Distamycin
Chemical compound
From Wikipedia, the free encyclopedia
Distamycin is a polyamide-antibiotic, which acts as a minor groove binder, binding to the small furrow of the double helix.[1]
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| 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) |
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| ChemSpider | |
| ECHA InfoCard | 100.026.823 |
PubChem CID |
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| UNII | |
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| 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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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.