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Current Organic Chemistry

Current Organic Chemistry

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ISSN (Online): 1875-5348

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Research Article

Synthesis of 5-[4ʹ-(phenoxydimethylenoxy)-phenyl]-10,15,20-tris(N-methylpyridinium- 3ʹ-yl)porphyrin Triiodide and the Study of its Interaction with Representative Oligonucleotides poly[d(AT)2] and poly[d(GC)2]

Author(s): Natalya Lebedeva*orcid of author, Elena Yurinaorcid of author, Sabir Guseinovorcid of author, Ksenia Mamaevaorcid of author, Sergey Syrbuorcid of author, Aleksei Kiselevorcid of author and Yana Kibirevaauthors OrcID

Volume 29, Issue 20, 2025

Published on: 20 May, 2025

Page: [1547 - 1554] Pages: 8

DOI: 10.2174/0113852728378664250507060849

Price: $65

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Abstract

Porphyrins and their analogues, due to their unique physicochemical properties, have a wide range of applications. Synthetic tetraarylporphyrins with an asymmetric substituent system are of particular interest. In this regard, an asymmetric porphyrin was synthesized, containing a phenyl fragment on the periphery of the porphyrin macrocycle. Subsequent quaternization of the compound with methyl iodide was carried out in order to obtain water-soluble porphyrin. Its structure was confirmed by 1H NMR spectroscopy and MALDI-TOF spectrometry. The photochemical properties and structural features of the complexation of synthesized porphyrin with representative oligonucleotides poly[d(AT)2] and poly[d(GC)2] have been studied. According to the results obtained, the studied compound forms a highly stable complex with poly[d(GC)2] by the intercalation mechanism. In the case of poly[d(AT)2], porphyrin binds in the minor groove.

Keywords: Synthesis, asymmetrically substituted water-soluble porphyrin, oligonucleotides, intercalation, neoplastic cells, tumor tissue.

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Graphical Abstract

Graphical abstract illustrating key findings of the study

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