Fluorescent sensor compounds for detecting saccharides
First Claim
Patent Images
1. A fluorescent sensor compound having the formula:
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wherein L is selected from the group consisting of alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, and arylalkyloxyl;
each m, m′
, n, n′
, p, and p′
is independently an integer from 0 to 4, inclusive; and
each R1, R′
1, R2, R′
2, R3 and R′
3 is independently selected from the group consisting of hydrogen, alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, arylalkyloxyl, halo, substituted and unsubstituted amino, and substituted and unsubstituted thiol.
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Accused Products
Abstract
Fluorescent sensor compounds having the formula:
- wherein L is selected from the group consisting of alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, and arylalkyloxyl;
- each m, m′, n, n′, p, and p′ is independently an integer from 0 to 4, inclusive; and
- each R1, R′1, R2, R′2, R3 and R′3 is independently selected from the group consisting of hydrogen, alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, arylalkyloxyl, halo, substituted and unsubstituted amino, and substituted and unsubstituted thiol, are useful for the selective detection of saccharides such as glucose and sialyl Lewis X. The compounds find particular use in detecting saccharides in biological samples, and in detecting cancer cells that express cell surface polysaccharides such as sialyl Lewis X.
29 Citations
25 Claims
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1. A fluorescent sensor compound having the formula:
-
wherein L is selected from the group consisting of alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, and arylalkyloxyl;
each m, m′
, n, n′
, p, and p′
is independently an integer from 0 to 4, inclusive; and
each R1, R′
1, R2, R′
2, R3 and R′
3 is independently selected from the group consisting of hydrogen, alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, arylalkyloxyl, halo, substituted and unsubstituted amino, and substituted and unsubstituted thiol. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13)
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14. A method of detecting glucose in a biological sample, comprising contacting a biological sample with a fluorescent sensor compound having the formula:
-
wherein L is selected from the group consisting of alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, and arylalkyloxyl;
each m, m′
, n, n′
, p, and p′
is independently an integer from 0 to 4, inclusive;
each R1, R′
1, R2, R′
2, R3 and R′
3 is independently selected from the group consisting of hydrogen, alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, arylalkyloxyl, halo, substituted and unsubstituted amino, and substituted and unsubstituted thiol; and
detecting the presence or absence of fluorescence in the sample, wherein the presence of fluorescence indicates the presence of glucose in the sample. - View Dependent Claims (15, 16, 17)
correlating the amount of fluorescence in the sample with a concentration of glucose in the sample.
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16. The method according to claim 14, wherein m, m′
- , n, n′
, p, and p′
are each zero and L is;
- , n, n′
-
17. The method according to claim 14, wherein the fluorescent sensor compound is provided in an implantable sensor device.
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18. A method of detecting sialyl Lewis X in a biological sample, comprising contacting a biological sample with a fluorescent sensor compound having a formula:
-
wherein L is selected from the group consisting of alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, and arylalkyloxyl;
each m, m′
, n, n′
, p, and p′
is independently an integer from 0 to 4, inclusive; and
each R1, R′
1, R2, R′
2, R3 and R′
3 is independently selected from the group consisting of hydrogen, alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, arylalkyloxyl, halo, substituted and unsubstituted amino, and substituted and unsubstituted thiol; and
detecting the presence or absence of fluorescence in the sample, wherein the presence of fluorescence indicates the presence of sialyl Lewis X in the sample. - View Dependent Claims (19, 20)
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21. A method of detecting cancer cells that express sialyl Lewis X in a biological sample, comprising contacting a biological sample with a fluorescent sensor compound of the formula:
-
wherein L is selected from the group consisting of alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, and arylalkyloxyl;
each m, m′
, n, n′
, p, and p′
is independently an integer from 0 to 4, inclusive; and
each R1, R′
1, R2, R′
2, R3 and R′
3 is independently selected from the group consisting of hydrogen, alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, arylalkyloxyl, halo, substituted and unsubstituted amino, and substituted and unsubstituted thiol; and
detecting the presence or absence of fluorescence in the sample, wherein the presence of fluorescence indicates the presence of cancerous in the sample. - View Dependent Claims (22, 23, 24, 25)
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Specification
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Current AssigneeNorth Carolina State University (University of North Carolina System)
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Original AssigneeNorth Carolina State University (University of North Carolina System)
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InventorsWang, Binghe, Yang, Wenqian, Weston, Brent
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Primary Examiner(s)Snay, Jeffrey R.
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Application NumberUS10/437,362Publication NumberTime in Patent Office791 DaysField of Search436/63, 436/64, 436/94, 436/95, 436/172, 250/458.1, 250/459.1, 600/316, 600/317, 600/319US Class Current436/63CPC Class CodesA61K 31/69 Boron compoundsC07F 5/025 Boronic and borinic acid co...G01N 33/57492 involving compounds localiz...G01N 33/66 involving blood sugars, e.g...Y10T 436/143333 Saccharide [e.g., DNA, etc.]Y10T 436/144444 Glucose
