3-O-Methylviridicatin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04502 |
| CAS | 6152-57-4 |
| Molecular Weight | 366.3 |
| Molecular Formula | C17H18O9 |
| Purity | ≥99% |
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Description
O-Methylviridicatin is a metabolite produced by several species of Penicillium. It blocks TNF-alpha activation of the HIV LTR in the Hela-based system, with an IC50 of 5 mM, and inhibits virus production in the OM-10.1 cell line, a model of chronic infection responsive to induction by TNF-alpha, with an IC50 of 2.5 mM.
Specification
| Synonyms | 3-O-Methylviridicatin;6152-57-4;3-Methoxy-4-phenyl-1H-quinolin-2-one;O-methylviridicatin;3-methoxy-4-phenylquinolin-2(1h)-one;Methylviridicatin, O-;AIDS-089094, 3-Methoxy-4-phenyl-1H-quinolin-2-one;CHEMBL235425;DTXSID30210514;CHEBI:201725;HY-122786;CS-0089351; |
| Storage | Please store the product under the recommended conditions in the Certificate of Analysis. |
| IUPAC Name | 3-methoxy-4-phenyl-1H-quinolin-2-one |
| Canonical SMILES | C1=CC=C2C(=C1)C(=CC(=C2O)C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O |
| InChI | InChI=1S/C16H13NO2/c1-19-15-14(11-7-3-2-4-8-11)12-9-5-6-10-13(12)17-16(15)18/h2-10H,1H3,(H,17,18) |
| InChI Key | NDTLHHOQSHJIMX-UHFFFAOYSA-N |
Properties
| Appearance | Solid |
| Antibiotic Activity Spectrum | Viruses |
| Boiling Point | 476.5°C at 760 mmHg |
| Melting Point | 184.2°C |
| Density | 1.25 g/cm3 |
| Solubility | Soluble in DMSO, DMF, Ethanol, Methanol, Water |
Reference Reading
1. A new isoquinolone alkaloid from an endophytic fungus R22 of Nerium indicum
Yang-Min Ma,Ke Qiao,Zhi Miao,Chao Fan,Yang Kong,Lin-Xin Guo,Meng-Yun Li Nat Prod Res . 2017 Apr;31(8):951-958. doi: 10.1080/14786419.2016.1258556.
A new isoquinolone alkaloid named 5-hydroxy-8-methoxy-4-phenylisoquinolin-1(2H)-one (3), together with two known quinolinone alkaloids 3-O-methylviridicatin (1) and viridicatol (2) were isolated from the fermentation of an endophytic fungus Penicillium sp. R22 in Nerium indicum. Their structures were elucidated by NMR, IR and MS data, and were also confirmed by comparing with the reported data in the literature. Meanwhile, the antibacterial and antifungal activities of all compounds were tested, and the results showed that three compounds had strong antifungal activity. Among them, compound 2 revealed potent antibacterial activity against Staphylococcus aureus with MIC value of 15.6 μg/mL.
2. Synthesis of 3-O-methylviridicatin analogues with improved anti-TNF-alpha properties
Ludivine Fetzer,Jean Peluso,Nigel Ribeiro,Can Nebigil,Serge Dumont,Christian D Muller,Laurent Désaubry,Helena Tabaka Bioorg Med Chem Lett . 2007 Oct 15;17(20):5523-4. doi: 10.1016/j.bmcl.2007.08.036.
We synthesized 3-O-methylviridicatin and several analogues of this fungal metabolite. We showed that replacement of the methoxy moiety by a thiomethyl enhanced dramatically its ability to inhibit TNF-alpha secretion. These results strongly suggest that 4-phenyl-3-methylthioquinolinone may provide the basis for the development of new anti-inflammatory agents.
3. Isolation and characterization of the fungal metabolite 3-O-methylviridicatin as an inhibitor of tumour necrosis factor alpha-induced human immunodeficiency virus replication
B Katz,D Feineis,C Pearce,D L Taylor,P Cai,A S Tyms,A Heguy,R Michitsch,S Russo,P Meyn,G Bringmann,D Houck Antivir Chem Chemother . 1998 Mar;9(2):149-55. doi: 10.1177/095632029800900206.
The cytokine tumour necrosis factor alpha (TNF-alpha) has been shown to play a role in human immunodeficiency virus (HIV) replication by activating transcription of the provirus in both T cells and macrophages. Therefore, agents that block TNF-alpha-induced HIV expression could have therapeutic value in the treatment of AIDS. We have sought to identify antiviral agents that block TNF-alpha induction of HIV LTR-directed transcription, using a cell-based, virus-free assay system in automated high-throughput screening. HeLa cells were transfected with an HIV LTR-luciferase reporter plasmid and a stable line was isolated in which TNF-alpha increased luciferase production by two- to threefold. This cell line was used to screen approximately 15,000 fungal extracts. An inhibitory activity specific for TNF-alpha-induced HIV LTR transcription was observed in culture OS-F67406. The active component was isolated and identified as a known metabolite, 3-O-methylviridicatin, by NMR and mass spectrometry. No biological activity has been associated with this compound previously. This compound blocks TNF-alpha activation of the HIV LTR in the HeLa-based system, with an IC50 of 5 microM, and inhibited virus production in the OM-10.1 cell line, a model of chronic infection responsive to induction by TNF-alpha, with an IC50 of 2.5 microM.
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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 ╳
