Distamycin

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

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
CAS Number	6576-51-8 Y
3D model (JSmol)	Interactive image
ChemSpider	3003 N
ECHA InfoCard	100.026.823
PubChem CID	24894001
UNII	F6010N240F Y
InChI InChI=1S/C22H27N9O4/c1-29-9-13(26-12-32)6-17(29)21(34)28-15-8-18(31(3)11-15)22(35)27-14-7-16(30(2)10-14)20(33)25-5-4-19(23)24/h6-12H,4-5H2,1-3H3,(H3,23,24)(H,25,33)(H,26,32)(H,27,35)(H,28,34) Key: UPBAOYRENQEPJO-UHFFFAOYSA-N N
SMILES [H]/N=C(/CCNC(=O)c1cc(cn1C)NC(=O)c2cc(cn2C)NC(=O)c3cc(cn3C)NC=O)\N
Properties
Chemical formula	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). N (what is YN ?) Infobox references

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

• Lexitropsin
• Netropsin
• Hoechst 33258
• DAPI