A concise synthesis of the pennsylvania green fluorophore and labeling of intracellular targets with O 6-benzylguanine derivatives

Laurie F. Mottram; Ewa Maddox; Markus Schwab; Florent Beaufils; Blake R. Peterson

doi:10.1021/ol7015093

A concise synthesis of the pennsylvania green fluorophore and labeling of intracellular targets with O ⁶-benzylguanine derivatives

Laurie F. Mottram, Ewa Maddox, Markus Schwab, Florent Beaufils, Blake R. Peterson

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35 Scopus citations

Abstract

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 O ⁶-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O ⁶-benzyiguanine (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.

Original language	English
Pages (from-to)	3741-3744
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	19
DOIs	https://doi.org/10.1021/ol7015093
State	Published - Sep 13 2007

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abstract = "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 O 6-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O 6-benzyiguanine (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.",

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AU - Mottram, Laurie F.

AU - Maddox, Ewa

AU - Schwab, Markus

AU - Beaufils, Florent

AU - Peterson, Blake R.

PY - 2007/9/13

Y1 - 2007/9/13

N2 - 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 O 6-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O 6-benzyiguanine (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.

AB - 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 O 6-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O 6-benzyiguanine (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.

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U2 - 10.1021/ol7015093

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JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

A concise synthesis of the pennsylvania green fluorophore and labeling of intracellular targets with O ⁶-benzylguanine derivatives

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