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An understanding of the N-terminal position in the final pore and its role in membrane insertion and pore stability is essential to define the precise molecular mechanism of pore formation

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lipid membranes and helps to stabilize the transmembrane pore

Katarina Kristan1, Gabriella Viero2, Peter Mac˘ek1, Mauro Dalla Serra2and Gregor Anderluh1

1 Department of Biology, Biotechnical Faculty, University of Ljubljana, Ljubljana, Slovenia

2 ITC-CNR Institute of Biophysics, Unit at Trento, Trento, Italy

Pore-forming toxins (PFTs) comprise one of the most

widespread groups of natural toxins They have the

unusual characteristic of existing in two different

states: they are synthesized as soluble monomers,

which spontaneously insert into cellular and model

membranes to form transmembrane pores that are

per-meable to various compounds [1,2] The formation of

transmembrane pores disrupts ion gradients, which

leads to osmotic swelling and ultimately to cell death

PFTs differ in sequence and structure, but the major

steps of pore formation are similar The first step is attachment to the membrane surface, which is a non-specific or a non-specific process, with the receptor being a membrane protein or a lipid molecule; for example, cholesterol-dependent cytolysins from Gram-positive bacteria only bind to membranes including cholesterol [3] Binding to the membrane is essential for oligomeri-zation, as it enables a high concentration and correct orientation of molecules on the host cell membrane After initial attachment, PFTs undergo a series of

Keywords

actinoporin; equinatoxin; planar lipid

membrane; pore-forming toxin; pore

structure

Correspondence

M Dalla Serra, ITC-CNR Institute of

Biophysics, Unit at Trento, Via Sommarive

18, 38050 Povo, Trento, Italy

Fax: +39 0461 810628

Tel: +39 0461 314156

E-mail: mdalla@itc.it

G Anderluh, Department of Biology,

Biotechnical Faculty, University of Ljubljana,

Vec˘na pot 111, 1000 Ljubljana, Slovenia

Fax: +386 1 257 3390

Tel: +386 1 42 333 88

E-mail: gregor.anderluh@bf.uni-lj.si

(Received 27 August 2006, revised 11

November 2006, accepted 21 November

2006)

doi:10.1111/j.1742-4658.2006.05608.x

Equinatoxin II is a cytolytic protein isolated from the sea anemone Acti-nia equina It is a member of the actinoporins, a family of eukaryotic pore-forming toxins with a unique mechanism of pore formation Equinatoxin II

is a 20 kDa cysteineless protein, with sphingomyelin-dependent activity Recent studies showed that the N-terminal region of the molecule requires conformational flexibility during pore formation An understanding of the N-terminal position in the final pore and its role in membrane insertion and pore stability is essential to define the precise molecular mechanism of pore formation The formation of pores and their electrophysiologic char-acteristics were studied with planar lipid membranes We show that amino acids at positions 1 and 3 of equinatoxin II are exposed to the lumen of the pore Moreover, sulfhydryl reagents and a hexa-histidine tag attached

to the N-terminus revealed that the N-terminus of the toxin extends through the pore to the other (trans) side of the membrane and that negat-ively charged residues inside the pore are crucial to define the electrophysio-logic characteristics of the channel Finally, we detected a new, less stable, state with a lower conductance by using a deletion mutant in which the first five N-terminal amino acids were removed We propose that the first five amino acids help to anchor the amphipathic helix on the trans side of the membrane and consequently stabilize the final transmembrane pore

Abbreviations

EqtII, equinatoxin II; His6–EqtII, fusion protein with hexa-histidine tag attached to the N-terminus of equinatoxin II; MTS,

methane-thiosulfonate; MTSEA+, (2-aminoethyl)-methanethiosulfonate hydrobromide; MTSES–, sodium (2-sulfonato-ethyl)-methanethiosulfonate; MTSET + , (2-trimethylamonium)-ethyl methanethiosulfonate; PFT, pore-forming toxin; PLM, planar lipid membrane; SM, sphingomyelin.

