Microwave Synthesis, Basic Spectral and Biological Evaluation of Some Copper (II) Mesoporphyrinic Complexes

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-carboxymethylphenyl)-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 OPEN ACCESSMolecules 2010, 15 3732 (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.

Organic Nanoparticle-Based Fluorescent Chemosensor for Selective Switching ON and OFF of Photodynamic Therapy (PDT)

“…For example, an iminium salt of copper octaethylbenzochlorins showed efficient PDT activity in contrast to its Cu II ‐free form . Since copper is the most bio‐essential element among all transition metals, many organic copper complexes have been explored for efficient tumor suppression . Thus, selective coordination of the PS with Cu II has garnered great attention for tumor‐specific PDT.…”

Trends in Interdisciplinary Studies Revealing Porphyrinic Compounds Multivalency Towards Biomedical Application

“…The Q bands of the free base porphyrins consist of four absorption peaks which are typical to the Qx(0,0), Qx(0,1), Qy(0,0), Qy(0,1) transitions in the free base porphyrin (D 2h symmetry). Upon complexation with a metal ion, the number of Q bands decreases due to the enhancement of the molecular symmetry from D 2h to D 4h (Boscencu et al, 2008;Boscencu et al, 2010). The molecular electronic absorption spectra are usually used for the quantitative determination of compounds, but in the case of porphyrinic compounds they give real "fingerprints" that can be used to predict the usefulness of a certain compound as photosensitizer.…”

“…8): the condensation process involving pyrrole and various aldehydes, reaction mixture involved also in MW assisted procedures, the combination of substituted pyrroles carrying the desired future porphyrin substituents or via bilane structure; this last option was successfully applied on ABCD substituted porphyrins via synthesis of a protected acylbilane (by acid-catalyzed condensation of a acyldipyrromethane and protected dipyrromethane-n-carbinol) (Dogutan et al, 2007) and insertion of the substituents in meso positions in the already formed porphyrin core. The unsymmetrical porphyrins were chosen as our main synthetic target (Boscencu, 2008(Boscencu, , 2010) because a. they are easy to prepare either via the Adler route (Adler et al, 1976) or by microvawe (MW) irradiation b. the phenolic hydroxy group is a suitable site on which to build a different substituent (Milgrom LR, 1983) c. the 4-methoxycarbonyl side-chains of the other meso-substituents may be de-esterified to convert a hydrophobic porphyrin into a hydrophilic one.…”

mTHPC – A drug on its way from second to third generation photosensitizer?

“…Despite problems with regard to their absorption a range of 5,15-disubstituted or 5,10,15,20-tetrasubstituted hydroxyphenylporphyrins such as 5 and -chlorins closely related to mTHPC have been prepared and initial testing underlines their potential as photosensitizers (Fig. 2) [26,27,28,29,30]. An example for a simple symmetric system is 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin 6 which was incorporated into NPs.…”