Hydrogels and hydrogel arrays made from reactive prepolymers crosslinked by [2 + 2] cycloaddition

Inactive Publication Date: 2002-08-22
GE HEALTHCARE BIO SCI CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

0010] Polyacrylamide hydrogels that incorporate [2+2] photoreactive sites are disclosed. The hydrogels are especially useful for microarray formation and are made from prepolymers, including polyacrylamide reactive prepolymers. The photoreactive sites allow use of [2+2] cycloaddition reactions to not only crosslink the polyacrylamide reactive prepolymers forming the hydrogel, but also for later atta

Problems solved by technology

1. The coating process is difficult and expensive to automate because the film thickness is controlled with a spacer and top glass plate. The removal of the top glass plate must be done manually. Due to difficulties automating the process (e.g., viscosity too low for commercial coating methods), the coating of the monomer solution currently is done manually.
2. The reaction time of the acrylamide is excessively long (e.g., typically from about 15 to about 90 minutes at a short wavelength of about 254 nm), making the UV polymeri

Method used

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  • Hydrogels and hydrogel arrays made from reactive prepolymers crosslinked by [2 + 2] cycloaddition
  • Hydrogels and hydrogel arrays made from reactive prepolymers crosslinked by [2 + 2] cycloaddition
  • Hydrogels and hydrogel arrays made from reactive prepolymers crosslinked by [2 + 2] cycloaddition

Examples

Experimental program
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example 1

Method For Synthesizing a 20:1 DMI PRP

[0082] The 20:1 dimethyl maleimide (DMI) based PRP (as depicted in FIG. 1) is a copolymer of acrylamide and bifunctional N-(6-acroloylhexyl)-2,3-dim-ethyl-maleimide co-monomers. Thus, the PRP is polyacrylamide co-N-(6-acryloylhexyl)-2,3-dimethyl-maleimide.

[0083] First, 17.06 gram (0.24 mol.) of acrylamide (Fluka BioChemica, electrophoresis grade), 3.35 gram (0.012 mol.) of N-(6-acroloylhexyl)-2,3--dimethyl-maleimide, 0.39 gram (0.00156 mol.) of copper(II)sulfate pentahydrate, and 0.3 gram (0.00111 mol.) of potassium peroxodisulfate were dissolved in 81.6 gram of n-propanol / water 2:1 in a 250 mL-3-neck flask equipped with a condenser, a stirrer, and a gas inlet / outlet. The solution was deoxygenated with argon gas for 15 minutes, and then heated to 65.degree. C. and stirred for 4 hours. After cooling to room temperature, the salts were removed from the solution by filtration over a column filled with ion exchange resin (Dowex Monosphere 450).

[0084...

example 2

Method for Synthesizing a 15:1 Glycidyl Acrylate PRP

[0085] 15:1 glycidyl acrylate based PRP was formed by using acrylic acid as a second monomer and glycidyl acrylate as a [2+2] photocyclizable compound (as depicted in FIG. 3) or by using glycidyl acrylate as a second monomer and acrylic acid as a [2+2] photocyclizable compound. In the latter case, the polymer backbone was initially a copolymer of acrylamide and glycidyl methacrylate. Thus, the first copolymer formed was polyacrylamide co-glycidyl methacrylate. This first copolymer was further modified with acrylic acid to produce the PRP.

[0086] First, 15.99 gram (0.225 mol.) of acrylamide (Fluka BioChemica, electrophoresis grade), 2.13 gram (0.015 mol.) of glycidyl methacrylate, 0.39 gram (0.00156 mol.) of copper(II)sulfate pentahydrate, and 0.3 gram (0.00111 mol.) of potassium peroxodisulfate were dissolved in 82.5 gram of n-propanole / water 2:1 in a 250 mL-3-neck flask equipped with a condenser, a stirrer, and a gas inlet / outlet. ...

example 3

Photocrosslinking the 20:1 DMI PRP

[0088] A 20% by weight solids aqueous solution (range of from about 2% to about 40% solids) of 20:1 DMI PRP and 1% by weight anthroquinone 2-sulfonic acid sodium salt was coated on a solid support to a wet thickness of about 25 .mu.m (range of from about 2 nanometers to about 5 .mu.m). The coating was then exposed with UV radiation (less than about 1,000 milliJoules / cm.sup.2) through a photomask containing a grid array pattern of pads (pad size of from about 1 .mu.m to about 500 .mu.m) to cyclize the exposed PRP into a water insoluble, crosslinked, hydrogel (FIG. 1). Although not shown in FIG. 1, the PRP was simultaneously crosslinked to a glass solid support modified with [2+2] photoreactive sites. The unexposed, and therefore still water-soluble PRP, was then selectively removed by an aqueous developer solution, leaving an array pattern of the crosslinked, porous, hydrogel. Optionally, the solid support was then diced into individual biochips, eac...

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Abstract

Reactive prepolymers incorporating [2+2] photoreactive sites are synthesized. Upon exposure to UV light, these prepolymers undergo [2+2] cycloaddition to crosslink. When crosslinked, the reactive prepolymers form a hydrogel. Selective hydrogel formation is provided through selective exposure of the reactive prepolymer to UV light. Supports and other molecules may be attached or incorporated into the hydrogel through [2+2] cycloaddition with uncrosslinked [2+2] photoreactive sites present in the hydrogel.

Description

REFERENCE TO RELATED APPLICATIONS[0001] This application is a continuation-in-part of U.S. Nonprovisional Application No. 09 / 344,217, filed Jun. 25, 1999, entitled "Polyacrylamide Hydrogels and Hydrogel Arrays Made from Polyacrylamide Reactive Prepolymers," which claimed the benefit of U.S. Provisional Application No. 60 / 109,821, filed Nov. 25, 1998 entitled "Polyacrylamide Hydrogels and Hydrogel Arrays Made from Polyacrylamide Reactive Prepolymers."[0002] Acrylamide (CH.sub.2.dbd.CHC(O)NH.sub.2; C.A.S. 79-06-1; also known as acrylamide monomer, acrylic amide, propenamide, and 2-propenamide) is an odorless, free-flowing white crystalline substance that may be polymerized to form polyacrylamides. The resulting high molecular weight polymers have a variety of uses and further can be modified to optimize nonionic, anionic, or cationic properties for specified uses.[0003] Polyacrylamide hydrogels are used as molecular sieves for the separation of nucleic acids, proteins, peptides, oligo...

Claims

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Application Information

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IPC IPC(8): C08F2/46C08F8/00
CPCC08F8/00C08F20/54B01J2219/00621B01J2219/00637B01J2219/00644B01J2219/00659B01J2219/00722Y10T428/31725
Inventor BEUHLER, ALLYSONMCGOWEN, JOHN
Owner GE HEALTHCARE BIO SCI CORP
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