Back to results
US 6,054,271 AGranted
Methods of using synthetic molecules and target sequences
AssigneeThe Regents of the University of California
InventorsRoger Y. Tsien, B. Albert Griffin
Life of this patent
Estimating the term…
Abstract
The present invention features biarsenical molecules and target sequences that specifically react with the biarsenical molecules. Methods of using the biarsenical molecules, tetraarsenical molecules and the target sequences are included.
Claims20
A method of labeling a carrier molecule, comprising:
- a) providing a bonding partner comprising said carrier molecule and a target sequence, and
- b) contacting said bonding partner with a biarsenical molecule under conditions wherein said biarsenical molecule specifically reacts with said target sequence,
- said target sequence comprising one or more cysteines capable of specifically reacting with said biarsenical molecule, said biarsenical molecule having the following formula:
- ##STR12## and tautomers, anhydrides, and salts thereof;
- wherein
- each X.sup.1 or X.sup.2, independently, is Cl, Br, I OR.sup.a, or SR.sup.a, or
- X.sup.1 and X.sup.2 together with the arsenic atom form a ring having the formula:
- ##STR13## R.sup.a is H, C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2 OH, CH.sub.2 COOH or CN;
- Z is 1,2-ethanediyl, 1,2, benzenediyl, 4-methyl-1,2-benzyenediyl, 1,2-cyclopentanediyl, 1,2-cyclohexanediyl, 3-hydroxy-1,2-propanediyl, 3-sulfo-1,2-propanediyl, or 1,2-bis(carboxy)-1,2-ethanediyl;
- Y.sup.1 and Y.sup.2, independently, are H or CH.sub.3 ;
- or
- Y.sup.1 and Y.sup.2, together form a ring such that the biarsenical molecule has the formula:
- ##STR14## where M is O, S, CH.sub.2, C(CH.sub.3).sub.2, or NH;
- R.sup.1 and R.sup.2, independently, are OR.sup.a, OAc, NR.sup.a R.sup.b, or H;
- R.sup.3 and R.sup.4, independently, are H, F, Cl, Br, I, OR.sup.a, or R.sup.a ;
- or
- R.sup.1 together with R.sup.3, or R.sup.2 together with R.sup.4, or both, form a ring in which
- (i) one of R.sup.1 or R.sup.3 is a alkyl comprising two or three carbon atoms attached to the other, wherein the other is NR.sup.a and
- (ii) one of R.sup.2 and R.sup.4 is a alkyl comprising two or three carbon atoms attached to the other, wherein the other is NR.sup.a ;
- R.sup.b is H, C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2, CH.sub.2 COOH or CN;
- Q is CR.sup.a R.sup.b, CR.sup.a OR.sup.b, C.dbd.O, or a spirolactone having the formula:
- ##STR15## wherein the Spiro linkage is formed at C.sub.1.
19 more elements
A method of removing a label from a carrier molecule, comprising:
- a) providing a bonding partner, comprising a carrier molecule, a target sequence and a biarsenical molecule,
- wherein said target sequence comprises two or more cysteins, further wherein said target sequence is bound to said biarsenical molecule, further wherein said biarsenical molecule has the following formula:
- ##STR16## and tautomers, anhydrides, and salts thereof;
- wherein
- each X.sup.1 or X.sup.2, independently, is Cl, Br, I OR.sup.a, or SR.sup.a, or
- X.sup.1 and X.sup.2 together with the arsenic atom form a ring having the formula:
- ##STR17## R.sup.a is H, C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2 OH, CH.sub.2 COOH or CN;
- Z is 1,2-ethanediyl, 1,2, benzenediyl, 4-methyl-1,2-benzyenediyl, 1,2-cyclopentanediyl, 1,2-cyclohexanediyl, 3-hydroxy-1,2-propanediyl, 3-sulfo-1,2-propanediyl, or 1,2-bis(carboxy)-1,2-ethanediyl;
- Y.sup.1 and Y.sup.2, independently, are H or CH.sub.3 ;
- or
- Y.sup.1 and Y.sup.2, together form a ring such that the biarsenical molecule has the formula:
- ##STR18## where M is O, S, CH.sub.2, C(CH.sub.3).sub.2, or NH;
- R.sup.1 and R.sup.2, independently, are OR.sup.a, OAc, NR.sup.a R.sup.b, or H;
- R.sup.3 and R.sup.4, independently, are H, F, Cl, Br, I, OR.sup.a, or R.sup.a ;
- or
- R.sup.1 together with R.sup.3, or R.sup.2 together with R.sup.4, or both, form a ring in which
- (i) one of R.sup.1 or R.sup.3 is a alkyl comprising two or three carbon atoms attached to the other, wherein the other is NR.sup.a and
- (ii) one of R.sup.2 and R.sup.4 is a alkyl comprising two or three carbon atoms attached to the other, wherein the other is NR.sup.a ;
- R.sup.b is H, C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2, CH.sub.2 COOH or CN;
- Q is CR.sup.a R.sup.b, CR.sup.a OR.sup.b, C.dbd.O, or a spirolactone having the formula:
- ##STR19## wherein the Spiro linkage is formed at C.sub.1, and b) dissociating said biarsenical molecule from said target sequence.
18 more elements
Dependencies are inferred from the claim text.