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MedKoo Cat#: 413835 | Name: Stallimycin free base

Description:

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

Stallimycin, also known as distamycin A is an antibacterial and antitumor compound. It is able to bind to the minor groove of double-stranded B-DNA in a non intercalative manner, where it forms strong reversible complex preferentially at the nucleotide sequences consisting of 4-5 adjacent AT base pairs. The pyrrole-amide skeleton of distamycin A has been also used as DNA sequence selective vehicles for the delivery of alkylating functions to DNA targets, leading to a sharp increase of its cytotoxicity, in comparison to that, very weak, of distamycin itself.

Chemical Structure

Stallimycin free base
Stallimycin free base
CAS#636-47-5 (free base)

Theoretical Analysis

MedKoo Cat#: 413835

Name: Stallimycin free base

CAS#: 636-47-5 (free base)

Chemical Formula: C22H27N9O4

Exact Mass: 481.2186

Molecular Weight: 481.52

Elemental Analysis: C, 54.88; H, 5.65; N, 26.18; O, 13.29

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 #
636-47-5 (free base) 6576-51-8 (HCl)
Synonym
Stallimycin free base; distamycin A; NSC82150; NSC-82150; NSC 82150; MEN 10399; MEN-10399; MEN10399;
IUPAC/Chemical Name
1H-Pyrrole-2-carboxamide, N-(5-(((3-amino-3-iminopropyl)amino)carbonyl)-1-methyl-1H-pyrrol-3-yl)-4-(((4-(formylamino)-1-methyl-1H-pyrrol-2-yl)carbonyl)amino)-1-methyl- (9CI)
InChi Key
UPBAOYRENQEPJO-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(C1=CC(NC(C2=CC(NC=O)=CN2C)=O)=CN1C)NC3=CN(C)C(C(NCCC(N)=N)=O)=C3
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 481.52 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: Khalaf AI, Al-Kadhimi AA, Ali JH. DNA Minor Groove Binders-Inspired by Nature. Acta Chim Slov. 2016 Dec;63(4):689-704. doi: 10.17344/acsi.2016.2775. PMID: 28004090. 2: Baraldi PG, Tabrizi MA, Pavani MG, Nuñez Mdel C, Makaeva R, Gambari R, La Colla P, Romagnoli R. Design, synthesis and in vitro cytotoxicity of a cis- dichloroplatinum (II) complex linked to the minor groove binder stallimycin. Arzneimittelforschung. 2003;53(2):107-13. doi: 10.1055/s-0031-1297080. PMID: 12642966. 3: Drach JC, Shipman C Jr. The selective inhibition of viral DNA synthesis by chemotherapeutic agents: an indicator of clinical usefulness? Ann N Y Acad Sci. 1977 Mar 4;284:396-409. doi: 10.1111/j.1749-6632.1977.tb21976.x. PMID: 212984. 4: Haider SM, Neidle S, Parkinson GN. A structural analysis of G-quadruplex/ligand interactions. Biochimie. 2011 Aug;93(8):1239-51. doi: 10.1016/j.biochi.2011.05.012. Epub 2011 May 26. PMID: 21635933. 5: Moriarty HT, Webster LR. Fragile sites and bladder cancer. Cancer Genet Cytogenet. 2003 Jan 15;140(2):89-98. doi: 10.1016/s0165-4608(02)00650-7. PMID: 12645645. 6: Kutyavin I, Lokhov S, Lukhtanov E, Reed MW. Chemistry of minor groove binder- oligonucleotide conjugates. Curr Protoc Nucleic Acid Chem. 2003 Aug;Chapter 8:Unit 8.4. doi: 10.1002/0471142700.nc0804s13. PMID: 18428916. 7: Felbor U, Feichtinger W, Schmid M. The rare human fragile site 16B. Cytogenet Genome Res. 2003;100(1-4):85-8. doi: 10.1159/000072841. PMID: 14526167. 8: Dabrowiak JC. Sequence specificity of drug-DNA interactions. Life Sci. 1983 Jun 27;32(26):2915-31. doi: 10.1016/0024-3205(83)90642-2. PMID: 6191168. 9: Denny WA. DNA minor groove alkylating agents. Curr Med Chem. 2001 Apr;8(5):533-44. doi: 10.2174/0929867003373283. PMID: 11281840. 10: Wemmer DE. Designed sequence-specific minor groove ligands. Annu Rev Biophys Biomol Struct. 2000;29:439-61. doi: 10.1146/annurev.biophys.29.1.439. PMID: 10940255.