Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria.
Anti-Bacterial Agents
/ chemical synthesis
Cations
/ chemistry
Dose-Response Relationship, Drug
Fluorine
/ chemistry
Gram-Negative Bacteria
/ drug effects
Gram-Positive Bacteria
/ drug effects
Indoles
/ chemistry
Isoindoles
Microbial Sensitivity Tests
Molecular Structure
Photochemotherapy
Photosensitizing Agents
/ chemical synthesis
Structure-Activity Relationship
Amphiphile
Bacteria
Cationic
Photodynamic inactivation
Phthalocyanine
Journal
European journal of medicinal chemistry
ISSN: 1768-3254
Titre abrégé: Eur J Med Chem
Pays: France
ID NLM: 0420510
Informations de publication
Date de publication:
01 Feb 2020
01 Feb 2020
Historique:
received:
11
10
2019
revised:
22
11
2019
accepted:
08
12
2019
pubmed:
22
12
2019
medline:
11
3
2020
entrez:
22
12
2019
Statut:
ppublish
Résumé
Herein, we report the synthesis and characterization of new amphiphilic phthalocyanines (Pcs), the study of their singlet oxygen generation capabilities, and biological assays to determine their potential as photosensitizers for photodynamic inactivation of bacteria. In particular, Pcs with an ABAB geometry (where A and B refer to differently substituted isoindole constituents) have been synthesized. These molecules are endowed with bulky bis(trifluoromethylphenyl) groups in two facing isoindoles, which hinder aggregation and favour singlet oxygen generation, and pyridinium or alkylammonium moieties in the other two isoindoles. In particular, two water-soluble Pc derivatives (PS-1 and PS-2) have proved to be efficient in the photoinactivation of S. aureus and E. coli, selected as models of Gram-positive and Gram-negative bacteria.
Identifiants
pubmed: 31864170
pii: S0223-5234(19)31109-2
doi: 10.1016/j.ejmech.2019.111957
pii:
doi:
Substances chimiques
Anti-Bacterial Agents
0
Cations
0
Indoles
0
Isoindoles
0
Photosensitizing Agents
0
Fluorine
284SYP0193
phthalocyanine
V5PUF4VLGY
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
111957Informations de copyright
Copyright © 2019. Published by Elsevier Masson SAS.