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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

New Conjugatable Platinum(II) Chlorins: Synthesis, Reactivity and Singlet Oxygen Generation

by
José Almeida
1,*,
Giampaolo Barone
2,
Luís Cunha-Silva
1,
Ana F. R. Cerqueira
3,
Augusto C. Tomé
3,
Maria Rangel
4 and
Ana M. G. Silva
4,*
1
LAQV-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, 4169-007 Porto, Portugal
2
Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche, Università di Palermo, Viale delle Scienze, Edificio 17, 90128 Palermo, Italy
3
LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
4
LAQV-REQUIMTE, Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, 4050-313 Porto, Portugal
*
Authors to whom correspondence should be addressed.
Molecules 2025, 30(12), 2496; https://doi.org/10.3390/molecules30122496
Submission received: 6 May 2025 / Revised: 31 May 2025 / Accepted: 3 June 2025 / Published: 6 June 2025
(This article belongs to the Section Colorants)
Versions Notes

Abstract

An efficient protocol was developed for the microwave-mediated metallation of 5-(4-methoxycarbonylphenyl)-10,15,20-tris(pentafluorophenyl)porphyrin (P1) with bis(benzonitrile)platinum dichloride salt and subsequent 1,3-dipolar cycloaddition of the resulting PtP1 with an azomethine ylide to give two isomeric metallochlorins: PtC1 (main isomer) and PtC3. The methyl ester group of metalloporphyrin PtP1 and metallochlorin PtC1 was successfully hydrolysed in an alkaline medium to yield the corresponding derivatives PtP2 and PtC2 in moderate-to-good yields. As a proof of concept of the reactivity of the carboxy group in PtP2 and PtC2, these compounds were conjugated with a hydroxylated derivative of indomethacin, a known potent non-steroidal anti-inflammatory, obtaining the conjugates PtP2-Ind and PtC2-Ind. The obtained platinum(II) porphyrins and chlorins were characterized by UV-Vis, NMR spectroscopy and mass spectrometry. The structure of PtP1 was also confirmed by X-ray crystallography. Singlet oxygen generation studies were carried out, as well as theoretical calculations, which demonstrated that the prepared Pt(II) complexes can be considered potential photosensitizers for PDT.
Keywords: chlorins; metallochlorins; platinum(II) complexes; microwave-mediated metallation; optical properties; singlet oxygen generation chlorins; metallochlorins; platinum(II) complexes; microwave-mediated metallation; optical properties; singlet oxygen generation

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MDPI and ACS Style

Almeida, J.; Barone, G.; Cunha-Silva, L.; Cerqueira, A.F.R.; Tomé, A.C.; Rangel, M.; Silva, A.M.G. New Conjugatable Platinum(II) Chlorins: Synthesis, Reactivity and Singlet Oxygen Generation. Molecules 2025, 30, 2496. https://doi.org/10.3390/molecules30122496

AMA Style

Almeida J, Barone G, Cunha-Silva L, Cerqueira AFR, Tomé AC, Rangel M, Silva AMG. New Conjugatable Platinum(II) Chlorins: Synthesis, Reactivity and Singlet Oxygen Generation. Molecules. 2025; 30(12):2496. https://doi.org/10.3390/molecules30122496

Chicago/Turabian Style

Almeida, José, Giampaolo Barone, Luís Cunha-Silva, Ana F. R. Cerqueira, Augusto C. Tomé, Maria Rangel, and Ana M. G. Silva. 2025. "New Conjugatable Platinum(II) Chlorins: Synthesis, Reactivity and Singlet Oxygen Generation" Molecules 30, no. 12: 2496. https://doi.org/10.3390/molecules30122496

APA Style

Almeida, J., Barone, G., Cunha-Silva, L., Cerqueira, A. F. R., Tomé, A. C., Rangel, M., & Silva, A. M. G. (2025). New Conjugatable Platinum(II) Chlorins: Synthesis, Reactivity and Singlet Oxygen Generation. Molecules, 30(12), 2496. https://doi.org/10.3390/molecules30122496

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