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conformational changes that expose previously hidden

hydrophobic parts for the interaction with the

membrane lipids PFTs are commonly divided into

two subgroups according to structural elements of

the transmembrane pore The pores of b-PFTs are

transmembrane b-barrels formed by interconnected

b-hairpins Examples include the well-known

Staphylo-coccus aureus a-toxin, cholesterol-dependent cytolysins

and anthrax toxin protective antigen [4,5] On the

other hand, a-PFTs build pores from amphipathic

a-helices [6] The most notable examples are colicins

[7] and actinoporins [8] Transmembrane b-barrel pores

are structurally stable, whereas pores formed by

a-helices are unstable, and consequently there is less

structural information available Because of the

above-mentioned properties, PFTs comprise a useful and

unique model with which to study protein unfolding

on the surface of the lipid bilayer [9], oligomerization

in a hydrophobic environment and membrane protein

structure [10], protein–protein interactions on the

surface of the membrane [11], etc In addition, PFTs

are particularly interesting as potential tools in

biotechnology; that is, they can be used for selective

killing of cancer cells, with built-in biological ‘triggers’

that activate in response to specific biological stimuli

[12,13], or they can be used in biosensor technology [14]

Actinoporins, cytolytic toxins synthesized by sea

anemones, comprise a unique group of PFTs [8] They

comprise a group of 20 kDa, cysteineless proteins,

whose activity depends on the presence of

sphingomye-lin (SM) in the membrane The most studied

represen-tative actinoporins are equinatoxin II (EqtII), isolated

from the sea anemone Actinia equina, and

sticho-lysin II, from Stichodactyla helianthus Actinoporins

form cation-selective pores approximately 2 nm in

diameter on the surface of the target cell [15,16],

lead-ing to cell lysis through colloid osmotic shock The

three-dimensional structures of EqtII and sticholysin II

monomers were determined in solution [17–19] The

molecule is composed of a tightly folded hydrophobic

b-sandwich core, flanked on two faces by a-helices

(Fig 1A) The first 30 N-terminal amino acids,

inclu-ding an amphipathic a-helix, form the only part that

can detach from the core of the molecule without

disrupting the general fold of the protein [17,19]

Recently, it has been shown that this is the only part

of the molecule that undergoes major conformational

changes during pore formation, and that its flexibility

is essential for formation of the final pore [20,21]

Act-inoporin pore formation proceeds in distinct steps The

initial attachment to the membrane is achieved by a

cluster of exposed aromatic amino acids situated on

the broad loops at the bottom of the molecule and the

C-terminal a-helix [20,22,23], and by a recently defined phosphorylcholine-binding site [19] In the next step, the N-terminal a-helix detaches from the core of the molecule and inserts into the lipid–water interface, where it lies flat on the membrane [19,20,24] Finally, four toxin monomers oligomerize and form the pore

by inserting the N-terminal a-helix through the mem-brane [24] The final functional pore is thus composed

of four amphipathic helices from four monomers [15,16,25] and most probably also by membrane lipids

in a so-called toroidal pore arrangement [26,27] The pores formed by actinoporins have not yet been directly visualized Most previous experiments were focused on the N-terminal a-helix, which extends from Ser15 to Leu26 in solution [17,18] and from Asp10 to Asn28 in a hydrophobic membrane environment [24] The question remains of how the region that comprises residues 1–10 is organized in the final pore, and what the nature of the contacts is between the monomers, which should stabilize the toroidal pore [19] Thus, the purpose of this work was to gain further insight into the structure of the EqtII pore, especially the topology

of the first five N-terminal amino acids We demon-strated that the N-terminus is positioned on the trans side of the membrane Furthermore, the amino acids

at positions 1 and 3 are exposed to the ion conductive pathway, and the N-terminus helps to stabilize the final pore

Results

Characterization of transmembrane channels formed by EqtII, single cysteine and deletion mutants

In this study, we used planar lipid membranes (PLMs) and three N-terminal EqtII mutants to study the topo-logy of the N-terminus in the final transmembrane pore (Fig 1C) We chose to study the S1C mutant, as the modification of a thiol group with methanethiosulf-onate (MTS) reagents allows incorporation of a posit-ive charge by using (2-aminoethyl)-MTS hydrobromide (MTSEA+) and (2-trimethylamonium)-ethyl MTS (MTSET+), or a negative charge by using sodium (2-sulfonato-ethyl)-MTS (MTSES–) In order to clarify the effect of the first five residues on the electrophysio-logic properties and stability of the pore, the deletion mutant D5 was used This mutant lacks one negative charge (Asp3) and three hydrophobic residues (Fig 1C,D) Finally, a His6–EqtII variant contains a hexa-histidine tag and prolongs the N-terminus of EqtII for 13 amino acid residues, adding a strong positively charged region to the N-terminal helix at

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pH 5.5; at this pH, the majority of the histidines

should be protonated [28] (Fig 1C) All of the mutants

were produced in Escherichia coli and purified to

homogeneity as shown by SDS⁄ PAGE gels (Fig 1B)

