Method of inhibiting vertebrate collagenase activity using peptide hydroxamic acid derivatives

• US 4,720,486 A
• Filed: 01/07/1987
• Issued: 01/19/1988
• Est. Priority Date: 10/18/1985
• Status: Expired due to Term

• Current Assignee: Monsanto Company (Bayer AG)
• Original Assignee: Monsanto Company (Bayer AG)
• Inventors: Spilburg, Curtis A., Moore, William M.
• Primary Examiner(s): Phillips, Delbert R.
• Assistant Examiner(s): Nutter, Nathan M.
• Application Number:
  US07/001,265
• Time in Patent Office: 377 Days
• Field of Search: 514/18, 525/54.1
• US Class Current: 514/17.2
• CPC Class Codes: C07K 5/0823 and Pro-amino acid; Derivatives thereof
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

Novel peptide hydroxamic acid derivatives having useful collagenase inhibitory activity and capable of forming affinity resins for the purification of vertebrate collagenase are defined by the following structural formula:

R--Pro--Leu--Gly--NHOH

wherein R=H or N-protecting group or agarose.

Claims

1. A method of inhibiting vertebrate collagenase activity comprising treating a vertebrate collagenase-containing substrate with a collagenase inhibitory effective amount of a peptide hydroxamic acid derivative having the following structural formula:

space="preserve" listing-type="equation">R--Pro--Leu--Gly--NHOH

wherein R=H or N-protecting group or agarose.

2. The method of claim 1 in which the collagenase-containing substrate is human synovial collagenase.

3. The method of claim 1 in which the collagenase-containing substrate is human skin fibroblast collagenase.

4. A method of isolating vertebrate collagenase comprising treating a vertebrate collagenase-containing substrate with an affinity resin comprising agarose covalently coupled to the peptide hydroxamic acid derivative Pro--Leu--Gly--NHOH.