US2022290005A1PendingUtilityA1
Coatings with tunable amine density
Est. expiryNov 9, 2036(~10.3 yrs left)· nominal 20-yr term from priority
C08G 65/336C08G 77/26G01N 33/543G01N 33/544C07F 7/1804C08G 77/14B01J 2219/00605C08F 30/08C09D 183/08B05D 1/60C09D 143/04C07F 7/087G01N 33/68
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Claims
Abstract
Molecules or salts thereof are provided, having the structure in Formula I, wherein n 2 and n 4 are the same or different and are independently 1, 2, or 3, and n 3 is 1 to 20; X is oxygen, nitrogen, or sulfur; wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are as described herein. Methods are also provided for the synthesis of and use of the provided molecules in applications for diagnostic testing.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A molecule or salt thereof, having the structure:
wherein R 1 and R 2 are the same or different and are independently hydrogen, alkyl, alkenyl, aryl, heteroaryl, alkynyl, arylalkyl, arylalkenyl, haloalkyl, cycloalkyl, sulfonamidyl, acyl, or —CO 2 R 8 , wherein R 8 is alkyl, alkenyl, aryl, arylalkyl, arylalkenyl, haloalkyl, cycloalkyl, cycloalkylalkyl, or arylcycloalkylalkyl; or wherein R 1 and R 2 and the N to which they are bound form a ring; or wherein at least one of R 1 or R 2 comprise a nucleoside, nucleotide, polynucleotide, peptide, peptoid, saccharide, polysaccharide, aptamer, or antibody or fragment thereof;
R 3 , oriented from N to X, is alkyl, heteroalkyl, amino-substituted alkyl, amino-substituted heteroalkyl, amidoalkyl, amidoheteroalkyl, amino-substituted amidoheteroalkyl, each optionally substituted with an alkyl, heteroalkyl, amino-substituted alkyl, amino-substituted heteroalkyl, amidoalkyl, amidoheteroalkyl, or amino-substituted amidoheteroalkyl; or wherein R 3 is —(CR 9 R 10 CR 11 R 12 ) n — wherein n is 1 to 100, and R 9 , R 10 , R 11 , and R 12 are the same or different and are independently hydrogen, halo, alkyl, heteroalkyl, amino-substituted alkyl, amino-substituted heteroalkyl, amidoalkyl, amidoheteroalkyl, amino-substituted amidoheteroalkyl; or wherein R 3 is
wherein n 2 and n 4 are the same or different and are independently 1, 2, or 3, and n 3 is 1 to 20; or
wherein R 3 is a polymer comprising alkyl, heteroalkyl, amino-substituted alkyl, aminoheteroalkyl, and amidoalkyl;
X is O, NR 13 , or S, wherein R 13 is hydrogen or alkyl;
R 4 , oriented from X to C, is alkyl, alkylether, and alkylthioether, wherein each of alkyl, alkylether, and alkylthioether is optionally substituted with hydroxyl, thiol, amino, or halo;
R 5 , R 6 , and R 7 are the same or different and are independently hydrogen, alkyl, silyl, or siloxy; and
wherein at least one of R 5 , R 6 , or R 7 optionally further comprises a solid phase.
2 . The molecule or salt of claim 1 , comprising a solid phase.
3 . The molecule or salt of claim 2 , wherein said solid phase comprises a silicon atom.
