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We showed VT binding in paediatric glomeruli, whereas, little or no binding was seen in the glomeruli of adult human renal sections [34].. Renal frozen section binding of VT1, VT2 and an

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Differential carbohydrate epitope recognition of globotriaosyl

ceramide by verotoxins and a monoclonal antibody

Role in human renal glomerular binding

Davin Chark1,2, Anita Nutikka1, Natasha Trusevych1,3, Julia Kuzmina1,3and Clifford Lingwood1,2,3

1 Research Institute, Division of Infection, Immunity, Injury and Repair, The Hospital for Sick Children, Ontario, Canada;

2

Department of Laboratory Medicine & Pathobiology and3Department of Biochemistry, University of Toronto, Canada

The role of renal expression of the glycosphingolipid

verotoxin receptor, globotriaosylceramide, in susceptibility

to verotoxin-induced hemolytic uremic syndrome is unclear

We show that a single glycosphingolipid can discriminate

multiple specific ligands Antibody detection of

globo-triaosylceramide in renal sections does not necessarily

pre-dict verotoxin binding The deoxyglobotriaosylceramide

binding profile for verotoxin 1, verotoxin 2 and monoclonal

anti-globotriaosylceramide are distinct

Anti-globotriaosyl-ceramide had greater dependency on the intact a-galactose

and reducing glucose of globotriaosylceramide than

vero-toxin 1, while verovero-toxin 2 was intermediate These ligands

differentially stained human kidney sections

Glomerulo-pathy is the primary verotoxin-associated pathology in

hemolytic uremic syndrome For most samples, verotoxin 1

immunostaining within adult glomeruli was observed (type

A) Some samples, however, lacked glomerular binding

(type B) Anti-globotriaosylceramide (and less effectively,

verotoxin 2) stained all glomeruli Verotoxin

1/anti-globo-triaosylceramide tubular staining was comparable Type B

glomerular/tubular globotriaosylceramide showed minor,

but significant, fatty acid compositional differences

Vero-toxin 1 type B glomerular binding became evident following

pretreatment with cold acetone, or methyl-b-cyclodextrin, used to deplete cholesterol Direct visualization, using fluo-rescein isothiocyanate-verotoxin 1B, showed paediatric, but no adult glomerular staining; this was confirmed by anti-fluorescein isothiocyanate immunostaining Acetone induced fluorescein isothiocyanate-verotoxin 1B glomerular staining in type A, but poorly in type B samples Compar-ison of fluorescein isothiocyanate-verotoxin 1B and native verotoxin 1B deoxyglobotriaosylceramide analogue binding showed an alteration in subspecificity These studies indicate

a marked heterogeneity of globotriaosylceramide expression within renal glomeruli and differential binding of vero-toxin 1/verovero-toxin 2/anti-globotriaosylceramide to the same glycosphingolipid Verotoxin 1 derivatization can induce subtle changes in globotriaosylceramide binding to signifi-cantly affect tissue binding Heterogeneity in glomerular globotriaosylceramide expression may play a significant (cholesterol-dependent?) role in determining renal pathology following verotoxemia

Keywords: Membrane glycosphingolipid receptor; lipid isoforms; carbohydrate presentation; hemolytic uremic syndrome; cholesterol

The glycosphingolipid (GSL) globotriaosylceramide

(Gala1–4Galb1–4glucosyl ceramide, Gb3), is the functional

receptor for the verotoxins (VTs, also termed Shiga toxins,

or Stx’s) produced by Escherichia coli [1] Gastrointestinal

infection with E coli producing such toxins can result in

hemorrhagic colitis which may progress to hemolytic uremic

syndrome (HUS), particularly in young children [2] Gb3

is also CD77, a differentiation marker of human germinal

centre B cells [3], the Pk blood group antigen [4] and a

marker of certain tumour cells [5–8], such that VT1 can be used as an antineoplastic agent [9,10] Afraction of Gb3

is found in cell surface cholesterol-enriched lipid micro-domains – rafts [11,12] This organization appears to regulate the intracellular routing of the verotoxin–Gb3 complex [13], such that protein synthesis can be induced, rather than inhibited, by VT for cells in which Gb3is not raft-associated As for all GSLs, heterogeneity of fatty acid, and to a lesser extent, of sphingoid base, generates a spectrum of lipid isoforms of Gb3 Both the lipid structure [14–17] and the local membrane phospholipid microenvi-ronment [18] impinge upon verotoxin–Gb3 binding In addition, there are variants of verotoxin, primarily VT1, VT2 and VT2c [19], which differentially bind to the carbohydrate moiety of Gb3, as determined by differential binding to deoxyGb3analogues [20] and Gb3lipid isoforms [14,16] These variants are also differentially involved in disease [21,22]

Gb3is also involved in the signal transduction of CD19 [23] and a2-interferon [24,25], due to N-terminal sequence similarity between the verotoxin B subunit and the

Correspondence to C Lingwood, Research Institute, Division of

Infection, Immunity, Injury and Repair, The Hospital for Sick

Children, Ontario M5G 1X8, Canada.

Fax: + 1 416 813 5993, Tel.: + 1 416 813 5998,

E-mail: cling@sickkids.ca

Abbreviations: AP, alkaline phosphatase; FITC, fluorescein

isothio-cyanate; Gb 3 , globotriaosylceramide; GSL, glycosphingolipid; NGS,

normal goat serum; SGC, sulfogalactosyl ceramide; TBS,

Tris-buffered saline; VT, verotoxin; VTEC, verotoxigenic E coli.

(Received 15 October 2003, accepted 24 November 2003)

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N-terminus of CD19 [26] and the a2-interferon receptor [27].

