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US5714360A
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Photoactivatable water soluble cross-linking agents containing an onium group
Assignee: Surmodics Coatings LLC
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Filing: 1995-11-03
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Granted: 1998-02-03
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Expires: 2015-11-03
Abstract
Abstract A chemical linking agent is formed of a di- or higher functional photoactivatable compound having at least one group that is charged under the conditions of use in order to provide improved water solubility. The linking agent contains two or more photoreactive groups in order to allow the agent to be used as a cross-linking agent in aqueous systems. The charged group can be provided by a radical that includes one or more salts of organic acids, onium compounds, or protonated amines, (and optionally one or more additional photoreactive groups) and the photoreactive groups can be provided by two or more radicals that include an aryl ketone. The onium compound can provide a quaternary ammonium, sulfonium or phosphonium group. A surface can be coated with a target molecule such as a synthetic polymer, carbohydrate, protein, lipid, nucleic acid, drug, vitamin, cofactor or dye by forming an aqueous solution of the linking agent and the target molecule, placing the solution in contact with the surface and activating the photoreactive groups of the linking agent to cross-link the target molecule to the surface.
Inventors
- 👤 Dale G. Swan
- 👤 Richard A. Amos
- 👤 Terrence P. Everson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 19:14
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/10; C07D295/112; C07C; C07C225/00; C07C225/02; C07C225/14; C07C225/16; C07C309/00; C07C309/01; C07C309/02; C07C309/03; C07C309/13; C07C309/14; C07C45/00; C07C45/61; C07C45/63; C07K; C07K17/00; C07K17/02; C07K17/06; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/53; G01N33/543; G01N33/54353; Y; Y10; Y10S; Y10S530/00; Y10S530/81; Y10S530/812; Y10S530/815; Y10S530/816
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
63 words
A photoactivatable chemical linking agent capable, upon activation, of covalent attachment to a surface and/or target molecule, the agent comprising a charged, nonpolymeric di- or higher functional photoactivatable compound comprising two or more photoreactive groups, each capable of being activated to form a covalent bond with the surface or target molecule, and one or more charged groups, each comprising, independently, an onium group.
Claim 2
Dependent Claim
63 words
A photoactivatable chemical linking agent capable, upon activation, of covalent attachment to a surface and/or target molecule, the agent comprising a charged, nonpolymeric di- or higher functional photoactivatable compound comprising two or more photoreactive groups, each capable of being activated to form a covalent bond with the surface or target molecule, and one or more charged groups, each comprising, independently, an onium group.
Claim 3
Dependent Claim
35 words
The linking at rent according to claim 1 wherein the charged groups are sufficient to allow the agent to be used as a cross-linking agent in a solvent system having water as a major component.
Claim 4
Dependent Claim
28 words
The linking agent according to claim 1 wherein each onium group is, independently, selected from the group consisting of quaternary ammonium, sulfonium, and phosphonium groups, and combinations thereof.
Claim 5
Dependent Claim
23 words
The linking agent according to claim 1 wherein the photoreactive groups are provided by two or more radicals each containing an aryl ketone.
Claim 6
Dependent Claim
29 words
The linking gent according to claim 4 wherein each aryl ketone is selected from the group consist of acetophenone, benzophenone, anthraquinone, enthrone, and anthrone-like heterocycles, and their substituted derivatives.
Claim 7
Dependent Claim
94 words
A photoactivatable cross-linking agent comprising a compound of the formula: X--Y--X wherein each X, independently, is a radical containing a photoreactive group and Y is a radical containing one or more charged groups, wherein the number and/or type of charged group(s) is sufficient to provide the molecule with sufficient aqueous solubility to allow the agent to be used in a solvent system having water as the major component, and wherein each charged group comprises, independently, an onium group, provided however, that Y itself contains no more than one photoreactive group for each charged group.
Claim 8
Dependent Claim
94 words
A photoactivatable cross-linking agent comprising a compound of the formula: X--Y--X wherein each X, independently, is a radical containing a photoreactive group and Y is a radical containing one or more charged groups, wherein the number and/or type of charged group(s) is sufficient to provide the molecule with sufficient aqueous solubility to allow the agent to be used in a solvent system having water as the major component, and wherein each charged group comprises, independently, an onium group, provided however, that Y itself contains no more than one photoreactive group for each charged group.
Claim 9
Dependent Claim
28 words
The linking agent according to claim 6 wherein each onium group is, independently, selected from the group consisting of quaternary ammonium, sulfonium, and phosphonium groups, and combinations thereof.
Claim 10
Dependent Claim
21 words
The linking agent according to claim 6 wherein each X comprises a photoreactive groups in the form of an aryl ketone.
Claim 11
Dependent Claim
29 words
The linking agent according to claim 8 wherein each aryl ketone is selected from the group consisting of acetophenone, benzophenone, anthraquinone, anthrone, and anthrone-like heterocycles, and their substituted derivatives.