4 . A molecule or salt thereof having the structure:
wherein R 1 and R 2 are the same or different and are independently hydrogen, alkyl, alkenyl, aryl, heteroaryl, alkynyl, arylalkyl, arylalkenyl, haloalkyl, cycloalkyl, sulfonamidyl, acyl, or —CO 2 R 8 , wherein R 8 is alkyl, alkenyl, aryl, arylalkyl, arylalkenyl, haloalkyl, cycloalkyl, cycloalkylalkyl, or arylcycloalkylalkyl; or wherein R 1 and R 2 and the N to which they are bound form a ring; or wherein at least one of R 1 or R 2 comprise a nucleoside, nucleotide, polynucleotide, peptide, peptoid, saccharide, polysaccharide, aptamer, or antibody or fragment thereof;
R 3 , oriented from NR 1 R 2 to NH is alkyl, heteroalkyl, amino-substituted alkyl, amino-substituted heteroalkyl, amidoalkyl, amidoheteroalkyl, amino-substituted amidoheteroalkyl, each optionally substituted with an alkyl, heteroalkyl, amino-substituted alkyl, amino-substituted heteroalkyl, amidoalkyl, amidoheteroalkyl, or amino-substituted amidoheteroalkyl ; or wherein R 3 is —(CR 7 R 8 CR 9 R 10 ) n —, wherein n is 1 to 100, and R 7 , R 8 , R 9 , and R 10 are the same or different and are hydrogen, halo, alkyl, heteroalkyl, amino-substituted alkyl, amino-substituted heteroalkyl, amidoalkyl, amidoheteroalkyl, amino-substituted amidoheteroalkyl; or wherein R 3 is
wherein n 2 and n 4 are the same or different and are independently 1, 2, or 3, and n 3 is 1 to 20; or wherein R 3 is a polymer or dendrimer comprising alkyl, heteroalkyl, amino-substituted alkyl, amino-substituted heteroalkyl, amidoalkyl, and amino-substituted amidoalkyl, amidoheteroalkyl, or amino-substituted amidoheteroalkyl;
R 4 , R 5 , and R 6 are the same or different and are independently hydrogen, alkyl, silyl, or siloxy;
(*) is a carbon center, wherein said carbon center is in an R-configuration or S-configuration; and
wherein at least one of R 4 , R 5 , or R 6 optionally further comprises a solid phase.
5 . The molecule or salt of claim 4 , wherein said carbon center is in an R-configuration.
6 . The molecule or salt of claim 4 , wherein said carbon center is in an S-configuration.
7 . The molecule or salt of any one claims 4 to 6 , comprising said solid phase.
8 . The molecule or salt of claim 7 , wherein said solid phase comprises a silicon atom.
9 . The molecule or salt of any one of claims 4 to 8 , wherein R 3 is alkyl, aminoheteroalkyl, polyamidoaminoalkyl, or polyaminoalkyl.
10 . A molecule or salt thereof having the structure:
wherein:
n 1 =1, 2, 3, 4, 5, 6, or 7;
n 2 and n 3 are the same or different and are independently about 1 to about 1000;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , and R 20 are the same or different and are hydrogen, alkyl, alkenyl, aryl, heteroaryl, alkynyl, arylalkyl, arylalkenyl, haloalkyl, cycloalkyl, sulfonamidyl, acyl, or —CO 2 R 24 , wherein R 24 is alkyl, alkenyl, aryl, arylalkyl, arylalkenyl, haloalkyl, cycloalkyl, cycloalkylalkyl, or arylcycloalkylalkyl; or wherein R 1 and R 2 and the N to which they are bound, R 3 and R 4 and the N to which they are bound, R 5 and R 6 and the N to which they are bound, R 7 and R 8 and the N to which they are bound, R 9 and R 10 and the N to which they are bound, R 11 and R 12 and the N to which they are bound, R 13 and R 14 and the N to which they are bound, R 15 and R 16 and the N to which they are bound, R 17 and R 18 and the N to which they are bound, and R 19 and R 20 and the N to which they are bound independently optionally form a ring;
R 3 , R 4 , and R 5 are the same or different and are independently hydrogen, alkyl, silyl, or siloxy;
(*), (**), and (***) are carbon centers, wherein said carbon centers are independently in an R-configuration or S-configuration, or can be achiral centers;
(****) is a second carbon center, wherein said second carbon center is in an R-configuration or S-configuration; and
wherein at least one of R 21 , R 22 , or R 23 optionally further comprises a solid phase.
11 . The molecule of claim 10 , wherein said carbon center is in an R-configuration.
12 . The molecule of claim 10 , wherein said carbon center is in an S-configuration.
13 . A molecule or salt of any one of claims 10 to 12 , comprising a solid phase.
14 . A molecule or salt of claim 13 , wherein said solid phase comprises a silicon atom.
15 . A method of synthesizing the molecule or salt of any one of claims 1 to 14 , comprising:
a. forming an oxygen-silicon covalent bond between a solid substrate and a first molecule comprising:
i. said silicon at a first end and an epoxide, isocyanate, or thioisocyanate at a second end;
b. forming a Y-carbon covalent bond between a carbon atom of said epoxide, isocyanate, or thioisocyanate and a second molecule comprising an amino group;
wherein Y is nitrogen, oxygen, sulfur, or selenium;
wherein said epoxide, isocyanate, or isothiocyanate and said silicon are linked by a group comprising an alkyl, alkylether, or alkylthioether, wherein each of alky, alkylether, or alkylthioether is optionally substituted with hydroxyl, thiol, amino, or halo.
