Oxidized cationic polysaccharide-based polymer tissue adhesive for medical use
First Claim
1. A kit comprising:
- a) at least one oxidized polysaccharide containing aldehyde groups and amine groups, wherein said amine groups are not primary amine groups, having a weight-average molecular weight of about 1,000 to about 1,000,000 Daltons, said oxidized polysaccharide having an equivalent weight per aldehyde group of about 90 to about 1500 Daltons and an amine substitution level of about 5% to about 50%; and
b) at least one water-dispersible, multi-arm amine wherein at least three of the arms are terminated by a primary amine group, wherein the multi-arm amine has a number-average molecular weight of about 450 to about 200,000 Daltons.
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Abstract
A tissue adhesive formed by reacting an oxidized cationic polysaccharide containing aldehyde groups and amine groups with a multi-arm amine is described. The oxidized cationic polysaccharide-based polymer tissue adhesive may be useful for medical applications including wound closure, supplementing or replacing sutures or staples in internal surgical procedures such as intestinal anastomosis and vascular anastomosis, ophthalmic procedures, drug delivery, anti-adhesive applications and as a bulking agent to treat urinary incontinence. Additionally, due to the presence of the positively charged amine groups on the oxidized polysaccharide, the polymer tissue adhesive disclosed herein may promote wound healing and blood coagulation, and may possess antimicrobial properties.
87 Citations
25 Claims
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1. A kit comprising:
- a) at least one oxidized polysaccharide containing aldehyde groups and amine groups, wherein said amine groups are not primary amine groups, having a weight-average molecular weight of about 1,000 to about 1,000,000 Daltons, said oxidized polysaccharide having an equivalent weight per aldehyde group of about 90 to about 1500 Daltons and an amine substitution level of about 5% to about 50%; and
b) at least one water-dispersible, multi-arm amine wherein at least three of the arms are terminated by a primary amine group, wherein the multi-arm amine has a number-average molecular weight of about 450 to about 200,000 Daltons. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8)
- a) at least one oxidized polysaccharide containing aldehyde groups and amine groups, wherein said amine groups are not primary amine groups, having a weight-average molecular weight of about 1,000 to about 1,000,000 Daltons, said oxidized polysaccharide having an equivalent weight per aldehyde group of about 90 to about 1500 Daltons and an amine substitution level of about 5% to about 50%; and
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9. A dried hydrogel product formed by a process comprising the steps of:
- a) reacting in a solvent (i) at least one oxidized polysaccharide containing aldehyde groups and amine groups, wherein said amine groups are not primary amine groups, having a weight-average molecular weight of about 1,000 to about 1,000,000 Daltons, said oxidized polysaccharide having an equivalent weight per aldehydes group of about 90 to about 1500 Daltons and an amine substitution level of about 5% to about 50%;
with (ii) at least one water-dispersible, multi-arm amine wherein at least three of the arms are terminated by a primary amine group, wherein the multi-arm amine has a number-average molecular weight of about 450 to about 200,000 Daltons to form a hydrogel; and
b) treating the hydrogel to remove at least a portion of said solvent to form the dried hydrogel. - View Dependent Claims (10, 11, 14, 23, 24, 25)
- a) reacting in a solvent (i) at least one oxidized polysaccharide containing aldehyde groups and amine groups, wherein said amine groups are not primary amine groups, having a weight-average molecular weight of about 1,000 to about 1,000,000 Daltons, said oxidized polysaccharide having an equivalent weight per aldehydes group of about 90 to about 1500 Daltons and an amine substitution level of about 5% to about 50%;
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12. A composition for coating an anatomical site, the composition comprising the reaction product of:
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a) at least one oxidized polysaccharide containing aldehyde groups and amine groups, wherein said amine groups are not primary amine groups, having a weight-average molecular weight of about 1,000 to about 1,000,000 Daltons, said oxidized polysaccharide having an equivalent weight per aldehyde group of about 90 to about 1500 Daltons and an amine substitution level of about 5% to about 50%; and b) at least one water-dispersible, multi-arm amine wherein at least three of the arms are terminated by a primary amine group, wherein the multi-arm amine has a number-average molecular weight of about 450 to about 200,000 Daltons.
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13. A composition for bonding at least two anatomical sites together, the composition comprising the reaction product of:
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a) at least one oxidized polysaccharide containing aldehyde groups and amine groups, wherein said amine groups are not primary amine groups, having a weight-average molecular weight of about 1,000 to about 1,000,000 Daltons, said oxidized polysaccharide having an equivalent weight per aldehyde group of about 90 to about 1500 Daltons and an amine substitution level of about 5% to about 50%; and b) at least one water-dispersible, multi-arm amine wherein at least three of the arms are terminated by a primary amine group, wherein the multi-arm amine has a number-average molecular weight of about 450 to about 200,000 Daltons.
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15. A method for applying a coating to an anatomical site on tissue of a living organism, the method comprising applying to the site:
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a) at least one oxidized polysaccharide containing aldehyde groups and amine groups, wherein said amine groups are not primary amine groups, having a weight-average molecular weight of about 1,000 to about 1,000,000 Daltons, said oxidized polysaccharide having an equivalent weight per aldehyde group of about 90 to about 1500 Daltons and an amine substitution level of about 5% to about 50%;
followed byb) at least one water-dispersible, multi-arm amine wherein at least three of the arms are terminated by a primary amine group, wherein the multi-arm amine has a number-average molecular weight of about 450 to about 200,000 Daltons;
or applying (b) followed by (a); andmixing (a) and (b) on the site;
orpremixing (a) and (b) and applying the resulting mixture to the site;
orapplying (a) and (b) simultaneously to the site. - View Dependent Claims (16, 17, 18)
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19. A method for bonding at least two anatomical sites together comprising applying to at least one of the at least two anatomical sites:
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a) at least one oxidized polysaccharide containing aldehyde groups and amine groups, wherein said amine groups are not primary amine groups, having a weight-average molecular weight of about 1,000 to about 1,000,000 Daltons, said oxidized polysaccharide having an equivalent weight per aldehyde group of about 90 to about 1500 Daltons and an amine substitution level of about 5% to about 50%;
followed byb) at least one water-dispersible, multi-arm amine wherein at least three of the arms are terminated by a primary amine group, wherein the multi-arm amine has a number-average molecular weight of about 450 to about 200,000 Daltons;
or applying (b) followed by (a); andmixing (a) and (b) on the at least one site;
orpremixing (a) and (b) and applying the resulting mixture to the at least one site;
orapplying (a) and (b) simultaneously to the at least one site; and contacting the at least two anatomical sites together. - View Dependent Claims (20, 21, 22)
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Specification