Structural basis for bifunctional peptide recognition at human δ-opioid receptor

被引：142

作者：

Fenalti, Gustavo ^{[1
]}

Zatsepin, Nadia A. ^{[2
]}

Betti, Cecilia ^{[3
,4
]}

Giguere, Patrick ^{[5
,6
,7
]}

Han, Gye Won ^{[1
]}

Ishchenko, Andrii ^{[1
]}

Liu, Wei ^{[1
]}

Guillemyn, Karel ^{[3
,4
]}

Zhang, Haitao ^{[1
]}

James, Daniel ^{[2
]}

Wang, Dingjie ^{[2
]}

Weierstall, Uwe ^{[2
]}

Spence, John C. H. ^{[2
]}

Boutet, Sebastien ^{[8
]}

Messerschmidt, Marc ^{[8
]}

Williams, Garth J. ^{[8
]}

Gati, Cornelius ^{[9
]}

Yefanov, Oleksandr M. ^{[9
]}

White, Thomas A. ^{[9
]}

Oberthuer, Dominik ^{[9
,10
]}

Metz, Markus ^{[9
,11
]}

Yoon, Chun Hong ^{[9
,12
]}

Barty, Anton ^{[9
]}

Chapman, Henry N. ^{[9
,11
]}

Basu, Shibom ^{[13
,14
]}

Coe, Jesse ^{[13
,14
]}

Conrad, Chelsie E. ^{[13
,14
]}

Fromme, Raimund ^{[13
,14
]}

Fromme, Petra ^{[13
,14
]}

Tourwe, Dirk ^{[3
,4
]}

Schiller, Peter W. ^{[15
]}

Roth, Bryan L. ^{[5
,6
,7
]}

Ballet, Steven ^{[3
,4
]}

Katritch, Vsevolod ^{[1
]}

Stevens, Raymond C. ^{[1
]}

Cherezov, Vadim ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Integrat Struct & Computat Biol, La Jolla, CA 92037 USA

[2] Arizona State Univ, Dept Phys, Tempe, AZ 85287 USA

[3] Vrije Univ Brussel, Dept Chem, Brussels, Belgium

[4] Vrije Univ Brussel, Dept Bioengn Sci, Brussels, Belgium

[5] Univ N Carolina, Chapel Hill Med Sch, NIMH, Psychoact Drug Screening Program, Chapel Hill, NC USA

[6] Univ N Carolina, Chapel Hill Med Sch, Dept Pharmacol, Chapel Hill, NC USA

[7] Univ N Carolina, Chapel Hill Med Sch, Div Chem Biol & Med Chem, Chapel Hill, NC USA

[8] SLAC Natl Accelerator Lab, Linac Coherent Light Source, Menlo Pk, CA USA

[9] Deutsch Elektronen Synchrotron DESY, Ctr Free Elect Laser Sci, Hamburg, Germany

[10] Univ Hamburg, Inst Biochem & Mol Biol, Hamburg, Germany

[11] Univ Hamburg, Dept Phys, Hamburg, Germany

[12] European Xray Free Electron Laser Facil XFEL GmbH, Hamburg, Germany

[13] Arizona State Univ, Dept Chem & Biochem, Tempe, AZ USA

[14] Arizona State Univ, Biodesign Inst, Ctr Appl Struct Discovery, Tempe, AZ USA

[15] Clin Res Inst Montreal, Lab Chem Biol & Peptide Res, Montreal, PQ H2W 1R7, Canada

来源：

NATURE STRUCTURAL & MOLECULAR BIOLOGY | 2015年 / 22卷 / 03期

基金：

加拿大健康研究院; 美国国家科学基金会; 美国国家卫生研究院;

关键词：

SERIAL FEMTOSECOND CRYSTALLOGRAPHY; MU AGONIST/DELTA ANTAGONIST; POTENT; TOLERANCE; DEPENDENCE; MORPHINE; BOND; DMT;

D O I：

10.1038/nsmb.2965

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Bifunctional mu- and delta-opioid receptor (OR) ligands are potential therapeutic alternatives, with diminished side effects, to alkaloid opiate analgesics. We solved the structure of human delta-OR bound to the bifunctional delta-OR antagonist and mu-OR agonist tetrapeptide H-Dmt-Tic-Phe-Phe-NH2 (DIPP-NH2) by serial femtosecond crystallography, revealing a cis-peptide bond between H-Dmt and Tic. The observed receptor-peptide interactions are critical for understanding of the pharmacological profiles of opioid peptides and for development of improved analgesics.

