Electrochemically degradable polymers

• US 8,834,901 B2
• Filed: 10/14/2005
• Issued: 09/16/2014
• Est. Priority Date: 10/14/2004
• Status: Expired due to Fees

• Current Assignee: Trustees of Tufts College
• Original Assignee: Trustees of Tufts College
• Inventors: d'Alarcao, Marc, Calias, Pericles
• Primary Examiner(s): Shen, Wu-Cheng Winston
• Assistant Examiner(s): CORNET, JEAN P
• Application Number:
  US11/665,234
• Publication Number:
  US 20090024074A1
• Time in Patent Office: 3,259 Days
• Field of Search: 514/772.7, 514/772.4, 604/20, 424/426, 528/220, 526/312
• US Class Current: 424/400
• CPC Class Codes: A61K 41/00 Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
• CPC Class Codes: A61K 47/32 Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers , poly(meth)acrylates, or polyvinyl pyrrolidone
• CPC Class Codes: A61K 47/34 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers A61K47/10 takes precedence
• CPC Class Codes: A61K 47/38 Cellulose; Derivatives thereof
• CPC Class Codes: A61K 9/0009 involving or responsive to electricity, magnetism or acoustic waves; Galenical aspects of sonophoresis, iontophoresis, electroporation or electroosmosis microelectromechanical systems A61K9/0097
• CPC Class Codes: C08F 8/50 Partial depolymerisation

Abstract

The present invention discloses polymeric materials that incorporate a modified quinone moiety, either to cross-link the polymer or as a monomeric unit of the polymer. These polymeric materials can be efficiently degraded through electrochemical reduction of the quinone leading to rapid hydrolysis of the pendant chemical groups and degradation of the polymer. Quinone-containing compositions and methods of producing electrochemically degradable polymers are disclosed. The methods and compositions of the present invention can be used in a wide variety of applications, including, but not limited to, drug delivery, tissue regeneration, biomedical implants, and electronic systems.

Claims

1. An electrically-degradable polymer comprising:

polymer moieties comprising monomeric units, and

a quinone moiety, which is a crosslinking agent between non-terminal monomeric units in the polymer moieties, and the quinone moiety has the formula;

2. The electrically-degradable polymer moiety of claim 1, wherein the polymer further comprises monomers selected from styrene, acrylates, methacrylates, 1,3-butadiene, isoprene, 2-vinylpyridine, ethylene oxide, acrylonitrile, methyl vinyl ketone, alpha-cyanoacrylate vinylidene cyanide, propylene, butene, isobutylene, phosphorus acid, phosphonous acid, phosphinous acid, phosphoric acid, phosphonic acid, phosphinic acid, methylene bis(phosphonic acid), poly(vinylphosphonic acid), aziridine, spermine, cadaverine, and putrescine.

3. The electrically-degradable polymer moiety of claim 1, wherein the polymer is capable of degrading upon exposure to a change in electric potential of at least 0.05 V.