8-(anilino)-1-naphthalenesulfonate analogs

• US 6,218,571 B1
• Filed: 10/27/1999
• Issued: 04/17/2001
• Est. Priority Date: 10/27/1999
• Status: Expired due to Term

• Current Assignee: Cilag Gmbh International (Johnson & Johnson)
• Original Assignee: Lifescan Incorporated (Duv Holding Corporation)
• Inventors: Zheng, Xiaoling, Yu, Yeung Siu, Yani, Adva, Huang, Paing C.
• Primary Examiner(s): Geist, Gary
• Assistant Examiner(s): Calve, John N
• Application Number:
  US09/428,296
• Time in Patent Office: 538 Days
• Field of Search: 562/61
• US Class Current: 562/61
• CPC Class Codes: C07C 309/47 having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
• CPC Class Codes: C09B 27/00 Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation
• CPC Class Codes: C12Q 1/28 involving peroxidase
• CPC Class Codes: C12Q 1/54 involving glucose or galactose
• CPC Class Codes: C12Q 2326/00 Chromogens for determinations of oxidoreductase enzymes
• CPC Class Codes: C12Q 2326/32 3-Methyl-2-benzothiazolinone hydrazone hydrochloride hydrate, i.e. MBTH

Abstract

8-(anilino)-1-naphthalenesulfonate (ANS) analogs and methods for their use in analyte detection assays are provided. The subject ANS analogs are characterized by having at least one non-hydrogen substituent on their phenyl moiety and producing a reaction product with 3-methyl-2-benzothiazolinone hydrazone hydrchloride (MBTH) or an analog thereof, e.g. MBTHSB, that exhibits reduced drift. In certain preferred embodiments, the subject ANS analogs are described by the formula:

wherein: n is 1 to 5; and X is a substituent other than H. The subject ANS analogs find use in a variety of applications, particularly in analyte detection assays, such as glucose detection assays.

Claims

1. An 8-(anilino)-1-naphthalenesulfonate (ANS) analog which is capable of reacting with 3-methyl-2-benzothiazolinone hydrazone hydrochloride (MBTH), or an analog thereof, to produce a dye product having reduced drift as compared to the dye product produced upon reaction of ANS and MBTH or an analog thereof, wherein said ANS analog comprises at least one alkyl substituent bonded to the phenyl moiety, with the proviso that when said substituent is methyl, said substituent is not present at positions 3′

,4′

or 5′

.

2. The ANS analog according to claim 1, wherein said alkyl substituent comprises 1 to 6 carbon atoms.

3. The ANS analog according to claim 1, wherein said alkyl substituent is branched.

4. The ANS analog according to claim 1, wherein said alkyl substituent is linear.

5. A compound or the salt thereof of the formula:

wherein;

n is 1 to 5; and

X is independently an alkyl group of from 1 to 6 carbon atoms, with the proviso that when X is at position 3′

, 4′

or 5′

, X is not methyl.

6. The compound according to claim 5, wherein n is 1 or 2.

7. The compound according to claim 5, wherein said alkyl group is linear.

8. The compound according to claim 5, wherein said alkyl group is branched.

9. The compound according to claim 5, wherein said alkyl group is methyl, isopropyl or tert-butyl.

10. A compound or the salt thereof of the formula:

wherein;

n is 1 or 2; and

X is independently an alkyl moiety selected from the group consisting of methyl, isopropyl and tert-butyl, with the proviso that when X is at position 3′

, 4′

or 5′

, X is not methyl.

11. The compound according to claim 10, wherein n is 1.

12. The compound according to claim 11, wherein X is 2′

methyl.

13. The compound according to claim 11, wherein X is 4′

tert-butyl.

14. The compound according to claim 11, wherein X is 4′

isopropyl.

15. The compound according to claim 11, wherein X is 2′

tert-butyl.

16. The compound according to claim 10, wherein n is 2.

17. The compound according to claim 16, where a first X is 3′

tert-butyl and a second X is 5′

tert-butyl.

18. A reaction product produced by the reaction of an 8-(anilino)-1-naphthalenesulfonate (ANS) analog having at least one non-hydrogen substituent on its phenyl moiety and 3-methyl-2-benzothiazolinone hydrazone hydrochloride (MBTH) or an MBTH analog, wherein said reaction product has a reduced drift as compared to the reaction product produced upon reaction of ANS and MBTH or the MBTH analog.

19. The reaction product according to claim 18, wherein said substituent of said ANS analog is an alkyl group.

20. The reaction product according to claim 19, wherein said reaction product is a reaction product of said ANS analog and MBTHSB.

25. A composition of matter comprising a reaction product according to claim 18.

26. The composition of matter according to claim 25, wherein said reaction product is present on a porous substrate.

27. The composition of matter according to claim 26, wherein said porous substrate is a strip.

21. A compound produced upon reaction of MBTH or an analog thereof with an ANS analog in the presence of oxygen, an oxidizing agent and a peroxidase, wherein said ANS analog has the structural formula:

wherein;

n is from 1 to 5; and

X is independently a substituent other than H.

22. The compound according to claim 21, wherein X is an alkyl group.

23. The compound according to claim 22, wherein said alkyl group is from 1 to 6 carbon atoms.

24. The compound according to claim 23, wherein said alkyl group is methyl, isopropyl or tert-butyl.

28. A composition of matter comprising:

MBTH or an analog thereof; and

an ANS analog or the salt thereof of the formula;

wherein;

n is from 1 to 5; and

X is independently a substituent other than H.

29. The composition of matter according to claim 28, wherein said ANS analog and MBTH or analog thereof are present on a porous substrate.

30. The composition of matter according to claim 29, wherein said porous substrate is a strip.

31. The composition of matter according to claim 29, wherein said composition of matter further comprises an oxidase and a peroxidase.

32. A method of producing a chromogenic reaction product, said method comprising:

reacting a compound or the salt thereof of the formula;

wherein

n is 1 to 5; and

X is a substituent other than H;

with

MBTH or an analog thereof in the presence of oxygen, hydrogen peroxide and a peroxidase.

33. The method according to claim 32, wherein n is 1 to 2.

34. The method according to claim 32, wherein X is an alkyl group of from 1 to 6 carbon atoms.

35. In a method for detecting the presence of an analyte in a sample in which a dye couple comprising MBTH or an analog thereof and a second dye compound are employed, the improvement comprising:

employing as said second dye compound a compound or the salt thereof of the formula;

wherein

n is 1 to 5; and

X is a substituent other than H.

36. The method according to claim 35, wherein said X is an alkyl group of from 1 to 6 carbon atoms.

37. The method according to claim 35, wherein n is 1 or 2.

38. The method according to claim 35, wherein said analyte is glucose.