Porphyrins with combinations of 4-carboxyphenyl and 4-hydroxyphenyl substituents in meso-positions as anti-HIV-1 agents

  • Sci Rep. 2024 May 1;14(1):10006. doi: 10.1038/s41598-024-60728-w.
Debdulal Sharma  #  1 ,  Aradhana Singh  #  2 ,  Sanaullah Safi  2 ,  Ritu Gaur  3 ,  Devashish Sengupta  4
Affiliations
  • 1. Department of Chemistry, Assam University, Silchar, Assam, 788011, India.
  • 2. Faculty of Life Sciences and Biotechnology, South Asian University, New Delhi, 110068, India.
  • 3. Faculty of Life Sciences and Biotechnology, South Asian University, New Delhi, 110068, India. [email protected].
  • 4. Department of Chemistry, Assam University, Silchar, Assam, 788011, India. [email protected].
  • # Contributed equally.
PMID: 38693160 DOI: 10.1038/s41598-024-60728-w
Abstract

A series of 4-carboxyphenyl/4-hydroxyphenyl meso-substituted porphyrins were synthesized, purified, and characterized. The compounds exhibited anti-HIV-1 activities, in vitro, under both non-photodynamic (non-PDT) and photodynamic (PDT) conditions. Specifically, the porphyrins inhibited HIV-1 virus entry, with c-PB2(OH)2 and PB(OH)3 showing significant anti-HIV-1 activity. All of the porphyrins inhibited HIV-1 subtype B and C virus entry under PDT conditions. Our study demonstrated that the compounds bearing combinations of 4-carboxyphenyl/4-hydroxyphenyl moieties were not toxic even at higher concentrations, as compared to the reference porphyrins 5,10,15,20-tetra-(4-carboxyphenyl)porphyrin (TCPP) and 5,10,15,20-tetra-(4-hydroxyphenyl)porphyrin (THPP), under PDT conditions. This study underscores the promising potential of these compounds as HIV entry inhibitors in both non-PDT and PDT scenarios.

Keywords
Photodynamic therapy; Photoinactivation of viruses; Photosensitizers; Porphyrins.
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