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Calicheamicin CAS: 108212-75-5

Category: Inhibitors
Product Name: Calicheamicin
Cat No: I000356
CAS No: 108212-75-5
Molecular Formula: C55H74IN3O21S4
Molecular Weight: 1368.35
SMILES: O=C(S[C@@H]1[C@@H](C)O[C@@H](ON[C@@H]2[C@@H](C)OC(O[C@@H](C#C/C=C\C#C[C@@]3(O)C4)C(/C3=C\CSSSC)=C(NC(OC)=O)C4=O)[C@H](O[C@H]5C[C@H](OC)[C@@H](NCC)CO5)[C@H]2O)C[C@@H]1O)C6=C(OC)C(OC)=C(O[C@H]7[C@H](O)[C@H](OC)[C@@H](O)[C@H](C)O7)C(I)=C6C
InChI: None
InChIKey: None
Solubility: DMSO: 20 mg/mL
Target: Antibacterial
CAS 108212-75-5,Calicheamicin
  • Description

Calicheamicin is a potent DNA-binding cytotoxic antibiotic.
Target: Antibacterial
Calicheamicin being the most notable enediyne antitumor antibiotics derived from the bacterium Micromonospora echinospora. Calicheamicin targets DNA and cause strand scission. Calicheamicin binds 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 to be due to the aryltetrasaccharide group of the molecule.

  • Spec

Appearance:Solid powder
Purity: > 98%

  • References

1:Liver Microvascular Injury and Thrombocytopenia of Antibody-Calicheamicin Conjugates in Cynomolgus Monkeys-Mechanism and Monitoring. Guffroy M, Falahatpisheh H, Biddle K, Kreeger J, Obert L, Walters K, Goldstein R, Boucher G, Coskran T, Reagan W, Sullivan D, Huang C, Sokolowski S, Giovanelli R, Gerber HP, Finkelstein M, Khan N.Clin Cancer Res. 2017 Apr 1;23(7):1760-1770. doi: 10.1158/1078-0432.CCR-16-0939. Epub 2016 Sep 28. PMID: 27683177
2:Structural dynamics of a methionine γ-lyase for calicheamicin biosynthesis: Rotation of the conserved tyrosine stacking with pyridoxal phosphate. Cao H, Tan K, Wang F, Bigelow L, Yennamalli RM, Jedrzejczak R, Babnigg G, Bingman CA, Joachimiak A, Kharel MK, Singh S, Thorson JS, Phillips GN Jr.Struct Dyn. 2016 Apr 29;3(3):034702. doi: 10.1063/1.4948539. eCollection 2016 May. PMID: 27191010 Free PMC Article
3:Loop dynamics of thymidine diphosphate-rhamnose 3'-O-methyltransferase (CalS11), an enzyme in calicheamicin biosynthesis. Han L, Singh S, Thorson JS, Phillips GN Jr.Struct Dyn. 2016 Feb 18;3(1):012004. doi: 10.1063/1.4941368. eCollection 2016 Jan. PMID: 26958582 Free PMC Article
4:Structural Characterization of CalS8, a TDP-α-D-Glucose Dehydrogenase Involved in Calicheamicin Aminodideoxypentose Biosynthesis. Singh S, Michalska K, Bigelow L, Endres M, Kharel MK, Babnigg G, Yennamalli RM, Bingman CA, Joachimiak A, Thorson JS, Phillips GN Jr.J Biol Chem. 2015 Oct 23;290(43):26249-58. doi: 10.1074/jbc.M115.673459. Epub 2015 Aug 3. PMID: 26240141 Free PMC Article
5:Crystal structure of O-methyltransferase CalO6 from the calicheamicin biosynthetic pathway: a case of challenging structure determination at low resolution. Tsodikov OV, Hou C, Walsh CT, Garneau-Tsodikova S.BMC Struct Biol. 2015 Jul 15;15:13. doi: 10.1186/s12900-015-0040-6. PMID: 26170207 Free PMC Article
6:Anti-EFNA4 Calicheamicin Conjugates Effectively Target Triple-Negative Breast and Ovarian Tumor-Initiating Cells to Result in Sustained Tumor Regressions. Damelin M, Bankovich A, Park A, Aguilar J, Anderson W, Santaguida M, Aujay M, Fong S, Khandke K, Pulito V, Ernstoff E, Escarpe P, Bernstein J, Pysz M, Zhong W, Upeslacis E, Lucas J, Lucas J, Nichols T, Loving K, Foord O, Hampl J, Stull R, Barletta F, Falahatpisheh H, Sapra P, Gerber HP, Dylla SJ.Clin Cancer Res. 2015 Sep 15;21(18):4165-73. doi: 10.1158/1078-0432.CCR-15-0695. Epub 2015 May 26. PMID: 26015513 Free Article
7:Novel insights on the DNA interaction of calicheamicin γ₁(I). Sissi C, Moro S, Crothers DM.Biopolymers. 2015 Aug;103(8):449-59. doi: 10.1002/bip.22591. PMID: 25411012
8:Identification and characterization of a methionine γ-lyase in the calicheamicin biosynthetic cluster of Micromonospora echinospora. Song H, Xu R, Guo Z.Chembiochem. 2015 Jan 2;16(1):100-9. doi: 10.1002/cbic.201402489. Epub 2014 Nov 17. PMID: 25404066
9:Characterization of the calicheamicin orsellinate C2-O-methyltransferase CalO6. Singh S, Nandurkar NS, Thorson JS.Chembiochem. 2014 Jul 7;15(10):1418-21. doi: 10.1002/cbic.201402119. PMID: 24978950 Free PMC Article
10:Structural and functional characterization of CalS11, a TDP-rhamnose 3'-O-methyltransferase involved in calicheamicin biosynthesis. Singh S, Chang A, Helmich KE, Bingman CA, Wrobel RL, Beebe ET, Makino S, Aceti DJ, Dyer K, Hura GL, Sunkara M, Morris AJ, Phillips GN Jr, Thorson JS.ACS Chem Biol. 2013 Jul 19;8(7):1632-9. doi: 10.1021/cb400068k. Epub 2013 May 23. PMID: 23662776 Free PMC Article

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