Enhanced Functionalization of Carbon Nanoparticles for Biomedical Applications


The invention pertains to methods of increasing the density of carboxylic acids on the surface of a carbon nanoparticle that can be functionalized with biologically relevant molecules, such as antibodies or peptides, for biomedical applications. Advantageously, the method could increase functionalization of a nanoparticle by at least about 1x107 functional groups/g of nanoparticle. The method includes contacting an oxygen-containing functional group on a surface of a carbon nanoparticle with a reducing agent to provide a hydroxyl group; reacting the hydroxyl group with a diazoacetate ester in the presence of a transition metal catalyst to provide an ester and then cleaving the ester to provide a carboxylic acid group. The carboxylic acid can further be secondarily functionalized to an acyl chloride, an amide, pegylated, a biotinylate, a folate, a thiol, a maleimide, an active ester, an amine, a chelated gadolinium, an azide, an alkyne, a protein tag, or a dendrimer. Examples of notable nanoparticles that can be derivatized using this method include carbon nanoparticles such as carbon nanotubes, fullerenes, graphenes, graphene oxides, and nanodiamonds; with or without fluorescent properties. Fluorescent nanoparticles are of particular interest for functionalization as they are applicable to both research and diagnostic applications and can be visualized through microscopy.

Potential Commercial Applications: Competitive Advantages:
  • Imaging
  • Therapeutics
 
  • Higher degree of functionalization for carbon nanoparticles


Inventors:

Keir Neuman (NHLBI)  ➽ more inventions...

Rolf Swenson (NHLBI)  ➽ more inventions...

Ganesh Shenoy (NHLBI)  ➽ more inventions...

Chandrasekhar Mushti (NHLBI)  ➽ more inventions...


Intellectual Property:
US Application No. 62/402,339
PCT Application No. PCT/US2017/054351
US Application No. 16/336,709

Publications:
Mochalin VN, et al. PMID 22179567
Aller E, et al. DOI: 10.1021/jo00119a023
Huang J, et al. PMID 22222582
Nystrom RF, Brown WG. DOI: 10.1021/ja01197a060
Nystrom RF, Brown WG. DOI: 10.1021/ja01202a082
Hoehnel S, Lutolf MP. PMID 26079967
Chang BM, et al. DOI: 10.1002/adfm.201301075
Moon WK, et al. PMID 12757377
Fu CC, et al. PMID 17213326

Licensing Contact:
Michael Shmilovich, J.D.
Email: shmilovm@mail.nih.gov
Phone: 301-435-5019

OTT Reference No: E-207-2016-0
Updated: Oct 13, 2016