title: Monoglycoconjugated phthalocyanines: effect of sugar and linkage on photodynamic activity.
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.
  
  
  METHODS
  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.
  
  
  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.
authors.affiliation: Laboratoire de Chimie Organique II-Glycochimie ICBMS-UMR 5246, CNRS-Université Claude Bernard Lyon 1, Université de Lyon, Batiment Curien, 43 Bd du 11 Novembre, 69622 Villeurbanne Cedex, France.
authors.forename: Dominique
authors.initials: D
authors.lastname: Lafont
authors.forename: Yunus
authors.initials: Y
authors.lastname: Zorlu
authors.forename: Huguette
authors.initials: H
authors.lastname: Savoie
authors.forename: Florian
authors.initials: F
authors.lastname: Albrieux
authors.forename: Vefa
authors.initials: V
authors.lastname: Ahsen
authors.forename: Ross W
authors.initials: RW
authors.lastname: Boyle
authors.forename: Fabienne
authors.initials: F
authors.lastname: Dumoulin
mesh_terms: D017209:Apoptosis / Q000187:drug effects*; D057930:Click Chemistry / Q000379:methods; D003432:Cross-Linking Reagents / Q000528:radiation effects; D004339:Drug Compounding / Q000379:methods; D006001:Glycoconjugates / Q000737:chemistry*; D019073:HT29 Cells; D006801:Humans; D007211:Indoles / Q000008:administration & dosage* / Q000737:chemistry*; D054833:Isoindoles; D008027:Light; D009005:Monosaccharides / Q000737:chemistry*; D010778:Photochemotherapy / Q000379:methods; D017319:Photosensitizing Agents / Q000008:administration & dosage* / Q000138:chemical synthesis*; D016896:Treatment Outcome
chemical_list: D003432:Cross-Linking Reagents; D006001:Glycoconjugates; D007211:Indoles; D054833:Isoindoles; D009005:Monosaccharides; D017319:Photosensitizing Agents; C013647:phthalocyanine
keywords: Carbohydrate; Click chemistry; Photodynamic therapy; Photosensitiser; Phthalocyanine