Esperamicin A1
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| Category | Antibiotics |
| Catalog number | BBF-05709 |
| CAS | 99674-26-7 |
| Molecular Weight | 1325.55 |
| Molecular Formula | C59H80N4O22S4 |
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Description
Esperamicin A1 is an enediyne antineoplastic antibiotic hybrid containing an anthranilate moiety. Esperamicin A1 is isolated from the bacterium Actinomadura verrucosospora.
Specification
| Synonyms | Esperamicin A(sub 1) |
| IUPAC Name | [(2S,3R,4S,6S)-3-hydroxy-6-[[(2S,5Z,9R,10S,13E)-9-hydroxy-2-[(2R,3R,4S,5S,6R)-4-hydroxy-5-[[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-methylsulfanyloxan-2-yl]oxyamino]-3-[(2S,4S,5S)-4-methoxy-5-(propan-2-ylamino)oxan-2-yl]oxy-6-methyloxan-2-yl]oxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-10-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-methyloxan-4-yl] 4,5-dimethoxy-2-(2-methoxyprop-2-enoylamino)benzoate |
| Canonical SMILES | CC1C(C(C(C(O1)OC2C#CC=CC#CC3(C(C(=O)C(=C2C3=CCSSSC)NC(=O)OC)OC4CC(C(C(O4)C)O)OC(=O)C5=CC(=C(C=C5NC(=O)C(=C)OC)OC)OC)O)OC6CC(C(CO6)NC(C)C)OC)O)NOC7CC(C(C(O7)C)SC)O |
| 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+/t29-,30+,31-,36+,37+,38+,39+,42+,43+,44+,45+,47-,49-,50+,52-,53-,54-,57+,59-/m1/s1 |
| InChI Key | LJQQFQHBKUKHIS-IIZLOWFNSA-N |
Properties
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
Reference Reading
1. Heat-induced DNA cleavage by esperamicin antitumor antibiotics
Y Uesawa, Y Sugiura Biochemistry . 1991 Sep 24;30(38):9242-6. doi: 10.1021/bi00102a016.
Esperamicin A1 effectively breaks DNA strands upon heating at 50 degrees C. The preferential DNA cutting sites of heat-activated esperamicin A1 are random and clearly differ from those of thiol- or UV-light-mediated DNA breakage with esperamicin A1. The absence of heat-induced DNA cleavage by esperamicin Z and the induction of the DNA breakage by esperamicin A1 disulfide indicate that (1) the enediyne core plays a significant role in this DNA strand scission and (2) the DNA cutting with the heat-activated esperamicin antibiotics does not necessarily require a trisulfide trigger in the aglycon portion. On the basis of the present results, a probable mechanism for the heat-induced DNA cleavage of esperamicin A1 has been proposed.
2. Light-induced DNA cleavage by esperamicin and neocarzinostatin
Y Uesawa, Y Sugiura, J Kuwahara Biochem Biophys Res Commun . 1989 Oct 31;164(2):903-11. doi: 10.1016/0006-291x(89)91544-1.
Ultraviolet radiation of the enediyne drugs is effective in causing nicks in supercoiled DNA. Of special interest is the fact that the observed nucleotide cleaving specificity for the UV light- and thiol-activated antibiotics was the same with esperamicin A1, but was different with neocarzinostatin. In addition to the preferred cutting of T and A bases, the light-activated neocarzinostatin attacked certain G bases which were rarely cleaved by the thiol-activated neocarzinostatin. It should be noted that these enediyne antibiotics lose the DNA breakage activity after light-exposure for 30 min.
3. The effect of cerulenin on the production of esperamicin A1 by Actinomadura verrucosospora
K S Lam, J A Veitch, D R Gustavson, S Forenza J Ind Microbiol . 1993 Feb;12(2):99-102. doi: 10.1007/BF01569908.
Addition of cerulenin (0.25-1.0 mM) to cultures of Acinomadura verrucosospora before the onset of esperamicin synthesis inhibited the production of esperamicin A1 by the microorganism. This result indicates that esperamicin A1 is biosynthesized in part by the polyketide pathway. Addition of cerulenin to the cultures during the active production phase led to a net decrease in esperamicin A1 production. The 14C-acetate labeling pattern of esperamicin A1 in the cultures with or without addition of cerulenin at the active production phase also demonstrated the instability of esperamicin A1 in the fermentation. This suggests that esperamicin A1 is unstable and degradation occurs during the active production phase. Addition of the neutral resin Diaion HP-20 (1%) to the fermentation enhanced the production of esperamicin A1 by 53%.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
