Distamycin

Distamycin
Names
IUPAC name
N-{5-[(5-{[(3Z)-3-Amino-3-iminopropyl]carbamoyl}-1-methyl-1H-pyrrol-3-yl)carbamoyl]-1-methyl-1H-pyrrol-3-yl}-4-formamido-1-methyl-1H-pyrrole-2-carboxamide
Other names
Distamycin A, Herperetin, Stallimycin
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.026.823
Properties
C22H27N9O4
Molar mass 481.508 g/mol
Appearance White powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[1][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

References

  1. 1 2 M. P. Barrett, C. G. Gemmell, C. J. Suckling: Minor groove binders as anti-infective agents. In: Pharmacology & Therapeutics. 139(1), Juli 2013, 12–23. doi:10.1016/j.pharmthera.2013.03.002. PMID 23507040.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ 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.
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