Synthesis and antitumor evaluation of methyl spongoate analogs

被引：21

作者：

Jiang, Cheng-Shi ^{[1
]}

Huang, Cai-Guo ^{[2
]}

Feng, Bo ^{[2
]}

Li, Jia ^{[1
]}

Gong, Jing-Xu ^{[1
]}

Kurtan, Tibor ^{[3
]}

Guo, Yue-Wei ^{[1
]}

机构：

[1] Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

[2] Second Mil Med Univ, Shanghai 200433, Peoples R China

[3] Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary

来源：

STEROIDS | 2010年 / 75卷 / 13-14期

基金：

美国国家科学基金会;

关键词：

Synthesis; Methyl spongoate analogs; Cytotoxicity; Michael acceptor; ALPHA; BETA-UNSATURATED KETONES; ACID; STEROIDS; CYTOTOXICITY; DERIVATIVES; APOPTOSIS; BINDING;

D O I：

10.1016/j.steroids.2010.08.002

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：

A series of novel methyl spongoate (1) analogs has been synthesized and evaluated for their in vitro cytotoxic properties. It was found that the nature of the C-20 side chain had significant effects on their bioactivities and some analogs showed higher cytotoxicity than 1 against A549, HCT-116, HepG2, SW-1990, MCF-7 and NCl-H460 tumor cell lines. The pharmacological results confirmed that the alpha,beta-unsaturated carbonyl moiety, a Michael acceptor in ring A, plays a pivotal role in the cytotoxic effect of these derivatives. The compiled pharmacological data may be useful for the design of novel analogous anticancer drugs. (C) 2010 Elsevier Inc. All rights reserved.

引用

页码：1153 / 1163

页数：11

共 36 条

[1] Steroids from sponges: Recent reports
Aiello, A
Fattorusso, E
Menna, M
[J]. STEROIDS, 1999, 64 (10) : 687 - 714
[2] Synthesis of [26,27-2H6] brassinosteroids from 23,24-bisnorcholenic acid methyl ester
Antonchick, AP
Schneider, B
Zhabinskii, VN
Khripach, VA
[J]. STEROIDS, 2004, 69 (10) : 617 - 628
[3] Elucidation of thioredoxin as a molecular target for antitumor quinols
Bradshaw, TD
Matthews, CS
Cookson, J
Chew, EH
Shah, M
Bailey, K
Monks, A
Harris, E
Westwell, AD
Wells, G
Laughton, CA
Stevens, MFG
[J]. CANCER RESEARCH, 2005, 65 (09) : 3911 - 3919
[4] The triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid and its derivatives elicit human lymphoid cell apoptosis through a novel pathway involving the unregulated mitochondrial permeability transition pore
Brookes, Paul S.
Morse, Kimberly
Ray, Denise
Tompkins, Andrew
Young, Sara M.
Hilchey, Shannon
Salim, Suhail
Konopleva, Marina
Andreeff, Michael
Phipps, Richard
Bernstein, Steven H.
[J]. CANCER RESEARCH, 2007, 67 (04) : 1793 - 1802
[5] Development of a commercial process to produce oxandrolone
Cabaj, John E.
Kairys, David
Benson, Thomas R.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) : 378 - 388
[6] The cinnamon-derived Michael acceptor cinnamic aldehyde impairs melanoma cell proliferation, invasiveness, and tumor growth
Cabello, Christopher M.
Bair, Warner B., III
Lamore, Sarah D.
Ley, Stephanie
Bause, Alexandra S.
Azimian, Sara
Wondrak, Georg T.
[J]. FREE RADICAL BIOLOGY AND MEDICINE, 2009, 46 (02) : 220 - 231
[7] KIHEISTERONES, NEW CYTOTOXIC STEROIDS FROM A MAUI SPONGE
CARNEY, JR
YOSHIDA, WY
SCHEUER, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) : 6637 - 6640
[8] Anti-inflammatory steroids from the octocoral Dendronephthya griffini
Chao, Chih-Hua
Wen, Zhi-Hong
Chen, I-Ming
Su, Jui-Hsin
Huang, Ho-Cheng
Chiang, Michael Y.
Sheu, Jyh-Horng
[J]. TETRAHEDRON, 2008, 64 (16) : 3554 - 3560
[9] Synthesis and evaluation of some steroidal oximes as cytotoxic agents: Structure/activity studies (I)
Cui, Jian-Guo
Fan, Lei
Huang, Li-Liang
Liu, Hong-Li
Zhou, Ai-Min
[J]. STEROIDS, 2009, 74 (01) : 62 - 72
[10] Synthesis and biological evaluation of certain α,β-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents
El-Subbagh, HI
Abu-Zaid, SM
Mahran, MA
Badria, FA
Al-Obaid, AM
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (15) : 2915 - 2921

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