Compounds having improved fluorescence in fluorescence polarization immunoassays and immunoassays utilizing same

• US 5,315,015 A
• Filed: 11/10/1992
• Issued: 05/24/1994
• Est. Priority Date: 11/10/1992
• Status: Expired due to Fees

• Current Assignee: Roche Diagnostics Corporation (Roche Holding AG)
• Original Assignee: Hoffmann-La Roche Incorporated (Roche Holding AG)
• Inventors: Hui, Raymond A., Schwenzer, Kathryn S.
• Primary Examiner(s): Raymond, Richard L.
• Application Number:
  US07/974,397
• Time in Patent Office: 560 Days
• Field of Search: 549/223, 549/225, 549/224, 549/226, 549/227
• US Class Current: 549/223
• CPC Class Codes: G01N 33/582 with fluorescent label
• CPC Class Codes: G01N 33/94 involving narcotics or drugs or pharmaceuticals, neurotransmitters or associated receptors

Abstract

Compounds of the formula ##STR1## wherein F is a fluorescing compound; Y is --NH-- or a single covalent bond; Z is a straight or branched alkylene chain of 2 to 10 carbon atoms which is substituted by at least one hydrophilic group; Q is oxygen or sulfur; and X is a ligand-analog, the ligand-analog capable of being recognized by an antibody specific to the corresponding ligand. These compounds have improved properties in fluorescence polarization immunoassays by possessing either a better intensity and/or a larger span.

Claims

1. A compound of the formula:

##STR12## wherein F is a fluorescent group;

Y is --NH-- or a single covalent bond;

Z is straight or branched alkylene chain of two to ten carbon atoms which is substituted with at least one hydrophilic group;

Q is oxygen or sulfur; and

X is a ligand-analog capable of being recognized by an antibody specific to the corresponding ligand.

2. The compound according to claim 1, wherein X is a tetrahydrocannabinoid analog.

3. The compound according to claim 1, wherein X is a carbamazepine analog.

4. The compound according to claim 1, wherein X is a phenytoin analog.

5. The compound according to claim 1, wherein the polar hydrophilic group is selected from the group consisting of hydroxy, carboxy, carboxylate esters, carbamyl, thiocarbamyl, amino, substituted amino, sulfino, sulfo, sulfamyl, phosphono, nitro, hydroxyalkoxy, or aminoalkoxy.

6. The compound according to claim 2, wherein Y is a single covalent bond;

Q is oxygen; and

Z is 2-hydroxy propylene.

7. The compound according to claim 2, wherein Y is --NH--, and Q is oxygen.

8. The compound according to claim 5, wherein the tetrahydrocannabinoid analog is 6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-yl.

9. The compound according to claim 5, wherein the tetrahydrocannabinoid analog is 6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-yl.

10. The compound according to claim 1, wherein F is 5-fluoresceinyl.

11. The compound according to claim 1, wherein F is 6-fluoresceinyl.

12. The compound according to claim 6, wherein F is 5-fluoresceinyl.

13. The compound according to claim 6, wherein F is 6-fluoresceinyl.