Glucose sensor molecule
View Patent ↗The present invention provides a glucose sensor having a glucose receptor containing a binding site of formula (I): wherein X, n, m and R 1 are defined herein. Also provided is a glucose sensor molecule for use in such a glucose sensor, the glucose sensor molecule containing the binding site of formula (I). The binding site has been found to have particularly good selectivity for glucose.
1. A glucose sensor comprising a membrane and a glucose receptor having a binding site of formula (Ia):
wherein p is from 1 to 4;
q is from 0 to 3, and p+q is 4;
X is N;
each R 1 is the same or different and represents hydrogen, C 1-4 alkyl or C 3-7 cycloalkyl; and
ring A is a C 3-7 cycloalkyl group or a 5- to 7-membered heterocyclyl group.
2. A process for preparation of the glucose sensor of claim 1 , wherein the process comprises reductive amination of (III) in the presence of (IV), followed by deprotection of the boronic acid group:
wherein p is from 1 to 4;
q is from 0 to 3, and p+q is 4;
X is N;
each R 1 is the same or different and represents hydrogen, C 1-4 alkyl or C 3-7 cycloalkyl; and
ring A is a C 3-7 cycloalkyl group or a 5- to 7-membered heterocyclyl group;
wherein B(PG) is a boronic acid group protected by a protecting group.
3. A method of detecting or quantifying the amount of glucose in an analyte, the method comprising contacting the analyte with a glucose receptor comprising a binding site of formula (Ia):
wherein p is from 1 to 4;
q is from 0 to 3, and p+q is 4;
X is N;
each R 1 is the same or different and represents hydrogen, C 1-4 alkyl or C 3-7 cycloalkyl; and
ring A is a C 3-7 cycloalkyl group or a 5- to 7-membered heterocyclyl group.
4. A method according to claim 3 , wherein the method is a fluorescence sensing method comprising detecting a change in the fluorescence of the sensor when glucose is bound to the glucose receptor.
5. A method according to claim 4 , wherein the change in fluorescence is a change in fluorescence lifetime.
6. A method according to claim 4 , wherein the change in fluorescence is a change in fluorescence intensity.