US2004126897A1PendingUtilityA1
Colorimetric sensors constructed of diacetylene materials
Assignee: 3M INNOVATIVE PROPERTIES COPriority: Dec 19, 2002Filed: Dec 19, 2002Published: Jul 1, 2004
Est. expiryDec 19, 2022(expired)· nominal 20-yr term from priority
G01N 33/521Y10S530/812
46
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Claims
Abstract
Colorimetric sensors comprising a receptor incorporated within polydiacetylene assemblies to form a transducer capable of indicating a color change when contacted with an analyte are disclosed. Methods of using the colorimetric sensor and a kit for the colorimetric detection of an analyte are also disclosed.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A colorimetric sensor for detecting an analyte, comprising:
a receptor; and and a polymerized composition comprising at least one compound of the formula wherein R 1 comprises R 2 comprises R 3 , R 8 , R 13 , R 21 , R 31 , R 24 , R 31 and R 33 are independently C 1 -C 20 alkyl; R 4 , R 5 , R 7 , R 14 , R 16 , R 19 , R 20 , R 22 , R 25 , and R 32 are independently C 1 -C 14 alkylene; R 6 , R 15 , R 18 , and R 26 are independently C 1 -C 14 alkylene, C 2 -C 8 alkenylene, or C 6 -C 13 arylene; R 9 is C 1 -C 14 alkylene or —NR 34 —; R 10 , R 12 , R 27 , and R 29 are independently C 1 -C 14 alkylene or (C 1 -C 14 alkylene)-(C 2 -C 8 arylene); R 11 and R 28 are independently C 2 -C 30 alkynyl; R 17 is an ester-activating group; R 23 is C 6 -C 13 arylene; R 30 is C 1 -C 14 alkylene or —NR 36 —; R 34 , and R 36 are C 1 -C 4 alkyl; p is 1-5; n is 1-20; wherein R 1 and R 2 are not the same; wherein the receptor is incorporated into the polymerized composition to form a transducer; and wherein the transducer exhibits a color change when contacted with an analyte.
2 . The sensor of claim 1 , wherein R 1 is dodecyl or hexadecyl.
3 . The sensor of claim 1 , wherein R 3 is undecyl or pentadecyl.
4 . The sensor of claim 1 , wherein R 24 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, or dodecyl.
5 . The sensor of claim 1 , wherein R 33 is dodecyl, tetradecyl, hexadecyl, or octadecyl.
6 . The sensor of claim 1 , wherein R 4 is methylene, trimethylene, or tetramethylene.
7 . The sensor of claim 1 , wherein R 5 is ethylene or trimethylene.
8 . The sensor of claim 1 , wherein R 7 , R 16 , R 19 , R 20 and R 25 are independently ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, or nonamethylene.
9 . The sensor of claim 1 , wherein R 20 is methylene, trimethylene, or tetramethylene.
10 . The sensor of claim 1 , wherein R 22 is ethylene, trimethylene, or tetramethylene.
11 . The sensor of claim 1 , wherein R 32 is ethylene, trimethylene, tetramethylene, pentamethylene, or hexamethylene.
12 . The sensor of claim 1 , wherein R 6 , R 15 , R 18 , and R 26 are independently ethylene, trimethylene, ethenylene, or phenylene.
13 . The sensor of claim 1 , wherein R 8 and R 31 are independently C 1 -C 14 alkyl.
14 . The sensor of claim 15 , wherein R 8 and R 31 are independently butyl, pentyl or hexyl.
15 . The sensor of claim 1 , wherein R 9 and R 30 are independently methylene, —NH—, —N(CH 2 CH 3 )—, or —N(CH 3 )—.
16 . The sensor of claim 1 , wherein R 10 , R 12 , R 27 , and R 29 are independently methylene, ethylene, trimethylene, tetramethylene, —C(CH 3 ) 2 —, —CH((CH 2 ) t-4 CH 3 )—, or —CH 2 -phenylene.
17 . The sensor of claim 1 , wherein R 11 and R 28 are independently C 2 -C 30 alkynyl having at least two carbon-carbon triple bonds.
18 . The sensor of claim 19 , wherein R 11 and R 28 are independently —(CH 2 ) 8 —C≡C—C≡C—(CH 2 ) 9 CH 3 , or —(CH 2 ) 8 —C≡C—C≡C—(CH 2 ) 11 CH 3 .
