For research use only. Not for therapeutic Use.
Calicheamicin(Cat No.:I000356) is a potent DNA-binding cytotoxic antibiotic derived from the bacterium Micromonospora echinospora. It belongs to the enediyne class of antitumor antibiotics. Calicheamicin exerts its cytotoxic effects by targeting DNA and causing strand scission. It binds to DNA in the minor groove and undergoes a reaction similar to the Bergman cyclization, forming a diradical species known as 1,4-didehydrobenzene. This diradical then abstracts hydrogen atoms from the deoxyribose backbone of DNA, leading to DNA strand scission. The specificity of Calicheamicin’s binding to the minor groove of DNA is attributed to its aryl tetrasaccharide group. Calicheamicin is known for its potent antitumor activity and has been extensively studied for its therapeutic potential in cancer treatment.
| Catalog Number | I000356 |
| CAS Number | 108212-75-5 |
| Molecular Formula | C55H74IN3O21S4 |
| Purity | 95% |
| Target | Antibacterial |
| Solubility | DMSO: 20 mg/mL |
| Appearance | Solid powder |
| Storage | 3 years -20C powder |
| Analysis method | HPLC |
| IUPAC Name | S-[(2R,3S,4S,6S)-6-[[(2R,3S,4S,5R,6R)-5-[(2S,4S,5S)-5-(ethylamino)-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-[[(2S,5Z,9R,13Z)-9-hydroxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-2-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-methyloxan-3-yl]amino]oxy-4-hydroxy-2-methyloxan-3-yl] 4-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5-iodo-2,3-dimethoxy-6-methylbenzenecarbothioate |
| InChI | InChI=1S/C55H74IN3O21S4/c1-12-57-30-24-73-35(22-34(30)68-6)78-48-43(63)40(26(3)75-53(48)77-33-17-15-13-14-16-19-55(67)23-32(61)41(58-54(66)72-10)38(33)29(55)18-20-82-84-81-11)59-80-36-21-31(60)50(28(5)74-36)83-51(65)37-25(2)39(56)46(49(71-9)45(37)69-7)79-52-44(64)47(70-8)42(62)27(4)76-52/h13-14,18,26-28,30-31,33-36,40,42-44,47-48,50,52-53,57,59-60,62-64,67H,12,20-24H2,1-11H3,(H,58,66)/b14-13-,29-18-/t26-,27+,28-,30+,31+,33+,34+,35+,36+,40-,42+,43+,44-,47-,48-,50-,52+,53+,55+/m1/s1 |
| InChIKey | HXCHCVDVKSCDHU-GPCZLZLMSA-N |
| SMILES | CCN[C@H]1CO[C@H](C[C@@H]1OC)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3C#C/C=C\C#C[C@@]\4(CC(=O)C(=C3/C4=C/CSSSC)NC(=O)OC)O)C)NO[C@H]5C[C@@H]([C@@H]([C@H](O5)C)SC(=O)C6=C(C(=C(C(=C6OC)OC)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)OC)O)I)C)O)O |
| Reference | <br /> |
