Optically-detectable enzyme substrates and their method of use

• US 8,865,891 B2
• Filed: 09/13/2012
• Issued: 10/21/2014
• Est. Priority Date: 01/21/2004
• Status: Expired due to Fees

• Current Assignee: Life Technologies Corporation (Thermo Fisher Scientific Incorporated)
• Original Assignee: Life Technologies Corporation (Thermo Fisher Scientific Incorporated)
• Inventors: Corry, Schuyler, Downey, William, Filanoski, Brian, Gee, Kyle, Greenfield, Lawrence, Hirsch, James, Johnson, Iain, Rukavishnikov, Aleksey
• Primary Examiner(s): Shameem, Golam M M
• Assistant Examiner(s): DANIEL, LAURA M
• Application Number:
  US13/614,948
• Publication Number:
  US 20130090470A1
• Time in Patent Office: 768 Days
• Field of Search: 540/217, 540/219, 540/221, 540/230
• US Class Current: 540/222
• CPC Class Codes: C07D 499/00 Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula: , e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
• CPC Class Codes: C07D 501/00 Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula: , e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
• CPC Class Codes: C07D 501/58 with a nitrogen atom, which is a member of a hetero ring, attached in position 7
• CPC Class Codes: C07D 501/60 with a double bond between positions 3 and 4
• CPC Class Codes: C07D 503/00 Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula: , e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
• CPC Class Codes: C07D 519/00 Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
• CPC Class Codes: C07F 5/022 without C-boron linkages
• CPC Class Codes: C12Q 1/34 involving hydrolase
• CPC Class Codes: C12Q 2334/00 O-linked chromogens for determinations of hydrolase enzymes, e.g. glycosidases, phosphatases, esterases
• CPC Class Codes: G01N 2333/986 acting on amide bonds in cyclic amides (3.5.2), e.g. beta-lactamase (penicillinase, 3.5.2.6), creatinine amidohydrolase (creatininase, EC 3.5.2.10), N-methylhydantoinase (3.5.2.6)
• CPC Class Codes: G01N 33/581 with enzyme label (including co-enzymes, co-factors, enzyme inhibitors or substrates)

Abstract

The present invention relates to compounds that are substrates for an enzyme, and upon reaction with the enzyme provide a detectable response, such as an optically detectable response. In particular, the compounds have utility in detecting the presence of a β-lactamase in a sample. In addition to the compounds, methods are disclosed for analyzing a sample for the presence of a β-lactamase, for example, as an indicator of expression of a nucleic acid sequence including a sequence coding for a β-lactamase. Kits are disclosed that include the disclosed compounds and additional components, for example, cells, antibodies, a β-lactamase or instructions for using the components in an assay.

Claims

1. A compound having a structure of the formula: