Luminescence indicator including ionophoric moiety

• US 6,001,999 A
• Filed: 05/27/1998
• Issued: 12/14/1999
• Est. Priority Date: 05/30/1997
• Status: Expired due to Term

• Current Assignee: Roche Diagnostics Corporation (Roche Holding AG)
• Original Assignee: AVL Medical Instruments
• Inventors: Huber, Christian, Werner, Tobias, Leiner, Marco Jean Pierre, Wolfbeis, Otto S., Boila-Gockel, Andrei, Gareis, Thomas, Kollmannsberger, Matthias, Daub, Jorg, Heinl, Stefan
• Primary Examiner(s): Raymond, Richard L.
• Assistant Examiner(s): Sripada, Pavanaram K
• Application Number:
  US09/085,812
• Time in Patent Office: 566 Days
• Field of Search: 540/468, 540/469, 540/472, 544/229, 544/106, 544/336, 548/410
• US Class Current: 540/468
• CPC Class Codes: C07F 5/022 without C-boron linkages
• CPC Class Codes: G01N 31/22 using chemical indicators G01N31/02 takes precedence

Abstract

The invention relates to a compound having the general Formula I in which one of the groups R₁,R₂,R₃,R₄,R₅,R₆ and R₇ represents an ionophoric moiety and the remaining groups each independently are hydrogen, a lipophilic or hydrophilic group or a reactive group for coupling to a polymer or a biomolecule, or R₂ forms an aromatic ring system together with R₃ and R₅ forms an aromatic ring system together with R₆.

the compound of the invention is useful as a luminescence indicator for cations.

Claims

1. Compound having the general Formula I ##STR5## in which one of the groups R₁, R₂, R₃, R₄, R₅, R₆ and R₇ represents an ionophoric moiety and the remaining groups each independently are hydrogen, a lipophilic or hydrophilic group or a reactive group for coupling to a polymer or a biomolecule, or R₂ forms an aromatic ring system together with R₃ and R₅ forms an aromatic ring system together with R₆.

2. Compound according to claim 1 wherein R₇ is an ionophoric moiety and R₃ and R₆ are independently hydrogen or methyl.

3. Compound according to claim 1 wherein R₁ and R₄ are each a lipophilic group.

4. Compound according to claim 1 wherein o and p are each 1.

5. Compound according to claim 2 wherein R₁ and R₄ are a lipophilic group.

6. Compound according to claim 1 wherein R₁ and R₄ are each a tertiary butyl group.

7. Compound according to claim 2 wherein R₁ and R₄ are each a tertiary butyl group.

8. Compound according to any one of claims 1, 2, 3, 4, 5 or 6 wherein the ionophoric moiety is a diaza-cryptand having the general formula II ##STR6## in which o and p independently is 0, 1 or 2 or is one selected from the following groups ##STR7## wherein R₈ =alkyl with 1-20 carbon atoms.

9. Compound according to claim 8 wherein o and p are zero.

10. Compound according to claim 8 wherein o and p are different and selected from the group of 0 and 1.

11. Method for detecting lithium ions in a sample comprising the steps of:

contacting the sample with a luminescence indicator comprising a compound according to claim 5;

measuring the luminescence of the luminescence indicator; and

detecting the presence of lithium in the sample based on the measured luminescence.

12. Method for detecting sodium ions in a sample comprising the steps of:

contacting the sample with a luminescence indicator comprising a compound according to claim 6;

measuring the luminescence of the luminescence indicator; and

detecting the presence of sodium in the sample based on the measured luminescence.

13. Method for detecting potassium ions in a sample comprising the steps of:

contacting the sample with a luminescence indicator comprising a compound according to claim 7;

measuring the luminescence of the luminescence indicator; and

detecting the presence of potassium in the sample based on the measured luminescence.