Rational design, synthesis and biological evaluation of modular fluorogenic substrates with high affinity and selectivity for PTP1B

ChemBioChem

Volumn 15, Issue 7, 2014, Pages 961-976

  Sanchini, Silvano ^a   Perruccio, Francesca ^a   Piizzi, Grazia ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

enzyme catalysis; fluorescent probes; fluorogenic substrates; modular probes; PTP1B; structure activity relationships

Indexed keywords

2 BROMO 3,5 DIFLUORO 4 (PHOSPHONOOXY)BENZYL (4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMATE; 2,3,5,6 TETRAFLUORO 4 (PHOSPHONOOXY)BENZYL (4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMATE; 3,5 DIFLUORO 4 (PHOSPHONOOXY)BENZYL (4 METHYL 2 OXO 2H CHROMEN 7YL)CARBAMATE; 4 HYDROXYBENZYL ALCOHOL; 4 [[BIS(BENZYLOXY)PHOSPHORYL]OXY] 2 BROMO 3,5 DIFLUOROBENZYL (4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMATE; 4 [[BIS(BENZYLOXY)PHOSPHORYL]OXY] 2,3,5,6 TETRAFLUOROBENZYL (4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMATE; 4 [[BIS(BENZYLOXY)PHOSPHORYL]OXY] 3,5 DIFLUOROBENZYL (4 METHYL 2 OXO2H CHROMEN 7 YL)CARBAMATE; 7 [2,4 DIFLUORO 6 [[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL] 3 (PHOSPHONOOXY)PHENYL] 2,2 DIMETHYLHEPTANOIC ACID; ASPARTIC ACID; BENZYL DERIVATIVE; CYSTEINE; ETHYL 7 [2 FLUORO 4 HYDROXY 6 [[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL] 3 (PHOSPHONOOXY)PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [2 FLUORO 4 METHOXY 6 [[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL] 3 (PHOSPHONOOXY)PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [2,4 DIFLUORO 6 [[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL] 3 (PHOSPHONOOXY)PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [3 [BIS(BENZYLOXY)PHOSPHORYL]OXY] 2 FLUORO 4 (METHOXYMETHOXY) 6 [[[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL]PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [3 [BIS(BENZYLOXY)PHOSPHORYL]OXY] 2 FLUORO 4 METHOXY 6 [[[[(4METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL]PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [3 [BIS(BENZYLOXY)PHOSPHORYL]OXY] 2,4 DIFLUORO 6 [[[[(4 METHYL2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL]PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [3 [BIS(BENZYLOXY)PHOSPHORYL]OXY] 4 CHLORO 2 FLUORO 6 [[[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL]PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [3 [BIS(BENZYLOXY)PHOSPHORYL]OXY] 4 FLUORO 2 (2 METHOXYETHOXY) 6 [[[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL]PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [3 [BIS(BENZYLOXY)PHOSPHORYL]OXY] 4 FLUORO 2 METHOXY 6 [[[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL]PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [4 CHLORO 2 FLUORO 6 [[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL] 3 (PHOSPHONOOXY)PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [4 FLUORO 2 HYDROXY 6 [[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL] 3 (PHOSPHONOOXY)PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [4 FLUORO 2 METHOXY 6 [[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL] 3 (PHOSPHONOOXY)PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [4 METHOXY 2 [[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL] 5 (PHOSPHONOOXY)PHENYL] 2,2 DIMETHYLHEPTANOATE; ETHYL 7 [5 [BIS(BENZYLOXY)PHOSPHORYL]OXY] 4 METHOXY 2 [[[[(4 METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL]PHENYL] 2,2 DIMETHYLHEPTANOATE; GLUTAMINE; PROTEIN TYROSINE PHOSPHATASE 1B; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; TERT BUTYL 7 [3 [[BIS(BENZYLOXY)PHOSPHORYL]OXY] 2,4 DIFLUORO 6 [[[[(4METHYL 2 OXO 2H CHROMEN 7 YL)CARBAMOYL]OXY]METHYL]PHENYL] 2,2 DIMETHYLHEPTANOATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; FLUORESCENT DYE; RECOMBINANT PROTEIN;

ARTICLE; BINDING AFFINITY; CHROMATOPHORE; DEBENZYLATION; DEPHOSPHORYLATION; DRUG BINDING; DRUG DESIGN; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME CONFORMATION; ENZYME MECHANISM; ENZYME RELEASE; ENZYME SUBSTRATE COMPLEX; FLUORESCENCE; IN VITRO STUDY; MOLECULAR DOCKING; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; BINDING SITE; BIOCATALYSIS; BIOSYNTHESIS; CHEMISTRY; ENZYME ACTIVE SITE; ENZYME SPECIFICITY; GENETICS; HUMAN; KINETICS; METABOLISM; STEREOISOMERISM; SYNTHESIS;

BINDING SITES; BIOCATALYSIS; CATALYTIC DOMAIN; FLUORESCENT DYES; HUMANS; KINETICS; MOLECULAR DOCKING SIMULATION; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; RECOMBINANT PROTEINS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 84899634456     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201400033     Document Type: Article

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