Anticancer Activity of the Bioreductive and Non-Bioreductive Zerumbone Derivatives

被引：11

作者：

Pitchuanchom, Siripit ^{[1
,2
]}

Songsiang, Uraiwan ^{[1
,2
]}

Weerapreeyakul, Natthida ^{[3
]}

Yenjai, Chavi ^{[1
,2
]}

机构：

[1] Khon Kaen Univ, Dept Chem, Nat Prod Res Unit, Khon Kaen 40002, Thailand

[2] Khon Kaen Univ, Fac Sci, Ctr Innovat Chem, Khon Kaen 40002, Thailand

[3] Khon Kaen Univ, Fac Pharmaceut Sci, Ctr Res & Dev Herbal Hlth Prod, Khon Kaen 40002, Thailand

来源：

LETTERS IN DRUG DESIGN & DISCOVERY | 2011年 / 8卷 / 06期

关键词：

Bioreductive; KB; NCI-H187; MCF-7; Zerumbone derivatives; Zingiber zerumbet Smith; SESQUITERPENE; CELLS; ACTIVATION; APOPTOSIS; ESTERS;

D O I：

10.2174/157018011795906811

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Zerumbonoquinone 10 and zerumbonaminone 11 have been designed to release toxic moieties selectively and preferentially under reductive conditions. These compounds were synthesized by coupling the quinone delivery system with zerumbone alcohol 8 and amine 9. All compounds were evaluated for cytotoxicity against KB (non reductase over-expressing cells), NCI-H187 and MCF-7 (reductase overexpressing cells) and normal cells (Vero cells). Bioreductive compounds 10 and 11 were found to act as bioreductive anticancer agents exhibiting less cytotoxicity than the parents 8 and 9 in KB cells with good stability, and were partially bioreductively active against MCF-7 and NCI-H187 cells.

引用

页码：536 / 543

页数：8

共 50 条

[31] Toxicity, cellular uptake and DNA crosslinking studies on the novel bioreductive anticancer drug RH1
Ward, TH
Coe, N
Hargreaves, R
Butler, J
McGown, AT
BRITISH JOURNAL OF CANCER, 2000, 83 : 66 - 66
[32] Novel Derivatives Based on Zerumbone Scaffold as Potential Anticancer Inhibitors
Hieu, Luu Xuan
Ha, Tran Thi Hong
Chi, Hoang Kim
Vu, Tran Khac
Van Chung, Pham
Hung, Truong Ngoc
Van Chinh, Luu
LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (12) : 1062 - 1069
[33] POTENTIAL BIOREDUCTIVE ALKYLATING-AGENTS .3. SYNTHESIS AND ANTINEOPLASTIC ACTIVITY OF ACETOXYMETHYL AND CORRESPONDING ETHYL CARBAMATE DERIVATIVES OF BENZOQUINONES
LIN, AJ
SHANSKY, CW
SARTOREL.AC
JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (05) : 558 - 561
[34] NOVEL BIOREDUCTIVE ACTIVATION MECHANISM OF MITOMYCIN-C DERIVATIVES BEARING A DISULFIDE SUBSTITUENT IN THEIR QUINONE
HE, QY
MARUENDA, H
TOMASZ, M
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) : 9349 - 9350
[35] Enhancement of bioreductive drug toxicity in murine tumours by inhibition of the activity of nitric oxide synthase
SA Butler
PJ Wood
S Cole
C Williams
GE Adams
IJ Stratford
British Journal of Cancer, 1997, 76 : 438 - 444
[36] Enhancement of bioreductive drug toxicity in murine tumours by inhibition of the activity of nitric oxide synthase
Butler, SA
Wood, PJ
Cole, S
Williams, C
Adams, GE
Stratford, IJ
BRITISH JOURNAL OF CANCER, 1997, 76 (04) : 438 - 444
[37] Sulforaphane Preconditioning Sensitizes Human Colon Cancer Cells towards the Bioreductive Anticancer Prodrug PR-104A
Erzinger, Melanie M.
Bovet, Cedric
Hecht, Katrin M.
Senger, Sabine
Winiker, Pascale
Sobotzki, Nadine
Cristea, Simona
Beerenwinkel, Niko
Shay, Jerry W.
Marra, Giancarlo
Wollscheid, Bernd
Sturla, Shana J.
PLOS ONE, 2016, 11 (03):
[38] Immune response to haptenized tumor antigen as possible mechanism of anticancer action of hypoxic bioreductive agents at low doses
Schepetkin, I
CANCER BIOTHERAPY AND RADIOPHARMACEUTICALS, 1999, 14 (04) : 291 - 296
[39] Reductive and bioreductive activation is controlled by electronic properties of substituents in conformationally-constrained anticancer drug delivery systems
Weerapreeyakul, N
Visser, P
Brummelhuis, M
Gharat, L
Chikhale, PJ
MEDICINAL CHEMISTRY RESEARCH, 2000, 10 (03) : 149 - 163
[40] Efficient synthesis of 2-nitroimidazole derivatives and the bioreductive clinical candidate Evofosfamide (TH-302)
O'Connor, Liam J.
Cazares-Koerner, Cindy
Saha, Jaideep
Evans, Charles N. G.
Stratford, Michael R. L.
Hammond, Ester M.
Conway, Stuart J.
Organic Chemistry Frontiers, 2015, 2 (09): : 1026 - 1029

← 1 2 3 4 5 →