19 . The sensor of claim 1 , wherein R 13 is C 1 -C 4 alkyl.
20 . The sensor of claim 1 , wherein R 14 is C 1 -C 4 alkylene.
21 . The sensor of claim 1 , wherein R 17 is 2,5-dioxo-1-pyrrolidinyl.
22 . The sensor of claim 1 , wherein R 23 is phenylene.
23 . The sensor of claim 1 , wherein n is 1-20, 3-17, 6-14, or 9-11.
24 . The sensor of claim 1 , wherein p is 1 or 2.
25 . The sensor of claim 1 wherein R 1 is
wherein R 7 is ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, or nonamethylene, and R 1 is ethylene, trimethylene, ethenylene, or phenylene; and
wherein R 2 is
wherein R 20 is ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, or nonamethylene, and wherein R 21 is undecyl, tridecyl, pentadecyl, heptadecyl; and
wherein p is 1.
26 . The sensor of claim 25 , wherein R 1 is
R 7 is ethylene; and
R 2 is
R 20 is tetramethylene, and wherein R 21 is tridecyl; and
p is 1.
27 . The sensor of claim 1 , wherein the receptor is selected from the group consisting of phospholipid and glycerol.
28 . The sensor of claim 1 , wherein the transducer is dispersed in an aqueous solution.
29 . The sensor of claim 1 , wherein the transducer is coated on a substrate.
30 . The sensor of claim 29 , wherein the substrate exhibits a contact angle less than 50 degrees using methylene iodide.
31 . The sensor of claim 30 , wherein the substrate is selected from the group consisting of silica gel plate, paper, glass, textured photo paper, gloss photo paper, and microporous film.
32 . The sensor of claim 1 , wherein the receptor is integrated into the polymerized composition by physical mixing.
33 . The sensor of claim 1 , wherein the receptor is covalently bonded to the polymerized composition.
34 . A method for the detection of an analyte, comprising
forming a colorimetric sensor, comprising a receptor and a polymerized composition of the formula wherein R 1 comprises R 2 comprises R 3 , R 8 , R 13 , R 21 , R 24 , R 31 and R 33 are independently C 1 -C 20 alkyl; R 4 , R 5 , R 7 , R 14 , R 16 , R 19 , R 20 , R 22 , R 25 , and R 32 are independently C 1 -C 14 alkylene; R 6 , R 15 , R 18 , and R 26 are independently C 1 -C 14 alkylene, C 2 -C 8 alkenylene, or C 6 -C 13 arylene; R 9 is C 1 -C 14 alkylene or —NR 34 —; R 10 , R 12 , R 27 , and R 29 are independently C 1 -C 14 alkylene or (C 1 -C 14 alkylene)-(C 2 -C 8 arylene); R 11 and R 28 are independently C 2 -C 30 alkynyl; R 17 is an ester-activating group; R 23 is C 6 -C 13 arylene; R 30 is C 1 -C 14 alkylene or —NR 36 —; R 34 , and R 36 are C 3 -C 4 alkyl; p is 1-5; n is 1-20; , wherein R 1 and R 2 are not the same; wherein the receptor is incorporated into the polymerized composition to form a transducer capable of exhibiting a color change; contacting the sensor with an analyte; and observing a color change if the analyte is present.
35 . The sensor of claim 34 , wherein the transducer is dispersed in an aqueous solution.
36 . The method of claim 34 , wherein the transducer is coated on a substrate.
37 . The method of claim 36 , wherein the substrate exhibits a contact angle less than 50 degrees using methylene iodide.
38 . The sensor of claim 30 , wherein the substrate is selected from the group consisting of silica gel plate, paper, glass, textured photo paper, gloss photo paper, and microporous film.
39 . The sensor of claim 34 , wherein the receptor is integrated into the polymerized composition by physical mixing.
40 . The sensor of claim 34 , wherein the receptor is covalently bonded to the polymerized composition.
