Cation-sensing composite structure and compounds for use therein

• US 5,474,743 A
• Filed: 10/21/1993
• Issued: 12/12/1995
• Est. Priority Date: 10/21/1993
• Status: Expired due to Term

• Current Assignee: Terumo Cardiovascular Systems Corporation (Terumo Corporation)
• Original Assignee: 3M Company
• Inventors: Kipke, Cary A., Trend, John E., Patil, Sanjay L., Yafuso, Masao, Rossman, Mitchell A.
• Primary Examiner(s): Warden, Robert J.
• Assistant Examiner(s): BHAT, NINA NMN
• Application Number:
  US08/140,257
• Time in Patent Office: 782 Days
• Field of Search: 436/172, 436/166, 436/140, 422/82.07, 422/82.08, 422/82.11, 540/468, 540/469, 558/44
• US Class Current: 422/82.07
• CPC Class Codes: C07C 43/23 containing hydroxy or O-metal groups
• CPC Class Codes: C07C 45/513 the singly bound functional group being an etherified hydroxyl group
• CPC Class Codes: C07C 45/60 in six-membered rings
• CPC Class Codes: C07C 47/575 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07D 498/18 Bridged systems
• CPC Class Codes: G01N 33/84 involving inorganic compounds or pH

Abstract

A fluorescent ionophoric compound comprises a cryptand portion and a coumarin portion substituted at the 3-position with an electron withdrawing or polarizable group. The compound, which exhibits good photostability, can be incorporated into cation-sensing composite structures useful in biological and environmental testing, which can be used with conventional glass optics, by means of convenient points of covalent attachment.

Claims

1. A fluorescent ionophoric compound having the general formula ##STR7## wherein m and n are independently 0 or 1,

R is at least one of an electron withdrawing group and a polarizable group, and

Z is oxygen or N--R" where R" is H or a C₁ to C₄ alkyl group,

said compound having an absorbance maximum in the range of 350 to 440 nm.

2. The ionophoric compound of claim 1 wherein R is selected from the group consisting of carboxyl, carboxamide, sulfonylaryl, ester, keto-alkyl ester, and aromatic groups.

3. The ionophoric compound of claim 2 wherein R is a carboxyl group.

4. The ionophoric compound of claim 2 wherein R is an ethyl ester group.

5. The ionophoric compound of claim 2 wherein said keto-alkyl ester group has the formula ##STR8##

6. The ionophoric compound of claim 2 wherein said sulfonylaryl or aromatic group is substituted by a group selected from the class consisting of amine, carboxylic acid, and sulfonic acid groups.

7. The ionophoric compound of claim 2 wherein said aromatic group is selected from the group consisting of phenyl, benzimidazolyl, benzoxazolyl, and benzthiazolyl groups.

8. The ionophoric compound of claim 1 having the formula ##STR9##

9. A cation-sensing composite structure comprising a substrate and the fluorescent ionophoric compound of claim 1 wherein said compound is covalently bound to said substrate through R, defined as above, by means of one of a bond and a linking group, said linking group comprising functionalities at both ends, the functionality at one end of said linking group being complementary to the functionality of R and the functionality at the other end being complementary to a functional group on said substrate.

10. The sensing composite structure according to claim 9 wherein said functionalities of said linking group are independently selected from the group consisting of amine, amide, ester, oxirane, olefin, urea, silanol, carbamate, isocyanate, thioisocyanate, sulfonamide, sulfonyl chloride, carboxyl, chlorotriazine, hydrazine, hydrazide, and aldehyde groups.

11. The sensing composite structure according to claim 9 wherein said linking group is hydrophilic.

12. The sensing composite structure according to claim 11 wherein said substrate is selectively permeable to protons or the hydronium ion.

13. The sensing composite structure according to claim 12 wherein said sensing composite structure is a pH sensor.

14. The sensing composite structure according to claim 9 wherein said linking group comprises a longest chain including 5 to 125 carbon or hetero atoms.

15. The sensing composite structure according to claim 14 wherein said longest chain of said linking group comprises 10 to 70 carbon or hetero atoms.

16. The sensing composite structure according to claim 9 wherein said substrate is hydrophilic.

17. The sensing composite structure according to claim 9 wherein said substrate comprises a polymeric material.

18. The sensing composite structure according to claim 17 wherein said polymer is coated on a membrane.

19. The sensing composite structure according to claim 18 wherein said coated polymer is selected from the group consisting of polyvinylchloride, copolymers and terpolymers of polyvinylchloride, copolymers of styrene and at least one of maleic acid and maleic anhydride, copolymers of polyalkylvinylether and at least one of maleic acid and maleic anhydride, polymers and copolymers of vinyldimethyl azlactone, and copolymers of one of acrylate esters, methacrylate esters, acrylamides, and methacrylamides with one of acrylic acid and methacrylic acid.

20. The sensing composite structure according to claim 18 wherein said membrane is hydrophilic porous polypropylene.

21. The sensing composite structure according to claim 17 wherein said polymeric material comprises silica.

22. The sensing composite structure according to claim 17 wherein said polymeric material possesses a net negative charge.

23. The sensing composite structure according to claim 9 wherein said substrate is substantially planar in shape.

24. The sensing composite structure according to claim 9 wherein said composite structure is a powder.

25. The sensing composite structure according to claim 24 wherein said powder is adhered to a surface which is substantially planar.