Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
The calicheamicins are a class of enediyne antitumor antibiotics derived from the bacterium Micromonospora echinospora,[1] with calicheamicin γ1 being the most notable.[2] It was isolated originally in the mid-1980s from the chalky soil, or "caliche pits", located in Kerrville, Texas. The sample was collected by a scientist working for Lederle Labs.[3] It is extremely toxic to all cells and, in 2000, a CD33 antigen-targeted immunoconjugate N-acetyl dimethyl hydrazide calicheamicin was developed and marketed as targeted therapy against the non-solid tumor cancer acute myeloid leukemia (AML).[4] A second calicheamicin-linked monoclonal antibody, inotuzumab ozogamicin (marketed as Besponsa), an anti-CD22-directed antibody-drug conjugate, was approved by the U.S. Food and Drug Administration on August 17, 2017, for use in the treatment of adults with relapsed or refractory B-cell precursor acute lymphoblastic leukemia.[5] Calicheamicin γ1 and the related enediyne esperamicin are the two of the most potent antitumor agents known.[6]
^Maiese, William M; Lechevalier, Mary P; Lechevalier, Hubert A; Korshalla, Joseph; Kuck, Nydia; Fantini, Amadeo; Wildey, Mary Jo; Thomas, John; Greenstein, Michael (April 1989). "Calicheamicins, a novel family of antitumor antibiotics: taxonomy, fermentation and biological properties". Journal of Antibiotics. 42 (4): 558–63. doi:10.7164/antibiotics.42.558. PMID 2722671.
^Lee, May D.; Manning, Joann K.; Williams, David R.; Kuck, Nydia A.; Testa, Raymond T.; Borders, Donald B. (July 1989). "Calichemicins, a novel family of antitumor antibiotics. 3. Isolation, purification and characterization of calichemicins β1Br, γ1Br, α2I, α3I, β1I, γ1I, and Δ1I". Journal of Antibiotics. 42 (7): 1070–87. doi:10.7164/antibiotics.42.1070. PMID 2753814.
^
Total Synthesis and the Creative Process: An Interview with K.C. Nicolaou, Scripps Research Institute
^G.A. Ellestad (2011). "Structural and Conformational Features Relevant to the Anti-Tumor Activity of Calichemicin γ1I". Chirality. 23 (8): 660–671. doi:10.1002/chir.20990. PMID 21800378.
^"Newly Approved Drugs in ALL and NHL: How to Use Them in Practice". January 11, 2018.
^Calicheamicin and Esperamicin are the two most potent antitumor agents known to man Archived 2008-09-21 at the Wayback Machine, Univ Of Georgia, Chem 4500
The calicheamicins are a class of enediyne antitumor antibiotics derived from the bacterium Micromonospora echinospora, with calicheamicin γ1 being the...
against CD22 (inotuzumab), linked to a cytotoxic agent from the class of calicheamicins called ozogamicin. The US Food and Drug Administration (FDA) considers...
G.A. Ellestad; D. Kahne (1992). "Cleavage behavior of calicheamicin gamma 1 and calicheamicin T". Proc Natl Acad Sci USA. 89 (10): 4608–12. Bibcode:1992PNAS...
during a search for new anticancer products produced by microorganisms. Calicheamicin was one of the first such products identified and was originally found...
river Styx (modern-day Mavroneri in Arcadia, Greece) that contained calicheamicin, a dangerous compound produced by bacteria. Several natural causes (diseases)...
covalently attached to the cytotoxic antitumor antibiotic calicheamicin (N-acetyl-γ-calicheamicin) via a bifunctional linker (4-(4-acetylphenoxy)butanoic...
Peloponnesian peninsula. Its waters contain a significant amount of Calicheamicin, a dangerous compound produced by bacteria. Stanford University scientists...
gentamicin, mutamicin, netilmicin, retymicin, sisomicin, verdamicin, calicheamicin, and the recently found turbinmicin. Potent new antifungal drugs discovered...
containing the enediyne functional group that model the activity of the calicheamicin class of antibiotics. Sarpong received his Ph.D. in 2001. Sarpong moved...
glycosylation on peptide backbone conformation ; Part II. An NMR study of calicheamicin bound to DNA (Thesis). Princeton University. OCLC 30962578. "Dr. Amy...
common. Examples are N-tert-butylhydroxylamine or the glycosidic bond in calicheamicin. N,O-Dimethylhydroxylamine is a precursor to Weinreb amides. Similarly...
tumors. The calicheamicins are a sub-family of enediynes that were isolated from Micromonospora echinospora calichensis. All calicheamicin family members...
studied compound in this class. Esperamcin A1 and the related enediyne calicheamicin are the two most potent antitumor agents known. The esperamicins are...
monoclonal antibody to CD33 linked to a cytotoxic agent from the class of calicheamicins (ozogamicin). CD33 is expressed in most leukemic blast cells but also...
antitumor antibiotic agents, which includes: namenamicin, esperamicin and, calicheamicin. Due to its high potency from cytotoxicity, Shishjimicin A is currently...
indicates that they are linked to a cytotoxic agent from the class of calicheamicins. Gemtuzumab ozogamicin Inotuzumab ozogamicin "マイロターグ点滴静注用5mg インタビューフォーム"...
2021-08-24. Brummond, Kay Michille (1991). Synthetic approach to the calicheamicin/esperamicin bicyclo[7.3.1]tridencenediyne ring core and sulfones in...
(August 2003). "Antibody-targeted chemotherapy with immunoconjugates of calicheamicin". Current Opinion in Pharmacology. 3 (4): 386–90. doi:10.1016/S1471-4892(03)00083-3...
became topical with the discovery of enediyne "cytostatics", such as calicheamicin, which generates a 1,4-didehydrobenzene. A variety of natural products...
species of bacteria that is known for producing the enediyne antibiotic calicheamicins. Lee, May D.; Manning, Joann K.; Williams, David R.; Kuck, Nydia A.;...
immunoglobulin G4 humanized monoclonal antibody conjugated to calicheamicin. The mechanism by which calicheamicin destroys malignant cells is that it binds to DNA...
much lower temperature of 37 °C. Naturally occurring compounds such as calicheamicin contain the same 10-membered ring and are found to be cytotoxic. These...
aminopentose of which is also found appended to the 10-membered enediyne calicheamicin. Information for this pathway, along with those of K252a and STA, was...
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