Verotoxin B subunit and monoclonal anti-Gb3can induce

apoptosis [28,29], particularly in lymphoid cells [30] Tissue

screening with monoclonal anti-Gb3indicates a wider Gb3

distribution [31,32] than inferred from pathogenesis of HUS

or VT tissue targeting and pathology in animal models [33]

We have shown previously the expression of Gb3within

the renal glomerulus, as monitored by the binding of

fluorescein isothiocyanate (FITC)-labelled VT1, correlates

with the age-related incidence of HUS following

verotoxi-genic E coli (VTEC) infection [34] Ninety per cent of HUS

cases occur in children under 3 years of age We showed VT

binding in paediatric glomeruli, whereas, little or no binding

was seen in the glomeruli of adult human renal sections

[34] The distribution of Gb3 was thus implicated in the

epidemiology and hence, etiology, of VT-induced disease

[35] However, this differential renal glomerular Gb3

expression has recently been questioned At 4C, VT1

binds similarly to both adult and paediatric glomeruli [36]

Anti-Pk is used to type red cells, yet the binding of VT

to human red cells is only observed at 4C and is not

significant under physiological temperature conditions [37]

We therefore questioned whether anti-Gb3 and VT bind

Gb3in the same manner and whether any differences could

shed light on the Gb3expression in the human kidney in

relation to VT-induced disease Our present studies validate

our previous age-related binding [34], but show a marked

difference in Gb3recognition according to ligand This work

adds a new, clinically relevant, dimension to the

lipid-mediated heterogeneity of Gb3 recognition, which may

provide a precedent for other GSL receptor functions

Materials and methods

VT1, VT1B and VT2 were purified as described [38–40] Rat

mAb anti-Gb3(38.13) hybridoma was a generous gift from

J Wiels (Institut Gustave Roussy, Villejuif, France)

Culture supernatant was affinity purified using Gb3-celite

[41] SULF1 mAb anti-sulfogalactosyl ceramide (SGC)

culture supernatant [42] was kindly provided by P Fredman

(Department Clinical Neuroscience, University of

Gote-borg, Sweden) Rabbit anti-VT2e was supplied by C Gyles

(Department Microbiology, University of Guelph, Ontario)

Polyclonal rabbit anti-VT1B 6869 Ig was prepared in our

laboratory Biotin-conjugated goat anti-(rat IgM) serum

and biotin-conjugated goat anti-rabbit Ig were from

Jack-son Immunoresearch Laboratories (West Grove, PA,

USA) Horseradish peroxidase (HRP)-conjugated goat

anti-rabbit and HRP-conjugated goat anti-mouse Igs were

purchased from Sigma StreptABComplex/alkaline

phos-phatase (AP) were from Dako (Carpinteria, CA, USA)

Avidin/Biotin blocker was from Vector (Burlingame, CA,

USA) True Blue Peroxidase substrate and HistoMark

Red were from Kirkegaard & Perry Laboratories (KPL,

Gaithersburg, MD, USA)

Receptor enzyme linked immunosorbant assay (RELISA)

The wells of a 96-well Evergreen microtitre plate (DiaMed

Laboratory Supplies Inc Mississauga, ON, CA) were

incubated with 150 lL aliquots of 5% (w/v) BSAin

10 mM NaCl/P (pH 7.2) for 2 h at room temperature,

washed three times with ddH2O and allowed to dry completely Ten microliters of Gb3 (100 lgÆmL)1) in an 85% ethanolic solution was then added in duplicate to each well and dried overnight After blocking with 1% BSA/ NaCl/Pi(150 lL per well) for 1 h, wells were successively treated with 50 lL each of serially diluted VT1, VT2, or mAb 38.13 in 1% BSA/NaCl/Pi; corresponding antibodies (rabbit anti-VT1B 6869, rabbit anti-VT2e, or biotin-conju-gated goat anti-rat IgM, respectively, all at 1 : 2000 in 1% BSA/NaCl/Pi); and finally the corresponding horseradish peroxidase-conjugated goat anti-rabbit or HRP-conjugated streptavidin, both at 1 : 2000 in 1% BSA/NaCl/Pi) Each step consisted of a 1 h incubation (100 lL per well) followed by two washings with 1% BSA/NaCl/Pi A fter one final wash with NaCl/Pi, freshly prepared 2,2¢-azino-bis-3-ethylbenzthiazoline-6-sulfonic acid solution (ABTS; Sigma – 0.5 mgÆmL)1ABTS, 0.3 lLÆmL)130% hydrogen peroxide in 0.08Mcitrate/0.1Mphosphate buffer, pH 4.0) was added (100 lL per well) to the wells After a 40 min incubation at room temperature, absorbence at 405 nm in each well was measured with an ELISAplate reader (Dynatech Laboratories) The assay was also performed using VT1, VT2 or mAb 38.13 (each at 1 lgÆmL)1) on serially diluted concentrations of Gb3

Tissue preparation Human renal cortical tissue was harvested 24 h post mortem Grossly normal appearing tissue was excised, embedded in Tissue Tek OCT Compound (Sakura Finetek, Torrence, CA, USA), and snap-frozen in liquid nitrogen Frozen tissue was then sectioned (6 lm) and stored at )70 C Sections to be stained were dried overnight at room temperature and all subsequent steps were performed in a humid chamber

Staining with FITC-conjugated VT1B Sections were blocked with 1% normal goat serum (NGS) (Jackson Immunoresearch Laboratories, Westgrove, PA, USA) in 50 mM Tris-buffered saline (TBS) pH 7.4 for

20 min at room temperature NGS (1% in TBS) was used as the diluent for all toxins and antibodies Sections were stained with FITC-labelled VT1B, prepared as described [43] at 5 lgÆmL)1for 1 h at room temperature, extensively washed with TBS and fixed for 20 min in 4% paraformal-dehyde/NaCl/Pi After washing, sections were treated with

50 mMammonium chloride for 10 min, washed, mounted with fluorescent mounting media (Dako, Carpinteria, CA, USA), and observed under a Polyvar fluorescent micro-scope under incident UV illumination

Immunoperoxidase detection of FITC-VT1B Sections were blocked with endogenous peroxidase blocker (1 mM sodium azide, 1 UÆmL)1 glucose oxidase, 10 mM

glucose) at 37C for 1 h After extensive rinses with TBS, sections were blocked with 1% NGS/TBS for 20 min at room temperature Serial sections were stained with FITC– VT1B (1 lgÆmL)1) for 30 min, washed with TBS and incubated with either biotin-conjugated rabbit anti-FITC (1 : 1000) or rabbit anti-VT1B 6869 (1 : 1000) for 30 min

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After washing and a 30 min incubation with

