Distamycin

Distamycin

File:Distamycin A.svg
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 checkY
3D model (JSmol)	Interactive image
ChemSpider	3003 ☒N
ECHA InfoCard
E number
PubChem CID	24894001
UNII	F6010N240F checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
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 checkY☒N ?) Infobox references

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

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. Distamycin inhibits the transcription and increases the activity of the topoisomerase II. Derivates from distamycin are used as alkylating antineoplastic agents to combat tumours. Derivates with fluorophores are used as fluorescent tags for double-stranded DNA.

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