The hemolytic activity of S1C and D5 was as observed

previously [24,29] The addition of the His-tag to

the N-terminus of EqtII decreased the hemolytic

activity (cwt ¼ 0.21 lgÆmL)1± 0.03, cHisEqtII50 ¼ 0.98

lgÆmL)1± 0.04; n¼ 3–5 ± SD) (c50is the

concentra-tion of a protein that produces 50% of the maximal

rate of hemolysis)

Deletion mutant D5, S1C, chemically modified

ver-sions of S1C (S1C-MTSEA+, S1C-MTSET+,

S1C-MTSES–, in which S1C was chemically modified with

MTSEA+, MTSET+ and MTSES–, respectively), and

His6–EqtII were able to form pores in PLMs at final

concentrations of 1–5 nm (Figs 2 and 4)

EqtII and its mutants formed pores in PLMs with a

broad conductance distribution: 308 pS (wild-type),

329 pS (S1C), 349 pS (S1C-MTSEA+), 358 pS

(S1C-MTSET+), 247 pS (S1C-MTSES–) and 256 pS (D5)

(Fig 3A) D5 frequently showed two different types of

pore One was similar to the wild-type, and the other had a lower conductance and was less stable (Fig 2A, bottom trace, arrows) This behavior was not seen in the wild-type or other mutants used in this study, sug-gesting that it was a peculiarity of the deletion mutant These lower-conductance pores typically had conduct-ances of 100–150 pS (Fig 2B) and remained open for

a few seconds to 60 s (Fig 2A) After 5–10 min, when pores with higher conductance opened, such events were no longer observed, probably due to the typical total noise of EqtII multichannel recordings

All mutants showed cation selectivity, but to different extents (Fig 3B) Mutation of Ser1 to Cys did not affect the selectivity significantly (P+⁄ PWT ¼ 9.08;

P+⁄ PS1C¼ 10.14; p ¼ 0.321) (P+ and P) are the permeability of cation and anion, here K+ and Cl) respectively) The addition of a negative charge (S1C-MTSES–) leads to a significant increase in cationic selec-tivity (P+⁄ PMTSES¼ 15.1; p ¼ 0.021) On the other hand, the addition of positive charge (S1C-MTSEA+, S1C-MTSET+) or the deletion of a negative charge

in D5 caused a shift to less cationic selectivity

B

C

Fig 1 Structure of EqtII and alignments of

actinoporin N-terminal sequences, EqtII and

mutants used in the study (A)

Three-dimen-sional structure of EqtII (Protein Data Bank

code 1IAZ) with its N-terminal amphipathic

a-helix shown in black (B) SDS ⁄ PAGE gel

of proteins used in this study

Approxi-mately 1 lg of each protein was resolved

on 12% SDS ⁄ PAGE gel and stained with

Coomassie Blue (C) Alignment of the

wild-type EqtII, mutants and fusion protein used.

Negatively charged amino acids are in black.

The position of the N-terminal amphipathic

a-helix (amino acids 15–26) is shown above

the alignment by letters h [17] The region

that was shown to be in an a-helical

arrangement in the final pore is underlined

[24] An arrow denotes the thrombin

clea-vage site (D) The alignment of known

N-ter-minal sequences of actinoporins compiled

from the literature [8,45–49] Hydrophobic

amino acids (AGVLIFWYP) are shown in

black, polar amino acids (TSMCNQ) are

shown in dark gray, and charged amino

acids (DEKHR) are shown in light gray The

numbering is according to EqtII.

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(P+⁄ PMTSEAþ¼ 5.07, p ¼ 0.0003; P+⁄ PMTSETþ ¼ 4.03, p¼ 0.0002; P+⁄ Pd5¼ 2.58, p< 0.0001) (Fig 3B)

To further evaluate the charge distribution through the pore and possibly the position of the N-terminus, the current–voltage characteristic (I⁄ V) was studied (Fig 3C) The symmetry of the I⁄ V curve for S1C, i.e

I+⁄ I–  1 (Fig 3C, inset), suggests that the distribu-tion of the charges along the lumen of the mutated pore was not significantly different from that of the wild-type pore The addition of a negative charge on S1 (S1C-MTSES–) slightly decreased the I+⁄ I– ratio (Fig 3C, inset) On the other hand, the addition of a positive charge (S1C-MTSET+) strongly increased the slope of the I+⁄ I– ratio vs applied voltage curve (Fig 3C, inset), which is consistent with the location

of that charge on the trans side A similar strong asymmetry in the I⁄ V curve was also observed for D5, which lacks the negative charge at position 3

