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Protein-ligand binding volume determined by FPSA, densitometry, and NMR Zigmantas Toleikis § , Vladimir A. Sirotkin , Gediminas Skvarnaviˇ cius § , Joana Smirnovien ˙ e § , Christian Roumestand , Daumantas Matulis § , and Vytautas Petrauskas § * *E-mail: [email protected] § Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Vilnius, Lithuania A.M. Butlerov Institute of Chemistry, Kazan Federal University, Kazan, Russia Centre de Biochimie Structurale, Université Montpellier I et II, Montpellier, France XIV International Conference of the Lithuanian Biochemical Society | June 28 – 30, 2016 | Druskininkai, Lithuania I NTRODUCTION We report the values of recombinant human heat shock pro- tein 90 (Hsp90) binding volumes (i.e., the changes in protein volume associated with ligand binding), which were obtained by three independent experimental techniques – fluorescent pressure shift assay (FPSA), vibrating tube densitometry, and high-pressure NMR. Within the error range all techniques pro- vide similar volumetric parameters of investigated protein- ligand systems. L IGANDS N H 2 N S N H N N N Cl N O H Cl O OH O H OH O O OH ICPD91 ICPD9 ICPD1 Cl O O O OH OH O O O OH O H Cl O O O OH AZ1 AZ2 AZ3 OH Cl O H N N S O OH O H N N S O OH Cl O H O O O O ICPD47 ICPD62 Radicicol F LUORESCENT P RESSURE S HIFT A SSAY (FPSA) System of equations describing a protein dosing curve – the relationship between concentration of added ligand, L t , total protein concentration, P t , and melting pressure, p m : L t = (exp(-ΔG U /RT ) - 1) P t 2 exp(-ΔG U /RT ) + 1 exp(-ΔG b /RT ) , (1) ΔG x G 0_x V x (p m - p 0 )+ Δβ x 2 (p m - p 0 ) 2 ; x = U, b, (2) where ΔG 0 , ΔV and Δβ are standard state Gibbs energy, volume and compressibility factor, respectively, and indexes U and b stand for the changes related to protein unfolding and protein- ligand binding. Fluorescence yield (a.u.) 1000 2000 3000 4000 p (MPa) 0 100 200 300 L t (μM of AZ2) 0 10 30 50 (a) Δp m (MPa) 0 50 100 150 200 L t (M) 0 10 −6 10 −5 10 −4 Hsp90αN + ICPD1 AZ2 ICPD91 ICPD9 pure Hsp90αN (b) F IGURE : (a) Unfolding profiles and (b) dosing curves of Hsp90αN. H IGH -P RESSURE NMR The K d ’s of Hsp90αN interaction with a ligand is calculated from the chemical shift change, Δδ , dependency on L t and P t : Δδ δ max Y - Y 2 - 4L t P t 2P t , Y = L t + P t + K d . F IGURE : (a) Δδ of Hsp90αN amino acids which were induced by AZ3 and ICPD9 ligands. (b) Δδ of Val92 as a function of ICPD9 concentration at 30 MPa, 120 MPa, and 150 MPa pres- sures. (c) AZ3-induced shifts in Hsp90αN (PDB ID: 1UYL). D ENSITOMETRY The partial molar volume of a protein, V 0 , and the change in protein volume associated with the ligand binding, ΔV b , are calculated using equations: V 0 = M d 0 - d - d 0 Cd 0 , (3) V 0 (R)= V 0 (0) + αΔV b , (4) where M and C are molecular mass and molar concentration of a protein, d 0 and d are densities of solvent and protein solution, respectively, and α is the fraction of ligand-bound protein: α =0.5 (1 + R + K d /P t ) - q 0.25 (1 + R + K d /) 2 - R. (5) Here K d is the dissociation constant of the protein-ligand complex and R = L t /P t . Solution density (g/cm 3 ) 0.9990 0.9992 0.9994 0.9996 0.9998 Ratio L t / P t 0 1 2 3 4 Hsp90αN + radicicol ICPD47 ICPD62 AZ3 (a) V 0 (cm 3 /mol) 21360 21400 21440 21480 Ratio L t / P t 0 1 2 3 4 Hsp90αN + AZ3 ICPD47 ICPD62 radicicol (b) F IGURE : (a) Raw densitometry data and (b) the partial molar volumes of Hsp90αN at various R. B INDING VOLUMES ΔV b (FPSA) ΔV b (Densitometry) ΔV b (NMR) K d ICPD91 -1 ± 5 cm 3 /mol n.d. n.d. 3 × 10 -5 M ICPD9 -2 ± 5 cm 3 /mol n.d. 20 ± 4 cm 3 /mol 2 × 10 -5 M AZ3 -7 ± 6 cm 3 /mol -10 ± 3 cm 3 /mol -9 ± 4 cm 3 /mol 9 × 10 -5 M AZ2 -9 ± 6 cm 3 /mol n.d. n.d. 1 × 10 -3 M ICPD1 -9 ± 6 cm 3 /mol n.d. n.d. 3 × 10 -5 M AZ1 -21 ± 11 cm 3 /mol n.d. n.d. 2 × 10 -3 M ICPD47 -40 ± 14 cm 3 /mol -49 ± 5 cm 3 /mol n.d. 5 × 10 -9 M ICPD62 n.d. -50 ± 4 cm 3 /mol n.d. 2 × 10 -9 M radicicol -170 ± 60 cm 3 /mol -124 ± 7 cm 3 /mol n.d. 2 × 10 -10 M A CKNOWLEDGEMENT This research was funded by a grant (no. MIP-004/2014) from the Research Council of Lithuania.

