Synthesis of Some New Porphyrins and Their Metalloderivatives As Potential Sensitizers in Photo-dynamic Therapy

Overview

Journal Res Pharm Sci

Specialty Chemistry

Date 2016 Jan 19

PMID 26779270

Citations 5

Authors

Mahboubeh Rostami

Leila Rafiee

Farshid Hassanzadeh

Ali Reza Dadrass

Ghadam Ali Khodarahmi

Affiliations

Soon will be listed here.

Abstract

Porphyrins are a ubiquitous large class of naturally occurring macrocyclic compounds with many significant biological representatives comprising heme and chlorophyll. Some novel adaptable methods for the synthesis of free-based porphyrins as promising sensitizers for the use in photo-dynamic therapy by the virtue of their known tumor affinity, low dark cytotoxicity, and easy synthesis in good to high yields have already been discussed. In the present study, two new porphyrins including TAPFA, as a novel folic acid targeted porphyrin sensitizer, and TAP-Schiff base, as a novel sensitizer with better light absorption, were prepared for the first time and their structures were confirmed by (1)H NMR, (13)C NMR, FT-IR and UV-Vis spectroscopy as well as CHNS analysis. The compounds were metalized with Zn(II) and Fe(II) metal ions to study how the metal ions can improve the light absorption wavelength and their water solubility. The structures of metalized compounds were also confirmed by FT-IR and UV-Vis spectroscopy.

Citing Articles

Substituent Effects in the Photophysical and Electrochemical Properties of Meso-Tetraphenylporphyrin Derivatives.

Millheim A, Ponzano E, Moyano A Molecules. 2024; 29(15).

PMID: 39125093 PMC: 11314014. DOI: 10.3390/molecules29153689.

Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived -Tetraarylporphyrin.

Dardouri N, Hrichi S, Torres P, Chaabane-Banaoues R, Sorrenti A, Roisnel T Molecules. 2024; 29(13).

PMID: 38999116 PMC: 11243641. DOI: 10.3390/molecules29133163.

Porphyrin Metal-organic Framework Sensors for Chemical and Biological Sensing.

Dhir R, Kaur M, Malik A J Fluoresc. 2024; .

PMID: 38607529 DOI: 10.1007/s10895-024-03674-0.

Microwave absorbing characteristics of porphyrin derivates: a loop of conjugated structure.

Dogari H, Peymanfar R, Ghafuri H RSC Adv. 2023; 13(32):22205-22215.

PMID: 37492511 PMC: 10363711. DOI: 10.1039/d3ra03927g.

Hematoma Resolution In Vivo Is Directed by Activating Transcription Factor 1.

Seneviratne A, Han Y, Wong E, Walter E, Jiang L, Cave L Circ Res. 2020; 127(7):928-944.

PMID: 32611235 PMC: 7478221. DOI: 10.1161/CIRCRESAHA.119.315528.

References

Nebert D, Dalton T . The role of cytochrome P450 enzymes in endogenous signalling pathways and environmental carcinogenesis. Nat Rev Cancer. 2006; 6(12):947-60. DOI: 10.1038/nrc2015. View

Schneider R, Schmitt F, Frochot C, Fort Y, Lourette N, Guillemin F . Design, synthesis, and biological evaluation of folic acid targeted tetraphenylporphyrin as novel photosensitizers for selective photodynamic therapy. Bioorg Med Chem. 2005; 13(8):2799-808. DOI: 10.1016/j.bmc.2005.02.025. View

Lu Y, Low P . Folate-mediated delivery of macromolecular anticancer therapeutic agents. Adv Drug Deliv Rev. 2002; 54(5):675-93. DOI: 10.1016/s0169-409x(02)00042-x. View

Otelo V, SantAna A, de Faria D, Menezes C . Molecular modeling and UV-vis spectroscopic studies on the mechanism of action of reversed chloroquine (RCQ). Bioorg Med Chem Lett. 2010; 21(1):250-4. DOI: 10.1016/j.bmcl.2010.11.019. View

