title: Antibacterial phototoxic effects of synthetic asymmetric and glycosylated curcuminoids in aqueous formulations: studies on curcumin and curcuminoids. LIV.
abstract: The aim of this study was to evaluate the in vitro phototoxic potential of synthetic asymmetric and glycosylated curcuminoids on planktonic model bacteria by counting the colony forming units. The Gram-positive Enterococcus faecalis and the Gram-negative Escherichia coli were exposed to aqueous solutions of the curcuminoids (⩽2.5 μM) in the presence or absence of selected pharmaceutical excipients (Pluronic F127, PEG 400 and HPγCD) in combination with a low irradiation dose (5 J/cm(2); λmax: 450 nm) of constant irradiance and time. All the asymmetric curcuminoids, but only one of the glycosylated curcuminoids demonstrated substantial phototoxic effect on E.faecalis (⩾4.7 log reduction). Only two of the asymmetric curcuminoids showed a moderate to low phototoxic effect on the more persistent E.coli. This study emphasized that aromatic hydroxyl substituents in the para-position are important to maintain the phototoxic potential of curcuminoids independent of molecular symmetry. Glycosylation of the aromatic substituents resulted in a substantial loss in phototoxicity towards planktonic bacteria, an apparent change in the non-radiative S₁-decay process and a weaker interaction with Pluronic F127 compared to the non-glycosylated curcuminoids. The selected excipients Pluronic F127, PEG 400 and HPγCD strongly influenced the phototoxic potential of the unsymmetrical, non-glycosylated compounds.
authors.affiliation: University of Oslo, School of Pharmacy, Department of Pharmacy, Oslo, Norway; Nordic Institute of Dental Materials (NIOM), Oslo, Norway.
authors.forename: Marianne Lilletvedt
authors.initials: ML
authors.lastname: Tovsen
authors.affiliation: Nordic Institute of Dental Materials (NIOM), Oslo, Norway.
authors.forename: Ellen
authors.initials: E
authors.lastname: Bruzell
authors.affiliation: Department of Chemistry, University of Modena and Reggio Emilia, Modena, Italy.
authors.forename: Erika
authors.initials: E
authors.lastname: Ferrari
authors.affiliation: Department of Chemistry, University of Modena and Reggio Emilia, Modena, Italy.
authors.forename: Monica
authors.initials: M
authors.lastname: Saladini
authors.affiliation: Faculty of Pharmaceutical Sciences, School of Health Sciences, University of Iceland, Reykjavik, Iceland; PCI Biotech AS, Lysaker, Norway.
authors.forename: Vivek S
authors.initials: VS
authors.lastname: Gaware
authors.affiliation: Faculty of Pharmaceutical Sciences, School of Health Sciences, University of Iceland, Reykjavik, Iceland.
authors.forename: Már
authors.initials: M
authors.lastname: Másson
authors.affiliation: Faculty of Pharmaceutical Sciences, School of Health Sciences, University of Iceland, Reykjavik, Iceland.
authors.forename: Solveig
authors.initials: S
authors.lastname: Kristensen
authors.affiliation: University of Oslo, School of Pharmacy, Department of Pharmacy, Oslo, Norway. Electronic address: h.h.tonnesen@farmasi.uio.no.
authors.forename: Hanne Hjorth
authors.initials: HH
authors.lastname: Tønnesen
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical; D003474:Curcumin / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013293:Enterococcus faecalis / Q000187:drug effects / Q000528:radiation effects; D004926:Escherichia coli / Q000187:drug effects / Q000528:radiation effects; D006031:Glycosylation; D008027:Light; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D020442:Poloxamer / Q000737:chemistry; D011092:Polyethylene Glycols / Q000737:chemistry; D047408:gamma-Cyclodextrins / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D017319:Photosensitizing Agents; D047408:gamma-Cyclodextrins; D020442:Poloxamer; D011092:Polyethylene Glycols; D003474:Curcumin
keywords: Antibacterial phototoxic effect; Asymmetric curcuminoids; Cyclodextrin; Glycosylated curcuminoids; Hydroxyl substituent; Pluronic®