The position of the N-terminus in the final pore His6–EqtII was used to analyze in a more direct way the position of the N-terminus in the final pore, i.e to which side of the membrane the N-terminus extends His6–EqtII pores are slightly less conductive than the wild-type [G ¼ 204 ± 36.6 pS (p ¼ 0.004; n ¼ 21 average ± SD) (G¼ conductance), compared to

308 pS for the wild-type] The selectivity was not chan-ged (P+⁄ PHis6EqtII¼ 9.37, p ¼ 0.807), suggesting that the positively charged His-tag is positioned far enough from the pore entrance Interestingly, when positive voltages (from + 40 to + 100 mV) were applied across the membrane, the current increased nonlinearly (Fig 4B, inset) When the positive voltages were switched to negative voltages, the channels rap-idly closed and the current dropped close to zero (Fig 4A) The pores reversibly opened again when a positive voltage was again established This behavior could be easily explained by the His-tag being on the trans side At this pH, histidines should not carry an excess of positive charge; however, there is an addi-tional arginine, which is part of a thrombin cleavage site in the spacer (Fig 1C) and possesses a positive charge, which contributes to the observed behavior Therefore, an applied negative potential forces the entire N-terminus with the His-tag and linker contain-ing arginine to become closer to the trans entrance of the pore, to enter the pore lumen and to clog it The rate of closures was voltage-dependent and increased with the magnitude of the negative applied voltage Furthermore, when the pH of the buffer was lowered

to 5.5, i.e below the pKA of His (pKA¼ 6.04), which

A

B

C

Fig 2 Formation of pores in PLMs by the wild-type EqtII and

mutants (A) PLMs were composed of

1,2-diphytanoyl-sn-glycero-phosphocholine and 20% (w ⁄ w) SM The wild-type EqtII and D5

were added at a final concentration of 1–5 n M to the cis side,

where a constant voltage (+ 40 mV) was applied The buffer was

10 m M Tris ⁄ HCl and 100 m M KCl (pH 8.0) on both sides Only the

initial few steps of pore formation are presented for the most

rep-resentative traces Transient currents observed in D5 are indicated

by arrows (B) Histograms show the distribution of pore sizes The

numbers of events from eight and 10 independent experiments

were 24 and 83 for the wild-type and D5, respectively (C) Pore

for-mation of S1C and its modified forms (S1C-MTSET+, S1C-MTSEA+,

S1C-MTSES – ) at a final concentration of 1–5 n M , under the same

experimental conditions as in (A) The representative traces of at

least two independent experiments are shown.

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drastically increases the positive charge of the His-tag

[28], the current at negative voltages was actually

com-pletely blocked (Fig 4A)

To gain additional insights into the position of the

N-terminus across the membrane, MTS reagents were

applied to the cis or trans side of S1C preformed pores

(Table 1) The variation in selectivity, which has been

shown to be the most sensitive parameter, was

meas-ured after the addition of MTS reagents (see Fig 3B

for details) When MTS reagents, which are

mem-brane-impermeable, were added to the cis side of the

membrane, small or no changes in reversal potential

(Urev) were observed (Table 1) Changes occurred only

when MTS reagents were added to the trans side of

the membrane, suggesting that the reagents had

reac-ted with the thiol group of S1C, and modified the pore

selectivity, confirming the trans position of the Ser1

residue

Finally, heterobifunctional maleimeide-poly(ethylene

glycol)-N-hydroxysuccinimide was used to chemically

modify the thiol group of S1C after pores were

already formed Maleimeide-poly(ethylene

glycol)-N-hydroxysuccinimide contains a maleimide group that

can react with the thiol group and could possibly

clog the channel when covalently attached close to

the pore entrance In multichannel recordings,

clo-sures could be seen only when maleimeide-poly(ethy-lene glycol)-N-hydroxysuccinimide was added to the trans side However, the extent of current reduction did not exceed 15–20% of the total current (Fig 5A,B) When we performed a three-channel recording, the addition of the maleimeide-poly(ethy-lene glycol)-N-hydroxysuccinimide reagent caused stepwise closures only after maleimeide-poly(ethylene glycol)-N-hydroxysuccinimide was added to the trans side of the membrane (Fig 5C)

Discussion

The molecular mechanism of actinoporin pore forma-tion has been unraveled in the last few years, with