Balaban T . Tailoring porphyrins and chlorins for self-assembly in biomimetic artificial antenna systems. Acc Chem Res. 2005; 38(8):612-23. DOI: 10.1021/ar040211z. View

Dewaele M, Maes H, Agostinis P . ROS-mediated mechanisms of autophagy stimulation and their relevance in cancer therapy. Autophagy. 2010; 6(7):838-54. DOI: 10.4161/auto.6.7.12113. View

Adachi S, Nagano S, ISHIMORI K, Watanabe Y, Morishima I, Egawa T . Roles of proximal ligand in heme proteins: replacement of proximal histidine of human myoglobin with cysteine and tyrosine by site-directed mutagenesis as models for P-450, chloroperoxidase, and catalase. Biochemistry. 1993; 32(1):241-52. DOI: 10.1021/bi00052a031. View

Low P, Henne W, Doorneweerd D . Discovery and development of folic-acid-based receptor targeting for imaging and therapy of cancer and inflammatory diseases. Acc Chem Res. 2007; 41(1):120-9. DOI: 10.1021/ar7000815. View

James N, Ohulchanskyy T, Chen Y, Joshi P, Zheng X, Goswami L . Comparative tumor imaging and PDT Efficacy of HPPH conjugated in the mono- and di-forms to various polymethine cyanine dyes: part - 2. Theranostics. 2013; 3(9):703-18. PMC: 3767117. DOI: 10.7150/thno.5923. View

10.

Smith B . Catalytic methods for the destruction of chemical warfare agents under ambient conditions. Chem Soc Rev. 2008; 37(3):470-8. DOI: 10.1039/b705025a. View

11.

Zakhariev O, Trautwein A, Veeger C . Porphyrin-Fe(III)-hydroperoxide and porphyrin-Fe(III)-peroxide anion as catalytic intermediates in cytochrome P450-catalyzed hydroxylation reactions: a molecular orbital study. Biophys Chem. 2001; 88(1-3):11-34. DOI: 10.1016/s0301-4622(00)00194-0. View

12.

Allen T . Ligand-targeted therapeutics in anticancer therapy. Nat Rev Cancer. 2002; 2(10):750-63. DOI: 10.1038/nrc903. View

13.

Leamon C, Reddy J . Folate-targeted chemotherapy. Adv Drug Deliv Rev. 2004; 56(8):1127-41. DOI: 10.1016/j.addr.2004.01.008. View

14.

Wang S, Low P . Folate-mediated targeting of antineoplastic drugs, imaging agents, and nucleic acids to cancer cells. J Control Release. 1998; 53(1-3):39-48. DOI: 10.1016/s0168-3659(97)00236-8. View

15.

Kudinova N, Berezov T . [Photodynamic therapy: search for ideal photosensitizer]. Biomed Khim. 2009; 55(5):558-69. View

16.

Vicente M . Porphyrin-based sensitizers in the detection and treatment of cancer: recent progress. Curr Med Chem Anticancer Agents. 2003; 1(2):175-94. DOI: 10.2174/1568011013354769. View

17.

de Visser S, Valentine J, Nam W . A biomimetic ferric hydroperoxo porphyrin intermediate. Angew Chem Int Ed Engl. 2010; 49(12):2099-101. DOI: 10.1002/anie.200906736. View

18.

Henderson B, Dougherty T . How does photodynamic therapy work?. Photochem Photobiol. 1992; 55(1):145-57. DOI: 10.1111/j.1751-1097.1992.tb04222.x. View

19.

Kessel D . Relocalization of cationic porphyrins during photodynamic therapy. Photochem Photobiol Sci. 2003; 1(11):837-40. DOI: 10.1039/b206046a. View

20.

Pinhassi R, Assaraf Y, Farber S, Stark M, Ickowicz D, Drori S . Arabinogalactan-folic acid-drug conjugate for targeted delivery and target-activated release of anticancer drugs to folate receptor-overexpressing cells. Biomacromolecules. 2009; 11(1):294-303. DOI: 10.1021/bm900853z. View