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Synthesis and pharmacological evaluation of free-base 5,10,15,20-tetrakis (4-hydroxyphenyl)porphyrin and its Zn, Cu, Co metalloderivatives

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Title Synthesis and pharmacological evaluation of free-base 5,10,15,20-tetrakis (4-hydroxyphenyl)porphyrin and its Zn, Cu, Co metalloderivatives
 
Creator Vega-Medina, Antonio
Pérez-Gutiérrez, Salud
Pérez-Ramos, Julia
Martínez-Nava, Cristina
Pérez-González, Cuauhtémoc
 
Subject Photodynamic therapy
hotosensitizer
Cancer
Anti-inflammatory
Porphyrin
Metalloporphyrin
 
Description 1124-1133
In this study, the 5,10,15,20-tetrakis-(4-hydroxyphenyl)porphyrin (TpOHPP) and its Zn, Cu, and Co complexes have
been synthesized and evaluated as photosensitizers and for anti-inflammatory activity. TpOHPP and its Zn (Zn-TpOHPP),
Cu (Cu-TpOHPP), and Co (Co-TpOHPP) ligands have been synthesized using the Alder-Longo method; their
photosensitizer activity has been screened by irradiating HeLa cells with red light, comparing their relative activity to those
of protoporphyrin IX (PpIX) and cisplatin (CDDP). The edema mouse model in which inflammation is induced with 12-Otetradecanoylphorbol
13-acetate (TPA) has been adopted. Finally, molecular modeling (docking) on the test drugs have been
conducted using the Autodock VINA software. TpOHPP induced time-dependent cell replication inhibition when the cells
are exposed to red light (IC50 = 16.35 μM, 2.3 μM, and 2.1 μM at 0, 15, and 30 minutes, respectively). Comparatively, Zn-
TpOHPP exerts essentially the same cell replication inhibitory profile with and without red light exposure (IC50 = 1.35 μM
and 1.38 μM respectively). The percent inhibition of inflammation determined for the test molecules are 54.16% for
TpOHPP, 60.38% for Zn-TpOHPP, 67.10% for Cu-TpOHPP, and 67.53% with Co-TpOHPP. TpOHPP and its Zn complex
show anti-proliferative activity at low micromolar levels and the four porphyrins exerted significant anti-inflammatory
activity in vivo.
 
Date 2022-10-21T04:38:41Z
2022-10-21T04:38:41Z
2022-10
 
Type Article
 
Identifier 2583-1321 (Online); 0019-5103 (Print)
http://nopr.niscpr.res.in/handle/123456789/60716
https://doi.org/10.56042/ijc.v61i10.67205
 
Language en
 
Publisher NIScPR-CSIR,India
 
Source IJC Vol.61(10) [Oct 2022]