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Distamycin
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Distamycin ist ein Polyamid-Antibiotikum, das an die kleine Furche einer DNA-Doppelhelix bindet.cite-ref-pmid-23507040-2-0[2]
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Eigenschaften
Distamycin gehört zur Klasse Pyrrol-Amidin-Antibiotika und ist ein Analogon von Netropsin und den Lexitropsinen. Im Gegensatz zu Netropsin besitzt Distamycin drei N-Methyl-Pyrrol-Einheiten. Distamycin wird aus Streptomyces distallicus isoliert. Es bindet bevorzugt an AT-reiche DNA-Sequenzen und Tetraden aus [TGGGGT]4.cite-ref-3[3]cite-ref-4[4]
Distamycin hemmt die Transkription und erhöht die Aktivität der Topoisomerase II.cite-ref-5[5]cite-ref-6[6]
Verschiedene Derivate von Distamycin werden als Alkylanzien zur Behandlung von Tumoren untersucht.cite-ref-7[7]cite-ref-pmid-23507040-2-1[2] Distamycinderivate mit Fluorophoren werden zur Fluoreszenzmarkierung von doppelsträngiger DNA verwendet.cite-ref-8[8]
Distamycin ist hygroskopisch, hydrolyse-, frost- und lichtempfindlich. Der Extinktionskoeffizient beträgt 37.000 M−1 cm−1 bei einer Wellenlänge von 303 nm.
Einzelnachweise
cite-note-sigma-11. Datenblatt Distamycin hydrochloride bei Sigma-Aldrich, abgerufen am 24. November 2013 (PDF).
cite-note-pmid-23507040-22. ↑ M. P. Barrett, C. G. Gemmell, C. J. Suckling: Minor groove binders as anti-infective agents. In: Pharmacology & Therapeutics. Band 139, Nummer 1, Juli 2013, S. 12–23. doi:10.1016/j.pharmthera.2013.03.002. PMID 23507040.
cite-note-33. ↑ M. L. Kopka, C. Yoon, D. Goodsell, P. Pjura, R. E. Dickerson: The molecular origin of DNA-drug specificity in netropsin and distamycin. In: Proceedings of the National Academy of Sciences of the United States of America. Band 82, Nummer 5, März 1985, S. 1376–1380. PMID 2983343. PMC 397264 (freier Volltext).
cite-note-44. ↑ B. Pagano, I. Fotticchia, S. De Tito, C. A. Mattia, L. Mayol, E. Novellino, A. Randazzo, C. Giancola: Selective Binding of Distamycin A Derivative to G-Quadruplex Structure [d(TGGGGT)](4). In: Journal of nucleic acids. 2010. doi:10.4061/2010/247137. PMID 20725616. PMC 2915651 (freier Volltext).
cite-note-55. ↑ P. Majumder, A. Banerjee, J. Shandilya, P. Senapati, S. Chatterjee, T. K. Kundu, D. Dasgupta: Minor groove binder distamycin remodels chromatin but inhibits transcription. In: PLOS ONE. Band 8, Nummer 2, 2013, S. e57693. doi:10.1371/journal.pone.0057693. PMID 23460895. PMC 3584068 (freier Volltext).
cite-note-66. ↑ M. Fesen, Y. Pommier: Mammalian topoisomerase II activity is modulated by the DNA minor groove binder distamycin in simian virus 40 DNA. In: The Journal of Biological Chemistry. Band 264, Nummer 19, Juli 1989, S. 11354–11359. PMID 2544590.
cite-note-77. ↑ P. G. Baraldi, D. Preti, F. Fruttarolo, M. A. Tabrizi, R. Romagnoli: Hybrid molecules between distamycin A and active moieties of antitumor agents. In: Bioorganic & Medicinal Chemistry. Band 15, Nummer 1, Januar 2007, S. 17–35. doi:10.1016/j.bmc.2006.07.004. PMID 17081759.
cite-note-88. ↑ T. Vaijayanthi, T. Bando, G. N. Pandian, H. Sugiyama: Progress and prospects of pyrrole-imidazole polyamide-fluorophore conjugates as sequence-selective DNA probes. In: ChemBioChem. Band 13, Nummer 15, Oktober 2012, S. 2170–2185. doi:10.1002/cbic.201200451. PMID 23023993.