Polyglutaraldehyde synthesis and protein bonding substrates

• US 4,369,226 A
• Filed: 02/17/1981
• Issued: 01/18/1983
• Est. Priority Date: 03/19/1979
• Status: Expired due to Fees

• Current Assignee: California Institute of Technology
• Original Assignee: California Institute of Technology
• Inventors: Rembaum, Alan
• Primary Examiner(s): Lesmes, George F.
• Assistant Examiner(s): BUFFALOW, EDITH
• Application Number:
  US06/235,043
• Time in Patent Office: 700 Days
• Field of Search: 428/403, 428/407, 428/406, 428/524, 428/334, 252/62.54, 427/127, 424/32, 424/12, 528/270, 528/263
• US Class Current: 428/334
• CPC Class Codes: A61K 39/44 Antibodies bound to carriers
• CPC Class Codes: A61K 9/50 Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals A61K9/2081 takes precedence; particles with a single coating comprising drug A61K9/167
• CPC Class Codes: C07K 14/805 Haemoglobins; Myoglobins
• CPC Class Codes: C08G 6/00 Condensation polymers of aldehydes or ketones only
• CPC Class Codes: C12N 11/089 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: G01N 2446/20 the magnetic material being present in the particle core
• CPC Class Codes: G01N 2446/30 the magnetic material being dispersed in the polymer composition before their conversion into particulate form
• CPC Class Codes: G01N 2446/40 the magnetic material being dispersed in the monomer composition prior to polymerisation
• CPC Class Codes: G01N 2446/60 the magnetic material being dispersed in a medium other than the main solvent prior to incorporation into the polymer particle
• CPC Class Codes: G01N 33/54313 the carrier being characterised by its particulate form
• CPC Class Codes: G01N 33/5434 using magnetic particle immunoreagent carriers which constitute new materials per se
• CPC Class Codes: G01N 33/585 with a particulate label, e.g. coloured latex
• CPC Class Codes: Y10T 428/263 Coating layer not in excess of 5 mils thick or equivalent
• CPC Class Codes: Y10T 428/2996 Glass particles or spheres
• CPC Class Codes: Y10T 428/2998 including synthetic resin or polymer
• CPC Class Codes: Y10T 428/31942 Of aldehyde or ketone condensation product

Abstract

Polyglutaraldehyde (PGL) is polymerized in aqueous base or in aqueous highly polar solvent basic media to prepare powders, castable films or coatings for substrates such as amine substituted microbeads. PGL microspheres can be prepared by suspension polymerization in presence of a surfactant or by precipitating PGL from solution containing surfactant. Magnetic PGL microspheres are formed by suspension polymerization in the presence of magnetic particles such as iron oxide. Polyglutaraldehyde can be converted to a fluorescent polymer by reaction with m-aminophenol or other reagent. Proteins can be readily covalently bound to the polyglutaraldehyde.

Claims

1. An article comprising a substrate having a 0.1 to 5 mil coating on a surface thereof of a solid polyglutaraldehyde having a repeating conjugated aldehyde containing structural unit of the formula:

##STR5##

2. An article according to claim 1 in which the substrate is particulate.

3. An article according to claim 2 in which the particulate substrate is a microbead having a diameter from 200 A to 100 microns formed of a synthetic organic polymer.

4. An article according to claim 3 in which the polymer is an acrylamide copolymer.

5. An article according to claim 4 in which the polymer is a copolymer containing at least 50% vinyl pyridine or hydroxyethylmethacrylate, 5 to 35% acrylamide and 0.1 to 30% of an addition polymerizable cross-linking agent.

6. An article according to claim 5 in which the microbead contains hydrazide groups.

7. An article according to claim 2 in which the glutaraldehyde coating is bound to an amine.

8. An article according to claim 7 in which the amine is a protein.

9. An article according to claim 8 in which the protein is selected from antibodies, antigens, immunoglobulins, lymphocytes or hemoglobin.

10. An article according to claim 2 in which the polyglutaraldehyde coating is fluorescent.

11. An article according to claim 1 in which the substrate has functional groups thereon reactive with aldehyde.

12. An article according to claim 11 in which the groups are selected from hydroxyl, amine and hydrazide.