Demethylbleomycin A2 (Technical Grade)

• CAT Number: C000395
• CAS Number: 41089-03-6
• Molecular Formula: C₅₄H₈₁N₁₇O₂₁S₃
• Molecular Weight: 1400.52
• Purity: ≥95%
• Synonyms: Bleomycin DM-A2, N1-[3-(Methylthio)propyl]bleomycinamide; (2R,3S,4S,5R,6R)-2-(((2R,3S,4R,5S,6S)-2-((1R,2S)-2-(6-Amino-2-((S)-3-amino-1-(((S)-2,3-diamino-3-oxopropyl)amino)-3-oxopropyl)-5-methylpyrimidine-4-carboxamido)-3-(((2R,3S,4S)-3-hydroxy-5-(((3R)-3-hydroxy-1-((2-(4-((3-(methylthio)propyl)carbamoyl)-[2,4′-bithiazol]-2′-yl)ethyl)amino)-1-oxobutan-2-yl)amino)-4-methyl-5-oxopentan-2-yl)amino)-1-(1H-imidazol-4-yl)-3-oxopropoxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl Carbamate
• Target: Antibiotic
• Solubility: Acetonitrile (Slightly), Water (Very Slightly)
• Appearance: White to Off-White Solid
• Storage: -20°C, Hygroscopic
• IUPAC Name: [(2R,3S,4S,5R,6R)-2-[(2R,3S,4S,5S,6S)-2-[(1R)-2-[[6-amino-2-[(1S)-3-amino-1-[[(2S)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[[(2R,3S,4S)-3-hydroxy-5-[[(2S,3R)-3-hydroxy-1-[2-[4-[4-(3-methylsulfanylpropylcarbamoyl)-1,3-thiazol-2-yl]-1,3-thiazol-2-yl]ethylamino]-1-oxobutan-2-yl]amino]-4-methyl-5-oxopentan-2-yl]amino]-1-(1H-imidazol-5-yl)-3-oxopropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] carbamate
• InChI: 1S/C54H81N17O21S3/c1-19-32(68-45(71-43(19)57)24(11-30(56)75)63-12-23(55)44(58)81)49(85)70-34(40(25-13-60-18-64-25)90-53-42(38(79)36(77)28(14-72)89-53)91-52-39(80)41(92-54(59)87)37(78)29(15-73)88-52)50(86)65-21(3)35(76)20(2)46(82)69-33(22(4)74)48(84)62-9-7-31-66-27(17-94-31)51-67-26(16-95-51)47(83)61-8-6-10-93-5/h13,16-18,20-24,28-29,33-42,52-53,63,72-74,76-80H,6-12,14-15,55H2,1-5H3,(H2,56,75)(H2,58,81)(H2,59,87)(H,60,64)(H,61,83)(H,62,84)(H,65,86)(H,69,82)(H,70,85)(H2,57,68,71)/t20-,21+,22+,23-,24-,28-,29+,33-,34?,35-,36+,37+,38-,39-,40-,41-,42-,52+,53-/m0/s1
• InChIKey: FWTQNWDTHLXHFI-UFIMUECKSA-N
• SMILES: CC1=C(N=C(N=C1N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)C(=O)NC([C@H](C2=CN=CN2)O[C@H]3[C@H]([C@H]([C@@H]([C@@H](O3)CO)O)O)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)OC(=O)N)O)C(=O)N[C@H](C)[C@H]([C@H](C)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCCC5=NC(=CS5)C6=NC(=CS6)C(=O)NCCCSC)O

Demethylbleomycin A₂(Cat No.: C000395) is a derivative of the glycopeptide antibiotic bleomycin, known for its DNA-cleaving and anticancer properties. It retains the ability to induce oxidative DNA damage by generating free radicals, leading to strand breaks and apoptosis. Demethylation alters its biochemical properties, potentially affecting potency and selectivity. It is studied in cancer research and antibiotic development to understand structure-activity relationships. As a modified bleomycin analog, it serves as a tool for exploring novel chemotherapeutic strategies and DNA interaction mechanisms.

Reference

Carter, Barbara J.et al.: J. Biol. Chem., 265,В 4193(1990); Tanaka, Wataru., et al.: Heterocycles, 13,В 469 (1979); Takita, Tomohisa; et al.: J. Antibiot.,В В 26,В 252(1973);Byrnes, Robert W., et al.: Cancer Res.,В В 50,В 5275(1990);