DNA minor groove binders as potential antitumor and antimicrobial agents

被引:339
作者
Baraldi, PG [1 ]
Bovero, A [1 ]
Fruttarolo, F [1 ]
Preti, D [1 ]
Tabrizi, MA [1 ]
Pavani, MG [1 ]
Romagnoli, R [1 ]
机构
[1] Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy
关键词
minor groove binders; DNA; hybrid molecules; clinical evaluation;
D O I
10.1002/med.20000
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
DNA minor groove binders constitute an important class of derivatives in anticancer therapy. Some of these compounds form noncovalent complexes with DNA (e.g., distamycin A, Hoechst 33258, and pentamidine) while others DNA-binding compounds (such as CC-1065) cause cleavages in the DNA backbone. In this article, we have reviewed the minor groove binders currently in preclinical evaluation in the last years. Diarylamidines such as DAPI, berenil, and pentamidine; bis-benzimidazoles such as Hoechst 33258; ecteinascidins, pyrrololo [2,1-c]-[1,4]-benzodiazepines (PBDs), CC-1065, and distamycins are the classes discussed in this review article. A special section has been dedicated to hybrid molecules resulted by the combination of two minor groove binders, especially for derivatives of naturally occurring antitumor agents, such as anthramycin or the alkylating unit of the antibiotic CC-1065, and distamycin frames. (C) 2004 Wiley Periodicals, Inc.
引用
收藏
页码:475 / 528
页数:54
相关论文
共 242 条
  • [1] New water-soluble duocarmycin derivatives:: Synthesis and antitumor activity of A-ring pyrrole compounds bearing β-heteroarylacryloyl groups
    Amishiro, N
    Nagamura, S
    Kobayashi, E
    Gomi, K
    Saito, H
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (04) : 669 - 676
  • [2] Synthesis and antitumor activity of duocarmycin derivatives: Modification at C-8 position of A-ring pyrrole compounds bearing the simplified DNA-binding groups
    Amishiro, N
    Nagamura, S
    Murakata, C
    Okamoto, A
    Kobayashi, E
    Asada, M
    Gomi, K
    Tamaoki, T
    Okabe, M
    Yamaguchi, N
    Yamaguchi, K
    Saito, H
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (02) : 381 - 391
  • [3] STRUCTURE + SYNTHESIS OF DISTAMYCIN A
    ARCAMONE, F
    NICOLELL.V
    PENCO, S
    OREZZI, P
    PIRELLI, A
    [J]. NATURE, 1964, 203 (494) : 1064 - +
  • [4] SYNTHESIS, DNA-BINDING PROPERTIES, AND ANTITUMOR-ACTIVITY OF NOVEL DISTAMYCIN DERIVATIVES
    ARCAMONE, FM
    ANIMATI, F
    BARBIERI, B
    CONFIGLIACCHI, E
    DALESSIO, R
    GERONI, C
    GIULIANI, FC
    LAZZARI, E
    MENOZZI, M
    MONGELLI, N
    PENCO, S
    VERINI, MA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (04) : 774 - 778
  • [5] STUDIES ON TOMAYMYCIN, A NEW ANTIBIOTIC .1. ISOLATION AND PROPERTIES OF TOMAYMYCIN
    ARIMA, K
    KOHSAKA, M
    TAMURA, G
    SAKAI, H
    IMANAKA, H
    [J]. JOURNAL OF ANTIBIOTICS, 1972, 25 (08) : 437 - &
  • [6] ARISTOFF PA, 1993, ADV MED CHEM, V2, P67
  • [7] Antitumor imidazotetrazines. 41. Conjugation of the antitumor agents mitozolomide and temozolomide to peptides and lexitropsins bearing DNA major and minor groove-binding structural motifs
    Arrowsmith, J
    Jennings, SA
    Clark, AS
    Stevens, MFG
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (25) : 5458 - 5470
  • [8] Pyrronamycin A and B, novel antitumor antibiotics containing pyrrole-amide repeating unit, produced by Streptomyces sp.
    Asai, A
    Sakai, Y
    Ogawa, H
    Yamashita, Y
    Kakita, S
    Ochiai, K
    Ashizawa, T
    Mihara, A
    Mizukami, T
    Nakano, H
    [J]. JOURNAL OF ANTIBIOTICS, 2000, 53 (01) : 66 - 69
  • [9] Synthesis and cytotoxicity of 5-amino-1-(chloromethyl)-3-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indole (amino-seco-CBI-TMI) and related 5-alkylamino analogues:: New DNA minor groove alkylating agents
    Atwell, GJ
    Tercel, M
    Boyd, M
    Wilson, WR
    Denny, WA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) : 9414 - 9420
  • [10] Recognition of ATGA sequences by the unfused aromatic dication DB293 forming stacked dimers in the DNA minor groove
    Bailly, C
    Tardy, C
    Wang, L
    Armitage, B
    Hopkins, K
    Kumar, A
    Schuster, GB
    Boykin, DW
    Wilson, WD
    [J]. BIOCHEMISTRY, 2001, 40 (33) : 9770 - 9779