HRP-conjugated streptavidin (1 : 500) or HRP-HRP-conjugated goat

anti-rabbit Ig (1 : 500), respectively, FITC–VT1B binding

was chromagenically visualized with True Blue Peroxidase

substrate incubated at room temperature for 5 min

Sections were immersed in water for 5 min, dehydrated

through an ethanolic series, cleared with xylene, and

mounted with Permount Negative control slides were

tre-ated without FITC–VT1B The sensitivity of the

immuno-peroxidase detection allowed for the use of 1 lgÆmL)1

FITC–VT1B instead of the 5 lgÆmL)1used for visualization

by fluorescence

Immunostaining with VT1, VT1B or VT2

The immunoperoxidase staining procedure for VT1 (or

VT1B) was performed as previously [44] but with

modifi-cations Sections were first blocked for endogenous

peroxi-dase as above, and blocked for 20 min with 1% (v/v)

NGS/TBS Sections were then successively incubated with

1 lgÆmL)1 VT1 (or VT1B), rabbit anti-VT1B 6869

(1 : 1000), and HRP-conjugated goat anti-rabbit Ig

(1 : 500) Each step consisted of a 30 min incubation

followed by extensive washing with TBS VT1 (or VT1B)

binding was visualized with True Blue then washed,

dehydrated cleared, and mounted as above

Temperature-dependent binding of VT1 was performed in the same

manner, except all binding steps were performed at either

4C or 37 C Sections to be stained with VT2 were blocked

with Avidin/Biotin blocker followed by 1% (v/v) NGS/TBS

as above, and successively treated with 10 lgÆmL)1VT2,

rabbit VT2e (1 : 1000), biotin-conjugated goat

anti-rabbit (1 : 1000), and StreptABComplex/AP Each step

consisted of a 30 min incubation followed by extensive

washing with TBS VT2 binding was visualized with

HistoMark Red AP substrate Sections were washed,

dehydrated, cleared, and mounted as above Control slides

were treated identically but not exposed to the toxins

Double immunostaining with VT1 and mAb 38.13

Renal sections to be double immunostained were treated

with endogenous peroxidase blocker, Avidin/Biotin blocker

and 1% (v/v) NGS/TBS as above, with TBS washing

between steps After a 30 min incubation with VT1 and

mAb 38.13 together (1 lgÆmL)1and 5 lgÆmL)1,

respect-ively), sections were successively treated with

biotin-conju-gated goat anti-rat IgM (1 : 1000), and StreptABComplex/

AP, in the same manner as above, and mAb 38.13 binding

was visualized with HistoMark Red substrate After

wash-ing with water and 20 min blockwash-ing with 1% (v/v) NGS/

TBS, sections were incubated with rabbit anti-VT1B 6869

(1 : 1000) and HRP-conjugated goat anti-rabbit Ig

(1 : 500), each step consisting of 30 min followed by TBS

washing VT1 binding was visualized with True Blue

Peroxidase substrate and slides were washed, dehydrated,

cleared, and mounted as above Serial tissue sections were

also stained with VT1 and mAb 38.13 independently

Negative control slides were treated without VT1 or with

a rat IgM isotype control for mAb 38.13 Using this

combination of substrates, True Blue Peroxidase must be

developed last as the blue product is soluble in TBS

Epitope unmasking treatments Frozen sections were either incubated with 1.8 UÆmL)1 neuraminidase from Clostridium perfringens (Sigma) in 0.1M acetate buffer (pH 4.7) for 3 h at 37C, 0.125% trypsin (Sigma) in NaCl/Pifor 30 min at room temperature, acetone for 5 min at 4C or 10 mMmethyl-b-cyclodextrin for 45 min at 37C After extensive washing with TBS, sections were blocked with endogenous peroxidase blocker and 1% (v/v) NGS/TBS as above, and successively treated with 1 lgÆmL)1 VT1, rabbit anti-VTB 6869, and HRP-conjugated goat anti-rabbit Ig in the same manner as described VT1 binding was visualized with True Blue Peroxidase substrate Direct binding of FITC–VT1B was also assayed as above after acetone treatment

Renal sulfatide staining Renal sections were treated with endogenous peroxidase blocker and 1% (v/v) NGS/TBS as above, and stained with mouse anti-SGC SULF1 (2 lgÆmL)1) followed by incuba-tion with HRP-conjugated goat anti-mouse Ig (1 : 500) Each step consisted of a 30 min incubation followed by TBS washing SULF1 binding was visualized with True Blue Peroxidase substrate

Thin layer chromatography overlay of deoxyGb3

analogues Deoxy derivatives of a synthetic Gb3analogue containing globotriaose in anomeric linkage to a bis-C16-alkyl sulfone aglycone were synthesized as described [45,46] Glycolipids (5 lg) were resolved on Sil G UV plastic-backed silica TLC plates (Machery-Nagel) with chloroform/methanol/water (65 : 25 : 4, v/v/v), dried, and one plate was stained with 0.5% (w/v) orcinol in 3M H2SO4 The remaining plates were blocked with 0.6% gelatin in water at 37C overnight After washing extensively with water, plates were incubated with VT1 (0.3 lgÆmL)1), VT1B (0.3 lgÆmL)1), VT2 (3 lgÆmL)1), undiluted mAb 38.13 culture supernatant, or FITC–VT1B (0.3 lgÆmL)1) for 2 h at room temperature (all dilutions in TBS) After three washings with TBS, plates were incubated with the corresponding antibody (rabbit anti-VTB 6869, rabbit anti-VT2e, biotin-conjugated goat anti-rat IgM, or biotin-conjugated rabbit anti-FITC) at

1 : 1000 for 1 h, followed, after washing, by HRP-conju-gated goat anti-rabbit or HRP-conjuHRP-conju-gated streptavidin as appropriate at 1 : 1000 for 1 h Finally, plates were washed extensively with TBS and developed with 4-chloro-1-naph-thol peroxidase substrate

Renal glomeruli purification Renal cortical tissue was obtained at autopsy from a 68 year-old Type B phenotype kidney was dissected and stored at )20 C Tissue was then thawed, minced with a razor blade into a paste-like consistency, and pushed through a 50 mesh/

