N-Acetyl calicheamicin

• CAS: 108212-76-6
• Catalog Number: ACM108212766
• Category: Others
• Molecular Weight: 1410.38
• Molecular Formula: C57H76IN3O22S4
• Description: N-Acetyl calicheamicin is a derivative of calicheamicin, and is a potent enediyne antitumor antibiotic. Calicheamicins target DNA and cause strand scission. Calicheamicins bind with DNA in the minor groove, wherein they then undergo a reaction analogous to the Bergman cyclization to generate a diradical species. This diradical, 1,4-didehydrobenzene, then abstracts hydrogen atoms from the deoxyribose (sugar) backbone of DNA, which ultimately leads to strand scission. The specificity of binding of calicheamicin to the minor groove of DNA was demonstrated by Crothers et al. (1999) to be due to the aryltetrasaccharide group of the molecule.
• Synonyms: N-Acetyl calicheamicin; N-Acetyl-γ-calicheamicin; N-Acetylcalicheamicin γ
• IUPAC Name: S-((2R,3S,4S,6S)-6-((((2R,3S,4S,5R,6R)-5-(((2S,4S,5S)-5-(N-ethylacetamido)-4-methoxytetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-(((2S,5Z,9R,13Z)-9-hydroxy-12-((methoxycarbonyl)amino)-13-(2-(methyltrisulfanyl)ethylidene)-11-oxobicyclo[7.3.1]trideca-1(12),5-dien-3,7-diyn-2-yl)oxy)-2-methyltetrahydro-2H-pyran-3-yl)amino)oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl) 4-(((2S,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3-iodo-5,6-dimethoxy-2-methylbenzothioate
• Canonical SMILES: O=C1C[C@]2(O)/C(C([C@]([H])(C#C/C=C\C#C2)O[C@@H]3O[C@H](C)[C@@H](NO[C@@H]4O[C@H](C)[C@@H](SC(C5=C(C)C(I)=C(O[C@H]6[C@H](O)[C@H](OC)[C@@H](O)[C@H](C)O6)C(OC)=C5OC)=O)[C@@H](O)C4)[C@H](O)[C@H]3O[C@H]7C[C@H](OC)[C@@H](N(CC)C(C)=O)CO7)=C1NC(OC)=O)=C\CSSSC
• InChI: InChI=1S/C57H76IN3O22S4/c1-13-61(30(6)62)32-25-76-37(23-36(32)71-7)81-50-45(66)42(27(3)78-55(50)80-35-18-16-14-15-17-20-57(70)24-34(64)43(59-56(69)75-11)40(35)31(57)19-21-85-87-84-12)60-83-38-22-33(63)52(29(5)77-38)86-53(68)39-26(2)41(58)48(51(74-10)47(39)72-8)82-54-46(67)49(73-9)44(65)28(4)79-54/h14-15,19,27-29,32-33,35-38,42,44-46,49-50,52,54-55,60,63,65-67,70H,13,21-25H2,1-12H3,(H,59,69)/b15-14-,31-19-/t27-,28+,29-,32+,33+,35+,36+,37+,38+,42-,44+,45+,46-,49-,50-,52-,54+,55+,57+/m1/s1
• InChI Key: WPDOZYZAJKUVRZ-DPACUSKXSA-N
• Solubility: To be determined
• Appearance: Solid powder
• Shelf Life: >2 years if stored properly
• Storage: Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
• Drug Formulation: To be determined
• Elemental Analysis: C, 48.54; H, 5.43; I, 9.00; N, 2.98; O, 24.96; S, 9.09
• Exact Mass: 1409.2848
• HS Tariff Code: 2934.99.9001
• Shipping: 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.
• Stock Solution Storage: 0-4 °C for short term (days to weeks), or -20 °C for long term (months).