Disulfide-containing dendritic polymers
First Claim
1. A dendritic polymer having a core containing a disulfide moiety and at least two dendrons emanating from the core, each dendron having at least two terminal groups.
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Abstract
Dendritic polymers containing disulfide functional groups which are essentially inert under non-reducing conditions, but which form sulfhydryl groups upon being subjected to a reducing agent are prepared by synthesizing dendritic polymers having a core with a disulfide linkage or by reacting a dendritic polymer with a molecule containing a disulfide linkage and reactive terminal groups. In one aspect of the invention, dendritic polymers having a single disulfide functional group at the core are provided. The single disulfide group at the core can be reduced to form two sulfhydryl groups to which other molecules, such as proteins, oligonucleotides, peptides, hormones, other dendritic polymers, non-dendritic polymers, etc., can be bound. Applications for the disulfide functionalized dendritic polymers include formation of differentiated dendrimers, formation of binding reagents for diagnostics, drug delivery, gene therapy and magnetic resins imaging, and in the preparation of self-assembled dendrimer monolayers on a quartz crystal resonators to provide dendrimer-modified electrodes which are useful for detecting various ions or molecules. In another aspect of the invention, dendritic polymers having sulfhydryl terminals are provided. The sulfhydryl terminated dendritic polymers can be used to prepare stable, curable resins composition which can undergo cross linking when subjected to a reducing agent.
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Citations
49 Claims
- 1. A dendritic polymer having a core containing a disulfide moiety and at least two dendrons emanating from the core, each dendron having at least two terminal groups.
- 6. A dendritic polymer having a core and a plurality of dendrons emanating from the core, each of the dendrons having branch arms which include a disulfide moiety which is essentially inert under non-reducing conditions, but which when subjected to a reducing agent will react with the reducing agent to form a dendritic polymer having sulfhydryl terminal groups.
- 8. A thin film coated substrate comprising a substrate which has been subjected to application of ions or ionizable compounds of the same charge over the surface of the substrate, and one or more layers of organic materials which in each layer contain ions of the same charge, the ions of the layer immediately adjacent the substrate having the opposite charge of the modified substrate and, in the case of further layers, each further layer having a charge opposite that of the previous layer, and at least one of the layers comprising a dendritic polymer.
- 10. A quartz crystal electrode comprising a metal coated quartz crystal electrode subjected to application of a dendritic polymer coating.
- 15. A differentiated dendritic polymer having a core with a disulfide moiety and at least two dendrons emanating from the core, each of the dendrons having at least two terminal groups, at least one of the dendrons having terminal groups that are different from those of the other dendron.
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17. A method of making a dendritic polymer having a core with a disulfide moiety and a plurality of dendrons emanating from the core, comprising:
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providing a core molecule having a disulfide moiety and a plurality of reactive terminal groups; and reacting the terminal groups of the core molecule with a plurality of dendrons, each dendron having a single reactive group which bonds to one of the reactive terminal groups of the core molecule. - View Dependent Claims (18, 19, 20)
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21. A method of making a dendritic polymer having a core with a disulfide moiety and a plurality of dendrons emanating from the core, comprising:
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providing a core molecule having a disulfide moiety and a plurality of reactive terminal groups; reacting the terminal groups of the core molecule with a first reagent to form a -1/2 generation dendrimer, each molecule of the fit reagent having at least a single reactive site which bonds with one of the reactive terminal groups of the core molecule and at least one reactive moiety which becomes a terminal reactive moiety on the -1/2 generation dendrimer; reacting each of the terminal reactive moieties on the -1/2 generation dendrimer with a second reagent to form a zero generation dendrimer, each molecule of the second reagent including at least one reactive site which bonds with a terminal reactive moiety on the -1/2 generation dendrimer and at least one reactive site which becomes a terminal reactive moiety on the zero generation dendrimer; and optionally employing additional reagents to synthesize a dendritic polymer of a desired generation. - View Dependent Claims (22, 23, 24, 25, 26)
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27. A method of making a dendritic polymer having a core and a plurality of dendrons emanating from the core, each of the dendrons having branched arms which include a disulfide moiety, comprising:
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providing a dendritic polymer having reactive terminal groups; and reacting the terminal groups of the dendritic polymer with a monomer having a disulfide moiety, each of the monomer molecules including a reactive site which bonds with one of the reactive terminal groups of the dendritic polymer. - View Dependent Claims (28, 29)
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30. A method of making a thin film coated substrate, comprising:
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providing a substrate which has been modified by application of ions or ionizable compounds of the same charge over the surface of the substrate; and applying one of more layers made of organic materials, the organic materials in each layer having ions of the same charge, the organic materials being applied from a solution of the organic materials to the substrate which has been modified, the organic material for the first layer having ions of the opposite charge relative to the charge of the ions of the substrate which has been modified and, in the case of further layers, each further layer containing ions of opposite charge relative to the charge of the ions in the previous layer, at least one of the layers comprising a dendritic polymer. - View Dependent Claims (31)
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32. A method of forming a differentiated dendritic polymer, comprising:
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providing a first dendritic polymer having a core with a disulfide moiety and at least two dendrons emanating from the core, each of the dendrons having at least two terminal groups; providing a second dendritic polymer having a core with a disulfide moiety and a plurality of dendrons emanating from the core, each of the dendrons of the second dendritic polymer having at least two terminal groups; combining and subjecting the first and second dendritic polymers to reducing conditions to form a mixture of two different types of dendritic molecules, each having a single reactive sulfhydryl group; and subjecting the mixture to aerobic, oxidizing conditions to form a mixture containing the first and second dendritic polymers, and a differentiated dendritic polymer comprised of a part of each of the original first and second dendritic polymers. - View Dependent Claims (33)
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34. A gel comprised of crosslinked dendritic polymers, comprising:
dendritic polymers, each having sulfhydryl terminal groups which react with sulfhydryl terminal groups of another dendritic polymer to form a crosslinked gel. - View Dependent Claims (35, 36, 37, 38, 39)
- 40. A dendritic polymer conjugate comprising a dendritic polymer having a sulfhydryl group and a first carried material having a sulfhydryl-reactive group, conjugated to the dendritic polymer at the sulfhydryl group.
Specification