Synthesis Strategy of Tetrapyrrolic Photosensitizers for Their Practical Application in Photodynamic Therapy

Койфман, О. И.; Агеева, Т. А.; Kuzmina, Natalia S.; Otvagin, Vasilii F.; Nyuchev, Alexander V.; Fedorov, Alexey Yu.; Белых, Д. В.; Лебедева, Н.С.; Yurina, Elena S.; Сырбу, С. А.; Koifman, Mikhail О.; Gubarev, Yury A.

doi:10.6060/mhc224870k

Cited by 29 publications

(25 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To increase solubility, different anionic, cationic, or uncharged groups are introduced into the phthalocyanine molecule. 32 It is known that one of the ways to deliver substituted MPc into a cancer cell is to create nanomicelles that are soluble in water and capable of penetrating the cancer cell. 33,34 In this connection, MPc with pyrazole-containing substituents, soluble in organic solvents, and insoluble in water, and nanomicelles based on them are of interest.…”

Section: Introductionmentioning

confidence: 99%

“…A limitation to the use of unsubstituted MPc is their low solubility in organic solvents and insolubility in water. To increase solubility, different anionic, cationic, or uncharged groups are introduced into the phthalocyanine molecule 32 . It is known that one of the ways to deliver substituted MPc into a cancer cell is to create nanomicelles that are soluble in water and capable of penetrating the cancer cell 33,34 .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Molecular brushes with long polyfluorene backbones and polymethacrylic acid side chains: Luminescent properties and self‐organization in solutions

Kaskevich,

Simonova,

Romasheva

et al. 2024

Journal of Polymer Science

View full text Add to dashboard Cite

A series of molecular brushes with a polyfluorene (PF) backbone and polymethacrylic acid side chains of varying lengths were prepared by atom transfer radical polymerization. The structure and composition of the synthesized compounds were confirmed by 1H NMR and IR spectroscopy. Effect of the length of the backbone on spectral and conformational parameters of the macromolecules in solutions was analyzed. The grafting density of side chains was about 90%. Spectral methods have been used to determine the dependence of side chain grafting on the luminescent properties of polymer solutions, including quantum yields. It was shown that an optimal length of polymethacrylic acid side chains provides solubility of the polymer brushes. Solutions of PF‐graft‐polymethacrylic acid complexes with the model substance curcumin were investigated. It was established that the molecular brushes containing curcumin form monomolecular micelles. Molecular brushes with zinc phthalocyanine, potential systems for photodynamic, and photothermal therapy, were studied.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Molecular brushes with long polyfluorene backbones and polymethacrylic acid side chains: Luminescent properties and self‐organization in solutions

Kaskevich,

Simonova,

Romasheva

et al. 2024

Journal of Polymer Science

View full text Add to dashboard Cite

show abstract

“…[2] Such tetrapyrrolic systems as porphyrins [Por] and phthalocyanines [Pc] and their analogs have long been attractive platforms for creating effective functional materials for different applications. [3,4] Among [Pc] analogues, their low homologues -subphthalocyanines [sPc] are especially interesting as potential photoactive compounds and are actively studied in fluorescence applications.…”

Section: Introductionmentioning

confidence: 99%

“…In this point of view, organic and coordination compounds have attracted much interest because of their potential applications as biomolecular labels, fluorescent probes, materials for dye sensitizers solar cells (DSSCs), [1] component for photovoltaics (OPVCs), and organic light‐emitting diode (OLEDs) [2] . Such tetrapyrrolic systems as porphyrins [Por] and phthalocyanines [Pc] and their analogs have long been attractive platforms for creating effective functional materials for different applications [3,4] . Among [Pc] analogues, their low homologues – subphthalocyanines [ s Pc] are especially interesting as potential photoactive compounds and are actively studied in fluorescence applications.…”

Section: Introductionmentioning

confidence: 99%

First Subphthalocyanine Analogue with Fused 6H‐1,4‐diazepine Ring and its Conversion to Aminobenzamide Derivative

Skvortsov,

Chufarin,

Zaitsev

et al. 2023

Asian J Org Chem

View full text Add to dashboard Cite

Mixed cyclization of 5,7‐diphenyl‐6H‐1,4‐diazepine 2,3‐dicarbonitrile and tetrafluorophthalonitrile in the presence of boron trichloride affords along with symmetrical perfluorinated subphthakocyanine, [F12sPc], two novel subporphyrazine‐type products which were isolated by column chromatography and characterized by mass‐sprectometry, NMR, IR, UV‐VIS and fluorescent spectroscopy. It was established that co‐cyclomerization of dinitriles is accompanied by electrophilic chlorination of 1,4‐diazepine ring by evolved Cl2 resulting in formation of dibenzosubporphyrazine [F8sPc1] with fused 6‐chloro‐5,7‐diphenyl‐6H‐1,4‐diazepine fragment. According to DFT modelling and 1H NMR data, a more stable diastereomer with an axial Cl atom is formed and no inversion of the 1,4‐diazepine ring is observed. Hydrolytic cleavage of the 1,4‐diazepine fragment in [F8sPc1] is observed upon chromatography or in the presence of a strong acid (CF3COOH) and leads to 2‐amino‐3‐benzamide substituted dibenzo subporphyrazine [F8sPc2]. Fluorescence of [F8sPc1] (ΦF=0.03) is ca 10 times lower than for [F12sPc] (ΦF=0.28) due to the combined effect of intramolecular charge transfer (ICT) from the donor diazepine ring to the acceptor sPc macrocycle and heavy atom effect of chlorine. Fluorescence of [F8sPc2] is almost completely quenched by ICT from −NH2 group to the electron‐deficient subporphyrazine core (ΦF<0.001), but addition of acid leads to protonation of the amino group and switch‐ON the fluorescence. Therefore, aminobenzamide substituted subporphyrazines can be considered as perspective pH‐sensitive fluorophores.

show abstract

“…Porphyrins are aromatic macrocyclic compounds with outstanding photoelectronic properties suitable for application in catalysis, 1–3 photodynamic therapy, 4–7 dye-sensitized solar cells (DSSCs), 8–10 nonlinear optics, 11–13 MOFs 14 and so on. 15 A particular advantage of the porphyrin macrocycle as a platform for the development of functional molecules consists in a variety of available synthetic approaches for their peripheral modification.…”

Section: Introductionmentioning

confidence: 99%

Noncovalent interactions in gold(iii) tetrakis(4-butoxyphenyl)porphyrinate structures

Bardina¹,

Makotchenko²,

Birin³

et al. 2023

CrystEngComm

View full text Add to dashboard Cite

show abstract

Synthesis Strategy of Tetrapyrrolic Photosensitizers for Their Practical Application in Photodynamic Therapy

Cited by 29 publications

References 0 publications

Molecular brushes with long polyfluorene backbones and polymethacrylic acid side chains: Luminescent properties and self‐organization in solutions

Molecular brushes with long polyfluorene backbones and polymethacrylic acid side chains: Luminescent properties and self‐organization in solutions

First Subphthalocyanine Analogue with Fused 6H‐1,4‐diazepine Ring and its Conversion to Aminobenzamide Derivative

Noncovalent interactions in gold(iii) tetrakis(4-butoxyphenyl)porphyrinate structures

Contact Info

Product

Resources

About