8-(anilino)-1-naphthalenesulfonate analogs

Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfonic acids or salts thereof

Reexamination Certificate

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Reexamination Certificate




The field of this invention is dye compositions, particularly dye compositions suitable for use in analyte detection assays, e.g. glucose detection assays.
Analyte detection in physiological fluids, e.g. blood or blood derived products, is of ever increasing importance to today's society. Analyte detection assays find use in a variety of applications, including clinical laboratory testing, home testing, etc., where the results of such testing play a prominent role in diagnosis and management in a variety of disease conditions. Analytes of interest include glucose for diabetes management, cholesterol, and the like. In response to this growing importance of analyte detection, a variety of analyte detection protocols and devices for both clinical and home use have been developed.
Many of the protocols and devices that have been developed to date employ a signal producing system to identify the presence of the analyte of interest in a physiological sample, such as blood. For example, one glucose detection system employed today uses a signal producing system that includes glucose oxidase, horseradish peroxidase, meta[3-methyl-2-benzothiazolinone hydrazone]N-sulfonyl benzenesulfonate monosodium (MBTHSB) and 8-(anilino)-1-naphthalenesulfonate (ANS). See U.S. Pat. No. 5,563,031. When glucose is combined with the above signal producing system in the presence of oxygen, the following reaction takes place:
Despite the good results that have been achieved with the MBTHSB-ANS dye couple as described above, there is room for improvement in this system. For example, the blue dye product produced by the above described MBTHSB/ANS dye couple signal producing system is subject to drift during the detection phase of the assay, which ultimately can cause inaccuracy in the results.
Accordingly, there is continued interest in the development of new compounds for use in signal producing systems for analyte detection. Of particular interest would be the development of an ANS substitute that would yield a blue reaction product that is not subject to drift during detection.
Relevant Literature
Patents of interest include: U.S. Pat. Nos. 4,935,346; 4,962,040; 5,453,360; 5,563,031; 5,776,719; and 5,922,530. Also of interest is: Kosower & Kanety, “Intramolecular Donor-Acceptor Systems. 10. Multiple Fluorescences from 8-(phenylamino)-1-naphthalenesulfonates,” J. Am. Chem. Soc. (1983) 105: 6236-6243.
ANS analogs and methods for their use are provided. The ANS analogs react with 3-methyl-2-benzothiazolinone hydrazone hydrochloride (MBTH) or analogs thereof, e.g. MBTHSB, to produce a reaction product that exhibits reduced drift as compared to the reaction product of ANS and MBTH, or the same MBTH analog. The subject ANS analogs are further characterized by having at least one non-hydrogen substituent present on their phenyl moiety. The subject analogs find use in a variety of applications and are particularly suited for use in analyte detection assays, such as glucose detection assays.

patent: 4935346 (1990-06-01), Phillips et al.
patent: 4962040 (1990-10-01), Hugl et al.
patent: 5453360 (1995-09-01), Yu
patent: 5563031 (1996-10-01), Yu
patent: 5776719 (1998-07-01), Douglas et al.
patent: 5922530 (1999-07-01), Yu
Kosower, Edward M., et al., “Intramolecular Donor-Acceptor Systems. 10. Multiple Fluorescences from 8-(Phenylamino)-1-Naphthalenesulfonates,”Journal of American Chemical Society(1983) vol. 105:6236-6243.


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