Distamycin Explained

Distamycin is a polyamide-antibiotic, which acts as a minor groove binder, binding to the small furrow of the double helix.[1]

Properties

Distamycin is a pyrrole-amidine antibiotic and analogous to netropsin and the class of lexitropsins. As opposed to netropsin, distamycin contains three N-methyl-pyrrole units. It is harvested from Streptomyces netropsis that also produces netropsin. Distamycin prefers AT-rich DNA-sequences and tetrades of [TGGGGT]4.[2] [3] Distamycin inhibits the transcription and increases the activity of the topoisomerase II.[4] [5] Derivates from distamycin are used as alkylating antineoplastic agents to combat tumours.[6] Derivates with fluorophores are used as fluorescent tags for double-stranded DNA.[7]

The compound is hygroscopic, and sensible to light, freeze and hydrolysis. Its molar attenuation coefficient is 37,000 M−1 cm−1 at a wavelength of 303 nm.

See also

Notes and References

  1. 10.1016/j.pharmthera.2013.03.002. 23507040. Minor groove binders as anti-infective agents. Pharmacology & Therapeutics. 139. 1. 12–23. 2013. Barrett. Michael P.. Gemmell. Curtis G.. Suckling. Colin J..
  2. 2983343. 397264. 1985. Kopka. M. L.. The molecular origin of DNA-drug specificity in netropsin and distamycin. Proceedings of the National Academy of Sciences of the United States of America. 82. 5. 1376–80. Yoon. C.. Goodsell. D.. Pjura. P.. Dickerson. R. E.. 10.1073/pnas.82.5.1376. 1985PNAS...82.1376K. free.
  3. 10.4061/2010/247137. 20725616. 2915651. Selective Binding of Distamycin a Derivative to G-Quadruplex Structure [d(TGGGGT)]4. Journal of Nucleic Acids. 2010. 1–7. 2010. Pagano. Bruno. Fotticchia. Iolanda. De Tito. Stefano. Mattia. Carlo A.. Mayol. Luciano. Novellino. Ettore. Randazzo. Antonio. Giancola. Concetta. free.
  4. 10.1371/journal.pone.0057693. 23460895. 3584068. Minor Groove Binder Distamycin Remodels Chromatin but Inhibits Transcription. PLOS ONE. 8. 2. e57693. 2013. Majumder. Parijat. Banerjee. Amrita. Shandilya. Jayasha. Senapati. Parijat. Chatterjee. Snehajyoti. Kundu. Tapas K.. Dasgupta. Dipak. 2013PLoSO...857693M. free.
  5. 2544590. 1989. Fesen. M.. Mammalian topoisomerase II activity is modulated by the DNA minor groove binder distamycin in simian virus 40 DNA. The Journal of Biological Chemistry. 264. 19. 11354–9. Pommier. Y.. 10.1016/S0021-9258(18)60471-5. free.
  6. 10.1016/j.bmc.2006.07.004. 17081759. Hybrid molecules between distamycin a and active moieties of antitumor agents. Bioorganic & Medicinal Chemistry. 15. 1. 17–35. 2007. Baraldi. Pier Giovanni. Preti. Delia. Fruttarolo. Francesca. Tabrizi. Mojgan Aghazadeh. Romagnoli. Romeo.
  7. 10.1002/cbic.201200451. 23023993. Progress and Prospects of Pyrrole-Imidazole Polyamide-Fluorophore Conjugates as Sequence-Selective DNA Probes. ChemBioChem. 13. 15. 2170–2185. 2012. Vaijayanthi. Thangavel. Bando. Toshikazu. Pandian. Ganesh N.. Sugiyama. Hiroshi. 1491900.

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