Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2010 May 25;15(5):3731-43.
doi: 10.3390/molecules15053731.

Microwave synthesis, basic spectral and biological evaluation of some copper (II) mesoporphyrinic complexes

Rica Boscencu  1 , Mihaela Ilie, Radu Socoteanu, Anabela Sousa Oliveira, Carolina Constantin, Monica Neagu, Gina Manda, Luis Filipe Vieira Ferreira
Affiliations

Microwave synthesis, basic spectral and biological evaluation of some copper (II) mesoporphyrinic complexes

Rica Boscencu et al. Molecules. .

Abstract

Cu(II) complexes with asymmetrical and symmetrical porphyrinic ligands were synthesized with superior yields using microwave irradiation. The paper presents the synthesis of 5-(3-hydroxyphenyl)-10,15,20-tris-(4-carboxymethylphenyl)-21,23-Cu(II)-porphine in comparison to its symmetrical complex 5,10,15,20-meso-tetrakis-(4-carboxy-methylphenyl)-21,23-Cu(II) porphine. The two compounds were characterized by FT-IR, UV-Vis and EPR spectroscopy, which fully confirmed the structures. The spectral molecular absorption properties of the porphyrinic complexes were studied in organic solvents (methanol, ethanol, iso-propanol, dimethyl sulfoxide, dimethylformamide and methylene chloride), and the influence of the solvent polarity on the absorbance maxima is described. In order to establish their future potential in biomedical applications preliminary toxicological studies consisting of viability and proliferation of standard tumor cell lines (MCF7 and B16) testing was performed. The obtained results indicate a low toxicity for both compounds and further recommends them for testing in light activation protocols.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Structures of 5-(3-hydroxyphenyl)-10,15,20–tris-(4-carboxymethylphenyl)–21, 23 Cu(II) porphine (Cu(II)TCMOHm) (top) and 5,10,15,20-meso-tetrakis-(4-carboxy-methylphenyl)-21,23-Cu(II) porphine (Cu(II)TCMP) (bottom).
Figure 2
Figure 2
Absorption spectra of 2.5 × 10-6 M Cu(II)TCMP in different solvents (a-Soret band; b-Q bands).
Figure 3
Figure 3
Absorption spectra of 2.5 × 10-6 M Cu(II)TCMPOHm in different solvents (a-Soret band; b-Q bands).
Figure 4
Figure 4
Cellular response of MCF7 line after 24 h incubation with Cu(II)TCMPOHm.
Figure 5
Figure 5
Cellular response of B16 line after 2 h incubation with Cu(II)TCMPOHm and Cu(II)TCMP (a – viability, b – proliferation).
See this image and copyright information in PMC

References

    1. Biesaga M., Pyrzyńska K., Trojanowicz M. Porphyrins in analytical chemistry. A review. Talanta. 2000;51:209–224. doi: 10.1016/S0039-9140(99)00291-X. - DOI - PubMed
    1. Moan J., Peng Q. An outline of history of PDT. In: Patrice T., editor. Photodynamic Therapy. Royal Society of Chemistry; Cambridge, UK: 2004. pp. 1–18.
    1. Stockert J.C., Cañete M., Juarranz A., Villanueva A., Horobin R.W., Borrell J.I., Teixidó J., Nonell S. Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer. Curr. Med. Chem. 2007;14:997–1026. doi: 10.2174/092986707780362934. - DOI - PubMed
    1. Banfi S., Caruso E., Caprioli S., Mazzagatti L., Canti G., Ravizza R., Gariboldia M., Montia E. Photodynamic effects of porphyrin and chlorin photosensitizers in human colon adenocarcinoma cells. Bioorg. Med. Chem. 2004;12:4853–4860. doi: 10.1016/j.bmc.2004.07.011. - DOI - PubMed
    1. Chen J.Y., Mak N.K., Yow C.M.N., Fung M.C., Chiu L.C., Leung W.N., Cheung N.H. The Binding Characteristics and Intracellular Localization of Temoporfin (mTHPC) in Myeloid Leukemia Cells: Phototoxicity and Mitochondrial Damage. Photochem. Photobiol. 2000;72:541–547. doi: 10.1562/0031-8655(2000)072<0541:TBCAIL>2.0.CO;2. - DOI - PubMed

Publication types

LinkOut - more resources