{{chembox | Verifiedfields = changed | Watchedfields = changed | ImageFile =Distamycin_A.svg | IUPACName = N-<nowiki/>{5-[(5-<nowiki/>{[(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 | OtherNames = Distamycin A, Herperetin, Stallimycin | Section1 = {{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 6576-51-8 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = F6010N240F | PubChem = 24894001 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 3003 | SMILES = [H]/N=C(/CCNC(=O)c1cc(cn1C)NC(=O)c2cc(cn2C)NC(=O)c3cc(cn3C)NC=O)\N | StdInChI = 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) | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = UPBAOYRENQEPJO-UHFFFAOYSA-N }} | Section2 = {{Chembox Properties | Formula = C<sub>22</sub>H<sub>27</sub>N<sub>9</sub>O<sub>4</sub> | MolarMass = 481.508 g/mol | Appearance = White powder }} }}

'''Distamycin''' is a polyamide-antibiotic, which acts as a minor groove binder, binding to the small furrow of the double helix.<ref name="PMID 23507040">{{cite journal | doi = 10.1016/j.pharmthera.2013.03.002| pmid = 23507040| title = Minor groove binders as anti-infective agents| journal = Pharmacology & Therapeutics| volume = 139| issue = 1| pages = 12–23| year = 2013| last1 = Barrett| first1 = Michael P.| last2 = Gemmell| first2 = Curtis G.| last3 = Suckling| first3 = Colin J.}}</ref>

== 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]<sub>4</sub>.<ref>{{cite journal | pmid = 2983343| pmc = 397264| year = 1985| last1 = Kopka| first1 = M. L.| title = The molecular origin of DNA-drug specificity in netropsin and distamycin| journal = Proceedings of the National Academy of Sciences of the United States of America| volume = 82| issue = 5| pages = 1376–80| last2 = Yoon| first2 = C.| last3 = Goodsell| first3 = D.| last4 = Pjura| first4 = P.| last5 = Dickerson| first5 = R. E.| doi = 10.1073/pnas.82.5.1376| bibcode = 1985PNAS...82.1376K| doi-access = free}}</ref><ref>{{cite journal | doi = 10.4061/2010/247137| pmid = 20725616| pmc = 2915651| title = Selective Binding of Distamycin a Derivative to G-Quadruplex Structure &#91;d(TGGGGT)&#93;4| journal = Journal of Nucleic Acids| volume = 2010| pages = 1–7| year = 2010| last1 = Pagano| first1 = Bruno| last2 = Fotticchia| first2 = Iolanda| last3 = De Tito| first3 = Stefano| last4 = Mattia| first4 = Carlo A.| last5 = Mayol| first5 = Luciano| last6 = Novellino| first6 = Ettore| last7 = Randazzo| first7 = Antonio| last8 = Giancola| first8 = Concetta| doi-access = free}}</ref> Distamycin inhibits the transcription and increases the activity of the topoisomerase II.<ref>{{cite journal | doi = 10.1371/journal.pone.0057693| pmid = 23460895| pmc = 3584068| title = Minor Groove Binder Distamycin Remodels Chromatin but Inhibits Transcription| journal = PLOS ONE| volume = 8| issue = 2| article-number = e57693| year = 2013| last1 = Majumder| first1 = Parijat| last2 = Banerjee| first2 = Amrita| last3 = Shandilya| first3 = Jayasha| last4 = Senapati| first4 = Parijat| last5 = Chatterjee| first5 = Snehajyoti| last6 = Kundu| first6 = Tapas K.| last7 = Dasgupta| first7 = Dipak| bibcode = 2013PLoSO...857693M| doi-access = free}}</ref><ref>{{cite journal | pmid = 2544590| year = 1989| last1 = Fesen| first1 = M.| title = Mammalian topoisomerase II activity is modulated by the DNA minor groove binder distamycin in simian virus 40 DNA| journal = The Journal of Biological Chemistry| volume = 264| issue = 19| pages = 11354–9| last2 = Pommier| first2 = Y.| doi = 10.1016/S0021-9258(18)60471-5| doi-access = free}}</ref> Derivates from distamycin are used as alkylating antineoplastic agents to combat tumours.<ref name="PMID 23507040" /><ref>{{cite journal | doi = 10.1016/j.bmc.2006.07.004| pmid = 17081759| title = Hybrid molecules between distamycin a and active moieties of antitumor agents| journal = Bioorganic & Medicinal Chemistry| volume = 15| issue = 1| pages = 17–35| year = 2007| last1 = Baraldi| first1 = Pier Giovanni| last2 = Preti| first2 = Delia| last3 = Fruttarolo| first3 = Francesca| last4 = Tabrizi| first4 = Mojgan Aghazadeh| last5 = Romagnoli| first5 = Romeo}}</ref> Derivates with fluorophores are used as fluorescent tags for double-stranded DNA.<ref>{{cite journal | doi = 10.1002/cbic.201200451| pmid = 23023993| title = Progress and Prospects of Pyrrole-Imidazole Polyamide-Fluorophore Conjugates as Sequence-Selective DNA Probes| journal = ChemBioChem| volume = 13| issue = 15| pages = 2170–2185| year = 2012| last1 = Vaijayanthi| first1 = Thangavel| last2 = Bando| first2 = Toshikazu| last3 = Pandian| first3 = Ganesh N.| last4 = Sugiyama| first4 = Hiroshi| s2cid = 1491900}}</ref>

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

== See also == * Lexitropsin * Netropsin * Hoechst 33258 * DAPI

== References == {{Reflist}}

Category:Peptides Category:Antibiotics Category:DNA-binding substances Category:Imidazoles Category:Pyrroles Category:Amines