16 . The method of claim 15 , wherein said second molecule is an alkylamine, heteroalkylamine, amino-substituted alkylamine, amino-substituted heteroalkylamine, amidoalkylamine, amidoheteroalkylamine, amino-substituted amidoheteroalkylamine, each optionally substituted with an alkyl, heteroalkyl, amino-substituted alkyl, amino-substituted heteroalkyl, amidoalkyl, amidoheteroalkyl, or amino-substituted amidoheteroalkyl.
17 . The method of claim 15 or 16 , wherein said forming an oxygen-silicon bond comprises a deposition reaction.
18 . The method of claim 17 , wherein said deposition reaction is performed in the gas phase.
19 . The method of claim 18 , wherein said deposition reaction comprises a chemical vapor deposition reaction.
20 . The method of claim 19 , wherein said chemical vapor deposition reaction occurs at an elevated temperature.
21 . The method of claim 20 , wherein said elevated temperature is at least about 100° C., 110° C., 120° C., 130° C., 140° C., or 150° C.
22 . The method of any one of claims 15 to 21 , wherein step b further comprises the use of a diluent.
23 . The method of claim 22 , wherein said diluent is an alcohol.
24 . The method of claim 23 , wherein said alcohol is isopropyl alcohol.
25 . The method of any one of claim 15 or 24 , wherein said first molecule is 3-glycidoxypropyltrimethoxysilane (GPTMS).
26 . The method of any one of claims 15 to 25 , wherein said second molecule is ethylenediamine (EDA), (ethylenedioxy)bis(ethylamine) (EDBA), tris (2-aminoethyl)amine (TAEA), polyamidoamine (PAMAM), or polyallylamine (PAAm).
27 . The method of claim 26 , wherein said second molecule is PAAm.
28 . The method of claim 27 , wherein said PAAm has an average molecular weight of from about 1 KDa to about 100 KDa.
29 . The method of any one of claims 15 to 28 , wherein said second molecule has a boiling point of from about 100° C., to 300° C.
30 . The method of any one of claims 15 to 29 , further comprising coupling said amino group to a protected amino acid or salt thereof.
31 . The method of claim 30 , wherein said protected amino acid is a tert-butyl carbamate (Boc)- or 9-fluorenylmethyl carbamate (Fmoc)-protected amino acid.
32 . The method of claim 30 or 31 , wherein said amino acid is glycine.
33 . An amino coating comprising two or more molecules or salts of any one of claims 1 to 14 .
34 . A method of tuning the amino group density of the amino coating of claim 33 .
35 . An array comprising at least 2 molecules or salts of any one of claims 1 to 14 .
36 . The array of claim 35 , wherein said array comprises a density of said amino groups from about 1×10 10 groups per cm 2 to about 1×10 14 groups per cm 2 .
37 . The array of claim 35 or 36 , wherein said molecules or salts are stereoenriched or a racemate.
38 . The array of any one of claims 35 to 37 , wherein said molecules or salts have an enantiomeric excess of at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 85%, 90%, 95%, 96%, 97%, 98%, 99%, or 100%.
39 . The array of any one of claims 35 to 38 , wherein at least some of said molecules or their salts form a coating, wherein said coating has a thickness of from about 1 angstrom to about 25 angstroms.
40 . The array of any one of claims 35 to 39 , wherein said molecules or their salts are cross-linked.
41 . The array of any one of claims 35 to 40 , further comprising instructions for use.
42 . A method of making an array, comprising associating the molecule or salt of any one of claims 1 to 14 with a substrate.
43 . A method of making an array, comprising the method of any one of claims 20 to 32 .
44 . The method of claim 42 or 43 , wherein said array comprises a density of said amino groups from about 1×10 10 groups per cm 2 to about 1×10 14 groups per cm 2 .
45 . The method of any one of claims 42 to 44 , comprising tuning the density of said amino groups on said array.
46 . A kit, comprising the molecule or salt of any one of claims 1 to 14 and instructions for use.
47 . A kit, comprising the array of any one of claims 35 to 41 and instructions for use.
48 . The kit of claim 46 or 47 , further comprising a binding moiety.
49 . The kit of claim 48 , wherein said binding moiety comprises an antibody.
50 . The kit of claim 48 or 49 , wherein said binding moiety emits a signal.
51 . A method of making a kit, comprising forming the kit with the molecule or salt of any one of claims 1 to 14 .
52 . A molecule or salt thereof made by the process of any one of claims 15 to 32 .
53 . An array made by the process of any one of claims 42 to 45 .Join the waitlist — get patent alerts
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