Esperamicin

Esperamicin A1
Identifiers
CAS Number	99674-26-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL449274 ;
ChemSpider	4940320 ;
PubChem CID	6435576;
UNII	PLX8T21X8G ;
	InChI InChI=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+ Key: LJQQFQHBKUKHIS-WJHRIEJJSA-N ; 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+ Key: LJQQFQHBKUKHIS-WJHRIEJJBF;
	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;
Properties
Chemical formula	C59H80N4O22S4
Molar mass	1325.54 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[1] The esperamicins are extremely toxic DNA splicing compounds.^[2]

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).^[3]

References

^ Calicheamicin and Esperamicin are the two most potent antitumor agents known to man, Univ Of Georgia Chem 4500 Archived September 21, 2008, at the Wayback Machine
^ Long BH, Golik J, Forenza S, Ward B, Rehfuss R, Dabrowiak JC, et al. (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. 86 (1): 2–6. Bibcode:1989PNAS...86....2L. doi:10.1073/pnas.86.1.2. PMC 286391. PMID 2643098.
^ Sugiura Y, Uesawa Y, Takahashi Y, Kuwahara J, Golik J, Doyle TW (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. 86 (20): 7672–7676. Bibcode:1989PNAS...86.7672S. doi:10.1073/pnas.86.20.7672. PMC 298132. PMID 2813351.

[1] Calicheamicin and Esperamicin are the two most potent antitumor agents known to man, Univ Of Georgia Chem 4500 Archived September 21, 2008, at the Wayback Machine

[2] Long BH, Golik J, Forenza S, Ward B, Rehfuss R, Dabrowiak JC, et al. (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. 86 (1): 2–6. Bibcode:1989PNAS...86....2L. doi:10.1073/pnas.86.1.2. PMC 286391. PMID 2643098.

[3] Sugiura Y, Uesawa Y, Takahashi Y, Kuwahara J, Golik J, Doyle TW (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. 86 (20): 7672–7676. Bibcode:1989PNAS...86.7672S. doi:10.1073/pnas.86.20.7672. PMC 298132. PMID 2813351.

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Identifiers


CAS Number	99674-26-7^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL449274^N
ChemSpider	4940320^Y
PubChem CID	6435576
UNII	PLX8T21X8G^Y
InChI InChI=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+^Y Key: LJQQFQHBKUKHIS-WJHRIEJJSA-N^Y 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+ Key: LJQQFQHBKUKHIS-WJHRIEJJBF
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
Properties
Chemical formula	C₅₉H₈₀N₄O₂₂S₄
Molar mass	1325.54 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references