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MedKoo Cat#: 535134 | Name: Distamycin 2

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Distamycin 2 is a bioactive chemical.

Chemical Structure

Distamycin 2
Distamycin 2
CAS#56752-53-5

Theoretical Analysis

MedKoo Cat#: 535134

Name: Distamycin 2

CAS#: 56752-53-5

Chemical Formula: C16H21N7O3

Exact Mass: 359.1706

Molecular Weight: 359.39

Elemental Analysis: C, 53.47; H, 5.89; N, 27.28; O, 13.36

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Distamycin 2; Distamycin-2; Distamycin2
IUPAC/Chemical Name
1H-Pyrrole-2-carboxamide, N-(5-(((3-amino-3-iminopropyl)amino)carbonyl)-1-methyl-1H-pyrrol-3-yl)-4-(formylamino)-1-methyl-
InChi Key
RLINKTRQUWUNPA-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H21N7O3/c1-22-7-10(20-9-24)5-13(22)16(26)21-11-6-12(23(2)8-11)15(25)19-4-3-14(17)18/h5-9H,3-4H2,1-2H3,(H3,17,18)(H,19,25)(H,20,24)(H,21,26)
SMILES Code
O=C(C1=CC(NC=O)=CN1C)NC2=CN(C)C(C(NCCC(N)=N)=O)=C2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 359.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Arciszewska K, Pućkowska A, Wróbel A, Drozdowska D. Carbocyclic Analogues of Distamycin and Netropsin. Mini Rev Med Chem. 2019;19(2):98-113. doi: 10.2174/1389557518666181009143203. PMID: 30626311. 2: Ghosh S, Usharani D, De S, Jemmis ED, Bhattacharya S. Photophysical and duplex-DNA-binding properties of distamycin dimers based on 4,4'- and 2,2'-dialkoxyazobenzenes as the core. Chem Asian J. 2008 Nov 13;3(11):1949-61. doi: 10.1002/asia.200800151. PMID: 18810740. 3: Baraldi PG, Nûnez Mdel C, Espinosa A, Romagnoli R. Distamycin A as stem of DNA minor groove alkylating agents. Curr Top Med Chem. 2004;4(2):231-9. doi: 10.2174/1568026043451474. PMID: 14754456. 4: Marck C, Kakiuchi N, Guschlbauer W. Specific interaction of netropsin, distamycin-3 and analogs with LC duplexes: reversion towards the B form of the 2'-deoxy-.2'-deoxy-2'-fluoro-hybrid duplexes upon specific interaction with netropsin, distamycin-3 and analogs. Nucleic Acids Res. 1982 Oct 11;10(19):6147-61. doi: 10.1093/nar/10.19.6147. PMID: 6292869; PMCID: PMC320957. 5: Majumder P, Banerjee A, Shandilya J, Senapati P, Chatterjee S, Kundu TK, Dasgupta D. Minor groove binder distamycin remodels chromatin but inhibits transcription. PLoS One. 2013;8(2):e57693. doi: 10.1371/journal.pone.0057693. Epub 2013 Feb 27. PMID: 23460895; PMCID: PMC3584068. 6: Chetoni P, Monti D, Tampucci S, Matteoli B, Ceccherini-Nelli L, Subissi A, Burgalassi S. Liposomes as a potential ocular delivery system of distamycin A. Int J Pharm. 2015 Aug 15;492(1-2):120-6. doi: 10.1016/j.ijpharm.2015.05.055. Epub 2015 Jul 13. PMID: 26183332. 7: Pelton JG, Wemmer DE. Structural characterization of a 2:1 distamycin A.d(CGCAAATTGGC) complex by two-dimensional NMR. Proc Natl Acad Sci U S A. 1989 Aug;86(15):5723-7. doi: 10.1073/pnas.86.15.5723. PMID: 2762292; PMCID: PMC297702. 8: Prusov AN, Kolomijtseva GY, Smirnova TA. Differential scanning calorimetric study of antibiotic distamycin A binding with chromatin within isolated rat liver nuclei. Pharm Biol. 2017 Dec;55(1):687-690. doi: 10.1080/13880209.2016.1258427. PMID: 27982735; PMCID: PMC6130587. 