A porphycene-gentamicin conjugate for enhanced photodynamic inactivation of bacteria.
Amphiphilicity
Antimicrobial resistance
Photodynamic therapy
Photosensitizer conjugates
Porphycene
Singlet oxygen
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
04 2020
04 2020
Historique:
received:
07
10
2019
revised:
08
02
2020
accepted:
10
02
2020
pubmed:
23
2
2020
medline:
23
2
2021
entrez:
23
2
2020
Statut:
ppublish
Résumé
A novel photoantimicrobial agent, namely 2-aminothiazolo[4,5-c]-2,7,12,17-tetrakis(methoxyethyl)porphycene (ATAZTMPo-gentamicin) conjugate, has been prepared by a click reaction between the red-light absorbing 9-isothiocyanate-2,7,12,17-tetrakis(methoxyethyl)porphycene (9-ITMPo) and the antibiotic gentamicin. The conjugate exhibits submicromolar activity in vitro against both Gram-positive and Gram-negative bacteria (Staphylococcus aureus and Escherichia coli, respectively) upon exposure to red light and is devoid of any cytotoxicity in the dark. The conjugate outperforms the two components delivered separately, which may be used to enhance the therapeutic index of gentamicin, broaden the spectrum of pathogens against which it is effective and reduce its side effects. Additionally, we report a novel straightforward synthesis of 2,7,12,17-tetrakis(methoxyethyl) porphycene (TMPo) that decreases the number of steps from nine to six.
Identifiants
pubmed: 32086054
pii: S0045-2068(19)31428-2
doi: 10.1016/j.bioorg.2020.103661
pii:
doi:
Substances chimiques
Anti-Bacterial Agents
0
Gentamicins
0
Photosensitizing Agents
0
Porphyrins
0
porphycene
100572-96-1
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
103661Informations de copyright
Copyright © 2020 Elsevier Inc. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.