Zwitterionic materials

Details Zwitterionic materials Zwitterionic materials

1995-06-07

1997-07-08

Beck, Shrive

Coating processes

Medical or dental purpose product; parts; subcombinations;...

Implantable permanent prosthesis

4273935, B05D 302, A61L 2700

Patent

active

056458835

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to new materials which comprise a surface having pendent zwitterionic groups, processes for producing the materials, the use of compounds to provide such a material and to improve biocompatibility and to a device having such a surface. It also relates to new compounds useful in providing such materials.
Materials used in the manufacture of devices which, in use, come into contact with protein-containing or biological fluids must possess, as well as desirable physical and mechanical properties, good compatibility with protein-containing and/or biological fluids. Materials which do not possess such compatibility may for example promote the deposition of protein and, when brought into contact with blood, the activation of blood platelets which can have serious undesirable consequences such as the initiation of blood clotting. For example, materials which are used to produce contact lenses should desirably possess compatibility with the fluids in the eye which they come into contact with so as to reduce the deposition of protein upon them. Similarly, blood-contact devices, such as surgical implants and prostheses, should not lead to activation of blood platelets.
Several approaches have been used in the development of materials having good biocompatibility. One such approach has been to provide a surface having pendant groups which mimic the phospholipid zwitterionic groups which are found on the outside of cell surfaces. For example WO92/06719 and EP-A-32622 disclose natural and synthetic phospholipids which may be coated on a surface to provide improved biocompatibility and, in particular, haemocompatibility. Such phospholipids contain a phosphoryl choline head group, or a close analogue thereof. Further examples of materials which contain, at their surface, such head groups may be found in EP-A-157469, WO-A-86/02933, WO-A-88/00956, WO-A-91/13639, WO-A-92/07885, WO-A-92/07858, WO-A-92/21386 and WO-A-93/01221, and our as yet unpublished International patent application PCT/GB92/01580.
We have also found that compounds which contain such a phosphoryl choline headgroup or close analogue thereof, are able to reduce the tendency of microorganisms to adhere to and grow on surfaces. They may also be used more generally to reduce cellular adhesion at a surface. Materials which comprise such groups at their surface therefore have potentially wide utility wherever the growth of microorganisms such as bacteria, algae, yeast and fungi, particularly bacteria, occurs and is undesirable. Such compounds may therefore be used in both the medical field and also in other applications in industrial or domestic wherever it is desirable to prevent the growth of such microorganisms.
We have now found that compounds containing zwitterionic groups other than the naturally occurring phosphoryl choline groups and close analogues thereof, may also be used to improve the biocompatibility of a surface. In addition, such compounds may possess additional advantages over the use of compounds containing phosphoryl choline groups or close analogues thereof. For example, such compounds may possess improved solubility which renders them easier to treat a surface.
Accordingly, the present invention provides materials which comprise a surface having pendant zwitterionic groups Z comprising, as anion, a phosphate, sulphonate, carboxylate or phosphate-ester group or a phosphate ester group in which one or more of the ester oxygen atoms is replaced by --S--, --NH-- or by a valence bond and, as cation, an ammonium, phosphonium or sulphonium moiety, provided that where the anion is a phosphate-ester group or derivative thereof or sulphonate and the cation is a trialkyl quaternary ammonium group (the alkyl groups each containing from 1 to 4 carbon atoms) and the group linking the anion and cation moieties is an alkylene group, the alkylene group, contains at least 5, preferably at least 6, and more preferably at least 7, carbon atoms; ##STR1## in which the groups --B are the same or different and each is --CH.sub.2 -- or -

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