Monoglycoconjugated phthalocyanines: effect of sugar and linkage on photodynamic activity.

Authors :: Lafont D
Zorlu Y
Savoie H
Albrieux F
Ahsen V
Boyle RW
Dumoulin F
Source :: Photodiagnosis and photodynamic therapy [Photodiagnosis Photodyn Ther] 2013 Sep; Vol. 10 (3), pp. 252-9. Date of Electronic Publication: 2013 Feb 19.
Publication Year :: 2013
Abstract: Background: Click chemistry can be advantageously used to graft carbohydrates on phthalocyanines which are potent photosensitisers, but the effect of the presence of triazole moieties on photodynamic efficiency was not investigated systematically to date. The nature and linkage of the sugar were investigated in order to define structure-activity relationships.<br />Method: Two sets of monoglycoconjugated water-soluble phthalocyanines have been designed and their photodynamic activity and uptake investigated in HT-29 human colon adenocarcinoma cells. Carbohydrates: galactose, mannose or lactose were grafted onto Zn(II) phthalocyanines either by glycosylation or by click reaction.<br />Results: The triazole linkage formed by click conjugation lowered the biological efficiency for mannose and galactose, compared to classical glycosylation grafting. The mannose conjugate formed by glycosylation was the most photodynamically active, without correlation with the photosensitiser cell uptake.<br /> (Copyright © 2012 Elsevier B.V. All rights reserved.)

Subjects :: Click Chemistry methods
Cross-Linking Reagents radiation effects
Drug Compounding methods
HT29 Cells
Humans
Isoindoles
Light
Photochemotherapy methods
Treatment Outcome
Apoptosis drug effects
Glycoconjugates chemistry
Indoles administration & dosage
Indoles chemistry
Monosaccharides chemistry
Photosensitizing Agents administration & dosage
Photosensitizing Agents chemical synthesis

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