引用

页码：265 / 268

页数：4

共 19 条

[1] ABDELHAMID EE, 1991, J PHARMACOL EXP THER, V258, P299
[2] Conformationally constrained opioid ligands: The Dmt-Aba and Dmt-Aia versus Dmt-Tic scaffold
Ballet, Steven
Feytens, Debby
De Wachter, Rien
De Vlaeminck, Magali
Marczak, Ewa D.
Salvadori, Severo
de Graaf, Chris
Rognan, Didier
Negri, Lucia
Lattanzi, Roberta
Lazarus, Lawrence H.
Tourwe, Dirk
Balboni, Gianfranco
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (02) : 433 - 437
[3] Dmt and opioid peptides: A potent alliance
Bryant, SD
Jinsmaa, Y
Salvadori, S
Okada, Y
Lazarus, LH
[J]. BIOPOLYMERS, 2003, 71 (02) : 86 - 102
[4] INFLUENCE OF SAMPLE PH ON THE CONFORMATIONAL BACKBONE DYNAMICS OF A PSEUDOTRIPEPTIDE (H-TYR-TIC-PSI[CH2-NH]PHE-OH) INCORPORATING A REDUCED PEPTIDE-BOND - AN NMR INVESTIGATION
CARPENTER, KA
WILKES, BC
SCHILLER, PW
[J]. BIOPOLYMERS, 1995, 36 (06) : 735 - 749
[5] Molecular control of δ-opioid receptor signalling
Fenalti, Gustavo
Giguere, Patrick M.
Katritch, Vsevolod
Huang, Xi-Ping
Thompson, Aaron A.
Cherezov, Vadim
Roth, Bryan L.
Stevens, Raymond C.
[J]. NATURE, 2014, 506 (7487) : 191 - 196
[6] Structure of the δ-opioid receptor bound to naltrindole
Granier, Sebastien
Manglik, Aashish
Kruse, Andrew C.
Kobilka, Tong Sun
Thian, Foon Sun
Weis, William I.
Kobilka, Brian K.
[J]. NATURE, 2012, 485 (7398) : 400 - U171
[7] Synthesis, Modeling, and Pharmacological Evaluation of UMB 425, a Mixed μ Agonist/δ Antagonist Opioid Analgesic with Reduced Tolerance Liabilities
Healy, Jason R.
Bezawada, Padmavani
Shim, Jihyun
Jones, Jace W.
Kane, Maureen A.
MacKerell, Alexander D., Jr.
Coop, Andrew
Matsumoto, Rae R.
[J]. ACS CHEMICAL NEUROSCIENCE, 2013, 4 (09): : 1256 - 1266
[8] Serial Femtosecond Crystallography of G Protein-Coupled Receptors
Liu, Wei
Wacker, Daniel
Gati, Cornelius
Han, Gye Won
James, Daniel
Wang, Dingjie
Nelson, Garrett
Weierstall, Uwe
Katritch, Vsevolod
Barty, Anton
Zatsepin, Nadia A.
Li, Dianfan
Messerschmidt, Marc
Boutet, Sebastien
Williams, Garth J.
Koglin, Jason E.
Seibert, M. Marvin
Wang, Chong
Shah, Syed T. A.
Basu, Shibom
Fromme, Raimund
Kupitz, Christopher
Rendek, Kimberley N.
Grotjohann, Ingo
Fromme, Petra
Kirian, Richard A.
Beyerlein, Kenneth R.
White, Thomas A.
Chapman, Henry N.
Caffrey, Martin
Spence, John C. H.
Stevens, Raymond C.
Cherezov, Vadim
[J]. SCIENCE, 2013, 342 (6165) : 1521 - 1524
[9] Crystal structure of the μ-opioid receptor bound to a morphinan antagonist
Manglik, Aashish
Kruse, Andrew C.
Kobilka, Tong Sun
Thian, Foon Sun
Mathiesen, Jesper M.
Sunahara, Roger K.
Pardo, Leonardo
Weis, William I.
Kobilka, Brian K.
Granier, Sebastien
[J]. NATURE, 2012, 485 (7398) : 321 - U170
[10] Structural studies of [2′,6′-dimethyl-L-tyrosine1]endomorphin-2 analogues:: Enhanced activity and cis orientation of the Dmt-Pro amide bond
Okada, Y
Fujita, Y
Motoyama, T
Tsuda, Y
Yokoi, T
Li, TY
Sasaki, Y
Ambo, A
Jinsmaa, Y
Bryant, SD
Lazarus, LH
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (09) : 1983 - 1994

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