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Page 1: Protein-ligand binding volume determined byweb.vu.lt/.../uploads/2017/01/LBD14_poster.pdf · Protein-ligand binding volume determined by FPSA, densitometry, and NMR Zigmantas Toleikisx,

Protein-ligand binding volume determined byFPSA, densitometry, and NMRZigmantas Toleikis§, Vladimir A. Sirotkin†, Gediminas Skvarnavicius§, Joana Smirnoviene§,Christian Roumestand‡, Daumantas Matulis§, and Vytautas Petrauskas§**E-mail: [email protected]§Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Vilnius, Lithuania†A.M. Butlerov Institute of Chemistry, Kazan Federal University, Kazan, Russia‡Centre de Biochimie Structurale, Université Montpellier I et II, Montpellier, France

XIV International Conference of the Lithuanian Biochemical Society | June 28 – 30, 2016 | Druskininkai, Lithuania

INTRODUCTIONWe report the values of recombinant human heat shock pro-tein 90 (Hsp90) binding volumes (i.e., the changes in proteinvolume associated with ligand binding), which were obtainedby three independent experimental techniques – fluorescentpressure shift assay (FPSA), vibrating tube densitometry, andhigh-pressure NMR. Within the error range all techniques pro-vide similar volumetric parameters of investigated protein-ligand systems.

LIGANDS

NH2 N SNH

N

N

N

Cl

N

OH

Cl

OOH

OH OH

O

O

OH

ICPD91 ICPD9 ICPD1

Cl

O

OO

OH

OH

O

OO

OH

OH

Cl

O

OO

OH

AZ1 AZ2 AZ3

OH

Cl

OH

N N

S

O

OH

OH

N N

S

O

OH

Cl

OH

O

OO

O

ICPD47 ICPD62 Radicicol

FLUORESCENT PRESSURE SHIFT ASSAY (FPSA)System of equations describing a protein dosing curve – the relationship between concentrationof added ligand, Lt, total protein concentration, Pt, and melting pressure, pm:

Lt = (exp(−∆GU/RT )− 1)

(Pt

2 exp(−∆GU/RT )+

1

exp(−∆Gb/RT )

), (1)

∆Gx = ∆G0_x + ∆Vx(pm − p0) +∆βx

2(pm − p0)

2; x = U, b, (2)

where ∆G0, ∆V and ∆β are standard state Gibbs energy, volume and compressibility factor,respectively, and indexes U and b stand for the changes related to protein unfolding and protein-ligand binding.

