Cancer photocytotoxicity and anti-inflammatory response of cis-A(2)B(2) type meso-p-nitrophenyl and p-hydroxyphenyl porphyrin and its zinc(ii) complex: a synthetic alternative to the THPP synthon

This work establishes that in comparison with the popular synthetic synthon tetra-p-hydroxyphenyl porphyrin (THPP), used for developing various cancer photodynamic therapy (PDT) agents, the cis-A(2)B(2) type porphyrin derivative, synthesized by replacing two p-hydroxyphenyl groups at the meso-positi...

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Published inNew journal of chemistry Vol. 45; no. 4; pp. 2060 - 2068
Main Authors Sharma, Debdulal, Mazumder, Zeaul H., Sengupta, Devashish, Mukherjee, Avinaba, Sengupta, Mahuya, Das, Ranjan Kumar, Barbhuiya, Monjur Hassan, Palit, Partha, Jha, Tarun
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.01.2021
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
PYRIDYL
NANOPARTICLES
DESIGN
PHOTODYNAMIC THERAPY
PHOTOSENSITIZERS
TUMOR-ASSOCIATED MACROPHAGES
ANTICANCER DRUGS
GENE-EXPRESSION ANALYSIS
DERIVATIVES
PHENYL
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Summary:This work establishes that in comparison with the popular synthetic synthon tetra-p-hydroxyphenyl porphyrin (THPP), used for developing various cancer photodynamic therapy (PDT) agents, the cis-A(2)B(2) type porphyrin derivative, synthesized by replacing two p-hydroxyphenyl groups at the meso-positions with two p-nitrophenyl moieties, 5,10-bis-(4-hydroxyphenyl)-15,20-bis-(4-nitrophenyl)porphyrin PN2(OH)(2) and its zinc(ii) complex PN2(OH)(2)Zn have more promising photosensitizing and photobiological activities. The presence of the electron-withdrawing p-nitrophenyl moiety seems to strengthen and influence the photodynamic therapy (PDT) action against the A549 cell line by upregulating reactive oxygen species (ROS) and downregulating superoxide dismutase (SOD) in the same cancer cell line. Further, murine macrophage myeloperoxidase (MPO) inhibition and nitric oxide (NO) downregulation by PN2(OH)(2) and PN2(OH)(2)Zn are indicative of a concomitant immunoprotective nature towards noncancerous cells.
ISSN:1144-0546
1369-9261
DOI:10.1039/d0nj05106c