Cationic polymers for antimicrobial applications and delivery of bioactive materials

• US 8,709,466 B2
• Filed: 12/21/2011
• Issued: 04/29/2014
• Est. Priority Date: 03/31/2011
• Status: Expired due to Fees

• Current Assignee: Agency For Science Technology and Research, International Business Machines Corporation
• Original Assignee: Agency For Science Technology and Research, International Business Machines Corporation
• Inventors: Coady, Daniel Joseph, Engler, Amanda Catherine, Fukushima, Kazuki, Hedrick, James Lupton, Tan, Jeremy Pang Kern, Yang, Yi Yan
• Primary Examiner(s): Wax, Robert A
• Assistant Examiner(s): WORSHAM, JESSICA N
• Application Number:
  US13/333,930
• Publication Number:
  US 20120251608A1
• Time in Patent Office: 860 Days
• US Class Current: 424/423
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A01N 37/44 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
• CPC Class Codes: A61K 48/0041 the non-active part being polymeric
• CPC Class Codes: C08G 83/004 After treatment of dendrimers
• CPC Class Codes: C12N 15/88 using microencapsulation, e.g. using amphiphile liposome vesicle

Abstract

A cationic star polymer is disclosed of the general formula (1):
I′P′]_w′  (1),
wherein w′ is a positive number greater than or equal to 3, I′ is a dendritic polyester core covalently linked to w′ independent peripheral linear cationic polymer chains P′. Each of the chains P′ comprises a cationic repeat unit comprising i) a backbone functional group selected from the group consisting of aliphatic carbonates, aliphatic esters, aliphatic carbamates, aliphatic ureas, aliphatic thiocarbamates, aliphatic dithiocarbonates, and combinations thereof, and ii) a side chain comprising a quaternary amine group. The quaternary amine group comprises a divalent methylene group directly covalently linked to i) a positive charged nitrogen and ii) an aromatic ring.

Claims

1. A cationic graft polymer of formula (1):

I′

P′

]_w′

 

 

(1),

wherein

w′

is a positive number greater than or equal to 3,

I′

is a core comprising a multivalent linear aliphatic polycarbonate comprising carbonate repeat units,

the cationic graft polymer comprises w′

independent peripheral monovalent cationic polymer chains P′

, wherein each of the chains P′

is linked to a respective one of the carbonate repeat units of I′

, and

each of the chains P′

is a homopolymer of a cationic repeat unit selected from the group consisting of

2. The cationic graft polymer of claim 1, wherein I′

is a multivalent linear aliphatic polyestercarbonate.

3. The cationic graft polymer of claim 1, wherein I′

is free of carboxylic esters of phenolic alcohols.

4. The cationic graft polymer of claim 1, wherein the cationic graft polymer is biocompatible and/or enzymatically biodegradable.

5. A method of forming the cationic graft polymer of claim 1, comprising:

forming a mixture containing i) an organocatalyst, ii) an optional accelerator, iii) a solvent, iv) a cyclic carbonate monomer having the structure;

6. The method of claim 5, wherein the initiator is a linear aliphatic polyestercarbonate comprising 3 or more side chain nucleophilic groups capable of initiating a ring opening polymerization (ROP).

7. The method of claim 5, wherein the tertiary amine is TMEDA.

8. A method of killing a microbe comprising contacting the microbe with the cationic polymer of claim 1.

9. An injectable composition comprising an aqueous mixture of the cationic polymer of claim 1.

10. A method of treating a cell comprising contacting the cell with a composition comprising i) the cationic polymer of claim 1 and ii) a gene and/or a drug.

11. An article, comprising the cationic graft polymer of claim 1 disposed on a surface of a medical device.

12. The article of claim 11, wherein the medical device is selected from the group consisting of swabs, catheters, sutures, stents, bedpans, gloves, facial masks, absorbent pads, absorbent garments, internal absorbent devices, insertable mechanical devices, wound dressings, and surgical instruments.

13. A cationic graft polymer comprising i) a multivalent linear aliphatic polycarbonate core I′

comprising 3 or more side chains and ii) 3 or more independent monovalent cationic polymer chains P′

, wherein each of the side chains is linked to a respective end unit of one of the polymer chains P′

, each of the polymer chains P′

is an independent homopolymer of a cationic repeat unit selected from the group consisting of

14. The cationic polymer of claim 13, wherein the core I′

is a linear aliphatic polyestercarbonate comprising 3 or more side chains.