Two cationic meso-thiophenium porphyrins and their zinc-complexes as anti-HIV-1 and antibacterial agents under non-photodynamic therapy (PDT) conditions. (1st June 2022)

• Record Type: Journal Article
• Authors: Sengupta, Devashish; Rai, Madhu; Hoque Mazumdar, Zeaul; Sharma, Debdulal; Malabika Singha, K.; Pandey, Piyush; Gaur, Ritu
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 65(2022)
• Publication Date: 2022-06-01
• Subjects: Thiophenium porphyrins -- Zn-porphyrins -- Anti-HIV -- Anti-microbial -- Bactericidal; T2(OH)2MZn (cis-5, 10-bis(4-hydroxyphenyl)-15, 20-bis(2-methylthiophenium)-21, 23-Zn(II)-porphine) -- T(OH)3MZn (5, 10, 15-tris(4-hydroxyphenyl)-20-mono-(2-methylthiophenium)-21, 23-Zn(II) porphine) -- T2(OH)2M (cis-5, 10-bis(4-hydroxyphenyl)-15, 20-bis(2-methylthiophenium)porphyrin) -- T(OH)3M (5, 10, 15-tris(4-hydroxyphenyl)-20-mono-(2-methylthiophenium)porphyrin) -- CTPs cationic thiophenium porphyrins -- cPDT anti-cancer photodynamic therapy -- HIV human immunodeficiency virus -- SIVmac macaque simian immunodeficiency virus -- FIV feline immunodeficiency virus -- gp120 envelope glycoprotein 120 -- CD4 cluster of differentiation 4 -- CCR5 chemokine receptor type 5 -- CXCR4 chemokine receptor type 4 -- Env HIV-1 Envelope -- RT Reverse Transcriptase -- PR Viral Protease -- ZOI zone of inhibition -- MIC minimum inhibitory concentration; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2022.128699
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: The anti-HIV-1 and antimicrobial activities of novel cationic meso -thiophenium porphyrins and their zinc-complex are reported under in vitro non-photodynamic (PDT) conditions. While all the cationic porphyrins led to the inhibition of de novo virus infection, the Zn(II)-complexes of T2 (OH)2 M (A2 B2 -type) and T(OH)3 M (AB3 -type) displayed potent inhibition of HIV-1 entry with T2 (OH)2 MZn displaying maximal anti-HIV activity. The Zinc complex of both the thiophenium porphyrins T2 (OH)2 M and T(OH)3 M also depicted antibacterial activities against Escherichia coli (ATCC 25922) and more prominently against Staphylococcus aureus (ATCC 25923). Again, the antibacterial activity was more potent for T2 (OH)2 MZn . Our study highlighted that the presence of two thiophenium groups at the meso -positions of the A2 B2 -type porphyrins along with zinc strongly enhanced anti-HIV and antimicrobial properties of these novel thiophenium porphyrins under non-PDT conditions.