2024-03-28T16:42:47Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/1129842016-02-18T03:08:20Zcom_10261_34com_10261_5com_10261_33col_10261_287col_10261_286
Fluorescent labeling of alkyl chains of phosphocholine lipids by one-pot TMS cleavage-click reaction
Hornillos, Valentín
Amat-Guerri, Francisco
Acuña, A. Ulises
BODIPY
Fluorescent labeling
Click reaction
Alkynehydration
Lipid probes
Alkylphosphocholines
A simple click strategy for fluorescent tagging of azide-containing alkyl-chains of phosphocholine lipids is described, based on the easily prepared TMS-alkyne-BODIPY labeling reagent (1). Lipid labeling is carried out by one-pot Ag(I)-catalyzed deprotection of 1 followed by in situ Cu(I)-mediated cycloaddition of the alkyne-dye to the azide-phospholipid counterpart, under mild hydroalcoholic conditions with high yields. Since the reaction is compatible with the phosphocholine headgroup it was exemplified here by the synthesis of a fluorescent analog of n-hexadecylphosphocholine, a leishmanicidal drug (miltefosine). In addition, the preparation of a novel, strongly fluorescent 2-acyl BODIPY dye (6) by the unprecedented one-pot Ag(I)-catalyzed TMS-cleavage/alkyne-hydration of 1, is reported; this compound may also be a convenient labeling reagent for amino-containing biomolecules.
2015-03-26T11:45:33Z
2015-03-26T11:45:33Z
2012
2015-03-26T11:45:34Z
artículo
Journal of Photochemistry and Photobiology A: Chemistry 243: 56-60 (2012)
http://hdl.handle.net/10261/112984
10.1016/j.jphotochem.2012.06.005
eng
closedAccess
Elsevier