Syntheses and DNA binding of new cationic porphyrin–tetrapeptide conjugates

Abstract

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Oligo- and polypeptide conjugates of cationic porphyrins: binding, cellular uptake, and cellular localization

“…29 mg of TMPCP-AK conjugate was yielded. TMPCP content was determined spectrophotometrically (Hudecz et al 1993), using the molar absorptivity of TMPCP-4P at =436 nm (=4.62E5 M -1 cm -1 ) (Mező et al 2011). It was assumed that the TMPCP coupled to the -amino group of terminal alanine of the branch, has the same molar absorptivity as TMPCP coupled to -amino group of alanine in tetrapeptide Ac-Lys(H-Ala-D-Ala-Ala)-NH 2 .…”

“…The synthesis of Ac-Lys(H-Ala-D-Ala-Ala)-NH 2 model tetrapeptide was described previously (Mező et al 2011). Briefly, the Ac-Lys(H-Ala-D-Ala-Ala)-NH 2 was prepared by solid phase peptide synthesis on 4-methylbenzhydrilamine resin (MBHA) using standard Bocstrategy.…”

“…Conjugation of porphyrin derivatives was performed as described previously (Mező et al 2011). Briefly, the porphyrin derivatives were attached to the tetrapeptide in DMF solution by the aid of coupling agents, either BOP reagent or a water soluble carbodiimide EDC.…”

“…In these conjugates a tetrapeptide (Ac-Lys(H-Ala-D-Ala-Ala)-NH 2 ) (Mező et al 2011;Orosz et al 2013) was attached to meso-tri(4-N-methylpyridyl)-mono-(4-carboxyphenyl)porphyrin (TMPCP) or meso-5,10-bis(4-N-methylpyridyl)-15,20-di-(4-carboxyphenyl)porphyrin (BMPCP).…”

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

“…In recent years this research has expanded to incorporate bioactive functionalities for targeting. One such example was the introduction of amino acids/peptide conjugates to either increase cellular uptake of the porphyrin derivative or delivery of the peptidic units to nucleic acids [44,[371][372][373][374] . One such recent example includes cationic porphyrins with Mn complexation which have been covalently linked with peptide cell signaling sequences.…”