Photocleavable derivatives of hydroxyprenesulfonic acids

Claim 2

A compound of the formula ##STR13## wherein at least one of X, Y, and Z is --SO 3 H or --SO 3 --SALT; the remainder of X, Y and Z are independently --SO 3 H, --SO 3 --SALT, --OH, or H; where SALT is an alkali metal cation, ammonium, alkylammonium, polyalkylammonium, alkoxyammonium, or polyalkoxyammonium ion, the alkyl portions of each independently containing 1-6 carbon atoms; LINK is either --O-- or --O--(C═O)--O--; and BLOCK is described by the formula ##STR14## where R 1 is hydrogen, carboxylate (--CO 2 H), an alkyl group having 1-6 carbons, or ARYL; wherein ARYL is an unsubstituted phenyl, or phenyl substituted independently one or more times by --NO 2 , --OR 3 , where R 3 is an alkyl having 1-6 carbons; or --(CH) n --CO 2 --M, where n=0-3 and M is Li + , Na + , K + , or NH 4 + ; the remaining positions on the aromatic ring A are optionally independently substituted one or more times by --NO 2 , or --OR 3 ; or two adjacent positions on aromatic ring A, taken in combination, form a fused 6 membered ring to give a naphthyl structure; or substituents on two adjacent positions on aromatic ring A, taken in combination, form a methylenedioxy structure; or BLOCK is described by the formula ##STR15## where the remaining positions on aromatic rings B and C are optionally independently substituted one or more times by halogen, --NO 2 , --OR 4 , and --NR 5 R 6 , where R 4 , R 5 and R 6 are independently alkyl groups having 1-6 carbons; or LINK is --O-- and BLOCK is described by the formula ##STR16## wherein R 7 is H or Me; and R 2 is H, --OH, --OR 4 , or --NR 5 R 6 .

Claim 3

A compound according to claim 1, wherein BLOCK is described by the formula ##STR17## where R l is hydrogen, carboxylate (--CO 2 H), an alkyl group having 1-6 carbons, or ARYL; wherein ARYL is an unsubstituted phenyl, or phenyl substituted independently one or more times by --NO 2 , --OR 3 , where R 3 is an alkyl having 1-6 carbons; or --(CH) n --CO 2 --M, where n=0-3 and M is Li + , Na + , K + , or NH 4 + ; the remaining positions on the aromatic ring A are optionally independently substituted one or more times by --NO 2 , --OR 3 , or --(CH) n --CO 2 --M; or two adjacent positions on aromatic ring A, taken in combination, form a fused 6 membered ring to give a naphthyl structure; or substituents on two adjacent positions on aromatic ring A, taken in combination, form a methylenedioxy structure.

Claim 4

A compound according to claim 2, wherein LINK is --O--.

Claim 5

A compound according to claim 2, wherein X, Y, and Z are --SO 3 H or --SO 3 --SALT.

Claim 6

A compound according to claim 1, wherein BLOCK is described by the formula ##STR18## where R 1 is hydrogen, carboxylate (--CO 2 H), an alkyl group having 1-6 carbons, or ARYL; wherein ARYL is an alkoxy or nitro-substituted phenyl.

Claim 7

A compound according to claim 1 of the formula ##STR19## wherein LINK is --O--or --O--(C═O)--O--; and X, Y, and Z are --SO 3 H or --SO 3 --SALT.

Claim 8

A compound according to claim 1, wherein BLOCK is described by the formula ##STR20## where the remaining positions on aromatic rings B and C are optionally independently substituted one or more times by halogen, --NO 2 , --OR 4 , and --NR 5 R 6 , where R 4 , R 5 and R 6 are independently alkyl groups having 1-6 carbons.

Claim 9

A compound according to claim 7, wherein LINK is --O--and X, Y, and Z are --SO 3 H or --SO 3 --SALT.

Claim 10

A compound according to claim 7, wherein BLOCK is described by the formula ##STR21##

Claim 11

A compound according to claim 1, wherein X, Y, and Z are --SO 3 H or --SO 3 --SALT; LINK is --O--; and BLOCK is described by the formula ##STR22## wherein R 7 is H or Me; and R 2 is H, --OH, --OR 4 , or --NR 5 R 6 .