41 . A method for the detection of an analyte, comprising
forming a colorimetric sensor, comprising a receptor and a polymerized composition of the formula wherein R 1 comprises R 2 comprises R 3 , R 8 , R 13 , R 21 , R 24 , R 31 and R 33 are independently C 1 -C 20 alkyl; R 4 , R 5 , R 7 , R 14 , R 16 , R 19 , R 20 , R 22 , R 25 , and R 32 are independently C 1-1 alkylene; R 6 , R 15 , R 18 , and R 26 are independently C 1 -C 14 alkylene, C 2 -C 8 alkenylene, or C 6 -C 13 arylene; R 9 is C 1 -C 14 alkylene or —NR 34 —; R 10 , R 12 , R 27 , and R 29 are independently C 1 -C 14 alkylene or (C 1 -C 14 alkylene)-(C 2 -C 8 arylene); R 11 and R 28 are independently C 2 -C 30 alkynyl; R 17 is an ester-activating group; R 23 is C 6 -C 13 arylene; R 30 is C 1 -C 14 alkylene or —NR 36 —; R 34 and R 16 are C 1 -C 4 alkyl; p is 1-5; n is 1-20; wherein R 1 and R 2 are not the same; and wherein the receptor is incorporated into the polymerized composition to form a transducer capable of exhibiting a color change; contacting the transducer with an analyte; contacting the transducer with a probe that has an affinity for both the analyte and the receptor; and observing no color change if the analyte is present.
42 . The method of claim 41 , wherein the probe and analyte are combined to form a mixture before contacting the transducer.
43 . The method of claim 41 , wherein the transducer is dispersed in an aqueous solution.
44 . The method of claim 41 , wherein the transducer is coated on a substrate.
45 . The method of claim 44 , wherein the substrate exhibits a contact angle less than 50 degrees using methylene iodide.
46 . The method of claim 45 , wherein the substrate is selected from the group consisting of silica gel plate, paper, glass, textured photo paper, gloss photo paper, and microporous film.
47 . The method of claim 41 , wherein the receptor is integrated into the polymerized composition by physical mixing.
48 . The method of claim 41 , wherein the receptor is covalently bonded to the polymerized composition.
49 . The method of claim 41 , wherein the probe comprises a membrane disrupting peptide.
50 . The method of claim 49 , wherein the probe is selected from the group consisting of alamethicin, magainin, gramicidin, polymyxin B sulfate, and melittin.
51 . The method of claim 41 , wherein the analyte is selected from the group consisting of gram-negative bacteria and endotoxin.
52 . A disposable kit for detecting the presence of an analyte, comprising:
one or more transducers comprising a receptor and a polymerized composition of the formula wherein R 1 comprises R 2 comprises R 3 , R 8 , R 13 , R 21 , R 24 , R 31 and R 33 are independently C 1 -C 20 alkyl; R 4 , R 5 , R 7 , R 14 , R 16 , R 19 , R 20 , R 22 , R 25 and R 32 are independently C 1 -C 14 alkylene; R 6 , R 15 , R 18 , and R 26 are independently C 1 -C 14 alkylene, C 2 -C 8 alkenylene, or C 6 -C 13 arylene; R 9 is C 1 -C 14 alkylene or —NR 34 —; R 10 , R 12 , R 27 , and R 29 are independently C 1 -C 14 alkylene or (C 1 -C 14 alkylene)-(C 2 -C 8 arylene); R 11 and R 28 are independently C 2 -C 30 alkynyl; R 17 is an ester-activating group; R 23 is C 6 -C 13 arylene; R 30 is C 1 -C 14 alkylene or —NR 36 —; R 34 , and R 36 are C 1 -C 4 alkyl; p is 1-5; n is 1-20; wherein R 1 and R 2 are not the same; and wherein the receptor is integrated with the polymerized composition to form a transducer capable of exhibiting a color change; and a means for contacting the transducer with an analyte.
53 . The kit of claim 52 , further comprising one or more probes with an affinity to the receptor and one or more analytes; wherein the probe is physically separated from the transducer until the kit is used.
54 . The kit of claim 52 , wherein one or more transducers are dispersed in an aqueous solution.
55 . The kit of claim 52 , wherein one or more transducers are coated on a substrate to form an array.
56 . The method of claim 55 , wherein the substrate exhibits a contact angle less than 50 degrees using methylene iodide.
57 . The sensor of claim 56 , wherein the substrate is selected from the group consisting of silica gel plate, paper, glass, textured photo paper, gloss photo paper, and microporous film.
58 . The kit of claim 52 , wherein the receptor is integrated into the polymerized composition by physical mixing.
59 . The kit of claim 52 , wherein the receptor is covalently bonded to the polymerized composition.Join the waitlist — get patent alerts
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