230 lm stainless steel tissue sieve screen (Bellco Glass, Inc Vineland, NJ, USA) The filtrate containing intact glomeruli was washed through a 150 mesh/94 lm screen with NaCl/

Pi Glomerular cores were washed off the screen and collected separately from the final filtrate (tubular fraction)

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Purity of glomerular and tubular fractions was verified

microscopically Tissue retained by the 50 mesh sieve was

designated the glomeruli-depleted fraction Each fraction

was centrifuged at 2000 g for 3 min and pellets were

extracted in chloroform:methanol (2 : 1) overnight The

lower phase of a Folch partition was dried down and

saponified in 0.1MNaOH/100% methanol overnight After

neutralizing with HCl and desalting, lower phase lipids were

separated on TLC plates VT1 and mAb 38.13 overlays were

performed as described above

Mass spectrometry

The glomerular and tubular glycolipid fractions purified

from the type B kidney above were subject to mass

spectrometry to determine the ceramide heterogeneity

The lower phase GSL extracts (above) were saponified

with 1M NaOH in methanol, neutralized with HCl,

partitioned against water and washed twice GSLs were

isolated from the lower phase by elution from a silica

column in acetone/methanol (9 : 1, v/v) This fraction was

then passed through a DEAE column in methanol to

remove acidic GSLs Approximately 10 pmole Gb3 was

analyzed without further separation in the Mass

Spectro-metry Laboratory at the University of Toronto Saturated

2,5-dihydroxybenzoic acid in methanol was used as the

matrix solution The sample was dissolved in 20 lL

methanol and 1 lL was spotted on the sample target, and

then 1 lL of the saturated matrix solution loaded into the

mass spectrometer The MALDI MS was acquired in

DE-reflection, positive mode on an Applied Biosystems

Voyager-DE STR MALDI-TOF mass spectrometer

equipped with a 377 nm laser The accelerating voltage

was set at 20 KV, grid voltage at 94%, guide wire at 0.05%,

extraction delay time of 175 nsec and low mass gate at

800 Da The mass spectra were externally calibrated with

the molecular mass of a mixture of standard peptides

Results

Comparison of ligand/Gb3binding by RELISA

The binding of VT1, VT2, and mAb anti-Gb3 (38.13) to

Gb3 was assessed using a RELISAwhere binding was

determined as a function of the ligand concentration

(Fig 1A) and the immobilized Gb3concentration (Fig 1B)

While binding parameters cannot be calculated using this

assay, all three ligands showed similar dose-dependent,

saturable binding to Gb3

Binding to deoxyGb3analogues shows different hydroxyl

dependence for VT1and anti-Gb3

To examine the carbohydrate recognition epitopes of Gb3

for VT1, VT2, and mAb anti-Gb3, binding to a series of

synthetic monodeoxyGb3 analogues was assayed by TLC

overlay (Fig 2) The hydroxyl groups of the trisaccharide

moiety were each removed in turn Amarked difference

between the binding profile of the antibody and VT1

was clearly seen, while VT2, although more weakly,

bound many of the same deoxyGb3 analogues as the

mAb anti-Gb Deoxy substitutions within the terminal

a-galactose were less tolerated by mAb anti-Gb3than VT1, most notably at the 3¢ and 4¢ deoxy positions Similarly, deoxy substitutions in the b-glucose, proximal to the ceramide lipid, were more adverse for mAb anti-Gb3 Substitutions at the 2 or 6, but not 3-deoxy positions, were well tolerated by VT1, whereas 3-deoxyglucose but not 2 or

6 substitution allowed mAb anti-Gb3binding VT2 binding was sensitive to any glucose substitution and, like mAb anti-Gb3, little residual binding after any a-galactose hydroxyl substitution was seen With exception of the 3 position, hydroxyl substitutions within the b-galactose were not tolerated by all three ligands In general, all hydroxyls within the trisaccharide were required for full VT2 binding,

as binding to the deoxy analogues were much weaker than

to the parent Gb3bisalkyl analogue Also of note, VT2, but not VT1, required the presence of the hydroxyl at the 6-glucose position

Renal frozen section binding of VT1, VT2 and antiGb3

are not equivalent The binding of these three ligands to adult human renal tissue was then compared by overlay of frozen serial sections VT1, VT2 and mAb anti-Gb staining were

Fig 1 Binding of VT1, mAb anti-Gb 3 and VT2 to Gb 3 The binding of VT1 (d), mAb 38.13 (j), and VT2 (m) to immobilized Gb 3 as a function of (A) ligand concentration (at 1 lg Gb 3 per well) (B) Gb 3

concentration (at 1 lg ligand per mL), as determined by RELISA Similar saturable Gb 3 binding is seen for all three ligands.

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compared using double-label immunohistochemistry, where

HRP, staining blue, was used to detect VT1 binding, and

AP, staining red, was used to detect either VT2 or anti-Gb3

binding Immunolabelling resulted in a purple stain where

VT1 and anti-Gb3colocalized In the majority of samples,

the staining of anti-Gb3 and VT1 corresponded In some

cases, however, tubular staining by anti-Gb3 was distinct

from that of VT1 and this varied from sample-to-sample

More significantly, renal glomerular staining by anti-Gb3vs

VT1 could be quite distinct In all adult samples studied

(renal tissue from four autopsies ages 38, 46, 68 and 73 years

with no renal pathology), mAb anti-Gb3staining within the

glomerulus was observed (Fig 3Ac,g), while VT1 staining

within the glomerulus was present in three samples both in

single (Fig 3Aa) and double (Fig 3Ab) staining with

anti-Gb3 (designated type Aphenotype) In the other sample

(from a 68 year-old; designated type B phenotype), VT1

staining within the glomerulus was clearly absent both by

single immunostaining (Fig 3Ae) and double

immuno-staining with VT1 and anti-Gb3(Fig 3Af) of serial sections

Tubular staining was similar to that observed in type A

samples MAb anti-Gb3 and VT1 staining were, for the

most part, coincident However, some tubules stained by

anti-Gb3were not bound by VT1 (e.g some pink tubules

are seen in Fig 3Af) VT2 glomerular staining was seen in

all samples, although glomerular staining in the type B

sample was somewhat less (compare Fig 3Ad with h)

