Esperamicin
title: "Esperamicin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["antibiotics", "cancer-research", "enediynes", "isopropylamino-compounds", "carbamates", "secondary-alcohols", "amines", "phenol-ethers", "ethers", "methylthio-compounds", "alkene-derivatives", "anilides", "benzoate-esters", "methyl-esters", "ketones", "ten-membered-rings"] topic_path: "general/antibiotics" source: "https://en.wikipedia.org/wiki/Esperamicin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
|Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 399920724 |Name = Esperamicin A1 |ImageFile=Esperamicin.png |ImageSize=230px |ImageAlt = Structural formula of esperamicin A1 |ImageFile1 = Esperamicin A1 3D spacefill.png |ImageAlt1 = Ball-and-stick model of the Esperamicin A1 molecule |Section1={{Chembox Identifiers |ChemSpiderID_Ref = |ChemSpiderID = 4940320 |ChEMBL_Ref = |ChEMBL = 449274 |InChI = 1/C59H80N4O22S4/c1-28(2)60-36-27-77-43(25-39(36)73-8)83-52-50(66)47(63-85-45-24-37(64)53(86-12)31(5)79-45)29(3)80-57(52)82-38-18-16-14-15-17-20-59(71)34(19-21-88-89-87-13)46(38)48(62-58(70)76-11)51(67)54(59)84-44-26-42(49(65)30(4)78-44)81-56(69)33-22-40(74-9)41(75-10)23-35(33)61-55(68)32(6)72-7/h14-15,19,22-23,28-31,36-39,42-45,47,49-50,52-54,57,60,63-66,71H,6,21,24-27H2,1-5,7-13H3,(H,61,68)(H,62,70)/b15-14-,34-19+ |InChIKey = LJQQFQHBKUKHIS-WJHRIEJJBF |StdInChI_Ref = |StdInChI = 1S/C59H80N4O22S4/c1-28(2)60-36-27-77-43(25-39(36)73-8)83-52-50(66)47(63-85-45-24-37(64)53(86-12)31(5)79-45)29(3)80-57(52)82-38-18-16-14-15-17-20-59(71)34(19-21-88-89-87-13)46(38)48(62-58(70)76-11)51(67)54(59)84-44-26-42(49(65)30(4)78-44)81-56(69)33-22-40(74-9)41(75-10)23-35(33)61-55(68)32(6)72-7/h14-15,19,22-23,28-31,36-39,42-45,47,49-50,52-54,57,60,63-66,71H,6,21,24-27H2,1-5,7-13H3,(H,61,68)(H,62,70)/b15-14-,34-19+ |StdInChIKey_Ref = |StdInChIKey = LJQQFQHBKUKHIS-WJHRIEJJSA-N |CASNo_Ref = |CASNo=99674-26-7 |UNII_Ref = |UNII = PLX8T21X8G |PubChem = 6435576 |SMILES = O=C(C(\OC)=C)Nc1cc(OC)c(OC)cc1C(=O)OC2CC(OC(C)C2O)OC7C(=O)C(\NC(=O)OC)=C6/C(=C\CSSSC)C7(O)C#C\C=C/C#CC6OC5OC(C)C(NOC3OC(C)C(SC)C(O)C3)C(O)C5OC4OCC(NC(C)C)C(OC)C4 |Section2={{Chembox Properties |C=59 | H=80 | N=4 | O=22 | S=4
The esperamicins are chromoprotein enediyne antitumor antibiotics of bacterial origin. Esperamicin A1 is the most well studied compound in this class. Esperamcin A1 and the related enediyne calicheamicin are the two most potent antitumor agents known. The esperamicins are extremely toxic DNA splicing compounds.
Oxygen and active oxygen-radical scavengers have no significant influence upon DNA strand breakage by esperamicin, but the cleavage of DNA by esperamicin is greatly accelerated in the presence of thiol compounds. The preferential cutting sites of esperamicin are at thymidylate residues, and the frequency of nucleobase attacked (T greater than C greater than A greater than G) is different from that of calicheamicin (C much greater than T greater than A = G), neocarzinostatin (T greater than A greater than C greater than G), or bleomycin (C greater than T greater than A greater than G).
References
References
- [http://jlstasal.myweb.uga.edu/CaliEsp.htm Calicheamicin and Esperamicin are the two most potent antitumor agents known to man], Univ Of Georgia Chem 4500 {{webarchive. link. (September 21, 2008)
- (January 1989). "Esperamicins, a class of potent antitumor antibiotics: mechanism of action". Proceedings of the National Academy of Sciences of the United States of America.
- (October 1989). "Nucleotide-specific cleavage and minor-groove interaction of DNA with esperamicin antitumor antibiotics". Proceedings of the National Academy of Sciences of the United States of America.
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