Cytotoxic halogenoacrylic derivatives of distamycin A

被引：33

作者：

Cozzi, P

Beria, I

Caldarelli, M

Capolongo, L

Geroni, C

Mongelli, N

机构：

[1] Pharmacia & Upjohn Inc, Discovery Res Oncol, Dept Chem, I-20014 Milan, Italy

[2] Pharmacia & Upjohn Inc, Discovery Res Oncol, Dept Pharmacol, I-20014 Milan, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2000年 / 10卷 / 11期

关键词：

D O I：

10.1016/S0960-894X(00)00204-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The design, synthesis, in vitro and in vivo activities of a series of halogenoacrylic derivatives of distamycin A are described. The structure-activity relationships indicate a key role of the reactivity of alpha-halogenoacrylic moiety. The reactivity and the putative alkylating mechanism of these compounds are different from those of the nitrogen mustards and possibly based on a Michael type reaction. This supports the hypothesis that these compounds represent a class of minor groove binders mechanistically different from tallimustine. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1269 / 1272

页数：4

相关论文

共 16 条

[1] STRUCTURE + SYNTHESIS OF DISTAMYCIN A [J].

ARCAMONE, F ;

NICOLELL.V ;

PENCO, S ;

OREZZI, P ;

PIRELLI, A .

NATURE, 1964, 203 (494) :1064-+

[2] SYNTHESIS, DNA-BINDING PROPERTIES, AND ANTITUMOR-ACTIVITY OF NOVEL DISTAMYCIN DERIVATIVES [J].

ARCAMONE, FM ;

ANIMATI, F ;

BARBIERI, B ;

CONFIGLIACCHI, E ;

DALESSIO, R ;

GERONI, C ;

GIULIANI, FC ;

LAZZARI, E ;

MENOZZI, M ;

MONGELLI, N ;

PENCO, S ;

VERINI, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (04) :774-778

[3]

ARISTOFF PA, 1993, ADV MED CHEM, V2, P67

[4] Structure-activity relationship of novel tallimustine derivatives: Synthesis and antitumor activity [J].

Baraldi, PG ;

Beria, I ;

Cacciari, B ;

Capolongo, L ;

Cozzi, P ;

Mongelli, N ;

Romagnoli, R ;

Spalluto, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (11) :1247-1252

[5] A STUDY OF COMPARATIVE CHEMICAL AND BIOLOGICAL ACTIVITIES OF ALKYLATING AGENTS [J].

BARDOS, TJ ;

DATTAGUP.N ;

HEBBORN, P ;

TRIGGLE, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (02) :167-&

[6] DNA SEQUENCE-SPECIFIC ADENINE ALKYLATION BY THE NOVEL ANTITUMOR DRUG TALLIMUSTINE (FCE-24517), A BENZOYL NITROGEN-MUSTARD DERIVATIVE OF DISTAMYCIN [J].

BROGGINI, M ;

COLEY, HM ;

MONGELLI, N ;

PESENTI, E ;

WYATT, MD ;

HARTLEY, JA ;

DINCALCI, M .

NUCLEIC ACIDS RESEARCH, 1995, 23 (01) :81-87

[7] Cytotoxic α-bromoacrylic derivatives of distamycin analogues modified at the amidino moiety [J].

Cozzi, P ;

Beria, I ;

Caldarelli, M ;

Geroni, C ;

Mongelli, N ;

Pennella, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (11) :1273-1276

[8]

Cozzi P, 1998, CURR PHARM DESIGN, V4, P181

[9]

DALESSIO R, 1994, BIOORG MED CHEM LETT, V4, P1467

[10] DESIGN OF SEQUENCE-SPECIFIC DNA-BINDING MOLECULES [J].

DERVAN, PB .

SCIENCE, 1986, 232 (4749) :464-471