Ligand binding was examined routinely at room

tempera-ture However, for type B sections, the effect of temperature

on VT1 glomerular binding was determined At 37C, no

binding within the glomerulus was observed (Fig 3Aa), as seen at room temperature At 4C, VT1 glomerular binding was detected in a serial section (Fig 3Bb) Tubular VT1 staining was also more distinct and discriminatory at 37C (and at room temperature) compared with 4C

Type B glomerular and tubular Gb3are similar and bound by VT1

Renal glomeruli were isolated from this sample to determine whether the Gb3content was in any way unusual GSL was isolated from the residual tubular fraction also The glycolipid fraction from the glomeruli and tubules were subjected to VT1 and mAb anti-Gb3 TLC overlay (Fig 4A) No differences in the Gb3 species detected by such binding, as compared to the renal glomerular and glomerular-depleted fractions, were observed Mass spectro-metric analysis (Fig 4B) showed both the glomerular and tubular Gb3to be comprised primarily of C16, C22, C24 and C24:1 fatty acids C18 and C20 fatty acid Gb3 were detected in the tubular but not the glomerular fraction Hydroxylated C20 fatty acid was detected in glomerular but not tubular Gb3

Differential FITC–VT1B and VT1B renal section staining Amajor fraction of the adult renal samples used in this study were positive for VT1 glomerular staining (type A) using the indirect immunoperoxidase staining procedure This contrasts with our previous report in which no adult glomeruli were labelled by direct binding of FITC-conju-gated VT1 [34] We therefore compared the renal staining

of FITC-labelled VT1B with unmodified VT1B staining detected by the immunoperoxidase procedure (Fig 5) Adult renal medulla showed coincident FITC–VT1B (Fig 5A) and immunoperoxidase VT1B labelling (Fig 5B)

of the same tubules Some tubules were more reactive with VT1B than FITC–VT1B FITC–VT1B labelling within the renal cortex (Fig 5C,E) validated our previous results [34] that FITC-labelled toxin does not stain any adult renal glomeruli In a paediatric sample, FITC–VT1B staining of glomeruli (and some tubules) was evident (Fig 5G) as we had reported previously [34] Pediatric glomerular and tubular staining by VT1 by immunoperoxidase detection was also clear (Fig 5H) In type B adult renal sections (Figs 5E,F), immunoperoxidase anti-VT1 labelling of VT1B-treated serial sections confirmed the lack of glomer-ular staining However, in type Asamples, while FITC– VT1B glomerular staining was negative (Fig 5C), the immunoperoxidase staining of VT1B-treated serial sections showed renal glomeruli bound native VT1B (Fig 5D) To verify the distribution of FITC–VT1B in these renal frozen sections, we used an indirect peroxidase system using anti-FITC as the primary antibody (Fig 5I,K) This indirect immunoperoxidase assay, confirmed that the FITC-labelled toxin was not found within any adult renal glomeruli but restricted to the tubules (Fig 5I,K), as detected previously

by monitoring tissue section fluorescence directly (Fig 5A,C,E) However, when FITC-conjugated VT1B-treated type Aserial sections were visualized using the anti-VT1 peroxidase system, additional glomerular VT1B staining could be observed (Fig 5J), indicating the presence of

Fig 2 Comparison of VT1, mAb anti-Gb 3 and VT2 binding to

monodeoxyGb 3 analogues by TLC overlay DeoxyGb 3 analogues were

separated by TLC and visualized by (A) orcinol chemical detection.

Immunodetection of ligand binding was detected by TLC overlay for

(B) VT1, (C) mAb anti-Gb 3 or (D) VT2 Gb 3 analogues tested

for binding: lanes (1) parent Gb 3 bisalkyl analogue; (2) 2¢¢-deoxy;

(3) 3¢¢-deoxy; (4) 4¢¢-deoxy; (5) 6¢¢-deoxy; (6) 2¢-deoxy; (7) 3¢-deoxy;

(8) 6¢-deoxy; (9) 2-deoxy; (10) 3-deoxy and (11) 6-deoxy analogues.

Adistinct hydroxyl requirement is seen for each Gb 3 ligand.

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residual unlabelled VT1B within the FITC–VT1B

prepar-ation, binding to the type Aglomeruli Such anti-VT1

glomerular labelling was not seen for FITC–VT1B treated

type B sections (Fig 5L), and glomeruli were similarly

anti-FITC negative (Fig 5K)

FITC-conjugation alters VT1B deoxyGb3binding

Based on these results, we suspected that modification of

the VT1B by FITC-conjugation might have subtly altered

the ability of VT1B to bind Gb3 We therefore compared the

binding of FITC-labelled VT1B and native VT1B to the

series of deoxyGb3 analogues by TLC overlay Separate

binding assays were visualized using either the anti-FITC

peroxidase or the anti-VT peroxidase detection system

(Fig 6) Conjugation of VT1B with FITC significantly

affects the deoxyGb3analogue binding profile as monitored with anti-FITC (Fig 6C) when compared to the native VT1B-subunit (Fig 6A) Specifically, binding to the 6-deoxyglucose analogue is much reduced The binding of residual unconjugated toxin within the FITC–VT1B pre-paration was detected with anti-VT1 Fig 6B

Basis for lack of VT1B renal type B glomerular staining The basis of the differential VT1 and anti-Gb3binding of the type B renal sample was examined Cell surface GSLs may be cryptic [47] via masking by adjacent proteins or sialated glycoconjugates [48] Pretreatment of type B renal sections with either trypsin or neuraminidase/sialidase had

no effect on VT1 glomerular binding (Fig 7A,B); however, strong VT1 binding was observed after cold acetone

Fig 3 Comparison of VT1, mAb anti-Gb 3 and VT2 staining of adult renal frozen sections (A) Serial renal sections from the sample from the 46 year-old (a–d) and the 68 year-year-old (e–h) were stained with VT1 alone (a,e), VT1 and mAb 38.13 together (b,f), mAb 38.13 alone (c,g), or VT2 alone (d,h)

at room temperature In single immunostained sections: (a,e) VT1 (blue) (c,g) mAb anti-Gb 3 (red) (d,h) VT2 (red); colocalization of ligands stains purple in VT1/38.13 double immunostained sections (b,f) The sample from the 46 year-old is representative of type Aphenotype (VT1 positive glomeruli) and that from the 68 year-old of type B phenotype (VT1-negative glomeruli) MAb anti-Gb 3 stains all glomeruli (B) VT1 staining of a type B section at 37 C (a) is compared with staining of a serial section stained at 4 C (b) VT1 glomerular staining is seen at 4 C but is absent at

