6152-57-4 Usage
Uses
3-O-Methylviridicatin is a metabolite produced by several species of Penicillium. Recently, 3-O-methylviridicatin was shown to be a strong inhibitor of TNFα-induced replication of HIV. Lack of availability has hitherto restricted a more intensive investigation of this interesting metabolite.
Biological Activity
5 μm: blocks activation of the hiv long terminal repeat by tnf-α in hela cellso-methylviridicatin, a natural derivative of the alkaloid mycotoxin viridicatin, is produced by several species in the genus, penicillium. it is demonstrated that o-methylviridicatin, as an inhibitor, blocks the tumor necrosis factor alpha (tnfα)-induced replication of human immunodeficiency virus (hiv). tnfα increases the binding of the cellular transcription factor nf-κb to the hiv long terminal repeat (ltr), which directly triggers transcription of the latent provirus.
in vitro
o-methylviridicatin had an inhibitory effect on the tnfα-triggered replication of hiv ltr in hela cells. in addition, o-methylviridicatin dose-dependently dampened virus production in the om-10.1 cell line, which was measured by the output of p24 core antigen into the culture medium. it was demonstrated that the suppressive effect of o-methylviridicatin was not reversed even if the concentration of tnfα was increased 10-fold [1].
IC 50
2.5 μm: inhibits virus production in om-10.1 cells (hl-60 promyelocytes infected with hiv-1) treated with tnf-α.
references
[1]. heguy, a., cai, p., meyn, p., houck, d., russo, s., & michitsch, r. et al. isolation and characterization of the fungal metabolite 3-o-methylviridicatin as an inhibitor of tumour necrosis factor-induced human immunodeficiency virus replication. antiviral chemistry and chemotherapy. 1998; 9(2): 149-155.
Check Digit Verification of cas no
The CAS Registry Mumber 6152-57-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,1,5 and 2 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 6152-57:
(6*6)+(5*1)+(4*5)+(3*2)+(2*5)+(1*7)=84
84 % 10 = 4
So 6152-57-4 is a valid CAS Registry Number.
InChI:InChI=1/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)
6152-57-4Relevant articles and documents
Bicyclic alkaloid compound, preparation method and applications thereof
-
, (2018/11/03)
The present invention relates to a bicyclic alkaloid compound, or a tautomer, a stereoisomer, a racemate, the non-equal mixture of enantiomers, a geometric isomer, a solvate, a pharmaceutically acceptable salt or a prodrug thereof, and a pharmaceutical composition containing the compound. The invention further discloses uses of the compounds and the pharmaceutical composition thereof as drugs, especially as anti-inflammatory drugs and anti-fibrotic drugs.
Synthesis of 3-O-methylviridicatin analogues with improved anti-TNF-α properties
Ribeiro, Nigel,Tabaka, Helena,Peluso, Jean,Fetzer, Ludivine,Nebigil, Can,Dumont, Serge,Muller, Christian D.,Desaubry, Laurent
, p. 5523 - 5524 (2008/03/13)
We synthesized 3-O-methylviridicatin 1 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-α secretion. These results strongly suggest that 4-phenyl-3-methylthioquinolinone 3 may provide the basis for the development of new anti-inflammatory agents.
