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US 8,969,509 B2Granted
Signal amplified biological detection with conjugated polymers
AssigneeSirigen, Inc.
InventorsBin Liu, Chun Wang, Ruoyu Zhan, Glenn P. Bartholomew, Janice W. Hong, Jean M. Wheeler, Brent S. Gaylord
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Abstract
The devices and method are provided for detecting labeled and label-free analytes, such as nucleic acids and proteins, employing conjugated cationic, anionic and neutral polymers. The analytes can be immobilized on a solid support material. The solid support material can be disposed in the pre-fabricated patterns on a substrate. The chemical structures of the polymers employed by the various embodiments of the present invention are described herein.
Claims21
A polymer represented by the following formula:
- wherein:
- E, for each occurrence, is independently ethynyl, —N3, a trialkylsiloxy or an aryl group optionally substituted with a reactive group or a pendent reactive group capable of undergoing chain extension, conjugation, or crosslinking;
- A is an aryl or a heteroaryl, optionally substituted with one or more substituents selected from halogen, hydroxyl, C1-C12 alkyl, C2-C12 alkene, C2-C12 alkyne, C3-C12 cycloalkyl, C1-C12 haloalkyl, C1-C12 alkoxy, C6-C18 (hetero)aryloxy, C6-C18 (hetero)arylamino, a C6-C18 (hetero)aryl group and an ethylene glycol polymer;
- wherein the substituents for ring A are not ammonium group;
- L1, L1′, L2 and L2′ are each independently a covalent bond, a C1-C12 alkylene, a C3-C12 cycloalkylene, a C2-C12 alkenylene, a C2-C12 alkynylene, a (C6-C18)aryl(C1-C12)alkylene, a (C6-C18)aryl(C2-C12)alkenylene, a (C6-C18)aryl(C1-C12)alkynylene, a C6-C18 arylene group, —Y1-[O—Y2]p—, —O—Y1-[O—Y2]p— wherein each C1-C12 alkylene, C3-C12 cycloalkylene, (C6-C18)aryl(C1-C12)alkylene, or C6-C18 arylene group is optionally substituted with one or more halogen, hydroxyl, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl group, C1-C12 alkoxy, C1-C12 haloalkyl, —Y1-[O—Y2]p— or —O—Y1— [O—Y2]p—;
- q is 0 or an integer from 1 to 8;
- p is 0 or an integer from 1 to 24;
- Y1 and Y2 are each independently a covalent bond, or a C1-12 alkylene group, a C3-C12 cycloalkylene, a C6-C18 (hetero)arylene, a (C6-C18)aryl(C1-C12)alkylene, wherein each C1-12 alkylene group, C3-C12 cycloalkylene, C6-C18 (hetero)arylene, (C6-C18)aryl(C1-C12)alkylene is optionally substituted with one or more halogen, hydroxyl, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl group, C1-C12 alkoxy, or C1-C12 haloalkyl;
- each R6 and R7 is independently hydrogen, C1-C12 alkyl, C2-C12 alkene, C2-C12 alkyne, C3-C12 cycloalkyl or a C6-C18 (hetero)aryl group, wherein each C1-C12 alkyl, C2-C12 alkene, C2-C12 alkyne, C3-C12 cycloalkyl or C6-C18 (hetero)aryl group is optionally substituted with one or more halogen, hydroxyl, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl group, C1-C12 alkoxy, C1-C12 haloalkyl, cyano, or C2-C12 (hetero)alkynl;
- G1 and G1′ are each independently, ethynyl, —N3, hydrogen, C1-C6 alkyl, —OH, —OR, —COOH, —SH, —SR, —SHR+, SR2+, —SO3−, —PO4−, Br, —NH2, —NHR, —NR2, —NH3+, —NH2R+, —NHR2+ or —NR3+, wherein each R is independently a C1-C6 alkyl and —SHR+, SR2+, —SO3−, —PO4−, —NH3+, —NH2R+, —NHR2+ or —NR3+ each optionally has an associated counterion;
- and
- n is an integer from 1 to about 1,000.
9 more elements
A method of preparing a polymer represented by formula (I), comprising reacting a compound of formula (II)
- Br-{circle around (A)}-Br (II),
- with a compound of formula (III)
- thereby producing a polymer represented by the following formula:
- wherein:
- E, for each occurrence, is independently halogen, hydrogen, vinylene group, a trialkylsiloxy or an aryl group optionally substituted with a reactive group or a pendent reactive group capable of undergoing chain extension, conjugation, or crosslinking;
- A is an aryl or a heteroaryl, optionally substituted with one or more substituents selected from halogen, hydroxyl, C1-C12 alkyl, C2-C12 alkene, C2-C12 alkyne, C3-C12 cycloalkyl, C1-C12 haloalkyl, C1-C12 alkoxy, C6-C18 (hetero)aryloxy, C6-C18 (hetero)arylamino, a C6-C18 (hetero)aryl group and an ethylene glycol polymer;
- wherein the substituents for ring A are not ammonium group;
- L1, L1′, L2 and L2′ are each independently a covalent bond, a C1-C12 alkylene, a C3-C12 cycloalkylene, a C2-C12 alkenylene, a C2-C12 alkynylene, a (C6-C18)aryl(C1-C12)alkylene, a (C6-C18)aryl(C2-C12)alkenylene, a (C6-C18)aryl(C1-C12)alkynylene, a C6-C18 arylene group, —Y1-[O—Y2]p—, —O—Y1-[O—Y2]p— wherein each C1-C12 alkylene, C3-C12 cycloalkylene, (C6-C18)aryl(C1-C12)alkylene, or C6-C18 arylene group is optionally substituted with one or more halogen, hydroxyl, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl group, C1-C12 alkoxy, C1-C12 haloalkyl, —Y1-[O—Y2]p— or —O—Y1-[O—Y2]p—;
- q is 0 or an integer from 1 to 8;
- p is 0 or an integer from 1 to 24;
- Y1 and Y2 are each independently a covalent bond, or a C1-12 alkylene group, a C3-C12 cycloalkylene, a C6-C18 (hetero)arylene, a (C6-C18)aryl(C1-C12)alkylene, wherein each C1-12 alkylene group, a C3-C12 cycloalkylene, a C6-C18 (hetero)arylene, a (C6-C18)aryl(C1-C12)alkylene is optionally substituted with one or more halogen, hydroxyl, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl group, C1-C12 alkoxy, or C1-C12 haloalkyl;
- each R6 and R7 is independently hydrogen, C1-C12 alkyl, C2-C12 alkene, C2-C12 alkyne, C3-C12 cycloalkyl or a C6-C18 (hetero)aryl group, wherein each C1-C12 alkyl, C2-C12 alkene, C2-C12 alkyne, C3-C12 cycloalkyl or a C6-C18 (hetero)aryl group is optionally substituted with one or more halogen, hydroxyl, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl group, C1-C12 alkoxy, C1-C12 haloalkyl, cyano, or C2-C12 (hetero)alkynl;
- G1 and G1′ are each independently, hydrogen, C1-C6 alkyl, —OH, —COOH, —SH, —SR, —SHR+, SR2+, —SO3−, —PO4−, Br, —NH2, —NHR, —NR2, —NH3+, —NH2R+, —NHR2+ or —NR3+, wherein and each R is independently a C1-C6 alkyl and —SHR+, SR2+, —SO3−, —PO4−, —NH3+, —NH2R+, —NHR2+ or —NR3+ each optionally has an associated counterion;
- and
- n is an integer from 1 to about 1,000.
12 more elements
Dependencies are inferred from the claim text.