WO1996030540A3 - Substrates for beta-lactamase and uses thereof - Google Patents

Substrates for beta-lactamase and uses thereof Download PDF

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Publication number
WO1996030540A3
WO1996030540A3 PCT/US1996/004059 US9604059W WO9630540A3 WO 1996030540 A3 WO1996030540 A3 WO 1996030540A3 US 9604059 W US9604059 W US 9604059W WO 9630540 A3 WO9630540 A3 WO 9630540A3
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WO
WIPO (PCT)
Prior art keywords
group
lactamase
beta
substrates
fluorescent donor
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1996/004059
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French (fr)
Other versions
WO1996030540A2 (en
Inventor
Roger Y Tsien
Gregor Zlokarnik
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of California Berkeley
University of California San Diego UCSD
Original Assignee
University of California Berkeley
University of California San Diego UCSD
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to DE69612375T priority Critical patent/DE69612375T2/en
Priority to EP96912454A priority patent/EP0817785B1/en
Priority to CA002215310A priority patent/CA2215310C/en
Priority to AU55266/96A priority patent/AU723164B2/en
Priority to DK99118473T priority patent/DK0982398T3/en
Priority to US08/727,616 priority patent/US6291162B1/en
Priority to JP52957396A priority patent/JP3633940B2/en
Priority to DK96912454T priority patent/DK0817785T3/en
Application filed by University of California Berkeley, University of California San Diego UCSD filed Critical University of California Berkeley
Priority to AT96912454T priority patent/ATE200287T1/en
Publication of WO1996030540A2 publication Critical patent/WO1996030540A2/en
Publication of WO1996030540A3 publication Critical patent/WO1996030540A3/en
Anticipated expiration legal-status Critical
Priority to US09/481,756 priority patent/US6472205B1/en
Priority to US10/280,482 priority patent/US7157575B2/en
Priority to US11/447,691 priority patent/US20070020715A1/en
Priority to US11/606,642 priority patent/US8071761B2/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—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
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/36—Methylene radicals, substituted by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—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
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    • C12N15/09—Recombinant DNA-technology
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
    • C12N9/86—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in cyclic amides, e.g. penicillinase (3.5.2)
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    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/182—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system
    • C12P17/184—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system containing a beta-lactam ring, e.g. thienamycin
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    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/188—Heterocyclic compound containing in the condensed system at least one hetero ring having nitrogen atoms and oxygen atoms as the only ring heteroatoms
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    • C12P35/00—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin
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    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
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    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6897—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids involving reporter genes operably linked to promoters
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    • C12N2800/00—Nucleic acids vectors
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    • C12N2830/00—Vector systems having a special element relevant for transcription
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    • C12Q2334/00—O-linked chromogens for determinations of hydrolase enzymes, e.g. glycosidases, phosphatases, esterases
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
    • G01N2333/90—Enzymes; Proenzymes
    • G01N2333/914—Hydrolases (3)
    • G01N2333/978—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
    • G01N2333/986—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) 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)
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2415/00—Assays, e.g. immunoassays or enzyme assays, involving penicillins or cephalosporins
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
  • Cephalosporin Compounds (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)

Abstract

Substrates for β-lactamase of general formula (I) in which one of X and Y is a fluorescent donor moiety and the other is a quencher (which may or may not re-emit); R' is selected from the group consisting of H, lower (i.e., alkyl of 1 to about 5 carbon atoms) and (CH2)nOH, in which n is 0 or an integer from 1 to 5; R' is selected from the group consisting of H, physiologically acceptable metal and ammonium cations, -CHR2OCO(CH¿2?)nCH3, -CHR?2¿OCOC(CH¿3?)3, acylthiomethyl, acyloxy-alpha-benzyl, delta-butyrolactonyl, methoxycarbonyloxymethyl, phenyl, methylsulphinylmethyl, beta-morpholinoethyl, dialkylaminoethyl, acyloxyalkyl, dialkylaminocarbonyloxymethyl and aliphatic, in which R?2¿ is selected from the group consisting of H and lower alkyl; A is selected from the group consisting of S, O, SO, SO¿2? and CH2; and Z' and Z' are linkers for the fluorescent donor and quencher moieties. Methods of assaying β-lactamase activity and monitoring expression in systems using β-lactamase as a reporter gene also are disclosed.
PCT/US1996/004059 1995-03-20 1996-03-20 Substrates for beta-lactamase and uses thereof Ceased WO1996030540A2 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
DK96912454T DK0817785T3 (en) 1995-03-20 1996-03-20 Substrates for beta-lactamase and its use
EP96912454A EP0817785B1 (en) 1995-03-20 1996-03-20 Substrates for beta-lactamase and uses thereof
CA002215310A CA2215310C (en) 1995-03-20 1996-03-20 Substrates for beta-lactamase and uses thereof
AU55266/96A AU723164B2 (en) 1995-03-20 1996-03-20 Substrates for beta-lactamase and uses thereof
DK99118473T DK0982398T3 (en) 1995-03-20 1996-03-20 Nucleic acids and uses thereof for the study of beta-lactamase
US08/727,616 US6291162B1 (en) 1995-03-20 1996-03-20 Cytosolic forms of beta-lactamase and uses thereof
JP52957396A JP3633940B2 (en) 1995-03-20 1996-03-20 Substrate for β-lactamase and use thereof
DE69612375T DE69612375T2 (en) 1995-03-20 1996-03-20 SUBSTRATES FOR BETA LACTAMASE AND THEIR USE
AT96912454T ATE200287T1 (en) 1995-03-20 1996-03-20 SUBSTRATES FOR BETA-LACTAMASE AND THE USE THEREOF
US09/481,756 US6472205B1 (en) 1995-03-20 2000-01-11 Cytosolic forms for β-lactamase and uses thereof
US10/280,482 US7157575B2 (en) 1995-03-20 2002-10-24 Substrates for β-lactamase and uses thereof
US11/447,691 US20070020715A1 (en) 1995-03-20 2006-06-05 Novel fluorogenic substrates for beta-lactamase gene expression
US11/606,642 US8071761B2 (en) 1995-03-20 2006-11-29 Substrates for beta-lactamase and uses thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/407,544 1995-03-20
US08/407,544 US5741657A (en) 1995-03-20 1995-03-20 Fluorogenic substrates for β-lactamase and methods of use

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US08/407,544 Continuation-In-Part US5741657A (en) 1995-03-20 1995-03-20 Fluorogenic substrates for β-lactamase and methods of use

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US08/727,616 Continuation US6291162B1 (en) 1995-03-20 1996-03-20 Cytosolic forms of beta-lactamase and uses thereof

Publications (2)

Publication Number Publication Date
WO1996030540A2 WO1996030540A2 (en) 1996-10-03
WO1996030540A3 true WO1996030540A3 (en) 1997-01-09

Family

ID=23612529

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Application Number Title Priority Date Filing Date
PCT/US1996/004059 Ceased WO1996030540A2 (en) 1995-03-20 1996-03-20 Substrates for beta-lactamase and uses thereof

Country Status (13)

Country Link
US (5) US5741657A (en)
EP (3) EP1405922B1 (en)
JP (2) JP3633940B2 (en)
CN (2) CN1066731C (en)
AT (3) ATE521715T1 (en)
AU (1) AU723164B2 (en)
CA (1) CA2215310C (en)
DE (2) DE69630622T2 (en)
DK (2) DK0982398T3 (en)
ES (2) ES2156994T3 (en)
MX (1) MX9707213A (en)
PT (1) PT982398E (en)
WO (1) WO1996030540A2 (en)

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