desmethylanethol trithione

• CAT Number: M088061
• CAS Number: 18274-81-2
• Molecular Formula: C9H6OS3
• Molecular Weight: 226.326
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: 4-(5-sulfanyldithiol-3-ylidene)cyclohexa-2,5-dien-1-one
• InChI: InChI=1S/C9H6OS3/c10-7-3-1-6(2-4-7)8-5-9(11)13-12-8/h1-5,11H
• InChIKey: ROGBQLVTFIEBAV-UHFFFAOYSA-N
• SMILES: C1=CC(=O)C=CC1=C2C=C(SS2)S

ADT-OH is a derivative of anethole dithiolethione (ADT) and synthetic hydrogen sulfide (H2S) donor. In the in vitro glucose-oxygen deprivation (OGD) model, ADT-OH markedly attenuated tPA-enhanced Akt activation and VEGF expression in brain microvascular endothelial cells. Finally, ADT-OH improved functional outcomes in mice subjected to MCAO and tPA infusion. H2S donors reduced tPA-induced cerebral hemorrhage by possibly inhibiting the Akt-VEGF-MMP9 cascade. Administration of H2S donors has potential as a novel modality to improve the safety of tPA following stroke.

Reference

1:Eur J Med Chem. 2010 Jul;45(7):3005-10. doi: 10.1016/j.ejmech.2010.03.029. Epub 2010 Mar 25. Design, synthesis, and pharmacological evaluation of the aqueous prodrugs of desmethyl anethole trithione with hepatoprotective activity.Chen P,Luo Y,Hai L,Qian S,Wu Y, PMID: 20392547 DOI: 10.1016/j.ejmech.2010.03.029 Abstract: A metabolite-based prodrug strategy to increase the solubility of anethole trithione was reported to facilitate the clinical application of this hepatoprotective agent. Water-soluble analogs of anethole trithione were synthesized via substituting the methyl group of anethole trithione with the simple hydrophilic alkylamino group, and subjected to physiochemical, pharmacological and metabolic studies. The prodrugs displayed increased solubility as well as other physiochemical properties favorable for parenteral use. Among the analogs synthesized, the compound 5a exhibited best hepatoprotective activity at the dose of 2.0 mg/kg in mice equal to that of anethole trithione. The in vivo metabolic investigation demonstrated that the straight-side chain prodrug 5a could convert to desmethyl anethole trithione in vivo, while the ring-side chain prodrug 5d could not. The hepatoprotective activity of the prodrugs might result from the active metabolite desmethyl anethole trithione.Copyright (c) 2010 Elsevier Masson SAS. All rights reserved.