37 C Tubular staining is more distinct and discriminatory at 37 C Magnification, ·22.

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treatment (Fig 7C) As cold acetone may extract steroids,

we pretreated kidney sections with methyl-b-cyclodextrin to

deplete cholesterol more selectively [49] This induced

punctate VT1 glomerular staining (Fig 7D) in the type B

sample As cold acetone pretreatment was able to induce

renal glomerular VT1 binding in type B samples, the same

procedure was performed to examine whether the binding

of FITC-VT1B, which did not bind to any adult glomeruli,

could be similarly induced FITC–VT1B glomerular

bind-ing was induced by acetone treatment of type Asamples but

less significantly in type B (Fig 7E–H)

SGC is highly expressed in the kidney [50] and we have

described SGC as a deceptor which when present, can

inhibit VT1 binding to Gb3/cholesterol lipid domains

in vitro[51] We therefore stained serial sections with VT1 and mAb anti-SGC (Fig 7I–L) No glomerular anti-SGC staining was seen, but much of the anti-SGC staining was found for structures not stained by VT1 Similarly, VT1 staining was largely exclusive of anti-SGC binding This was apparent for all sections but was particular clear in type B samples

Discussion

Cell membrane GSL receptor recognition is a more complex process than the recognition of protein or glycoprotein receptors by their appropriate ligands Glycolipids are dynamic structures, both in terms of their lateral mobility and their organization within the plasma membrane The identification of cholesterol and sphingolipid enriched, detergent resistant plasma membrane lipid microdomains, which serve as foci for transmembrane signal transduction [52], has provided a strong impetus to consider GSLs as more than structural bilayer components [53] The hetero-geneity within the lipid moiety of GSLs generates a series of isoforms for each carbohydrate and this heterogeneity may determine or modulate their organization within rafts [54] and subsequent intracellular trafficking pathways [13,55] In the case of VT1–Gb3 binding, although the binding specificity is defined solely by amino acid/carbohydrate contacts [20,56] the lipid-free carbohydrate has a barely detectable binding affinity [15,17] Indeed, the lipid-free globotriaose oligosaccharide and Gb3 glycolipid bind in separate sites within the VT1B subunit pentamer [57] In addition, the fatty acid content of Gb3can markedly affect

VT binding and this effect is different for the different forms

of VT [14,16] Hydroxylation of specific Gb3 fatty acid isoforms for example, preferentially enhances VT2 binding, correlating the high renal hydroxylated fatty acid-Gb3 content [58] and VT2 susceptibility of mice [59] Gb3fatty acid heterogeneity also promotes VT binding [60] In a lipid bilayer, Gb3containing fatty acids shorter than C16 were not bound Increasing the chain length up to C22 increased VT1 binding while that of VT2c was preferential for C18 [14] Such effects can be modulated by the phospholipid acyl chain length within the GSL containing membrane micro-environment [18] Thus, the hydrophobic component and membrane play a central role in VT/Gb3 recognition We have proposed that this effect is mediated by an H-bond network within the interface region at the serine moiety of the GSL [61] to restrict sugar conformation and solvation Molecular modelling predicted two Gb3 binding sites within each monomer of the B subunit pentamer [20] with

site 1 being predominant, while cocrystallization studies identified three Gb3sites, with site 2 dominating [56] Our present studies are the first to identify substitutions within the glucose moiety of Gb3 that affect VT binding, and as such, are more consistent with site 1, rather than site 2,

Gb3 occupancy Moreover, the major difference between VT1 and VT2 binding was the lack of VT2 binding to the 6-deoxyglucose analogue, which is consistent with a predic-ted H-bond from this hydroxyl to VT2, but not VT1, when

Gb3 is docked in site 1 [20] The presence of multiple binding sites predicts that receptor multivalency plays a significant role in determining Gb binding avidity [62] but

Fig 4 Characterization of type B glomerular Gb 3 (A) Glycolipids

from purified renal fractions from a type B (VT1 glomerular-negative)

sample were separated by TLC and visualized by: (a) orcinol chemical

detection; (b) VT1 overlay; (c) mAb anti-Gb 3 overlay; lanes: (1)

gly-colipid standards at 1 lg each; (2) tubular fraction; (3) glomerular

fraction and (4) glomerular-depleted fraction Each lane represents

neutral lipids standardized for Gb 3 content Glycolipid standards are,

from top of the plate, glucosylceramide, galactosylceramide,

lactosyl-ceramide, Gb 3 , Gb 4 , Forssman glycolipid (B) MA LDITOF MS (a)

Tubular Gb 3 , (b) glomerular Gb 3 from type B kidney Only the Gb 3

mass range is shown The masses highlighted are the sodium adducts of

Gb 3 containing the indicated fatty acid.

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relating this to membrane Gb3glycolipid binding remains

unclear [57]

In the present study, we have shown five important new

findings: (i) VT1 binds deoxyGb3 analogues in a distinct

manner from VT2 and mAb anti-Gb3; (ii) all adult renal

glomeruli contain Gb3 as monitored by mAb anti-Gb3

binding; (iii) FITC-conjugation of VT1B alters the Gb3

binding such that adult renal glomerular Gb3is not bound;

(iv) unmodified VT1 (and VT1B) bind renal glomerular Gb3

within a significant fraction of adult samples and (v) VT1

(and VT1B) unreactive renal glomerular Gb3can be made accessible to FITC-VT1B/VT1 binding by cold acetone or methyl-b-cyclodextrin pretreatment Our studies also valid-ate our previous work [34] that FITC-VT1 glomerular binding is restricted to paediatric renal samples

Based on our present tissue staining results, we now propose two categories for Gb3expression within the adult renal glomerulus: (type A) Gb3 present and reactive with VT1, VT2, and mAb anti-Gb3; (type B) Gb3 present but only reactive with mAb anti-Gb, and to a lesser degree,