Claim 12

A mixture comprising an aqueous solution of a photoactive compound of the formula ##STR23## wherein at least one of X, Y, and Z is --SO 3 H or --SO 3 --SALT; the remainder of X, Y and Z are independently --SO 3 H, --SO 3 --SALT, --OH, or H; where SALT is an alkali metal cation, ammonium, alkylammonium, polyalkylammonium, alkoxyammonium, or polyalkoxyammonium ion, the alkyl portions of each independently containing 1-6 carbon atoms; LINK is either --O-- or --O----(C═O)--O--; and BLOCK is described by the formula ##STR24## where R 1 is hydrogen, carboxylate (--CO 2 H), an alkyl group having 1-6 carbons, or ARYL; wherein ARYL is an unsubstituted phenyl, or phenyl substituted independently one or more times by --NO 2 , --OR 3 , where R 3 is an alkyl having 1-6 carbons; or --(CH) n --CO 2 --M, where n=0-3 and M is Li + , Na + , K + , or NH 4 + ; the remaining positions on the aromatic ring A are optionally independently substituted one or more times by --NO 2 , --OR 3 , or --(CH) n --CO 2 --M; or two adjacent positions on aromatic ring A, taken in combination, form a fused 6 membered ring to give a naphthyl structure; or substituents on two adjacent positions on aromatic ring A, taken in combination, form a methylenedioxy structure; or BLOCK is described by the formula ##STR25## where the remaining positions on aromatic rings B and C are optionally independently substituted one or more times by halogen, --NO 2 , --OR 4 , and --NR 5 R 6 , where R 4 , R 5 and R 6 are independently alkyl groups having 1-6 carbons; or LINK is --O-- and BLOCK is described by the formula ##STR26## wherein R 7 is H or Me; and R 2 is H, --OH, --OR 4 , or --NR 5 R 6 ; wherein the concentration of said compound is greater than 10 nanogram per milliliter and less than 10 milligrams per milliliter.

Claim 13

A mixture comprising an aqueous solution of a photoactive compound of the formula ##STR23## wherein at least one of X, Y, and Z is --SO 3 H or --SO 3 --SALT; the remainder of X, Y and Z are independently --SO 3 H, --SO 3 --SALT, --OH, or H; where SALT is an alkali metal cation, ammonium, alkylammonium, polyalkylammonium, alkoxyammonium, or polyalkoxyammonium ion, the alkyl portions of each independently containing 1-6 carbon atoms; LINK is either --O-- or --O----(C═O)--O--; and BLOCK is described by the formula ##STR24## where R 1 is hydrogen, carboxylate (--CO 2 H), an alkyl group having 1-6 carbons, or ARYL; wherein ARYL is an unsubstituted phenyl, or phenyl substituted independently one or more times by --NO 2 , --OR 3 , where R 3 is an alkyl having 1-6 carbons; or --(CH) n --CO 2 --M, where n=0-3 and M is Li + , Na + , K + , or NH 4 + ; the remaining positions on the aromatic ring A are optionally independently substituted one or more times by --NO 2 , --OR 3 , or --(CH) n --CO 2 --M; or two adjacent positions on aromatic ring A, taken in combination, form a fused 6 membered ring to give a naphthyl structure; or substituents on two adjacent positions on aromatic ring A, taken in combination, form a methylenedioxy structure; or BLOCK is described by the formula ##STR25## where the remaining positions on aromatic rings B and C are optionally independently substituted one or more times by halogen, --NO 2 , --OR 4 , and --NR 5 R 6 , where R 4 , R 5 and R 6 are independently alkyl groups having 1-6 carbons; or LINK is --O-- and BLOCK is described by the formula ##STR26## wherein R 7 is H or Me; and R 2 is H, --OH, --OR 4 , or --NR 5 R 6 ; wherein the concentration of said compound is greater than 10 nanogram per milliliter and less than 10 milligrams per milliliter.

Claim 14

A mixture according to claim 11, further comprising a fluorescent dye of the formula ##STR27## wherein the fluroescent dye is the photolysis product of said photoactive compound, and X, Y, and Z are as defined for said photoactive compound.

Claim 15

A mixture according to claim 12, wherein the fluorescent dye is formed by photolysis of said photoactive compound using light having a wavelength of less than about 400 nanometers.

Claim 16

A mixture according to claim 13, wherein the fluorescent dye, when illuminated by light at a wavelength greater than about 425 nanometers, fluoresces at a wavelength greater than about 480 nanometers.

Claim 17

A mixture according to claim 14, wherein the fluorescence of said fluorescent dye is detected at a site that is remote from the site of the photolysis of said photoactive compound and is performed at a time that is at least 1 microsecond subsequent to the time of photolysis.

Claim 18

A mixture according to claim 12, wherein the aqueous solution is a biological fluid.

Claim 19

A mixture according to claim 16, wherein the biological fluid is present within a living organism or cell.