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Identifier

000421129

Title

Σύνθεση και χαρακτηρισμός δυάδων πορφυρίνης με Νιτριλοτριοξικό οξύ (NTA) για πιθανές βιολογικές εφαρμογές

Alternative Title

Synthesis and characterization of porphyrin dyads with Nitrilotriacetic acid (NTA) for potential biological applications

Author

Γλυμενάκη, Ελένη Ι.

Thesis advisor

Κουτσολέλος, Αθανάσιος

Reviewer

Μητράκη, Άννα
Βασιλικογιαννάκης, Γεώργιος

Abstract

The need to trace, monitor and understand the structure, interactions and processes occurring in biomolecules such as proteins, peptides, amino acids, antibodies, mRNA, etc has led to the development of a variety of methods for detecting them. Among the methods used to monitor such compounds, fluorescent probes (or tags) are very promising ones, due to their sensitivity and non-invasive character. The detection of biomolecules such as proteins and peptides can be performed mostly with fluorescent proteins and fluorescent chromophores. Fluorescent chromophores (fluorophores) can be chemically or non-chemically binding to the target region of the biomolecule. Various labeling strategies are emerging depending on the coupling between the chromophore and the biomolecule. One of the most commonly used labeling methods is the metallochelate binding between chromophores and the amino acids in the sequence of a peptide/protein. The most commonly used metallochelate motif for this purpose is chromophore-nitrilotriacetic acid (NTA)-Ni²⁺-His tag. The majority of chromophores that are used with the metallochelate motif consist of small and organic molecules. Few references from literature refer to the use of chromophores such as porphyrin derivatives for metallochelate labeling of peptides/proteins. In order to broaden the research on the use of porphyrins with a metallochelate coupling moiety (Ni²⁺-NTA) for peptide/protein labeling, we decided to synthetize two new porphyrin dyads bearing a nitrilo triacetic acid chelating ligand (NTA) for possible coupling via Ni²⁺ with a peptide containing histidine (His) at the C-terminal end. The first dyad consists of a tetraphenyl porphyrin which is linked via an amide bond with NTA at the meso position of the porphyrin. The second dyad constists of a tetraphenyl porphyrin with an -NH₂ group at the meso position. The coupling with the NTA moiety is accomplished via a cyanuric chloride bridge. The characterization of the non-hydrolyzed forms of the new dyads was performed by mass spectrometry (MALDI-TOF), nuclear magnetic resonance spectroscopy (NMR) and ultraviolet-visible (UV-Vis) absorption spectroscopy. The results from the coupling reaction with the peptide which are expected to be accomplished, may broaden the use of porphyrin dyads as potential probes for peptide and protein labeling both in vitro and in vivo.

Language

English

Subject

Fluorophore

Labeling

Metallochelate coupling (Ni2+-NTA)

Porphyrin

Μεταλλοχηλική σύζευξη (Ni2+-NTA)

Πορφυρίνη

Σήμανση

Φθοροφόρο

Issue date