Fig 5 Comparison of VT1B and FITC–VT1B staining of renal frozen sections Medullar staining by (A) FITC–VT1B visualized by incident UV illumination and (B) immunoperoxidase detection of VT1B binding to the corresponding serial frozen section Arrows highlight tubules labelled by both procedures Arrowheads indicate tubules preferentially labelled by native VT1B Sections are from a type A sample Type A and B phenotype renal cortical staining by FITC–VT1B (C,E), respectively, and immunoperoxidase detection of VT1B binding to the corresponding serial frozen section (D,F) Type Aand B are both negative for FITC–VT1B glomerular binding Only Type Aexhibits glomerular staining by immunoper-oxidase detection of VT1B FITC–VT1B (G) and VT1 immunoperimmunoper-oxidase (H) staining of paediatric glomeruli Anti-FITC staining of an FITC– VT1B treated Type Asection (I) and anti-VT1 staining of the FITC–VT1B treated corresponding serial section (J) Anti-FITC immunoperoxidase staining of an FITC–VT1B treated of Type B section (K) and anti-VT1 staining of the FITC–VT1B treated corresponding serial section (L) No glomerular anti-FITC staining is seen but anti-VT1 detects VT1B glomerular binding (due to residual unlabelled VT1B in the FITC–VT1B sample) but only in type Asections Magnification, ·11.

Fig 6 Comparison of FITC–VT1B and VT1B binding to deoxyGb 3 analogues The effect of FITC-conjugation on VT1B/Gb 3 binding was assessed

by TLC overlay Lane (1) parent Gb 3 bisalkyl analogue; (2) 2¢-deoxy; (3) 3¢-deoxy; (4) 4¢-deoxy; (5) 6¢-deoxy; (6) 2¢-deoxy; (7) 3¢-deoxy; (8) 6¢-deoxy; (9) 2-deoxy; (10) 3-deoxy and (11) 6-deoxy analogues VT1B binding detected by anti-VT1 (A); FITC–VT1B binding detected by anti-VT1B (B) or anti-FITC (C) FITC-labelling of VT1B reduced binding to the 6 deoxyglucosyl analogue (lane 11).

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VT2 We have reported this VT1 binding phenotype

previously [44] The relative frequency of these categories

and their relationship to the incidence of HUS following

gastrointestinal VTEC infection remains to be determined

Studies along similar lines may also shed light on the

incidence of HUS in children

Our use of serial frozen section staining allows the direct

comparison of ligand binding and the effect of tissue

modification Our findings greatly expand the physiological

significance of lipid-based heterogeneity of Gb3 receptor

function, which now may impinge on the epidemiology of

HUS following gastrointestinal VTEC infection Our renal

section sample size is very small and therefore the variation

in renal glomerular Gb3 expression in relation to HUS

cannot be addressed in this study Nevertheless our studies

identify the phenotypic prototypes we would expect to

influence the incidence of VT-induced renal disease and

suggest the mechanism separating them The binding of

VT2 to adult renal glomeruli, not bound by VT1, is

consistent with the more common association of this variant

with renal disease [63–65]

Binding studies of VT1, VT2, mAb anti-Gb3, and FITC–

VT1B to deoxyGb3analogues show differential binding to

the sugar moiety and support our contention that these

ligands can preferentially bind different isoforms of Gb3

However, our TLC overlay binding data does not

com-pletely rationalize the differences in renal tissue staining

observed This binding assay, though demonstrating distinct

Gb binding subspecificity, is an ineffective mimic of cell

membrane Gb3 presentation [15] It is clear that the deoxyGb3 binding of mAb anti-Gb3 and VT2 is more restricted than that of VT1 While this is consistent with the similar glomerular staining by mAb anti-Gb3and VT2 but not VT1 in type B samples, overall, mAb anti-Gb3 renal glomerular staining is more, rather than less, widespread than VT1 Deoxy substitution at Glcb2OH or Glcb6OH is not tolerated by mAb anti-Gb3 Access to these hydroxyls could be restricted due to the close apposition of the ceramide moiety [66] maintained by intramolecular H-bonding of the ceramide N-H with the anomeric oxygen [67,68] The Glcb6OH may form an H-bond with 2-hydroxy fatty acid containing GSLs [69] within the interface of the membrane bilayer Thus, particularly when such H-bonds are formed, mAb anti-Gb3 (and VT2) binding may be restricted; in contrast VT1 binding could be unaffected In contrast, the Glcb3OH is involved in an intramolecular H-bond with the b-galactose [20] and the lack of VT1, as opposed to mAb anti-Gb3 binding to this analogue may indicate that restriction of rotation around this anomeric linkage is more important for VT1, as compared to mAb anti-Gb3 and VT2 binding Such considerations could be used to explain the differential VT1, as opposed to mAb anti-Gb3, renal glomerular staining by proposing that excess membrane cholesterol may restrict the formation of the Glcb3OH/Galb5O intramolecular H-bond In terms of FITC–VT1B binding, the major difference is reduced binding to the 6-deoxyglucose analogue as compared to VT1B (or VT1) The glucose residue of Gb is closely

Fig 7 Modulation of glomerular VT1 staining Frozen renal sections of type B phenotype were treated by the following procedures prior toVT1/ peroxidase immunostaining: (A) trypsin; (B) sialidase; (C) acetone and (D) methyl-b-cyclodextrin FITC–VT1B staining of type A(E,F) and type B (G,H) renal sections without (E,G) and after (F,H) acetone treatment Serial frozen sections of type A(I,J) and type B (K,L) phenotype were stained with VT1 (I,K) and mAb anti-SGC (J,L) Only VT1 glomerular staining was seen for type A samples In type B, neither VT1 nor anti-SGC glomerular staining was observed VT1 and anti-SGC staining are largely exclusive (Arrows show structures stained with VT1 but not anti-SGC, and arrowheads show those stained with anti-SGC but not VT1) Magnification, ·11.