Fig 3 Properties of the channels formed by the wild-type and

mutants in PLMs (A) Average conductance of the wild-type and

mutant pores The dashed line shows the wild-type’s conductance

for comparison *p < 0.05; n ¼ 16–60, average ± SD The

experi-mental conditions were as in Fig 2A The bar corresponding to D5

refers to the normal channel, i.e the one with higher conductivity

in Fig 2B (B) Selectivity of pores formed by the wild-type EqtII

and mutants The wild-type and mutants were added at a final

con-centration of 1–5 n M to the cis side of the membrane Initially, both

sides were bathed in a symmetric solution of 10 m M Tris ⁄ HCl and

100 m M KCl (pH 8.0) The KCl concentration was increased

step-wise only on the trans side, to reach a final KCl concentration of

1 M (10-fold gradient) Urevvalues were converted to the reported

permeability ratio (P + ⁄ P – ) with the Goldman–Hodgkin–Katz equation

(Eqn 2) The dashed line shows the wild-type’s selectivity for

com-parison *p < 0.05; n ¼ 3–9, average ± SD (C) The dependence of

the single-channel current on the applied voltage for the wild-type

EqtII and mutants The I ⁄ V characteristics of the pores formed by

the wild-type EqtII (filled squares), S1C (filled diamonds),

S1C-MTSES – (open triangles), S1C-MTSET + (open inverted triangles)

and D5 (open circles) mutants are shown They were derived from

the amplitude of the current steps caused by square voltage pulses

in experiments with membranes containing 5–50 channels Current

values were then normalized at + 40 mV to the current flowing

through one single channel, as obtained from the histogram in

Fig 3 All conditions were as described in Fig 2A Inset: the ratio

of currents (I + ⁄ I – ; in absolute values) when positive and negative

voltages were applied n ¼ 3–9, average ± SD.

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particular emphasis on the role of the N-terminal

region It was shown that it needs to be flexible [20,21]

and that region 10–28 forms an amphipathic a-helix,

so far the only recognized structural element of the final pore [23] The present study provides additional information about the structure and formation of the EqtII pore The following conclusions can be drawn from the data presented here: (a) the first and third amino acids of EqtII are exposed to the lumen of the pore; (b) the N-terminal part of EqtII extends to the transside of the membrane in the final pore, i.e to the other side than the rest of the membrane-bound mole-cule; and (c) the first five amino acids help to stabilize the final pore

The position of the first and third amino acids

in the final pore The change in the fixed charge distribution through the pore affects the pore conductance [30] Therefore,

it can be used for determining the residues exposed to the lumen and the structural organization of the pore [24] In our experiments, the effects on pore properties were clearly shown for chemically modified S1C, for which large changes in cation selectivity were observed upon chemical modification with MTS reagents In Malovrh et al [24], modifications with MTS reagents and comparison of selectivity indices for chemically labeled mutants proved to be very useful for the detec-tion of sites exposed to the pore lumen, particularly the ratio of selectivity indices of a mutant that was chemically modified with MTSES– and MTSEA+ [(P+⁄ PMTSES)⁄ (P+⁄ PMTSEAþ)] This ratio is about

1 when the amino acid side chain is not facing the lumen of the pore, as was observed for most of the mutants in region 10–28 of EqtII [24] For the mutants exposed to the pore lumen, this ratio should be higher,

as selectivity increased with the negative charge attached and decreased with the positive charge This was indeed observed for the residues from the polar face of the amphipathic helix, with Asp10 showing the

Fig 4 The effect of the N-terminal histidine tag on the voltage-gating

properties (A) Proteins were added to the cis side at a final

concentra-tion of 2–20 n M , and the current across the membrane was followed.

The buffer was 10 m M Tris ⁄ HCl, 100 m M KCl, and 0.1 m M EDTA

(pH 8.0), on both sides, except in the lowest trace, where the buffer

was 10 m M Mes, 100 m M KCl, and 0.1 m M EDTA (pH 5.5) Other

con-ditions used were the same as described in Fig 2A The currents

when positive and negative voltages were applied are shown (B)

Cur-rent–voltage dependence of His6–EqtII The inset shows the ratio of

currents (I + ⁄ I – ; in absolute values) when positive and negative

vol-tages were applied The protein concentration was 5 n M

Table 1 MTS reagents were added to the cis or trans side in order

to study the accessibility of Cys1 Experiments were performed in asymmetric conditions, and Urevwas monitored from the first 15 s after the addition of MTS reagents until Urevstabilized (see Fig 3B for experimental details) The typical changes in U rev of 1–3 experi-ments are reported The concentration of KCl was 100 m M and 1 M

in the cis and trans chambers, respectively The Urevvalues for the S1C mutant before the addition of MTS reagents were 38.9 mV, 37.6 mV and 39.1 mV for MTSEA + , MTSET + and MTSES – , respect-ively.