9: Woynarowski JM, McHugh M, Sigmund RD, Beerman TA. Modulation of topoisomerase II catalytic activity by DNA minor groove binding agents distamycin, Hoechst 33258, and 4',6-diamidine-2-phenylindole. Mol Pharmacol. 1989 Feb;35(2):177-82. PMID: 2465485. 10: Inase A, Kodama TS, Sharif J, Xu Y, Ayame H, Sugiyama H, Iwai S. Binding of distamycin A to UV-damaged DNA. J Am Chem Soc. 2004 Sep 8;126(35):11017-23. doi: 10.1021/ja048851k. PMID: 15339187. 11: Pagano B, Virno A, Mattia CA, Mayol L, Randazzo A, Giancola C. Targeting DNA quadruplexes with distamycin A and its derivatives: an ITC and NMR study. Biochimie. 2008 Aug;90(8):1224-32. doi: 10.1016/j.biochi.2008.03.006. Epub 2008 Mar 28. PMID: 18420038. 12: Baliga R, Crothers DM. On the kinetics of distamycin binding to its target sites on duplex DNA. Proc Natl Acad Sci U S A. 2000 Jul 5;97(14):7814-8. doi: 10.1073/pnas.97.14.7814. PMID: 10884413; PMCID: PMC16627. 13: Inase A, Kodama TS, Sharif J, Xu Y, Ayame H, Sugiyama H, Iwai S. Analysis of distamycin A binding to UV-damaged DNA. Nucleic Acids Symp Ser (Oxf). 2004;(48):257-8. doi: 10.1093/nass/48.1.257. PMID: 17150576. 14: Prislan I, Khutsishvili I, Marky LA. Interaction of minor groove ligands with G-quadruplexes: thermodynamic contributions of the number of quartets, T-U substitutions, and conformation. Biochimie. 2011 Aug;93(8):1341-50. doi: 10.1016/j.biochi.2011.06.001. Epub 2011 Jun 12. PMID: 21684318. 15: Animati F, Arcamone FM, Conte MR, Felicetti P, Galeone A, Lombardi P, Mayol L, Paloma LG, Rossi C. Synthesis of two distamycin analogues and their binding mode to d(CGCAAATTTGCG)2 in the 2:1 solution complexes as determined by two- dimensional 1H-NMR. J Med Chem. 1995 Mar 31;38(7):1140-9. doi: 10.1021/jm00007a011. PMID: 7707317. 16: Fagan PA, Spielmann HP, Sigurdsson S, Rink SM, Hopkins PB, Wemmer DE. An NMR study of [d(CGCGAATTCGCG)]2 containing an interstrand cross-link derived from a distamycin-pyrrole conjugate. Nucleic Acids Res. 1996 Apr 15;24(8):1566-73. doi: 10.1093/nar/24.8.1566. PMID: 8628693; PMCID: PMC145811. 17: Lah J, Vesnaver G. Binding of distamycin A and netropsin to the 12mer DNA duplexes containing mixed AT.GC sequences with at most five or three successive AT base pairs. Biochemistry. 2000 Aug 8;39(31):9317-26. doi: 10.1021/bi000748u. PMID: 10924125. 18: Kawashima E, Nakanishi Y, Terui Y, Tomitori H, Kashiwagi K, Ohba Y, Kamaike K. Synthesis and evaluation of 2-pyrrolepolyamide-2'-deoxyguanosine 5'-phosphate. Nucleic Acids Symp Ser (Oxf). 2007;(51):263-4. doi: 10.1093/nass/nrm132. PMID: 18029687. 19: Geierstanger BH, Jacobsen JP, Mrksich M, Dervan PB, Wemmer DE. Structural and dynamic characterization of the heterodimeric and homodimeric complexes of distamycin and 1-methylimidazole-2-carboxamide-netropsin bound to the minor groove of DNA. Biochemistry. 1994 Mar 15;33(10):3055-62. doi: 10.1021/bi00176a039. PMID: 8130219. 20: Hiraku Y, Oikawa S, Kawanishi S. Distamycin A, a minor groove binder, changes enediyne-induced DNA cleavage sites and enhances apoptosis. Nucleic Acids Res Suppl. 2002;(2):95-6. doi: 10.1093/nass/2.1.95. PMID: 12903122.

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