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apposed to the interface between hydrophilic and lipophilic

components of the GSL As such, changes in the lipid

moiety or its membrane environment may more severely

impinge on this region to restrict FITC–VT1B binding to

explain the lack of adult renal glomerular binding

Our earlier studies showed that FITC-coupling at Lys53

of the VT1B subunit inhibited FITC-VT1B/Gb3 binding

[43] and that brief coupling times were necessary to avoid

this The modified Gb3 binding subspecificity we now

observe may be due to FITC-coupling to other lysine

residues within, or adjacent to, the Gb3binding site (e.g

Lys28) Brief FITC-coupling to VT1 has no effect on

cytotoxicity in vitro [43] and FITC–VT1B can compete with

native VT1 for Gb3binding [51]

These studies reveal a surprising complexity of tissue Gb3

receptor function Our finding that the same GSL can be

available for one specific ligand but not another,

demon-strates a new aspect to GSL receptor function This is

relevant to the recent report that VT1 and anti-Gb3induce

apoptosis via different signalling pathways, despite binding

to the same GSL [29] There are several other examples

where a single GSL is recognized by several ligands [61,69–

75] and differential recognition may also occur

The lack of VT1 (and VT1B) binding in glomeruli that

were mAb anti-Gb3 reactive (type B) is likely to be a

property of the membrane Gb3lipid environment as both

ligands were able to effectively bind purified glomerular Gb3

(from the same sample) by TLC overlay Mass spectrometry

of these samples showed a very similar fatty acid

compo-sition However there were differences in the minor species

[C18 and C20 for tubular and C20(OH) for glomerular Gb3]

which could have a bearing on VT1 reactivity Fatty acid

heterogeneity promotes VT1 binding [60] and hydroxylation

can preferentially increase VT2 binding [16] Our finding

that mAb anti-Gb3reactive glomerular structures become

VT1 reactive after cold acetone treatment is consistent with

a role of the membrane environment in Gb3 receptor

function While glycolipids and membrane phospholipids

are poorly, if at all, soluble in cold acetone,

immunolocal-ization of GSL after acetone treatment should nevertheless,

be interpreted with caution Solubility may be sufficient for

GSL diffusion However, as anti-Gb3reveals the presence of

Gb3 in the type B glomeruli, we favour an explanation

whereby Gb3presentation is altered by acetone to promote

VT1 binding Cholesterol is acetone soluble and might be

extracted from the glomerular membranes to achieve such

an effect This is the most likely interpretation, since

cholesterol depletion with methyl-b-cyclodextrin had a

similar effect to induce VT1 recognition, although this is

the first time methyl-b-cyclodextrin has been used to extract

tissue section cholesterol However, the selectivity of

methyl-b-cyclodextrin to deplete cholesterol has recently

been more rigorously investigated [76] The conditions used

in our study, while preferential for cholesterol, may also

extract some sphingomyelin, glycolipids and phosphatidyl

choline from cells Thus a role for cholesterol cannot be

inferred conclusively Cholesterol intercalates with

sphingo-lipids and cholesterol/Gb3enriched lipid microdomains play

a central role in determining VT1 cell sensitivity [13,77]

Although addition of cholesterol promotes VT1/Gb3

bind-ing in an in vitro lipid microdomain bindbind-ing assay we have

developed [51,78], excess cholesterol is inhibitory for VT1

(but not VT2) binding (C Lingwood & A Nutikka, unpublished observation) If glomerular membrane choles-terol was high, limited cholescholes-terol extraction might therefore selectively increase VT1 binding membrane Gb3 rafts to explain our observation The more aggregated VT1 staining seen after methyl-b-cyclodextrin treatment would be con-sistent with optimization of VT1/Gb3 raft binding Thus, potentially, the glomerular cholesterol content may be a risk factor for VT1 binding and hence, for the development of HUS This may also provide the basis of the age-related FITC–VT1B glomerular binding we have found

The lack of VT1 glomerular binding in type B samples is not due to SGC inhibition of VT1/Gb3 binding as these glomeruli lack SGC SGC is a major component of the renal GSL fraction [50] and may be involved in ion transport [79]

We have found the addition of SGC inhibits the binding of VT1 to Gb3/cholesterol microdomains prepared in vitro [51] The extensive expression of SGC in distal tubules could relate to their relative resistance to VT1 [80] VT1 and anti-SGC renal binding were found to be, for the most part, mutually exclusive This gross separation of Gb3and SGC implies functional distinction

Arecent report [36] has contested that there is no age-related difference in human glomerular Gb3 expression and reported that Gb3can be stained by VT1 or anti-Gb3

in all renal glomeruli In these studies, Gb3 was quant-itated by VT1/TLC overlay While suitable for compar-ison, this does not quantitate Gb3 in absolute terms Chemical detection or mass spectrometry is necessary to avoid bias due to preferential binding of VT1 to select

Gb3 isoforms Moreover, in this study, VT1 binding to renal sections at 4C was monitored, and 90% of the binding was reported lost at room temperature [36] The relevance of binding of VT1 to glomeruli (and to red blood cells [37]) at 4C only, to the pathophysiology of VT-induced disease is questionable It is possible that at

4C, the heterogenous Gb3 binding phenotypes we observe, are reduced to a common lower affinity mech-anism, universally present At 4C, the lateral mobility of

Gb3 will be less, reducing the entropic penalty on ligand binding Indeed, we found VT1 glomerular binding in type

B samples at 4C In addition, membrane lipid organ-ization will be altered below their phase transition temperatures [18] The lack of VT1 glomerular binding

in type B samples at room temperature, was also seen at

37C, validating our binding studies at room temperature

as physiologically relevant Tubular binding was also more restricted but more distinct at 37C as compared to 4 C This suggests heterogeneity of tubular VT1 sensitivity under physiological conditions

While the role of Gb3 in mediating VT cytotoxicity

in vitro[13,55,81] and in animal models [33,82,83] has been established, the role in human disease has yet to be defined Renal glomerulus-bound VT1 was found in paediatric, but not in adult cases of HUS [35] This is consistent with our original report [34] and present studies using FITC-VT1B The VT-dependent etiology of HUS in the elderly and the young may be different The reduced susceptibility of adults might be ascribed to a type B Gb3expression, but, though our numbers are small, type Aappears to predominate, implicating other factors Possibly renal Gb3expression can

be modulated Certainly renal Gb expression and VT1

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