Synthetic DNA minor groove-binding drugs
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文摘
In this review, both cationic and neutral synthetic ligands that bind in the minor groove of DNA are discussed. Certain bis-distamycins and related lexitropsins show activities against human immunodeficiency virus (HIV)-1 and HIV-2 at low nanomolar concentrations. DAPI binds strongly to AT-containing polymers and is located in the minor groove of DNA. DAPI intercalates in DNA sequences that do not contain at least three consecutive AT bp. Berenil can also exhibit intercalative, as well as minor groove binding, properties depending on sequence. Furan-containing analogues of berenil play an important role in their activities against Pneumocystis carinii and Cryptosporidium parvuam infections in vivo. Pt(II)-berenil conjugates show a good activity profile against HL60 and U-937 human leukemic cells. Pt-pentamidine shows higher antiproliferative activity against small cell lung, non-small cell lung, and melanoma cancer cell lines compared with many other tumor cell lines. trans-Butenamidine shows good anti-P. carinii activity in rats. Pentamidine is used against P. carinii pneumonia in individuals infected with HIV who are at high risk from this infection. A comparison of the cytotoxic potencies of adozelesin, bizelesin, carzelesin, cisplatin, and doxorubicin indicates that adozelesin is a potent analog of CC-1065. Naturally occurring pyrrolo[2,1-c][1,4]benzodiazepines such as anthramycin have a 2- to 3-bp sequence specificity, but a synthetic PBD dimer spans 6 bp, actively recognizing a central 5′-GATC sequence. The crosslinking efficiency of PBD dimers is much greater than that of other major groove crosslinkers, such as cisplatin, melphalan, etc. Neothramycin is used clinically for the treatment of superficial carcinoma of the bladder.
Publisher: Elsevier Science
Language of Publication: English
Item Identifier: S0163-7258(99)00021-2
Publication Type: Article
ISSN: 0163-7258
Cited by:
  1. Cortesi, Rita; Nastruzzi, Claudio,""Delivery systems for DNA-binding drugs as gene expression modulators""Drug Discovery Today2001pp. 893-904
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  2. Pavlov, Valentin; Kong Thoo Lin, Paul; Rodilla, Vicente,""Cytotoxicity, DNA binding and localisation of novel bis-naphthalimidopropyl polyamine derivatives""Chemico-Biological Interactions2001pp. 15-24
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  3. Helm, Mark; Kopka, Mary L.; Sharma, Sanjay K.; Lown, J. William; Giege, Richard,""RNase Activity of a DNA Minor Groove Binder with a Minimalist Catalytic Motif from RNase A""Biochemical and Biophysical Research Communications2001pp. 1283-1290
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  4. Rowe, Thomas C.; Weissig, Volkmar; Lawrence, Jeffrey W.,""Mitochondrial DNA metabolism targeting drugs""Advanced Drug Delivery Reviews2001pp. 175-187
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  5. Kiechle, Frederick L.; Zhang, Xinbo,""Apoptosis: biochemical aspects and clinical implications""Clinica Chimica Acta2002pp. 27-45
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  6. Sun, Xiao-Wen; Neidle, Stephen; Mann, John,""Synthesis of a novel dimeric bis-benzimidazole with site-selective DNA-binding properties""Tetrahedron Letters2002pp. 7239-7241
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  7. Woynarowski, Jan M.,""Targeting critical regions in genomic DNA with AT-specific anticancer drugs""Biochimica et Biophysica Acta (BBA)/Molecular Basis of Disease2002pp. 300-308
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  8. Canzonetta, Claudia; Caneva, Roberto; Savino, Maria; Scipioni, Anita; Catalanotti, Bruno; Galeone, Aldo,""Circular dichroism and thermal melting differentiation of Hoechst 33258 binding to the curved (A4T4) and straight (T4A4) DNA sequences""Biochimica et Biophysica Acta (BBA)/Gene Structure and Expression2002pp. 136-142
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  9. Krautbauer, Rupert; Pope, Lisa H.; Schrader, Tobias E.; Allen, Stephanie; Gaub, Hermann E.,""Discriminating small molecule DNA binding modes by single molecule force spectroscopy""FEBS Letters2002pp. 154-158
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  10. Johnson, Heather A.; Thomas, Neil R.,""Polyhydroxylated azepanes as new motifs for DNA minor groove binding agents""Bioorganic and Medicinal Chemistry Letters2002pp. 237-241
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  11. Satz, Alexander L.; Bruice, Thomas C.,""Recognition of Nine Base Pair Sequences in the Minor Groove of DNA at Subpicomolar Concentrations by a Novel Microgonotropen""Bioorganic and Medicinal Chemistry2002pp. 241-252
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  12. Wang, Lei; Kumar, Arvind; Boykin, David W.; Bailly, Christian; Wilson, W. David,""Comparative thermodynamics for monomer and dimer sequence-dependent binding of a heterocyclic dication in the DNA minor groove2""Journal of Molecular Biology2002pp. 361-374
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  13. Seaton, A.; Higgins, C.; Mann, J.; Baron, A.; Bailly, C.; Neidle, S.; van den Berg, H.,""Mechanistic and anti-proliferative studies of two novel, biologically active bis-benzimidazoles""European Journal of Cancer2003pp. 2548-2555
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  14. Li, Min; Wu, Robert S.; Tsai, Jane S.C.,""DAPI derivative: A fluorescent DNA dye that Can be covalently attached to biomolecules""Bioorganic and Medicinal Chemistry Letters2003pp. 4351-4354
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  15. Mazur, Suzann; Tanious, Farial A.; Ding, Daoyuan; Kumar, Arvind; Boykin, David W.; Simpson, Ian J.; Neidle, Stephen; Wilson, W.David,""A thermodynamic and structural analysis of DNA minor-groove complex formation3""Journal of Molecular Biology2000pp. 321-337
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Footnotes:

  1. Editor's Note: appear throughout text. Structures 1–271 appear together at the end of this article, although Structures 25, 111–147, 162–181, 182–188, and 241–255 also appear within .

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