Novel halogenated sulfonamides inhibit the growth of multidrug resistant MCF-7/ADR cancer cells

被引：91

作者：

Medina, JC ^{[1
]}

Roche, D ^{[1
]}

Shan, B ^{[1
]}

Learned, RM ^{[1
]}

Frankmoelle, WP ^{[1
]}

Clark, DL ^{[1
]}

Rosen, T ^{[1
]}

Jaen, JC ^{[1
]}

机构：

[1] Tularik Inc, S San Francisco, CA 94080 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 13期

关键词：

D O I：

10.1016/S0960-894X(99)00276-0

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In this report, we describe the synthesis of halogenated benzenesulfonamide compounds and their ability to inhibit the growth of HeLa, MCF-7 and MCF-7/ADR tumor cells in vitro. The multidrug resistance (MDR) phenotype of certain cells does not affect their sensitivity to these compounds. These agents belong to a family of compounds previously shown to bind irreversibly to cysteine-239 of beta-tubulin. Consistent with this mechanism of action, the cytotoxicities of these compounds appear to correlate with their ability to undergo nucleophilic aromatic substitution. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1843 / 1846

页数：4

相关论文

共 10 条

[1] A NEW RAPID AND SIMPLE NONRADIOACTIVE ASSAY TO MONITOR AND DETERMINE THE PROLIFERATION OF LYMPHOCYTES - AN ALTERNATIVE TO [H-3] THYMIDINE INCORPORATION ASSAY [J].

AHMED, SA ;

GOGAL, RM ;

WALSH, JE .

JOURNAL OF IMMUNOLOGICAL METHODS, 1994, 170 (02) :211-224

[2] AROMATIC POLYFLUORO-COMPOUNDS .8. PENTAFLUOROBENZALDEHYDE AND RELATED PENTAFLUOROPHENYL KETONES AND CARBOXYLIC ACIDS [J].

BARBOUR, AK ;

BUXTON, MW ;

COE, PL ;

STEPHENS, R ;

TATLOW, JC .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (MAR) :808-&

[3] A RATIONALIZATION OF ORIENTATION AND REACTIVITY IN NUCLEOPHILIC REPLACEMENT REACTIONS OF AROMATIC POLYHALO-COMPOUNDS [J].

BURDON, J .

TETRAHEDRON, 1965, 21 (12) :3373-&

[4] STUDIES IN CHEMISTRY OF POLYHALOGENOBENZENE COMPOUNDS - SYNTHESIS AND REACTIVITY OF "2,3,5,6-TETRACHLOROBENZENESULPHONYL AND "2,3,4,5-TETRACHLOROBENZENESULPHONYL CHLORIDES AND RELATED COMPOUNDS [J].

CHIVERS, GE ;

CREMLYN, RJW ;

CRONJIE, TN ;

MARTIN, RA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (07) :1573-1582

[5] BIOCHEMISTRY OF MULTIDRUG-RESISTANCE MEDIATED BY THE MULTIDRUG TRANSPORTER [J].

GOTTESMAN, MM ;

PASTAN, I .

ANNUAL REVIEW OF BIOCHEMISTRY, 1993, 62 :385-427

[6] THE USE OF PENTAFLUOROPHENYL DERIVATIVES FOR THE F-18 LABELING OF PROTEINS [J].

HERMAN, LW ;

FISCHMAN, AJ ;

TOMPKINS, RG ;

HANSON, RN ;

BYON, C ;

STRAUSS, HW ;

ELMALEH, DR .

NUCLEAR MEDICINE AND BIOLOGY, 1994, 21 (07) :1005-1010

[7]

MARCH J, 1992, ADV ORG CHEM, P649

[8] Novel antineoplastic agents with efficacy against multidrug resistant tumor cells [J].

Medina, JC ;

Shan, B ;

Beckmann, H ;

Farrell, RP ;

Clark, DL ;

Learned, RM ;

Roche, D ;

Li, A ;

Baichwal, V ;

Case, C ;

Baeuerle, PA ;

Rosen, T ;

Jaen, JC .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (19) :2653-2656

[9] Selective, covalent modification of β-tubulin residue Cys-239 by T138067, an antitumor agent with in vivo efficacy against multidrug-resistant tumors [J].

Shan, B ;

Medina, JC ;

Santha, E ;

Frankmoelle, WP ;

Chou, TC ;

Learned, RM ;

Narbut, MR ;

Stott, D ;

Wu, PG ;

Jaen, JC ;

Rosen, T ;

Timmermans, PBMWM ;

Beckmann, H .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (10) :5686-5691

[10]

YAKOBSON IL, 1985, SYNTHESIS FLUOROORGA, P185