Topopyrone C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02702 |
| CAS | |
| Molecular Weight | 338.27 |
| Molecular Formula | C18H10O7 |
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Description
It is produced by the strain of Phoma sp. BAUA 2861 and Penicillum sp. BAUA 4206. Topopyrone C selectively inhibits topoisomerase I with the IC50 of 4.88 ng/mL. It also has anti-Gram-positive bacteria activity.
Specification
| IUPAC Name | 5,9,11-trihydroxy-2-methylnaphtho[3,2-h]chromene-4,7,12-trione |
| Canonical SMILES | CC1=CC(=O)C2=C(C=C3C(=C2O1)C(=O)C4=C(C3=O)C=C(C=C4O)O)O |
| InChI | InChI=1S/C18H10O7/c1-6-2-10(20)15-12(22)5-9-14(18(15)25-6)17(24)13-8(16(9)23)3-7(19)4-11(13)21/h2-5,19,21-22H,1H3 |
| InChI Key | AWDAPFGGFWZKGB-UHFFFAOYSA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | >280°C |
Reference Reading
1. Identification and Heterologous Expression of the Topopyrone Nonaketide Synthase Gene from Phoma sp
Nobuyuki Kashiwa, Yutaka Ebizuka, Isao Fujii Chem Pharm Bull (Tokyo). 2016;64(7):947-51. doi: 10.1248/cpb.c16-00172.
Non-reducing iterative type I polyketide synthase genes, pnk1 and pnk2, were cloned from the fungus Phoma sp. BAUA2861, which produces the topoisomerase I inhibitors, topopyrones A to D. Heterologous expression of these polyketide synthase genes under the α-amylase promoter in Aspergillus oryzae was carried out to identify their functions. The pnk2 transformant produced topopyrones C, D, and haematommone. Therefore, the pnk2 gene was found to encode for the topopyrone nonaketide synthase.
2. Novel human topoisomerase I inhibitors, topopyrones A, B, C and D. II. Structure elucidation
D Ishiyama, Y Kanai, H Senda, W Iwatani, W Iwatani, H Konno, S Kanazawa J Antibiot (Tokyo). 2000 Sep;53(9):873-8. doi: 10.7164/antibiotics.53.873.
The structures of novel topoisomerase I inhibitors, topopyrones A, B, C and D were elucidated by spectral analysis of the chemical derivatives. These compounds are an anthraquinone type containing a fused 1,4-pyrone moiety. Topopyrones A and B contain a chlorine atom, however C and D do not. It was suggested that topopyrones B and D are converted from topopyrones A and C, respectively by Wessely-Moser type rearrangement.
3. Synthesis and cytotoxic activity of a new series of topoisomerase I inhibitors
Sabrina Dallavalle, Sonia Gattinoni, Stefania Mazzini, Leonardo Scaglioni, Lucio Merlini, Stella Tinelli, Giovanni L Beretta, Franco Zunino Bioorg Med Chem Lett. 2008 Feb 15;18(4):1484-9. doi: 10.1016/j.bmcl.2007.12.055. Epub 2007 Dec 25.
A series of structurally simple analogues of natural topopyrone C were synthesized and tested for cytotoxic and topoisomerase I inhibitory activities. The removal of the hydroxyl groups at the 5 and 9 positions resulted in an increased cytotoxic potency and ability to stabilize topoisomerase-mediated cleavage. In addition, the results suggest that some structural features, such as the pyrone ring and a polar group in position 11, are fundamental for topoisomerase I inhibitory effect. These structural requirements are also consistent with the cytotoxic activity.
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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 ╳
