Synthesis and structure-activity relationship of non-peptidic antagonists of neuropilin-1 receptor

被引：28

作者：

Liu, Wang-Qing ^{[1
]}

Megale, A. Valentino ^{[2
]}

Borriello, Lucia ^{[1
,2
,3
]}

Leforban, Bertrand ^{[1
,3
]}

Montes, Matthieu ^{[4
]}

Goldwaser, Elodie ^{[2
,3
]}

Gresh, Nohad ^{[1
,2
]}

Piquemal, Jean-Philip ^{[5
]}

Hadj-Slimane, Reda ^{[3
]}

Hermine, Olivier ^{[6
,7
,8
]}

Garbay, Christiane ^{[1
,2
]}

Raynaud, Francoise ^{[1
,2
]}

Lepelletier, Yves ^{[6
,7
,8
]}

Demange, Luc ^{[1
,2
,9
]}

机构：

[1] Univ Paris 05, Lab Mol & Cellular Pharmacochem, INSERM U648, Sorbonne Paris Cite,UFR Biomed St Peres, F-75270 Paris 06, France

[2] Univ Paris 05, Lab Chim & Biochim Pharmacol & Toxicol, UMR CNRS 8601, Sorbonne Paris Cite,UFR Biomed St Peres, F-75270 Paris 06, France

[3] Tragex Pharma, F-92100 Boulogne, France

[4] Conservatoire Natl Arts & Metiers, Chaire Bioinformat, Lab Genom Bioinformat & Applicat, EA 4627, F-75003 Paris, France

[5] Univ Paris 06, Sorbonne Univ, Chim Theor Lab, F-75252 Paris, France

[6] INSERM UMR 1163, Lab Cellular & Mol Basis Normal Hematopoiesis & H, F-75015 Paris, France

[7] Paris Descartes Univ, Imagine Inst, Sorbonne Paris Cite, F-75015 Paris, France

[8] CNRS ERL 8254, F-75015 Paris, France

[9] Univ Nice Sophia Antipolis, CNRS, UMR 7272, Inst Chim Nice, F-06108 Nice 1, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 17期

关键词：

Angiogenesis; Neuropilin; Protein-protein interaction; Docking to receptor; Heterocycles; ENDOTHELIAL GROWTH-FACTOR; END-RULE PEPTIDES; EFFICIENT SYNTHESIS; SEMAPHORIN-III; BREAST-CANCER; BINDING; ANGIOGENESIS; VEGF; OSTEOARTHRITIS; CORECEPTORS;

D O I：

10.1016/j.bmcl.2014.07.028

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Neuropilins (NRPs) are VEGF-A(165) co-receptors over-expressed in tumor cells, and considered as targets in angiogenic-related pathologies. We previously identified compound 1, the first non-peptidic antagonist of the VEGF-A(165)/NRP binding, which exhibits in vivo anti-angiogenic and anti-tumor activities. We report here the synthesis and biological evaluations of new antagonists structurally-related to compound 1. Among these molecules, 4a, 4c and 4d show cytotoxic effects on HUVEC and MDA-MB-31 cells, and antagonize VEGF-A(165)/NRP-1 binding. This study confirmed our key structure-activity relationships hypothesis and paved the way to compound 1 'hit to lead' optimization. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：4254 / 4259

页数：6

共 50 条

[21] Activation of the GLP-1 receptor by a non-peptidic agonist
Peishen Zhao
Yi-Lynn Liang
Matthew J. Belousoff
Giuseppe Deganutti
Madeleine M. Fletcher
Francis S. Willard
Michael G. Bell
Michael E. Christe
Kyle W. Sloop
Asuka Inoue
Tin T. Truong
Lachlan Clydesdale
Sebastian G. B. Furness
Arthur Christopoulos
Ming-Wei Wang
Laurence J. Miller
Christopher A. Reynolds
Radostin Danev
Patrick M. Sexton
Denise Wootten
Nature, 2020, 577 : 432 - 436
[22] DESIGN, SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIP STUDIES FOR IMIDAZOLYL QUINOXALINES AS AMPA RECEPTOR ANTAGONISTS
OHMORI, J
SHIMIZUSASAMATA, S
OKADA, M
SAKAMOTO, S
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 178 - MEDI
[23] Design, synthesis, and structure-activity relationship studies of himbacine derived muscarinic receptor antagonists
Doller, D
Chackalamannil, S
Czarniecki, M
McQuade, R
Ruperto, V
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (06) : 901 - 906
[24] A Novel Non-Peptidic Agonist of the Ghrelin Receptor with Orexigenic Activity In vivo
Pastor-Cavada, Elena
Pardo, Leticia M.
Kandil, Dalia
Torres-Fuentes, Cristina
Clarke, Sarah L.
Shaban, Hamdy
McGlacken, Gerard P.
Schellekens, Harriet
SCIENTIFIC REPORTS, 2016, 6
[25] Synthesis and structure-activity relationship of the potent antagonists of VLA-1 integrin
VanBrunt, Michael Pete
Kasar, Ramesh
Kolakowski, Gabrielle R.
Jacobson, Irina C.
Harris, Edith A. S.
Sui, Li-ming
Lupher, Mark L., Jr.
Staunton, Donald S.
Farouz, Francine
Thorsett, Eugene D.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[26] A Novel Non-Peptidic Agonist of the Ghrelin Receptor with Orexigenic Activity In vivo
Elena Pastor-Cavada
Leticia M. Pardo
Dalia Kandil
Cristina Torres-Fuentes
Sarah L. Clarke
Hamdy Shaban
Gerard P. McGlacken
Harriet Schellekens
Scientific Reports, 6
[27] Structure-activity and mechanistic studies of non-peptidic inhibitors of the PLK1 polo box domain identified through REPLACE
Craig, Sandra N.
Baxter, Merissa
Chapagai, Danda
Stafford, Jessy M.
Nurmemmedov, Elmar
Altomare, Diego
Wyatt, Michael D.
McInnes, Campbell
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2022, 227
[28] Structure-activity relationship for peptidic growth hormone secretagogues
Ferro, P.
Krotov, G.
Zvereva, I.
Rodchenkov, G.
Segura, J.
DRUG TESTING AND ANALYSIS, 2017, 9 (01) : 87 - 95
[29] Novel, non-peptidic somatostatin receptor subtype 5 antagonists improve glucose tolerance in rodents
Sprecher, Urs
Mohr, Peter
Martin, Rainer E.
Maerki, Hans Peter
Sanchez, Ruben Alvarez
Binggeli, Alfred
Kuennecke, Basil
Christ, Andreas D.
REGULATORY PEPTIDES, 2010, 159 (1-3) : 19 - 27
[30] Novel γ-aminobutyric acid ρ1 receptor antagonists;: Synthesis, pharmacological activity and structure-activity relationships
Kumar, Rohan J.
Chebib, Mary
Hibbs, David E.
Kim, Hye-Lim
Johnston, Graham A. R.
Salam, Noeris K.
Hanrahan, Jane R.
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (13) : 3825 - 3840

← 1 2 3 4 5 →