Bioresorbable and biocompatible compounds for surgical use

Abstract

A bioresorbable and biocompatible compound for surgical use is composed of functionalized collagen cross-linked with a glycosaminoglycan.

1 . A compound containing a functionalized collagen covalently bonded directly to a glycosaminoglycan without the use of a crosslinking agent. 
     
     
         2 . A compound as in  claim 1  wherein the functionalized collagen includes one or more reactive moieties selected from the group consisting of aldehydes, sulfones, vinylsulfones, isocyanates, and acid anhydrides. 
     
     
         3 . A compound as in  claim 1  wherein the collagen is functionalized by oxidative cleavage. 
     
     
         4 . The compounds of  claim 1  wherein the functionalized collagen includes one or more reactive moieties selected from the group consisting of —CO 2 N(COCH 2 ) 2 , —CO 2 N(COCH 2 ) 2 , —CO 2 H, —CHO, —CHOCH 2 , —N═C═O, —SO 2 CH═CH 2 , —N(COCH) 2 , and —S—S—(C 5 H 4 N). 
     
     
         5 . The compound of  claim 1  wherein the glycosaminoglycan is selected from the group consisting of dermatan surfate, hyaluronic acid, chondroitin sulfate, chitin, chitosan, heparin, keratan surfate, keratosulfate, deacylated hyaluronic acid and derivatives and combinations thereof. 
     
     
         6 . The compound of  claim 1  wherein the glycosaminoglycan is chitosan. 
     
     
         7 . The compound of  claim 1  wherein the glycosaminoglycan has a degree of acetylation of about 0 to about 60%. 
     
     
         8 . The compound of  claim 1  wherein the glycosaminoglycan has a degree of acetylation of about 0.5 to about 50%. 
     
     
         9 . A compound as in  claim 1  wherein the glycosaminoglycan solution includes a blend of chitosan with different degree of acetylation selected from about 0.5 to 60%. 
     
     
         10 . The compound of  claim 1  wherein the glycosaminoglycan has a molecular weight of about 164 to about 1,000,000 g/mol. 
     
     
         11 . The compound of  claim 1  wherein the glycosaminoglycan has a molecular weight of about 1500 to about 800,000 g/mol 
     
     
         12 . The compound of  claim 1  wherein the glycosaminoglycan has a polydisperity index between about 1.2 to about 1.8. 
     
     
         13 . A method of forming a bioresorbable compound comprising contacting a functionalized collagen with a glycosaminoglycan under reaction conditions under which the functionalized collagen covalently binds directly to the glycosaminoglycan without the use of a crosslinking agent. 
     
     
         14 . A method as in  claim 13  wherein the functionalized collagen includes one or more reactive moieties selected from the group consisting of aldehydes, sulfones, vinylsulfones, isocyanates, and acid anhydrides. 
     
     
         15 . A method as in  claim 13  wherein the collagen is functionalized by oxidative cleavage. 
     
     
         16 . A method as in  claim 13  wherein the functionalized collagen includes one or more reactive moieties selected from the group consisting of —CO 2 N(COCH 2 ) 2 , —CO 2 N(COCH 2 ) 2 , —CO 2 H, —CHO, —CHOCH 2 , —N═C═O, —SO 2 CH═CH 2 , —N(COCH) 2 , and —S—S—(C 5 H 4 N). 
     
     
         17 . A method as in  claim 13  wherein the glycosaminoglycan is selected from the group consisting of dermatan surfate, hyaluronic acid, chondroitin sulfate, chitin, chitosan, heparin, keratan surfate, keratosulfate, deacylated hyaluronic acid and derivatives and combinations thereof. 
     
     
         18 . A method as in  claim 13  wherein the glycosaminoglycan is chitosan. 
     
     
         19 . A method as in  claim 13  wherein the glycosaminoglycan has a degree of acetylation of about 0 to about 60%. 
     
     
         20 . A method as in  claim 13  wherein the glycosaminoglycan has a degree of acetylation of about 0.5 to about 50%. 
     
     
         21 . A method as in  claim 13  wherein the glycosaminoglycan has a molecular weight of about 164 to about 1,000,000 g/mol. 
     
     
         22 . A method as in  claim 13  wherein the glycosaminoglycan has a molecular weight of about 1500 to about 800,000 g/mol 
     
     
         23 . A method as in  claim 13  wherein the glycosaminoglycan has a polydisperity index between about 1.2 to about 1.8. 
     
     
         24 . An implant comprising a compound containing a functionalized collagen covalently bonded directly to a glycosaminoglycan without the use of a crosslinking agent. 
     
     
         25 . An implant as in  claim 24  comprising a sponge containing said compound. 
     
     
         26 . An implant as in  claim 24  comprising a textile containing said compound. 
     
     
         27 . An implant as in  claim 24  comprising a hydrogel containing said compound. 
     
     
         28 . An implant as in  claim 24  comprising threads containing said compound. 
     
     
         29 . An implant as in  claim 24  comprising a non knitted, non woven composite containing said compound. 
     
     
         30 . An implant as in  claim 24  comprising a film containing said compound. 
     
     
         31 . An implant as in  claim 24  comprising a mesh coated with a composition containing said compound. 
     
     
         32 . A composition comprising a compound containing a functionalized collagen covalently bonded directly to a glycosaminoglycan without the use of a crosslinking agent.