Preparation and use of polyethylene glycol propionaldehyde

• US 5,252,714 A
• Filed: 11/28/1990
• Issued: 10/12/1993
• Est. Priority Date: 11/28/1990
• Status: Expired due to Term

• Current Assignee: University of Alabama in Huntsville (University of Alabama System)
• Original Assignee: University of Alabama in Huntsville (University of Alabama System)
• Inventors: Sedaghat-Herati, M. R., Harris, J. Milton
• Primary Examiner(s): Russel, Jeffrey E.
• Application Number:
  US07/618,882
• Time in Patent Office: 1,049 Days
• Field of Search: 424/85.8, 530/350, 530/387, 530/389, 530/402, 530/812, 530/815, 530/391.7, 530/391.9, 530/406, 530/410, 514/2, 514/12, 526/273, 526/289, 568/41, 568/494, 568/613, 568/623, 568/57, 528/421, 528/380, 106/287.23, 106/287.24, 106/287.25, 106/287.26, 106/287.32, 525/512, 525/513, 525/515
• US Class Current: 530/391.9
• CPC Class Codes: C07C 323/22 containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
• CPC Class Codes: C07C 47/198 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07K 1/1077 by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids

Abstract

A new polyethylene glycol derivative (PEG) having the property of not being destroyed by water and also being able to retain reactivity in water and selectively react with amine groups. Also provided is a process for modifying organic or polymer surfaces in water by connecting PEG derivatives to exposed amine groups which provides a process whereby there is efficient linking to organic or polymer surfaces in water by use of the PEG derivatives.

Claims

1. A compound, as described by formula (I):

##STR3## wherein R₁ and R₃ each independently consist of an element selected from the group consisting of ##STR4## R₄ --N═

CH, and R₄ --NH--CH₂, wherein R₄ is an antibody; and

wherein X is selected from elements of the group consisting of O, and S; and

wherein R₂ is a C₁ to C₆ alkyl, or H, and;

wherein n is an integer, and n less than 10,000, and m is an integer selected from the group consisting of 2, 3, 4, 5, or 6.

2. A compound, as recited in claim 1, wherein R₁ and R₃ are ##STR5## X is an element selected from the group consisting of O and S, and R₂ is H, m=2 or 3.

3. A composition comprising a compound as recited in any of claims 1 or 2, further comprising water.

4. A compound, as recited in any one of claims 1, or 2, wherein n is between 10 and 1,000.

5. A process for amine modifications comprising the steps of:

preparing an amine comprising substance in a solution and adding a compound, I, ##STR6## wherein X=O or S, n<

10,000, and R₂ is a C₁ to C₆ alkyl, or H, and m is an integer selected from an element of the group consisting of 1, 2, 3, 4, 5, or 6.

6. A process for amine modification as recited in claim 5, further comprising the steps of:

waiting for a period of time sufficient for said compound to react with said amine comprising substance to form a final product;

separating said product from unreacted substance.

7. A process for amine modification, as recited in claim 5 or 6, wherein said amine comprising substance is essentially a protein.

8. A process for amine modification, as recited in claim 5 or 6, wherein said solution is water based.

9. A process for amine modification, as recited in claim 11 or 12, wherein said solution is buffered and contains enough reducing agent to reduce imine bonds occurring in an intermediate product of said amine comprising and said compound.

10. A process for amine modification, as recited in claim 9, wherein said solution is borate buffered with a pH between 8 and 10, and said reducing agent is cyanoborohydride.

11. A process for amine modification, as recited in claim 5 or 6, wherein said solution is at a temperature between 0 and 100°

C.

12. A process for amine modification, as recited in claim 5 or 6, wherein said compound in said solution is present with said amine comprising substance in said solution in a weight ratio of between 1:

1 and 10;

1.

13. A process for amine modification, as recited in claim 5 or 6, wherein the density of said amine comprising substance in solution is less than 100 grams per liter.

14. A process for amine modification, as recited in claim 7, wherein said protein is an antibody.

15. A process for amine modification, as recited in claim 5 or 6, further comprising the steps of:

then contacting an aminated surface with said solution;

then contacting said surface with a second solution which contains ##STR7## wherein X is selected from an element of the group consisting of O, and S, and n<

10,000, and R₂ is a C₁ to C₆ alkyl, or H, and m is an integer selected from an element of the group consisting of 2, 3, 4, 5 or 6, and R₃ is selected from an element of the group of ##STR8## and R₄ --NH--CH₂, wherein R₄ is selected from an element of the group consisting of organic compounds.

16. A process for amine modification, as recited in claim 6, wherein said separating is accomplished by dialysis against a phosphate buffered saline.

17. A process for amine modification, as recited in claim 16, wherein said amine comprising substance is an anti-alkaline phosphatase.

18. A process for amine modification, as recited in claim 16, wherein said substance is an anti-human RBC.

19. A process for amine modification as recited in claim 5 or 6, further comprising the steps of, then adding a second solution to said first solution wherein said second solution contains a second substance which comprises at least one amino group.