# Distamycin
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Distamycin
> Markdown URL: https://mediated.wiki/source/Distamycin.md
> Source: https://en.wikipedia.org/wiki/Distamycin
> Source revision: 1313839588
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| ImageFile =Distamycin_A.svg
| IUPACName = 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
| 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 = C22H27N9O4
| MolarMass = 481.508 g/mol
| Appearance = White powder
}}
}}
'''Distamycin''' is a [polyamide](/source/polyamide)-[antibiotic](/source/antibiotic), which acts as a [minor groove binder](/source/minor_groove), binding to the small furrow of the [double helix](/source/Nucleic_acid_double_helix).[{{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.}}]
== Properties ==
Distamycin is a [pyrrole](/source/pyrrole)-[amidine](/source/amidine) antibiotic and analogous to [netropsin](/source/netropsin) and the class of [lexitropsin](/source/lexitropsin)s. As opposed to netropsin, distamycin contains three N-methyl-pyrrole units. It is harvested from ''[Streptomyces netropsis](/source/Streptomyces_netropsis)'' that also produces netropsin. Distamycin prefers AT-rich DNA-sequences and tetrades of [TGGGGT]4.[{{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}}][{{cite journal | doi = 10.4061/2010/247137| pmid = 20725616| pmc = 2915651| title = Selective Binding of Distamycin a Derivative to G-Quadruplex Structure [d(TGGGGT)]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}}] Distamycin inhibits the [transcription](/source/transcription_(genetics)) and increases the activity of the [topoisomerase II](/source/topoisomerase_II).[{{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}}][{{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}}]
Derivates from distamycin are used as [alkylating antineoplastic agent](/source/alkylating_antineoplastic_agent)s to combat tumours.[{{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}}] Derivates with [fluorophore](/source/fluorophore)s are used as [fluorescent tag](/source/fluorescent_tag)s for double-stranded DNA.[{{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}}]
The compound is [hygroscopic](/source/Hygroscopy), and sensible to light, freeze and [hydrolysis](/source/hydrolysis). Its [molar attenuation coefficient](/source/molar_attenuation_coefficient) is 37,000 M−1 cm−1 at a wavelength of 303 nm.
== See also ==
* [Lexitropsin](/source/Lexitropsin)
* [Netropsin](/source/Netropsin)
* [Hoechst 33258](/source/Hoechst_33258)
* [DAPI](/source/DAPI)
== References ==
{{Reflist}}
Category:Peptides
Category:Antibiotics
Category:DNA-binding substances
Category:Imidazoles
Category:Pyrroles
Category:Amines
---
Adapted from the Wikipedia article [Distamycin](https://en.wikipedia.org/wiki/Distamycin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Distamycin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.