Topostatin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02704 |
| CAS | |
| Molecular Weight | 754.93 |
| Molecular Formula | C36H58N4O11S |
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Description
Topostatin is originally isolated from Thermomonos pora alba No. 1520. It has inhibitory effects on human tumor cells, and the IC50 of SNB-75 and SNB-78 were 0.4 μmol/L and 7 μmol/L, respectively.
Specification
| IUPAC Name | [1-amino-3-[(3S,6S)-6,13-dimethyl-10-methylidene-2,5,9,12-tetraoxo-14-[(5E,7E)-3,7,10-trimethyl-4-oxoheptadeca-5,7-dienyl]-1-oxa-4,8,11-triazacyclotetradec-3-yl]-1-oxopropan-2-yl] hydrogen sulfate |
| Canonical SMILES | CCCCCCCC(C)CC=C(C)C=CC(=O)C(C)CCC1C(C(=O)NC(=C)C(=O)NCC(C(=O)NC(C(=O)O1)CC(C(=O)N)OS(=O)(=O)O)C)C |
| InChI | InChI=1S/C36H58N4O11S/c1-8-9-10-11-12-13-22(2)14-15-23(3)16-18-29(41)24(4)17-19-30-26(6)34(44)39-27(7)35(45)38-21-25(5)33(43)40-28(36(46)50-30)20-31(32(37)42)51-52(47,48)49/h15-16,18,22,24-26,28,30-31H,7-14,17,19-21H2,1-6H3,(H2,37,42)(H,38,45)(H,39,44)(H,40,43)(H,47,48,49)/b18-16+,23-15+/t22?,24?,25-,26?,28-,30?,31?/m0/s1 |
| InChI Key | XLDIAUNLPWGNHO-NUPNHORYSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 179-186°C |
Reference Reading
1. Topostatin, a novel inhibitor of topoisomerases I and II produced by Thermomonospora alba strain No. 1520. III. Inhibitory properties
K Suzuki, M Yamaizumi, S Tateishi, Y Monnai, M Uyeda J Antibiot (Tokyo). 1999 May;52(5):460-5. doi: 10.7164/antibiotics.52.460.
A novel inhibitor of topoisomerases designated as topostatin was isolated from the culture filtrate of Thermomonospora alba strain No. 1520. The inhibitory activity of topostatin was shown to be pH- and temperature-dependent with a maximum around at pH 6 and 28 degrees C. The stability of topostatin decreased with decreasing pH and rising temperature. Topostatin inhibited topoisomerases I and II in a competitive manner with respect to DNA. The inhibitor also inhibited some restriction endonucleases such as Sca I, Hind III and Pst I, but not Alu I, Bam HI, Eco RI, RNase A, DNase I, DNase II and DNA ligase. Topostatin did not induce the nuclear accumulation of p53 protein by DNA damage in the normal human cells.
2. Topoisomerase I poisons and suppressors as anticancer drugs
C Bailly Curr Med Chem. 2000 Jan;7(1):39-58. doi: 10.2174/0929867003375489.
Inhibitors of topoisomerase I constitute a novel family of antitumor agents. The camptothecin derivatives topotecan and irinotecan represent new weapons in our arsenal for battling human cancer. These two drugs act specifically at the level of the topoisomerase I-DNA complex and stimulate DNA cleavage. This mechanism of action is not restricted to the camptothecins. Numerous topoisomerase I poisons including DNA minor groove binders such as Hoechst 33258 and DNA intercalators such as benzophenanthridine alkaloids and indolocarbazole derivatives have been discovered and developed. Another important group of topoisomerase I inhibitors contains drugs which prevent or reverse topoisomerase I-DNA complex formation. Many of these topoisomerase I suppressors are natural products (beta-lapachone, diospyrin, topostatin, topostin, flavonoids) which are believed to interact directly with the enzyme. This review is concerned with the different families of topoisomerase I poisons and suppressors. Their origin, chemical nature and mechanism of action are presented. The relationships between drug binding to DNA and topoisomerase I inhibition are discussed.
3. Topostatin, a novel inhibitor of Topoisomerases I and II produced by Thermomonospora alba strain No. 1520. II. Physico-chemical properties and structure elucidation
K Suzuki, S Yahara, Y Kido, K Nagao, Y Hatano, M Uyeda J Antibiot (Tokyo). 1998 Nov;51(11):999-1003. doi: 10.7164/antibiotics.51.999.
Topostatin is a new topoisomerase inhibitor isolated from the culture filtrate of Thermononospora alba strain No. 1520. The inhibitor inhibits topoisomerases I and II, and it has neither ability to stabilize the cleavable complex nor ability to intercalate into DNA strands. The molecular formula of topostatin was determined as C36H58N4O11S based on the FAB-MS analyses, and the structure was elucidated to be a novel 14-membered ring containing peptide and terpenoid by various NMR spectroscopies.
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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 ╳
