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US 2023/0057033 A1Published application
Fluorogenic beta-lactamase substrate and associated detection method
AssigneesMolsid, Ecole Normale Superieure De Lyon, Universite Claude Bernard Lyon 1, Centre National de la Recherche Scientifique (CNRS)
InventorsJens HASSERODT, Mathieu BORDY, Quentin GLENADEL, Charlie VERRIER
Life of this patent
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Abstract
Probes for the detection of β-lactamase-type enzymatic activity. In particular, novel fluorogenic substrates for detecting the presence of a catalytically active β-lactamase and a detection method using such substrates.
Claims20
A compound of formula (I):
- in which:
- W is —O— or —NR13—, with R13 being a C1-C4 alkyl or a hydrogen atom;
- R1 is such that HWR1, obtained after cleavage of the —C(O)—WR1 bond present in formula (I), belongs to the class of fluorophores;
- R2, R3 and R4 are defined as follows:
- either R2 is a C1-C4 alkyl, R3 is a C1-C4 alkyl or a hydrogen atom, and R4 is a C1-C4 alkyl;
- or R3 is a C1-C4 alkyl or a hydrogen atom and R2 and R4 are bonded to each other and form a —(CH2)p—Yq—(CH2)r— chain in direction of R2 toward R4, wherein
- Y is O, NR14, N(R14)2+or S,
- p=0, 1, 2, 3, 4 or 5,
- q=0 or 1,
- r=0, 1, 2, 3, 4 or 5,
- p+q+r=3,4,5, or 6,and
- each R14 represents independently a hydrogen atom, a C1-C6 alkyl, an amino protecting group, or -(L)q-GP, with q which is equal to 0 or 1, L which is a linking arm and GP which is a hydro solubilizing group;
- or R2 is a C1-C4 alkyl and R3 and R4 are bonded together and form, with the carbon atom to which they are bonded, an aliphatic carbocycle;
- R5 and R6 are identical or different and represent, independently of each other, a hydrogen atom, a C1-C4 alkyl, or a C5-C10 aryl;
- R7 is a hydrogen atom, or a group selected from C1-C4 alkyl and C1-C4 alkoxy;
- R8 represents a hydrogen atom;
- V represents an oxygen atom or a sulfur atom;
- n is 0 or 1;
- Z is —S—, —SO—or —CR9R10—;
- with R9 and R10 being identical or different and representing, independently of each other, a hydrogen atom or a C1-C4 alkyl;
- Q is H, a cation or R16, where R16 is selected from C1-C6 alkyl optionally substituted with an aryl or a —O(CO)—R, with R being independently selected from H, C1-C6 alkyl and C3-C6 cycloalkyl;
- and
- R11 is an organyl group, an organylamino group, an organyloxy group, or an organylthio group,
- X represents a bond, or a group selected from
21 more elements
Dependencies are inferred from the claim text.