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highest ratio of almost 10, suggesting it is located at

the constriction of the pore [24] In our case, the ratio

(P+⁄ PMTSES)⁄ (P+⁄ PMTSEAþ) was about 3 for the

S1C mutant, thus clearly indicating that this side chain

faces the lumen of the pore This value is

approxi-mately the same as the value observed for Asp17 [24],

and would place Ser1 at approximately the same

posi-tion with regard to the center of the pore

The introduced charges along the ion conductive pathway should also affect the conductance of pores Variation of the conductance upon addition of positive charge (MTSEA+ or MTSET+) or negative charge (MTSES–) has been observed for the solution-exposed amino acids of other PFTs [30,31] The observed chan-ges were explained primarily by the electrostatic nature

of these effects, on the assumption that the channel

Fig 5 The effect of maleimeide-poly(ethylene glycol)-N-hydroxysuccinimide on currents of the wild-type and S1C pores Multichannel recordings of EqtII (left) and S1C (right) in PLMs The lowest panel in S1C shows a three channel recording The concentration of the protein was 1 n M , except for oligochannel recording, where it was 200 p M Maleimeide-poly(ethylene glycol)-N-hydroxysuccinimide at a final concen-tration of 50 l M was added to the cis or trans compartment, as indicated by arrows The voltage applied was + 40 mV in all experiments.

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maintained a fixed structure In the present study, only

slight differences were observed in the conductance of

S1C, modified or not with MTS reagents (Fig 3A)

For a possible explanation of these small variations,

we must keep in mind that we modified the position at

the tip of a very flexible N-terminus [17,18,32] and that

EqtII forms toroidal pores [27] in which helices are not

rigidly arranged in the final pore Accordingly, the

high standard deviations in conductance values, which

are characteristics of EqtII pores, demonstrate that the

helix can slightly change position according to

circum-stances [24] As previously noted [24], we confirm here

that EqtII conductance is not the most sensitive

parameter with which to study the charge distribution

along the pore We therefore propose that the effects

of charges on the conductance of EqtII pores observed

for MTS-modified S1C and the low-conductance state

of the D5 mutant could be ascribed to an electrostatic

effect and to a pore structural rearrangement,

respect-ively

A strong effect on selectivity, as a result of the

change in the net charge, was observed for the D5

mutant This mutant showed significantly lower

cat-ion selectivity than the wild-type, which is consistent

with removal of a negative charge from the ion

conductive pathway The data obtained with D5

therefore suggest that Asp3 is exposed to the pore

lumen Similarly, the addition of a positive charge at

position 1 decreased the cation selectivity, and the

addition of a negative charge increased it According

to Malovrh et al [24], the modulation of negative

charges is crucial for defining the electrophysiologic

characteristics of EqtII In particular, selectivity is

the most sensitive electrophysiologic parameter and

the one that is most affected by charge modifications

in the pore lumen

Furthermore, current dependence on the applied

voltage was studied for chemically modified S1C and

D5 Deletion of the first five amino acid residues (D5)

and positive charge addition (S1C-MTSET+) had the

greatest effect The strong asymmetry of the I⁄ V

curves of D5 and S1C-MTSET+provides the first

indi-cation that the N-terminus is exposed to the trans side

of the membrane Furthermore, values of the I+⁄ I–

ratio larger than 1, as measured for those mutants,

strongly suggest a trans position of Ser1 (Fig 3C,

inset) In this case, the local trans concentration of

cat-ions is lower than the bulk concentration, due to the

repulsive effect of MTSET+, K+ (and Cl–), so they

move from cis to trans (or trans to cis) according to

both electrical and concentration gradients, leading to

a higher current The opposite happens when a

negat-ive voltage is applied

The position of the N-terminus in the final pore The asymmetry of the I⁄ V curves indicates that the first and third positions are exposed to the lumen of the pore Additional insights into the position of the N-terminus were obtained with the His-tagged version

of EqtII The data showed that His6–EqtII forms channels of lower conductance, has an asymmetric I⁄ V curve, and exhibits rapid closures of pores at a negat-ive applied potential voltage As we did not observe any changes in the selectivity of the pores formed by His6–EqtII, the changes in current must again be due

to changes in the pore structure and flexibility of the His-tag The above observations can be interpreted to mean that the His-tag is translocated to the trans side

