.alpha.-carboxy caged compounds
AssigneeMolecular Probes, Inc.
InventorsRichard P. Haugland, Kyle R. Gee
Life of this patent
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Abstract
The invention relates to caged compounds for the study of biological processes, where the caged compound has a photoremoveable .alpha.-carboxy-substituted o-nitrobenzyl group. Covalent attachment of the substituted o-nitrobenzyl to a parent compound yields a caged compound with biological and/or physical properties that are significantly altered from the original properties of the parent compound. Illumination of the caged compounds to cleave the photoremoveable group yields the parent compound with its original properties restored.
Claims23
A photolabile compound, having the formula ##STR4## wherein R.sup.1 and R.sup.2, which may be the same or different, are H, --(C.dbd.O)--Cl, CO.sub.2 R.sup.7,--OR.sup.8, --O--(CH.sub.2).sub.n --CO.sub.2 R.sup.7 ;
- wherein R.sup.7 is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3,
- or a carboxylate salt, and R.sup.8 is a linear or branched alkyl having 1-18 carbons;
- n=1-17;
- R.sup.3 is H or --NO.sub.2 ;
- R.sup.4, is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3, or a carboxylate salt;
- X is ##STR5## and R.sup.5 is selected so that photolysis of said photolabile compound generates a linear or branched, saturated or unsaturated, substituted or unsubstituted carboxylic acid that is a fatty acid having 3-32 carbons;
- or R.sup.5 is selected so that photolysis of said photolabile compound generates a glutamic acid, an aspartic acid, or a .gamma.-aminobutyric acid.
A photolabile compound, having the formula ##STR6## wherein R.sup.1 and R.sup.2 which may be the same or different, are H, --(C.dbd.O)--Cl, CO.sub.2 R.sup.7,--OR.sup.8, --O--(CH.sub.2).sub.n --CO.sub.2 R.sup.7, or R.sup.1 and R.sup.2 taken in combination are --O--CH.sub.2 --O--;
- wherein R.sup.7 is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3, ##STR7## or a carboxylate salt, and R.sup.8 is a linear or branched alkyl having 1-18 carbons;
- n=1-17;
- R.sup.3 is H or --NO.sub.2 ;
- R.sup.4 is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3, ##STR8## or a carboxylate salt;
- X is ##STR9## wherein R.sup.5 and R.sup.6 are selected so that photolysis of said photolabile compound generates an amino acid, peptide or protein;
- or X is ##STR10## and R.sup.5 is selected so that photolysis of said photolabile compound generates a linear or branched, saturated or unsaturated, substituted or unsubstituted carboxylic acid that is a fatty acid having less than 32 carbons.
A photolabile compound, having the formula ##STR13## wherein R.sup.1 and R.sup.2, which may be the same or different, are H, --(C.dbd.O)--Cl, --CO.sub.2 R.sup.7 --OR.sup.8, or --O--(CH.sub.2).sub.n --CO.sub.2 R.sup.7, or
- R.sup.1 and R.sup.2 taken in combination are --O--CH.sub.2 --O--;
- wherein R.sup.7 is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3, ##STR14## or a carboxylate salt, and R.sup.8 is a linear or branched alkyl having 1-18 carbons;
- n=1-17;
- R.sup.3 is H or --NO.sub.2 ;
- R.sup.4 is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3, ##STR15## or a carboxylate salt;
- X is ##STR16## wherein R.sup.5 and R.sup.6 are selected so that photolysis of said photolabile compound generates a carbohydrate that is a monosaccharide, disaccharide or a polysaccharide.
A photolabile compound, having the formula ##STR17## wherein R.sup.1 and R.sup.2, which may be the same or different, are H, --(C.dbd.O)-Cl, --CO.sub.2 R.sup.7, --OR.sup.8, or --O--(CH.sub.2).sub.n --CO.sub.2 R.sup.7, or R.sup.1 and R.sup.2 taken in combination are --O--CH.sub.2 --O--;
- wherein R.sup.7 is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3, ##STR18## or a carboxylate salt, and R.sup.8 is a linear or branched alkyl having 1-18 carbons;
- n=1-17;
- R.sup.3 is H or --NO.sub.2 ;
- R.sup.4 is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3, ##STR19## or a carboxylate salt;
- X is ##STR20## wherein R.sup.5 and R.sup.6 are selected so that photolysis of said photolabile compound generates a nucleoside, a nucleotide or an oligonucleotide.
A photolabile compound, having the formula ##STR21## wherein R.sup.1 and R.sup.2, which may be the same or different, are H, --(C.dbd.O)--Cl, --CO.sub.2 R.sup.7, --OR.sup.8, or --O--(CH.sub.2).sub.n --CO.sub.2 R.sup.7 ;
- wherein R.sup.7 is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3, ##STR22## or a carboxylate salt, and R.sup.8 is a linear or branched alkyl having 1-18 carbons;
- n=1-17;
- R.sup.3 is H or --NO.sub.2 ;
- R.sup.4 is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3, ##STR23## or a carboxylate salt;
- X is --O--(C.dbd.O)--R.sup.5 ;
- wherein R.sup.5 is selected so that photolysis of said photolabile compound generates a glutamic acid, an arachidonic acid, a .gamma.-aminobutyric acid, a N-methyl-D-aspartic acid, a kainate, a 1-aminocyclopentane-1,3-dicarboxylate, a quisqualate, or a glucuronic acid.
A photolabile compound, having the formula ##STR24## wherein R.sup.1 and R.sup.2 which may be the same or different, are H, --(C.dbd.O)--Cl, --CO.sub.1 R.sup.7,--OR.sup.8, or --O--(CH.sub.2).sub.n --CO.sub.2 R.sup.7, or R.sup.1 and R.sup.2 taken in combination are --O--CH.sub.2 --O--;
- wherein R.sup.7 is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3, ##STR25## or a carboxylate salt, and R.sup.8 is a linear or branched alkyl having 1-18 carbons;
- n=1-17;
- R.sup.3 is H or --NO.sub.2 ;
- R.sup.4 is H, a linear or branched alkyl ester having 1-6 carbons, --CH.sub.2 --O--(C.dbd.O)--CH.sub.3, ##STR26## or a carboxylate salt;
- and X is ##STR27##
Dependencies are inferred from the claim text.