Synthetic and Biological Studies of Sesquiterpene Polygodial: Activity of 9-Epipolygodial against Drug-Resistant Cancer Cells

被引：20

作者：

Dasari, Ramesh ^{[1
]}

De Carvalho, Annelise ^{[2
]}

Medellin, Derek C. ^{[1
]}

Middleton, Kelsey N. ^{[1
]}

Hague, Frederic ^{[3
]}

Volmar, Marie N. M. ^{[4
]}

Frolova, Liliya V. ^{[5
,6
]}

Rossato, Mateus F. ^{[7
,8
]}

De La Chapa, Jorge J. ^{[9
]}

Dybdal-Hargreaves, Nicholas F. ^{[10
]}

Pillai, Akshita ^{[11
]}

Mathieu, Veronique ^{[2
]}

Rogelj, Snezna ^{[5
,6
]}

Gonzales, Cara B. ^{[9
]}

Calixto, Joao B. ^{[7
,8
]}

Evidente, Antonio ^{[12
]}

Gautier, Mathieu ^{[3
]}

Munirathinam, Gnanasekar ^{[11
]}

Glass, Rainer ^{[4
]}

Burth, Patricia ^{[13
]}

Pelly, Stephen C. ^{[14
]}

van Otterlo, Willem A. L. ^{[14
]}

Kiss, Robert ^{[2
]}

Kornienko, Alexander ^{[1
]}

机构：

[1] SW Texas State Univ, Dept Chem & Biochem, San Marcos, TX 78666 USA

[2] Univ Libre Bruxelles, Lab Cancerol & Toxicol Expt, Fac Pharm, B-1050 Brussels, Belgium

[3] Univ Picardie Jules Verne, Fac Sci, Lab Physiol Cellulaire & Mol, F-80000 Amiens, France

[4] Univ Clin Munich, Neurosurg Res, D-81377 Munich, Germany

[5] New Mexico Inst Min & Technol, Dept Chem, Socorro, NM 87801 USA

[6] New Mexico Inst Min & Technol, Dept Biol, Socorro, NM 87801 USA

[7] Ctr Innovat & Preclin Studies, BR-88056000 Florianopolis, SC, Brazil

[8] Univ Fed Santa Catarina, Dept Pharmacol, Florianopolis, SC, Brazil

[9] Univ Texas Hlth Sci Ctr San Antonio, Dept Comprehens Dent, Canc Therapy & Res Ctr, San Antonio, TX 78229 USA

[10] Univ Texas Hlth Sci Ctr San Antonio, Dept Pharmacol, San Antonio, TX 78229 USA

[11] Univ Illinois, Coll Med, Dept Biomed Sci, Rockford, IL 61107 USA

[12] Univ Naples Federico II, Dipartimento Sci Chim, I-80126 Naples, Italy

[13] Fed Fluminense Outeiro Sao Joao Batista, Dept Biol Celular & Mol, Inst Biol, BR-24020140 Niteroi, RJ, Brazil

[14] Univ Stellenbosch, Dept Chem & Polymer Sci, ZA-7602 Matieland, South Africa

来源：

CHEMMEDCHEM | 2015年 / 10卷 / 12期

基金：

美国国家科学基金会; 新加坡国家研究基金会;

关键词：

capsaicin; capsazepine; ion channels; resiniferatoxin; vanilloid; VANILLOID RECEPTOR AGONISTS; STEM-CELLS; ENANTIOSELECTIVE SYNTHESIS; BIOMIMETIC CONDITIONS; MULTIDRUG-RESISTANCE; ANTIFEEDANT ACTIVITY; PRIMARY AMINES; EGF RECEPTOR; PAIN PATHWAY; HOT TASTE;

D O I：

10.1002/cmdc.201500360

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Polygodial, a terpenoid dialdehyde isolated from Polygonum hydropiperL., is a known agonist of the transient receptor potential vanilloid1 (TRPV1). In this investigation a series of polygodial analogues were prepared and investigated for TRPV1-agonist and anticancer activities. These experiments led to the identification of 9-epipolygodial, which has antiproliferative potency significantly exceeding that of polygodial. 9-Epipolygodial was found to maintain potency against apoptosis-resistant cancer cells as well as those displaying the multidrug-resistant (MDR) phenotype. In addition, the chemical feasibility for the previously proposed mechanism of action of polygodial, involving the formation of a Paal-Knorr pyrrole with a lysine residue on the target protein, was demonstrated by the synthesis of a stable polygodial pyrrole derivative. These studies reveal rich chemical and biological properties associated with polygodial and its direct derivatives. These compounds should inspire further work in this area aimed at the development of new pharmacological agents, or the exploration of novel mechanisms of covalent modification of biological molecules with natural products.

引用

页码：2014 / 2026

页数：13

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