Ligand functionalized polymers

Abstract

Ligand functionalized substrates, methods of making ligand functionalized substrates, and methods of using functionalized substrates are disclosed.

1 .- 23 . (canceled) 
     
     
         24 . A complex comprising:
 a) a water soluble or water-dispersible aminopolymer functionalized with pendent or catenary guanidinyl groups; and   b) a neutral or negatively charged target biological species derived from a cell culture or fermentation process.   
     
     
         25 . The complex of  claim 24 , wherein the aminopolymer functionalized with pendent or catenary guanidinyl groups is of the formula: 
       
         
           
           
               
               
           
         
       
       wherein
 R 2  is a H, C 1 -C 12  alkyl, C 5 -C 12  (hetero)aryl, or a residue of the polymer chain; 
 each R 3  is independently H, C 1 -C 12  alkyl, or C 5 -C 12  (hetero)aryl, 
 each R 4  is H, C 1 -C 12  alkyl or alkylene, C 5 -C 12  (hetero)aryl or (hetero)arylene, cyano, or —C(═NH)—N(R 2 )-Polymer, 
 Polymer is the aminopolymer chain; and 
 n is 1 or 2. 
 
     
     
         26 . The complex of  claim 24 , wherein said biomacromolecules are selected from proteins, enzymes, nucleic acids, and endotoxins. 
     
     
         27 . The complex of  claim 24 , wherein said biological species is selected from bacteria, viruses, cells, cell debris, and spores. 
     
     
         28 . The complex of  claim 24 , wherein the amino polymer is selected from the group consisting of polyethylenimine, polylysine, polyaminoamides, polyallylamine, polyvinylamine, polydimethylamine-epichlorohydrin-ethylenediamine, polyaminosiloxanes and dendrimers formed from polyamidoamine (PAMAM) and polypropylenimine. 
     
     
         29 . The complex of  claim 24 , wherein 0.1 to 100 mole percent of the available amino groups of the aminopolymer are functionalized with guanidinyl groups. 
     
     
         30 . The complex of  claim 24 , wherein the guanidinyl groups of the functionalized aminopolymer are pendent from the polymer chain. 
     
     
         31 . The complex of  claim 24 , wherein guanidinyl groups of the functionalized aminopolymer are in the aminopolymer chain. 
     
     
         32 . The complex of  claim 27 , wherein the cells are selected from archaea, bacteria, and eucaryota. 
     
     
         33 . The complex of  claim 24 , wherein the amount of ligand-functionalized polymer relative to the amount of target biological species is 0.01% to 100% by weight. 
     
     
         34 . The complex of  claim 24 , wherein a portion of the amino groups of the ligand-functionalized polymer further comprise alkyl or acyl groups. 
     
     
         35 . The complex of  claim 24 , wherein the functionalized aminopolymer is crosslinked. 
     
     
         36 . The complex of  claim 24 , wherein the functionalized aminopolymer is uncrosslinked. 
     
     
         37 . A method of separating a target biological species from a fluid comprising the target biological species comprising:
 a. contacting the fluid with a suspension or solution of water-soluble or water-dispersible aminopolymer functionalized with pendent or catenary guanidinyl groups represented by the following general formula:   
       
         
           
           
               
               
           
         
         wherein 
         R 2  is H, C 1 -C 12  alkyl, C 5 -C 12  (hetero)aryl, or a residue of the polymer chain; 
         each R 3  is independently H, C 1 -C 12  alkyl, or C 5 -C 12  (hetero)aryl, 
         each R 4  is H, C 1 -C 12  alkyl or alkylene, C 5 -C 12  (hetero)aryl or (hetero)arylene, cyano, or —C(═NH)—N(R 2 )-Polymer, 
         n is 1 or 2; and 
         “Polymer-N(R 2 )—” is the linkage formed between an amine group of the polyamino polymer and guanylating agent; 
         b. forming a complex in the fluid that comprises the aminopolymer functionalized with guanidinyl groups and the target biological species; and 
         c. separating the complex from the fluid; 
         wherein the target biological species is selected from biomacromolecules and microbiological species and wherein the fluid is a cell culture or fermentation broth.