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Synthesis of amphiphilic meso-tetrasubstituted porphyrin-L-amino acid and -heterocyclic conjugates based on $m$ -THPP

Division of Pharmaceutical and Drug Industries, Department of the Chemistry of Natural and Microbial Products, National Research Centre, El Buhouth Street, Dokki, 12622 Cairo, Egypt

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Mathias O. Senge

Medicinal Chemistry, Trinity Translational Medicine Institute, Trinity Centre for Health Sciences, Trinity College Dublin, The University of Dublin, St. James’s Hospital, Dublin 8, Ireland

E-mail Address: [email protected]

Corresponding author, tel: +353-1-896-8537, fax: +353-1-896-8536.

SPP full member in good standing.

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Sanaa M. Sh. Atta

Division of Pharmaceutical and Drug Industries, Department of the Chemistry of Natural and Microbial Products, National Research Centre, El Buhouth Street, Dokki, 12622 Cairo, Egypt

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Dalia S. Farrag

Division of Pharmaceutical and Drug Industries, Department of the Chemistry of Natural and Microbial Products, National Research Centre, El Buhouth Street, Dokki, 12622 Cairo, Egypt

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Abdel-Rahman H. Abdel-Rahman

Chemistry Department, Faculty of Science, Mansoura University, Mansoura, Egypt

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, and

Yasser M. Shaker

Division of Pharmaceutical and Drug Industries, Department of the Chemistry of Natural and Microbial Products, National Research Centre, El Buhouth Street, Dokki, 12622 Cairo, Egypt

E-mail Address: [email protected]

Corresponding author.

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https://doi.org/10.1142/S1088424618500979Cited by:6 (Source: Crossref)

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Abstract

Two series of amphiphilic meso-tetrasubstituted porphyrin conjugates based on 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin ( $m$ -THPP) covalently linked to L-amino acids and heterocycles were synthesized efficiently in the context of a program targeting new photosensitizers for PDT. 5,10,15-Tris(3-hydroxyphenyl)-20-(3-oxyacetic acid)phenyl]porphyrin and the respective trihexyl ether derivatives were conjugated with polar and non-polar natural L-amino acids such as glycine, L-proline, and L-tyrosine via an amide bond linker using $N, N, N^{'}, N^{'}$ -tetramethyl- $O$ -(1H-benzotriazol-1-yl)uroniumhexafluorophosphate in diisopropylethylamine (HBTU/DIPEA). $m$ -THPP was also conjugated with heterocyclic systems such as indole 3-acetic acid, 4-methylthiazole-5-carboxylic acid, and thiophene-2-carboxylic acid via ester linker using $N$ -(3-dimethylaminopropyl)- $N^{'}$ -ethylcarbodiimide hydrochloride in $N$ -hydroxysuccinamide or 1-hydroxybenzotriazole (EDCI, NHS or HOBt). The members of the two series were obtained in good yields and characterized by UV-vis, HRMS MALDI-TOF, ¹H NMR and ¹³C NMR spectroscopy.

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