Flu

ore

scen

ce y

ield

(a.u

.)

1000

2000

3000

4000

p (MPa)0 100 200 300

Lt (μM of AZ2) 0 10 30 50

(a)

Δp m

(MP

a)

0

50

100

150

200

Lt (M)

0 10−6 10−5 10−4

Hsp90αN + ICPD1 AZ2 ICPD91 ICPD9

pur

e H

sp90

αN

(b)

(a)

FIGURE: (a) Unfolding profiles and (b) dosing curves of Hsp90αN.

HIGH-PRESSURE NMRThe Kd’s of Hsp90αN interaction with a ligand is calculatedfrom the chemical shift change, ∆δ, dependency on Lt and Pt:

∆δ = ∆δmaxY −

√Y 2 − 4LtPt

2Pt,

Y = Lt + Pt +Kd.

FIGURE: (a) ∆δ of Hsp90αN amino acids which were inducedby AZ3 and ICPD9 ligands. (b) ∆δ of Val92 as a function ofICPD9 concentration at 30 MPa, 120 MPa, and 150 MPa pres-sures. (c) AZ3-induced shifts in Hsp90αN (PDB ID: 1UYL).

DENSITOMETRY

The partial molar volume of a protein, V 0, and the change in protein volume associated with theligand binding, ∆Vb, are calculated using equations:

V 0 =M

d0− d− d0

Cd0, (3) V 0(R) = V 0(0) + α∆Vb, (4)

where M and C are molecular mass and molar concentration of a protein, d0 and d are densitiesof solvent and protein solution, respectively, and α is the fraction of ligand-bound protein:

α = 0.5 (1 +R+Kd/Pt)−√

0.25 (1 +R+Kd/)2 −R. (5)

Here Kd is the dissociation constant of the protein-ligand complex and R = Lt/Pt.

Solu

tio

n d

ensi

ty (g

/cm

3 )

0.9990

0.9992

0.9994

0.9996

0.9998

Ratio Lt / Pt

0 1 2 3 4

Hsp90αN + radicicol ICPD47 ICPD62 AZ3

(a)

V 0

(cm

3 /m

ol)

21360

21400

21440

21480

Ratio Lt / Pt

0 1 2 3 4

Hsp90αN + AZ3 ICPD47 ICPD62 radicicol

(b)

FIGURE: (a) Raw densitometry data and (b) the partial molar volumes of Hsp90αN at variousR.

BINDING VOLUMES

∆Vb (FPSA) ∆Vb (Densitometry) ∆Vb (NMR) Kd

ICPD91 −1± 5 cm3/mol n.d. n.d. 3× 10−5 MICPD9 −2± 5 cm3/mol n.d. 20± 4 cm3/mol 2× 10−5 MAZ3 −7± 6 cm3/mol −10± 3 cm3/mol −9± 4 cm3/mol 9× 10−5 MAZ2 −9± 6 cm3/mol n.d. n.d. 1× 10−3 MICPD1 −9± 6 cm3/mol n.d. n.d. 3× 10−5 MAZ1 −21± 11 cm3/mol n.d. n.d. 2× 10−3 MICPD47 −40± 14 cm3/mol −49± 5 cm3/mol n.d. 5× 10−9 MICPD62 n.d. −50± 4 cm3/mol n.d. 2× 10−9 Mradicicol −170± 60 cm3/mol −124± 7 cm3/mol n.d. 2× 10−10 M

ACKNOWLEDGEMENTThis research was funded by a grant (no. MIP-004/2014) fromthe Research Council of Lithuania.