of the membrane and then blocks the channel when negative voltages are applied This is likely, because the His-tag with the linker possesses at least one posit-ive charge at the pH of the buffer used (pH 8), and can therefore act as a voltage-dependent gate At

pH 5.5 (Fig 4), most of the histidines are protonated and thus the N-terminus of His6–EqtII carries a large excess of positive charge Consistently, the rates of clo-sure and opening of the pore, as well as the blocking efficiency at negative voltages, are drastically increased The most likely mechanism by which it may close the pore is by inserting into the pore lumen and thus obstructing the ion permeability when a negative potential is applied This mechanism would be analog-ous to the ‘ball and chain’ mechanism of channel inac-tivation [33] The voltage-dependent closures of His6– EqtII pores are also extremely similar to those observed for His-tagged diphtheria toxin [33] In that study, it was shown that diphtheria toxin is able to translocate the His-tag at the N-terminal region across the lipid membrane The same occurs in the case of EqtII; how-ever, the pore formation efficiency of His6–EqtII is reduced, as this mutant is less hemolytically active A similar reduction in permeabilizing activity when the His-tag was present was reported for the homologs magnificalysin [34] and sticholysin II [35] In fact, the N-terminus is critical for the permeabilizing activity of EqtII, and longer tags rendered it inactive [20]

Topological experiments with thiol-modifiable rea-gents were also performed MTS rearea-gents were added

to either side of the membrane when S1C pores were already formed, but changes were observed only upon addition to the trans side of the membrane (Table 1) Finally, maleimeide-poly(ethylene glycol)-N-hydroxy-succinimide only had observable effects when added to the trans side (Fig 5C) Altogether, the data obtained indicate that the N-terminal part of EqtII is exposed to the trans side when the transmembrane pore is formed

Trang 9

Stabilization of pores by first five amino acids

The most unusual behavior was observed with D5

(Fig 2) Unstable pores with half the conductance of

the fully open D5 pores were observed The current

data cannot exclude the possibility that the smaller

currents are due to the formation of channels by only

three or even fewer monomers In this case, the

N-terminal end would help to assemble monomers in

the final pore However, we believe that these smaller

channels represent an intermediate on the way to the

final pore, where the lack of five amino acids

pre-vents stabilization of final fully open pores In this

model, the first five amino acids would act as an

anchor, which would help to restrict the N-terminus

to the trans side of the membrane Region 1–5 is

highly hydrophobic in actinoporins (Fig 1D) The

Asp present at position 3 in EqtII is an exception, as

most actinoporins possess a hydrophobic amino acid

at that position (Fig 1D) The fourth amino acid is a

bulkier hydrophobic Val or Leu and could actually

have the most important role The first five amino

acids are also highly flexible and were not resolved in

the crystal structure of EqtII [17] Recently, an NMR

structure of a peptide corresponding to region 1–32

was determined in the presence of

dodecylphospho-choline micelles It formed a continuous helix from

residues 6 to 28, but again the first five amino acids

showed the highest flexibility [32] This region would

have a similar role as in aerolysin, a b-pore-forming

toxin from bacteria, where hydrophobic amino acids

from the tip of the b-loop anchor the b-barrel in the

membrane [36]

Experimental procedures

Materials

Bovine brain SM and

1,2-diphytanoyl-sn-glycerophospho-choline were obtained from Avanti Polar Lipids (Alabaster,

AL) All other materials were from Sigma (Milan, Italy),

unless stated otherwise

Cloning, expression and isolation of the mutants

The construction of expression vectors of mutants S1C and

D5 (deleted first five amino acids of EqtII) has been

des-cribed previously (Fig 1C) [22,29] The wild-type EqtII,

S1C and D5 were expressed in an E coli BL21 (DE3) strain

and purified from the bacterial cytoplasm as described

else-where [37] The wild-type EqtII was also constructed as a

His6fusion protein, which contains an N-terminal

hexa-his-tidine tag and the thrombin cleavage site (Fig 1C) His6–

EqtII was expressed in an E coli BL21 (DE3) pLysS strain

and purified from the bacterial cytoplasm by Ni-chelate chromatography [38] All mutants, fusion proteins and the wild-type were purified to homogeneity on SDS⁄ PAGE gels

Hemolytic activity Hemolytic activity was measured by the use of a microplate reader (MRX; Dynex Technologies, Deckendorf, Ger-many) A suspension of bovine red blood cells was pre-pared in hemolysis buffer (0.13 m NaCl, 0.02 m Tris⁄ HCl,

pH 7.4) from well-washed erythrocytes One hundred microliters of erythrocyte suspension with A630¼ 0.5 was added to 100 lL of two-fold serially diluted proteins Hemolysis was then monitored turbidimetrically by measur-ing the absorbance at 630 nm for 20 min at room tempera-ture The results are presented as c50, which is the concentration of a protein that produces 50% of the max-imal rate of hemolysis

