Biocompatible surfaces and a method for their preparation

A method for masking biologically reactive sites on the surface of a synthetic polymeric or tissue derived prothesis comprising

• reacting nucleophilic moieties on a surface of a polymeric or tissue-derived prosthesis with a masking molecule having a formula:
• wherein
• A and B are sugars forming a repeating disaccharide unit in which A and B are joined covalently by a glycosidic bond between C-1 of sugar A and C-3 or C-4 of sugar B, and the repeating disaccharide units are joined covalently to form an oligosaccharide by a glycosidic bond between C-1 of sugar B of a first disaccharide unit and C-3 or C-4 of sugar A in a next successive disaccharide unit,
• B′ is a sugar at a non-reducing terminus of said oligosaccharide of ring structure identical to sugar B,
• A′ is an acyclic hexose joined covalently by a glycosidic bond between C-1 of sugar B at a terminus opposite the non-reducing terminus of said oligosaccharide and C-3 or C-4 of sugar A′,
• n is an integer from 2 to 20,
• L is an aliphatic, acyclic carbon chain which links Z′ to the 1-amino, 1-amido or 1-imino group attached to C-1 of sugar A′, the aliphatic, acyclic carbon chain containing one or more moieties selected from the group consisting of ether, thio ether, and amide;
• and
• Z′ is selected from the group consisting of an aldehyde, an activated ester of a carboxylic acid, a maleimide, an epoxide, a tosyl ester, a tresyl ester, and a halide.

A liposome composition comprising a mixture of a phospholipid and cholesterol in an aqueous phase, wherein the phospholipid has the formula:

• wherein
• FA is a fatty acid,
• Q is selected from the group consisting of choline, ethanolamine, serine, or inositol;
• A and B are sugars forming a repeating disaccharide unit in which A and B are joined covalently by a glycosidic bond between C-1 of sugar A and C-3 or C-4 of sugar B, and the repeating disaccharide units are joined covalently to form an oligosaccharide by a glycosidic bond between C-1 of sugar B of a first disaccharide unit and C-3 or C-4 of sugar A in a next successive disaccharide unit,
• B′ is a sugar at a non-reducing terminus of said oligosaccharide of ring structure identical to sugar B,
• A′ is an acyclic hexose joined covalently by a glycosidic bond between C-1 of sugar B at a terminus opposite the non-reducing terminus of said oligosaccharide and C-3 or C-4 of sugar A′,
• n is an integer from 2 to 20,
• L is an aliphatic, acyclic carbon chain which links Y to the 1-amino, 1-amido or 1-imino group attached to C-1 of sugar A′, the aliphatic, acyclic carbon chain containing one or more moieties selected from the group consisting of ether, thio ether, and amide;
• and
• Y is an acyl radical.

A compound comprising a prosthetic polymer having a polyolefinic surface and an oligosaccharide adsorbed to said polyolefinic surface by electrostatic interaction, said oligosaccharide having a formula:

• wherein
• A and B are sugars forming a repeating disaccharide unit in which A and B are joined covalently by a glycosidic bond between C-1 of sugar A and C-3 or C-4 of sugar B, and the repeating disaccharide units are joined covalently to form an oligosaccharide by a glycosidic bond between C-1 of sugar B of a first disaccharide unit and C-3 or C-4 of sugar A in a next successive disaccharide unit,
• B′ is a sugar at a non-reducing terminus of said oligosaccharide of ring structure identical to sugar B,
• A′ is an acyclic hexose joined covalently by a glycosidic bond between C-1 of sugar B at a terminus opposite the non-reducing terminus of said oligosaccharide and C-3 or C-4 of sugar A′,
• n is an integer from 2 to 20,
• L is an aliphatic, acyclic carbon chain which links Y to the 1-amino, 1-amido or 1-imino group attached to C-1 of sugar A′, the aliphatic, acyclic carbon chain containing one or more moieties selected from the group consisting of ether, thio ether, and amide;
• and
• Y is a linear n-alkyl radical having 5 to 30 carbon atoms.

A compound comprising a prosthetic polymer having a surface and an oligosaccharide adsorbed to said surface, said oligosaccharide having the formula:

• wherein
• A and B are sugars forming a repeating disaccharide unit in which A and B are joined covalently by a glycosidic bond between C-1 of sugar A and C-3 or C-4 of sugar B, and the repeating disaccharide units are joined covalently to form an oligosaccharide by a glycosidic bond between C-1 of sugar B of a first disaccharide unit and C-3 or C-4 of sugar A in a next successive disaccharide unit,
• B′ is a sugar at a non-reducing terminus of said oligosaccharide of ring structure identical to sugar B,
• A′ is an acyclic hexose joined covalently by a glycosidic bond between C-1 of sugar B at a terminus opposite the non-reducing terminus of said oligosaccharide and C-3 or C-4 of sugar A′,
• n is an integer from 2 to 20,
• L is an aliphatic, acyclic carbon chain which links Y to the 1-amino, 1-amido or 1-imino group attached to C-1 of sugar A′, the aliphatic, acyclic carbon chain containing one or more moieties selected from the group consisting of ether, thio ether, and amide;
• and
• Y is a linear perfluoronated radical having 5 to 30 carbon atoms.