Reducible compounds which provide aniline dyes, and analytical compositions, elements and methods using same

• US 5,196,519 A
• Filed: 12/04/1991
• Issued: 03/23/1993
• Est. Priority Date: 07/05/1988
• Status: Expired due to Term

• Current Assignee: Clinical Diagnostic Systems Inc.
• Original Assignee: Eastman Kodak Company
• Inventors: Mooberry, Jared B.
• Primary Examiner(s): Lee, Mary C.
• Assistant Examiner(s): Powers, Fiona
• Application Number:
  US07/819,162
• Time in Patent Office: 475 Days
• Field of Search: 534/732, 534/733, 552/299
• US Class Current: 534/733
• CPC Class Codes: C09B 29/06 from coupling components containing amino as the only directing group
• CPC Class Codes: C12Q 1/04 Determining presence or kind of microorganism; Use of selective media for testing antibiotics or bacteriocides; Compositions containing a chemical indicator therefor C12Q1/6897 takes precedence
• CPC Class Codes: C12Q 2304/20 Redox indicators
• CPC Class Codes: G01N 33/52 Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements immunological elements G01N33/54386; involving labelled immunochemicals G01N33/58; for haemoglobin or occult blood G01N33/72

Abstract

Certain reducible compounds are useful in analytical compositions, elements and methods, for example for the detection of bacterial cells. These compounds comprise a moiety which provides an aniline dye upon reduction. Structurally, the reducible compounds are quinones having suitable substituents which promote varying amounts of aniline dye release at physiological pH.

Claims

1. A reducible compound of the structure CAR--R¹ wherein CAR-- is the quinone structure ##STR8## R¹ is ##STR9## R² and R⁴ are independently hydrogen, alkyl, aryl or an electron withdrawing group,

R⁵ is methylene,

R³ is the same as --R⁵ --R¹, or is hydrogen, alkyl, aryl or an electron withdrawing group, or R³ and R⁴, taken together, represent the atoms necessary to complete a fused carbocyclic ring,

R⁶ is alkyl, aryl, cycloalkyl or a heterocyclic moiety, and

R⁷, together with the nitrogen atom forms an aniline dye, or R⁶ and R⁷ taken together form a ring that forms part of an aniline dye moiety which, upon release of R¹ from said quinone nucleus and decarboxylation, form an aniline dye.

2. The compound of claim 1 wherein at least two of R², R³ and R⁴ are independently electron withdrawing groups, or R³ and R⁴, taken together, represent the atoms necessary to complete a fused 5- to 7-member ring.

3. The compound of claim 2 wherein R³ and R⁴, taken together, represent the atoms necessary to complete a fused 5- to 7-membered ring, and R⁵ is methylene.

4. The compound of claim 1 selected from the following group of compounds:

##STR10##