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Claims for Patent: 6,409,990

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Claims for Patent: 6,409,990

Title: Macromolecular carrier for drug and diagnostic agent delivery
Abstract:New macromolecular carriers for drugs and diagnostic agents are described that make use of the chemical attachment of new leashes to oligomeric backbone structures. The synthesis of these leashes and their facile creation, reaction and conjugation with chelators and ligands makes them ideal candidates for use in medicine, and especially diagnostics.
Inventor(s): Vera; David R. (San Diego, CA)
Assignee: The Regents of the University of California (Oakland, CA)
Application Number:09/569,466
Patent Claims: 1. A carrier molecule comprising:

a backbone, wherein said backbone is dextran;

wherein said backbone having affixed thereto a plurality of groups having structure --O(CH.sub.2).sub.3 S(CH.sub.2).sub.2 NH.sub.2 ;

wherein said carrier is water soluble, non-toxic to humans and essentially cross-link free; and

comprises at least one additional chemical group conjugated to the amino group of at least one said groups having the structure --O(CH.sub.2).sub.3 S(CH.sub.2).sub.2 NH.sub.2.

2. The molecule of claim 1 produced by the reaction of an allyl group with aminoethanethiol.

3. The molecule of claim 1 wherein said at least one additional chemical group is selected from the group consisting of chelators, receptor ligands, enzymatic substrates, nucleic acids, peptides, polysaccharides, radiosensitizers, radioprotectors, antiviral agents and dyes.

4. The molecule of claim 3 wherein said at least one additional group is a chelator selected from the group consisting of tetraazacyclododecanetetraacetic acid (DOTA), mercaptoacetylglycylglycyl-glycine (MAG3), and diethylenetriamine pentaacetic acid (DTPA).

5. The molecule of claim 3 wherein said at least one additional group is a chelator capable of binding an atom selected from the group consisting of radioactive atoms, absorbing elements, and paramagnetic atoms.

6. The molecule of claim 5 wherein said molecule is useful for sentinel node imaging.

7. The molecule of claim 5 wherein said chelator is bound to gadolinium.

8. The molecule of claim 5 wherein said chelator is bound to ytterbium.

9. The molecule of claim 5 wherein said chelator is bound to Technetium-99m (Tc-99m).

10. The molecule of claim 5 wherein said chelator is bound to indium.

11. The molecule of claim 3 wherein said at least one additional group is a receptor ligand selected from the group consisting of mannose, galactose, monosaccharides, polysaccharides and peptides.

12. A magnetic resonance imaging (MRI) agent synthesized from the molecule of claim 1.

13. A computed tomography (CT) agent synthesized from the molecule of claim 1.

14. A method of producing a substantially cross-link-free carrier molecule having a plurality of amino terminated leashes, comprising:

providing a backbone molecule having a plurality of hydroxyl groups, allylating at least a portion of said hydroxyl groups on said backbone molecule to produce an allyl derivative of said backbone;

reacting said allyl groups of said allyl derivative with a compound comprising an amino terminus and a second terminus, said second terminus reactive with said allyl groups of said allyl derivative;

reacting said allyl derivative with said compound to produce a substantially cross-link-free carrier molecule having a plurality of amino terminated leashes wherein each leash consists of --O(CH.sub.2).sub.3 S(CH.sub.2).sub.2 NH.sub.2 ; and

wherein each leash comprises at least one additional chemical group conjugated to an amino group of each leash.

15. The method of claim 14 wherein said compound is aminoethanethiol.

16. The method of claim 15 further comprising conjugating said amino terminated leashes with at least one member selected from the group consisting of chelators, receptor ligands, enzymatic substrates, nucleic acids, peptides, polysaccharides, monosaccharides, radiosensitizers, radioprotectors, and dyes.

17. The method of claim 16 wherein said at least one member is a chelator selected from the group consisting of DOTA, MAG3, and DTPA, and wherein said receptor ligand is selected from the group consisting of mannose, galactose, monosaccharides, polysaccharides and peptides.

18. The method of claim 17 further comprising adding an atom having an affinity for chelators, said atom selected from the group consisting of radioactive atoms, absorbing elements, and paramagnetic atoms.

19. The method of claim 18 further comprising using said conjugated substantially cross-link-free carrier molecule in a diagnostic procedure.

20. The method of claim 19 wherein said diagnostic procedure is sentinel node imaging.

21. The method of claim 16 further comprising the use of said conjugated substantially cross-link-free carrier molecule in a therapeutic application.

22. An agent synthesized using the method of claim 21 wherein said backbone or backbone molecule is dextran.

23. An MRI agent synthesized using the method of claim 14.

24. A CT agent synthesized using the method of claim 14.

25. A sentinel node detection agent made according to the method of claim 14 and further comprising a receptor substrate, a chelator, and a radioactive atom.

26. The sentinel node detection agent of claim 25 wherein said chelator is selected from the group consisting of DOTA, DTPA and MAG3.

27. The sentinel node detection agent of claim 25 wherein said receptor substrate is mannose.

28. The sentinel node detection agent of claim 27 wherein said radioactive atom is Tc-99m and said chelator is selected from the group consisting of DOTA, DTPA and MAG3.

29. The sentinel node detection agent of claim 25 wherein said backbone is a polysaccharide.

30. The sentinel node detection agent of claim 29 wherein said polysaccharide is a dextran.

31. The molecule of claim 5 wherein said chelator is bound to dysprosium.
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