Caractérisation spectroscopique et structurale de nouveaux complexes porphyriniques de cadmium(II) et de vanadium(IV). Synthèse et étude photophysique de nouveaux composés porphyrine-peptides pour des applications thérapeutiques.

Résumé

In my thesis work, we have in a first part synthesized the 5,10,15,20-tetrakis [4- (chloro) phenyl] porphyrin (H2TClPP) which was subsequently metallated by cadmium to give the starting material [Cd (TClPP)]. The reaction between this complex and nitrogen ligands: 4,4'diaminophenylmethane (4,4'-mda), 2-aminopyridine (2NH2py), pipyrazine (pipyz) and morphine resulted in the formation of the four new complexes the following cadmium (II) porphyrins: - Compound (I): [Cd (TClPP) (2-NH2py)] -Compound (II): [Cd (TClPP) (4,4'-mda)] - Compound (III): [Cd (TClPP) (pipyz)] - Compound (IV): [Cd (TClPP) (morpholine)] The synthesized complexes were subsequently characterized by UV-visible, fluorescence, 1H NMR, IR and mass spectrometry (MALDI-TOF and ESI). The observed bathochromic effect on the absorption spectra confirms the complexation of ligands with the complex [Cd (TClPP)] and shows that in solution only the pentacoordinated porphyrinic complexes are trained. A structural study by single crystal x-ray diffraction was also carried out. In the second part of this thesis , we synthesized five new analogs of the peptide sequence TAT (37-53) (CFITKALGISYGRKKRR) by the technique from Ala-scan. These analogs are coupled to the 5- (4-carboxyphenyl) -10,15,20-triphenylporphyrin porphyrin called P1-COOH in order to obtain new peptide-porphyrin compounds. These derivatives were purified by HPLC and characterized by mass spectrometry. A photophysical study was also carried out on these products, this study indicates their effectiveness for applications in PDT. As a perspective we propose to perform a biological study to assess the affinity of each peptide-porphyrin compound as a peptide targeting LRP-1 for the treatment of glioblastoma.

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