Claim 12
Dependent Claim
20 words
The linking agent according to claim 6 wherein Y comprises an onium group comprising one or more quaternary ammonium groups.
Claim 13
Dependent Claim
118 words
A linking agent according to claim 10 wherein the onium group(s) comprises a linear or heterocyclic radical selected from the group consisting of: ##STR11## wherein each R 1 independently is a radical containing an alkylene, oxyalkylene, cycloalkylene, arylene, or aralkylene group, each R 2 independently is a radical containing an alkyl, oxyalkyl, cycloalkyl, aryl, or aralkyl group, and each R 3 independently is either a non-bonding pair of electrons, a hydrogen atom, or a radical of the same definition as R 2 , in which the R 1 , R 2 and R 3 groups can contain noninterfering heteroatoms or substituents, provided however, that when R 2 includes a photoactivatible group, R 3 cannot equal R 2 .
Claim 14
Dependent Claim
11 words
A photoactivatable cross-linking agent selected from the group consisting of: ##STR12##
Claim 15
Dependent Claim
11 words
A photoactivatable cross-linking agent selected from the group consisting of: ##STR12##
Claim 16
Independent Claim
121 words
A method of coating a surface with a target molecule, the method comprising the steps of: a) providing a photoactivatable chemical linking agent capable, upon activation, of covalent attachment to the surface and the target molecule, the agent comprising a charged, nonpolymeric di- or higher functional photoactivatable compound comprising two or more photoreactive groups, the compound comprising one or more charged groups, each charged group, independently, comprising an onium group; and forming a solvent system having water as the major component and comprising the linking agent and a target molecule; b) placing the solvent system in bonding proximity to the surface, and c) activating the photoreactive groups of the linking agent in order to cross-link the target molecule to the surface.
Claim 17
Independent Claim
121 words
A method of coating a surface with a target molecule, the method comprising the steps of: a) providing a photoactivatable chemical linking agent capable, upon activation, of covalent attachment to the surface and the target molecule, the agent comprising a charged, nonpolymeric di- or higher functional photoactivatable compound comprising two or more photoreactive groups, the compound comprising one or more charged groups, each charged group, independently, comprising an onium group; and forming a solvent system having water as the major component and comprising the linking agent and a target molecule; b) placing the solvent system in bonding proximity to the surface, and c) activating the photoreactive groups of the linking agent in order to cross-link the target molecule to the surface.
Claim 18
Dependent Claim
27 words
The method according to claim 13 wherein each onium group is, independently, selected from the group consisting of quaternary ammonium, sulfonium, and phosphonium groups, and combinations thereof.
Claim 19
Dependent Claim
22 words
The method according to claim 13 wherein the photoreactive groups are provided by two or more radicals each containing an aryl ketone.
Claim 20
Dependent Claim
28 words
The method according to claim 15 wherein each aryl ketone is selected from the group consisting of acetophenone, benzophenone, anthraquinone, anthrone, and anthrone-like heterocycles, and their substituted derivatives.
Claim 21
Dependent Claim
92 words
A surface bearing a coating comprising a target molecule cross-linked to the surface by the activation of a photoactivatable chemical linking agent, the agent comprising a charged, nonpolymeric di- or higher functional photoactivatable compound, the compound comprising two or more photoreactive groups activated to form covalent bonds with the surface and the target molecule and one or more charged groups sufficient to allow the agent to be used as a cross-linking agent in a solvent system having water as a major component, wherein the charged groups each comprise, independently, an onium group.
Claim 22
Dependent Claim
92 words
A surface bearing a coating comprising a target molecule cross-linked to the surface by the activation of a photoactivatable chemical linking agent, the agent comprising a charged, nonpolymeric di- or higher functional photoactivatable compound, the compound comprising two or more photoreactive groups activated to form covalent bonds with the surface and the target molecule and one or more charged groups sufficient to allow the agent to be used as a cross-linking agent in a solvent system having water as a major component, wherein the charged groups each comprise, independently, an onium group.
Claim 23
Dependent Claim
27 words
The surface according to claim 17 wherein each onium group is, independently, selected from the group consisting of quaternary ammonium, sulfonium, and phosphonium groups, and combinations thereof.
Claim 24
Dependent Claim
22 words
The surface according to claim 17 wherein the photoreactive groups are provided by two or more radicals each containing an aryl ketone.
Claim 25
Dependent Claim
28 words
The surface according to claim 19 wherein each aryl ketone is selected from the group consisting of acetophenone, benzophenone, anthraquinone, anthrone, and anthrone-like heterocycles, and their substituted derivatives.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2001-02-02 | 2001-08-04 | 2002-02-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2005-02-02 | 2005-08-04 | 2006-02-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2009-02-02 | 2009-08-04 | 2010-02-03 | $7700.00 | Window Closed / Lapsed |