Chemical modification using MTS derivatives Mutant S1C was chemically modified with MTS reagents

to introduce either a positive or a negative charge at the thiol group [30,39] MTSEA+ and MTSET+ were used for the introduction of positive charges, and MTSES–was used to introduce a negative charge (all from Biotium, Inc., Fremont, CA) S1C at a concentration of 10–

50 lgÆmL)1 (0.5–2 lm) in water was preincubated over-night in a 200 molar excess of dithiothreitol (0.1–0.4 mm) MTS reagents, freshly dissolved in water, were then added

at 1000 molar excess (0.5–2 mm) After 1 h of incubation

at room temperature, after which the majority of the rea-gent had been hydrolyzed according to the manufacturer’s specifications, the modified samples were used for PLM experiments The final concentrations of MTS reagents or dithiothreitol in the cis chamber after addition of the sample to the PLM were below 5 lm The pore propert-ies of the wild-type EqtII were not affected by the MTS reagents [24]

PLM experiments Solvent-free PLMs were composed of 1,2-diphytanoyl-sn-glycerophosphocholine and 20% SM (w⁄ w) [40] The chambers were made of Teflon, and the volume of the chambers was 2 mL The septum between the chambers was also made of Teflon and contained a 100 lm hole The protein was added at nanomolar concentrations to stable, preformed bilayers on the cis side only (the cis side is where the electrical potential was applied, and the trans side was grounded) All experiments were started in symmetric con-ditions, using a buffer comprising 10 mm Tris⁄ HCl and

100 mm KCl (pH 8.0) on both sides of the membrane For

Trang 10

experiments with His6–EqtII fusion protein, 0.1 mm

EDTA was included in the buffer A defined voltage,

generally + 40 mV, was applied across the membrane

Miniature magnetic stir bars stirred the solutions on both

sides of the membrane The currents across the bilayer were

measured, and the conductance (G) was determined as

follows [41]:

GðpSÞ ¼ IðpAÞ=UðVÞ ð1Þ where I is the current through the membrane, and U is the

applied transmembrane potential

Macroscopic currents were recorded by a patch clamp

amplifier (Axopatch 200, Axon Instruments, Foster City,

CA) A PC equipped with a DigiData 1200 A⁄ D converter

(Axon Instruments) was used for data acquisition The

current traces were filtered at 100 Hz and acquired at

500 Hz by the computer using axoscope 8 software (Axon

Instruments) All measurements were performed at room

temperature

For the selectivity measurement, KCl concentration was

increased stepwise on the trans side only to finally form a

10-fold gradient At each concentration, the potential

neces-sary to zero the transmembrane current (i.e the reversal

potential Urev), was determined From the reversal

poten-tial, the ratio of the cation over anion permeability

(P+⁄ P–) was calculated using the Goldman–Hodgkin–Katz

equation [42–44]:

Pþ= ¼ ½ðatrans=acisÞ expðeUrev=kTÞ  1=

½ðatrans=acisÞ  expðeUrev=kTÞ ð2Þ where atransand acis are the activities of KCl on the trans

side and the cis side, respectively [a, thermodynamic

activity on trans or cis side of membrane; Urev, reversal

potential; e, elementary charge; k, Boltzmann constant; T,

absolute temperature (at 23C kT/e ¼ 25 mV)] kT ⁄ e is

 25 mV at room temperature The P+⁄ P– values

repor-ted were measured at the same conditions, which were

100 mm KCl in the cis chamber and 1 m KCl in the

trans chamber

For topological experiments with the S1C mutant, the

protein was preincubated for 30 min with 20 mm

dithio-threitol and added to PLMs to allow pore formation MTS

reagents or heterobifunctional maleimeide-poly(ethylene

glycol)-N-hydroxysuccinimide (molecular mass¼ 3400 Da;

Nektar Therapeutics, Huntsville, AL) were then added to

the cis or trans solution The final concentrations used were

1 or 2 mm for MTS reagents and 50 lm for

maleimeide-poly(ethylene glycol)-N-hydroxysuccinimide

Acknowledgements

The Slovenian authors were supported by grants from

the Slovenian Research Agency (Ljubjana, Slovenia)

GV was supported by fellowships from the CNR

Insti-tute of Biophysics (Trento, Italy)

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