A concise synthesis of the Pennsylvania Green fluorophore and labeling of intracellular targets with O6-benzylguanine derivatives.
We report improved syntheses of the Pennsylvania Green and 4-carboxy-Pennsylvania Green fluorophores; the latter compound was prepared from methyl 4-iodo-3-methylbenzoate in a three-pot process (32% overall yield). Chinese hamster ovary cells expressing O6-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O6-benzylguanine (SNAP-Tag substrates). Analysis of living cells by confocal microscopy revealed that Pennsylvania Green derivatives exhibit substantially higher cell permeability than analogous Oregon Green-derived molecular probes.
Mottram
Laurie F
LF
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Maddox
Ewa
E
Schwab
Markus
M
Beaufils
Florent
F
Peterson
Blake R
BR
D019883:Alkyl and Aryl Transferases / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D017930:Genes, Reporter / Q000235:genetics; D006147:Guanine / Q000031:analogs & derivatives* / Q000737:chemistry; D006801:Humans; D008958:Models, Molecular; D015335:Molecular Probes / Q000737:chemistry; D015394:Molecular Structure
D005456:Fluorescent Dyes; D015335:Molecular Probes; C064976:O(6)-benzylguanine; D006147:Guanine; D019883:Alkyl and Aryl Transferases; C050956:DNA alkyltransferase