Light-stable reducible compounds and analytical compositions, elements and methods utilizing same
AssigneeEastman Kodak Company
InventorsAlbert J. Mura, Paul B. Merkel
Life of this patent
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Abstract
Certain reducible aromatic and quinone compounds having bulky groups on the carbamate nitrogen atom have improved stability to light. These compounds are useful in analytical compositions, elements and methods, e.g. for assays of bacterial cells. These compounds have suitable substituents that promote the release of phenalenone or benzphenalenone fluorescent dyes at physiological pH.
Claims18
A reducible compound of the structure CAR--R.sup.1).sub.n wherein n is 1 or 2, CAR-- is a substituted or unsubstituted aromatic or quinone nucleus selected from the group consisting of ##STR35## and the nucleus of a 1,2-, 1,4- or 9,10-anthraquinone, 4,4'-diphenoquinone, azuloquinone, or 1,6-anulenoquinone wherein R.sup.1 is attached to the nucleus adjacent to one of the oxo groups of the nucleus, and
- R.sup.1 is ##STR36## R.sup.2 and R.sup.4 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or an electron withdrawing group,
- R.sup.3 is the same as R.sup.1, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or an electron withdrawing group, provided that at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron withdrawing group, or R.sup.3 and R.sup.4, taken together, represent the atoms necessary to complete a substituted or unsubstituted strained fused carbocyclic ring,
- R.sup.5 is substituted or unsubstituted alkylene of 1 or 2 carbon atoms,
- R.sup.6 is a substituted or unsubstituted organic group having a molecular weight of at least 40, or together with R.sup.5 forms a divalent substituted or unsubstituted heterocyclic group having at least 5 atoms in the ring,
- Q is carbonyl or thiocarbonyl,
- FRAG is a moiety derived from a phenalenone or benzphenalenone dye selected from the group consisting of ##STR37## wherein R is hydroxy or mercapto, and m is 0 or 1,
- provided that when R.sup.1 is replaced with H, CAR-H has an E.sub.1/2 of at least about +100 mV when measured in water using a normal hydrogen electrode as a standard.
A composition buffered at a pH of 9 or less and comprising a reducible compound of the structure CAR--R.sup.1).sub.n wherein n is 1 or 2, CAR-- is a substituted or unsubstituted aromatic or quinone nucleus selected from the group consisting of ##STR39## and the nucleus of a 1,2-, 1,4- or 9,10-anthraquinone, 4,4'-diphenoquinone, azuloquinone, or 1,6-anulenoquinone wherein R.sup.1 is attached to the nucleus adjacent to one of the oxo groups of the nucleus, and
- R.sup.1 is ##STR40## R.sup.2 and R.sup.4 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or an electron withdrawing group,
- R.sup.3 is the same as R.sup.1, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or an electron withdrawing group, provided that at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron withdrawing group, or R.sup.3 and R.sup.4, taken together, represent the atoms necessary to complete a substituted or unsubstituted strained fused carbocyclic ring,
- R.sup.5 is substituted or unsubstituted alkylene of 1 or 2 carbon atoms,
- R.sup.6 is a substituted or unsubstituted organic group having a molecular weight of at least 40, or together with R.sup.5 forms a divalent substituted or unsubstituted heterocyclic group having at least 5 atoms in the ring,
- Q is carbonyl or thiocarbonyl,
- FRAG is a moiety derived from a phenalenone or benzphenalenone dye selected from the group consisting of ##STR41## wherein R is hydroxy or mercapto, and m is 0 or 1,
- provided that when R.sup.1 is replaced with H, CAR--H has an E.sub.1/2 of at least about +100 mV when measured in water using a normal hydrogen electrode as a standard.
A dry analytical element for the determination of an analyte comprising an absorbent carrier material and containing a reducible compound of the structure CAR--R.sup.1).sub.n wherein n is 1 or 2, CAR-- is substituted or unsubstituted aromatic or quinone nucleus selected from the group consisting of ##STR43## and the nucleus of a 1,2-, 1,4- or 9,10-anthraquinone, 4,4'-diphenoquinone, azuloquinone, or 1,6-anulenoquinone wherein R.sup.1 is attached to the nucleus adjacent to one of the oxo groups of the nucleus, and
- R.sup.1 is ##STR44## R.sup.2 and R.sup.4 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or an electron withdrawing group,
- R.sup.3 is the same as R.sup.1, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or an electron withdrawing group, provided that at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron withdrawing group, or R.sup.3 and R.sup.4, taken together, represent the atoms necessary to complete a substituted or unsubstituted strained fused carbocyclic ring,
- R.sup.5 is substituted or unsubstituted alkylene of 1 or 2 carbon atoms,
- R.sup.6 is a substituted or unsubstituted organic group having a molecular weight of at least 40, or together with R.sup.5 forms a divalent substituted or unsubstituted heterocyclic group having at least 5 atoms in the ring, p1 Q is carbonyl or thiocarbonyl,
- FRAG is a moiety derived from a phenalenone or benzphenalenone dye selected from the group consisting of ##STR45## wherein R is hydroxy or mercapto, and m is 0 or 1,
- provided that when R.sup.1 is replaced with H, CAR--H has an E.sub.1/2 of at least about +100 mV when measured in water using a normal hydrogen electrode as a standard.
A method for the determination of an analyte comprising the steps of:
- A. at a pH of 9 or less, contacting a sample of a liquid suspected of containing an analyte with a reducible compound of the structure CAR--R.sup.1).sub.n wherein n is 1 or 2, CAR-- is a substituted or unsubstituted aromatic or quinone nucleus selected from the group consisting of ##STR47## and the nucleus of a 1,2-, 1,4- or 9,10-anthraquinone, 4,4'-diphenoquinone, azuloquinone, or 1,6-anulenoquinone wherein R.sup.1 is attached to the nucleus adjacent to one of the oxo groups of the nucleus, and
- R.sup.1 is ##STR48## R.sup.2 and R.sup.4 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or an electron withdrawing group,
- R.sup.3 is the same as R.sup.1, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or an electron withdrawing group, provided that at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron withdrawing group, or R.sup.3 and R.sup.4, taken together, represent the atoms necessary to complete a substituted or unsubstituted strained fused carbocyclic ring,
- R.sup.5 is substituted or unsubstituted alkylene of 1 or 2 carbon atoms,
- R.sup.6 is a substituted or unsubstituted organic group having a molecular weight of at least 40, or together with R.sup.5 forms a divalent substituted or unsubstituted heterocyclic group having at least 5 atoms in the ring,
- Q is carbonyl or thiocarbonyl,
- FRAG is a moiety derived from a phenalenone or benzphenalenone dye selected from the group consisting of ##STR49## wherein R is hydroxy or mercapto, and m is 0 or 1,
- provided that when R.sup.1 is replaced with H, CAR--H has an E.sub.1/2 of at least about +100 mV when measured in water using a normal hydrogen electrode as a standard, and
- B. determining the phenalenone or benzphenalenone dye released as a result of the presence of said analyte.
Dependencies are inferred from the claim text.