N-Acetyl calicheamicin, enediyne antitumor antibiotic.

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.

Product information

CAS Number: 108212-76-6

Molecular Weight: 1410.38

Formula: C57H76IN3O22S4

Synonym:

N-Acetyl-Calicheamicin γ

N-Acetyl-γ-calicheamicin

Chemical Name: methyl N-[(1R, 8S, 13Z)-8-{[(2R, 3R, 4S, 5S, 6R)-5-({[(2S, 4S, 5S, 6R)-5-(4-{[(2S, 3R, 4R, 5S, 6S)-3, 5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3-iodo-5, 6-dimethoxy-2-methylbenzoylsulfanyl)-4-hydroxy-6-methyloxan-2-yl]oxy}amino)-3-{[(2S, 4S, 5S)-5-(N-ethylacetamido)-4-methoxyoxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-1-hydroxy-13-{2-[(methylsulfanyl)disulfanyl]ethylidene}-11-oxobicyclo[7.3.1]trideca-4, 9-dien-2, 6-diyn-10-yl]carbamate

Smiles: CSSSC/C=C1/C2[C@H](C#CC=CC#C[C@]/1(O)CC(=O)C=2NC(=O)OC)O[C@@H]1O[C@H](C)[C@@H](NO[C@H]2C[C@H](O)[C@H](SC(=O)C3=C(OC)C(OC)=C(O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](OC)[C@H]4O)C(I)=C3C)[C@@H](C)O2)[C@H](O)[C@H]1O[C@H]1C[C@H](OC)[C@H](CO1)N(CC)C(C)=O |c:11|

InChiKey: WPDOZYZAJKUVRZ-DPACUSKXSA-N

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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: To be determined

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

References:

1. Stasi R, et al. Gemtuzumab ozogamicin in the treatment of acute myeloid leukemia. Cancer Treat Rev. 2008 Feb;34(1):49-60.

Products are for research use only. Not for human use.