Issue 4, 2021
From the journal:

New Journal of Chemistry

Cancer photocytotoxicity and anti-inflammatory response of cis-A2B2 type meso-p-nitrophenyl and p-hydroxyphenyl porphyrin and its zinc(ii) complex: a synthetic alternative to the THPP synthon†

Debdulal Sharma, ORCID logo a   Zeaul H. Mazumder,a   Devashish Sengupta, ORCID logo *a   Avinaba Mukherjee,b   Mahuya Sengupta,c   Ranjan Kumar Das,a   Monjur Hassan Barbhuiya,a   Partha Palitd  and  Tarun Jha ORCID logo e  

* Corresponding authors

a Department of Chemistry, Assam University, Silchar, Assam, India
E-mail: devashish.sengupta@uni.sydney.edu.au

b Department of Zoology, Charuchandra College, University of Calcutta, Kolkata, India

c Department of Biotechnology, Assam University, Silchar, Assam, India

d Department of Pharmaceutical Sciences, Assam University, Silchar, India

e Department of Pharmaceutical Technology, Jadavpur University, Kolkata, India

Abstract

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-A2B2 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)2Zn 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)2Zn are indicative of a concomitant immunoprotective nature towards noncancerous cells.

Graphical abstract: Cancer photocytotoxicity and anti-inflammatory response of cis-A2B2 type meso-p-nitrophenyl and p-hydroxyphenyl porphyrin and its zinc(ii) complex: a synthetic alternative to the THPP synthon

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Article information

DOI
https://doi.org/10.1039/D0NJ05106C
Article type
Paper
Submitted
17 Oct 2020
Accepted
17 Dec 2020
First published
17 Dec 2020

New J. Chem., 2021,45, 2060-2068

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Cancer photocytotoxicity and anti-inflammatory response of cis-A2B2 type meso-p-nitrophenyl and p-hydroxyphenyl porphyrin and its zinc(II) complex: a synthetic alternative to the THPP synthon

D. Sharma, Z. H. Mazumder, D. Sengupta, A. Mukherjee, M. Sengupta, R. K. Das, M. H. Barbhuiya, P. Palit and T. Jha, New J. Chem., 2021, 45, 2060 DOI: 10.1039/D0NJ05106C

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