Microwave-assisted syntheses of BODIPY-sugar conjugates through click chemistry and conjugate assembly into liposomes

Ravi Shekar Yalagala; Sina Atrin Mazinani; Lucas A Maddalena; Jeffrey A Stuart; Fengyang Yan; Hongbin Yan

doi:10.1016/j.carres.2016.02.003

Microwave-assisted syntheses of BODIPY-sugar conjugates through click chemistry and conjugate assembly into liposomes

Carbohydr Res. 2016 Apr 7:424:15-20. doi: 10.1016/j.carres.2016.02.003. Epub 2016 Feb 23.

Authors

Ravi Shekar Yalagala¹, Sina Atrin Mazinani¹, Lucas A Maddalena², Jeffrey A Stuart², Fengyang Yan³, Hongbin Yan⁴

Affiliations

¹ Department of Chemistry, Brock University, 500 Glenridge Ave., St. Catharines, Ontario, Canada L2S 3A1.
² Department of Biological Sciences, Brock University, 500 Glenridge Ave., St. Catharines, Ontario, Canada L2S 3A1.
³ Sussex Research Laboratories Inc., 100 Sussex Drive, Ottawa, Ontario, Canada K1A 0R6.
⁴ Department of Chemistry, Brock University, 500 Glenridge Ave., St. Catharines, Ontario, Canada L2S 3A1. Electronic address: tyan@brocku.ca.

PMID: 26918516
DOI: 10.1016/j.carres.2016.02.003

Abstract

BODIPY fluorophores bearing azide or terminal alkyne functions were conjugated with glycans modified with terminal alkyne or azido through the Cu(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC) chemistry under microwave heating while these reactions did not proceed when heated in an oil-bath. The BODIPY-glycan conjugate product 8a undergoes self-assembly into liposomes when hydrated. Formation of liposomes was confirmed by both bright field and confocal microscopy. Fluorescent emission within the liposome was shifted from green to red due to effective high concentrations.

Keywords: BODIPY; CuAAC click chemistry; Fluorophore; Liposome; Microwave assisted synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Boron Compounds / chemistry*
Click Chemistry
Liposomes / chemistry
Liposomes / ultrastructure*
Microscopy, Confocal
Polysaccharides / chemistry*

Substances

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Boron Compounds
Liposomes
Polysaccharides