Calicheamicin

• CAT Number: I000356
• CAS Number: 108212-75-5
• PubChem Substance ID: 5359272
• Molecular Formula: C55H74IN3O21S4
• Molecular Weight: 1368.35
• Purity: 95%
• Target: Antibacterial
• Solubility: DMSO: 20 mg/mL
• Storage: 3 years -20C powder
• Analysis method: HPLC
• IUPAC Name: (1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
• InChI: InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1
• InChIKey: JAQUASYNZVUNQP-USXIJHARSA-N
• SMILES: CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)O

Calicheamicin(CAT: 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.

Reference

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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
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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