A New Bioorthogonal Reaction

Description:

Rapid and Efficient Bioorthogonal Ligation Reaction and Boron-Containing Heterocycles

 

“Click-Chemistry” reactions are widely used in highly diverse applications, rang-ing from diagnostics and therapeutics to polymer and materials sciences. Bioorthog-onal “click” reactions are chemical reactions that can selectively form a chemical bond in the presence of normal biomolecular functional groups. Applications of these reactions include conjugation of biomolecules with reporters, matrices, poly-mers and nanoparticles for use in targeted drug therapies, cellular and medical imag-ing, drug discovery and proteomics.

The present technology provides a bioorthogonal reaction. The reagents consist of an aromatic or heterocylic phenylboronic acid or ester that possesses a carbonyl containing functional group in the ortho- position and an alpha-effect amine. Com-bining the reagents results in very rapid dehydration reaction, forming a hydrazono or imino arylboronic acid product (A). The product from the dehydration reaction is frequently followed by a second reaction to form a heterocyclic ring that contains a boron atom, e.g., a 3,4-borazaisoquinoline (B) or a related boron-containing hetero-cycle such as a 1,2-dihydrobenzo[d][1,2,3]diazaborinin-1-uide (C).

 

The reaction generally approaches the ideal “click-chemistry” profile, with highly desirable properties such as rapid reaction at neutral pH using low concentrations of reagents and water soluble components with little to no toxicity. Control over the stability of the conjugate is accomplished by informed selection of structural features of the reactive pair

 

APPLICATIONS

 Targeted drug delivery (e.g. antibody-drug conjugates )

 Preparation of imaging probes (e.g. PET)

 Functionalized nanoparticles for biomedical applications

 Biomolecule immobilization (e.g. micoarrays , biosensors)

ADVANTAGES

 Reaction occurs in minutes at neutral pH & room tempera-ture

 High water solubility and low reagent toxicity

 Tunable product stability

I.P.

U.S. Patent Application 14/694,744

 

 

INVENTOR

Dr. Susan Bane is a Professor of Organic and Biological Chemistry at Binghamton University. Her research interests include design of novel tools and probes for bio-medical applications.

Patent Information:
For Information, Contact:
Scott Hancock
Director, IP Management and Licensing
Binghamton University
(607) 777-5874
shancock@binghamton.edu
Inventors:
Susan Bane Tuttle
Özlem Dilek
Kamalika Mukherjee
Keywords:
© 2017. All Rights Reserved. Powered by Inteum