Search results for "bioconjugation"

Kondrat'eva ligation: Diels-Alder-based irreversible reaction for bioconjugation.

2014

International audience; Diversification of existing chemoselective ligations is required to efficiently access complex and well-defined biomolecular assemblies with unique and valuable properties. The development and bioconjugation applications of a novel Diels-Alder-based irreversible site-specific ligation are reported. The strategy is based on a Kondrat'eva cycloaddition between bioinert and readily functionalizable 5-alkoxyoxazoles and maleimides that readily react together under mild and easily tunable reaction conditions to afford a fully stable pyridine scaffold. The potential of this novel bioconjugation is demonstrated through the preparation of fluorescent conjugates of biomolecul…

From Biocompatible to Biodegradable: Poly(Ethylene Glycol)s with Predetermined Breaking Points

2013

Poly(ethylene glycol) (PEG) is the gold standard polymer for biomedical applications. PEG is known for its biocompatibility and antifouling properties and is widely used for bioconjugation. However, like other synthetic polymers in the field, PEG is not biodegradable, limiting its use for parenteral formulations and protein conjugation to a molecular weight range with a specific upper limit (commonly 40–60 kDa) to avoid polyether accumulation in human tissue. For these biomedical applications, but also for other purposes such as cleavable hydrogels and templates for porous membranes, several routes for the insertion of in-chain biocleavable moieties, such as acetals or disulfides, into PEG …

A Versatile Grafting-to Approach for the Bioconjugation of Polymers to Collagen-like Peptides Using an Activated Ester Chain Transfer Agent

2009

DepartmentofMaterials Science and Engineering, University of Delaware, 201DuPont Hall, Newark, Delaware 19716,Received February 24, 2009Revised Manuscript Received April 24, 2009Biohybrid materials consisting of synthetic polymers andbiological moieties have gained more and more interest in therecent years.

Straightforward synthesis of bioconjugatable azo dyes. Part 2: Black Hole Quencher-2 (BHQ-2) and BlackBerry Quencher 650 (BBQ-650) scaffolds

2014

Abstract A further extension of the efficient synthetic methodology described in Part 1, to the aromatic bis-diazo scaffold of Black Hole Quencher-2 dye is presented. Bioconjugatable derivatives bearing either azido, terminal alkyne, or maleimide reactive group were easily obtained as well as the free-phenol form of BlackBerry® Quencher 650 (BBQ-650®) initially developed by Berry & Associates, Inc. Company. The efficient conjugation ability of azido- and maleimide-quenchers was demonstrated through the facile preparation of the first water-soluble and formylated BHQ-2 dyes and a FRET-based probe suitable for the in vitro/in cellulo detection of a cancer-associated protease namely urokinase-…

Amino-functional polyethers: versatile, stimuli-responsive polymers

2020

Due to the increasing demand for “smart” materials and systems e.g. for actuators, microvalves, but also for drug delivery, electrooptical devices and many other applications, multi-stimuli responsive materials such as amino-functional polymers are attracting increasing attention in recent years. The hydrophilic character and excellent biocompatibility of the polyether backbone, in combination with multi-stimuli responsive amine moieties, offer intriguing opportunities for a wide range of applications, such as bioconjugation, stimuli-responsive drug delivery and surface modification. Furthermore, the controlled introduction of amino-functionalities at the polyether backbone via copolymeriza…

Straightforward synthesis of bioconjugatable azo dyes. Part 1: Black Hole Quencher-​1 (BHQ-​1) scaffold

2014

Abstract Azo dyes are currently used to quench the fluorescence of energy donors in bioassays through Forster resonance energy transfer (FRET) phenomenon. Common examples of such dark quenchers are DABCYL and the three members of Black Hole Quencher® (BHQ) family. Yet, only carboxylic acid and phosphoramidite derivatives of such azo dyes are presently commercially available. This Letter presents a straightforward synthesis method to novel bioconjugatable quenchers derived from BHQ-1 scaffold and equipped with a reactive group being either azido, terminal alkyne, or maleimide. The potential utility of the ‘clickable’ azido and thiol-reactive derivatives was notably demonstrated through the p…

Cylindrical Brush Polymers with Polysarcosine Side Chains: A Novel Biocompatible Carrier for Biomedical Applications

2015

Cylindrical brush polymers constitute promising polymeric drug delivery systems (nanoDDS). Because of the densely grafted side chains such structures may intrinsically exhibit little protein adsorption (“stealth” effect) while providing a large number of functional groups accessible for bioconjugation reactions. Polysarcosine (PSar) is a highly water-soluble, nonionic and nonimmunogenic polypeptoid based on the endogenous amino acid sarcosine (N-methyl glycine). Here we report on the synthesis, characterization and biocompatibility of cylindrical brush polymers with either polysarcosine side chains or poly-l-lysine-b-polysarcosine side chains. The latter leads to block copolypept(o)id based…

Efficient Synthesis of 1,4,7-Triazacyclononane and 1,4,7-Triazacyclononane-Based Bifunctional Chelators for Bioconjugation (Eur. J. Org. Chem. 35/201…

2014

Efficient Synthesis of 1,4,7-Triazacyclononane and 1,4,7-Triazacyclononane-Based Bifunctional Chelators for Bioconjugation

2014

The reaction of diethylenetriamine with chloroacetaldehyde yielded a bicyclic aminal intermediate for the synthesis of 1,4,7-triazacyclononane (TACN), a macrocyclic polyamine the derivatives of which find applications as catalysts, bleaching agents, and chelators for medical imaging. This new synthetic protocol outperforms the synthetic methods described so far because it does not involve any cyclization step. Moreover, this aminal intermediate allowed access to a new family of TACN derivatives functionalized on the carbon skeleton, for example, C-aminomethyl-TACN. This novel compound is a precursor of valuable bifunctional chelating agents for nuclear medicine, in particular, for the prepa…

Recombinant nanocapsid for targeted theranostic delivery

2017

Developments in diagnostic and therapeutic delivery are trending towards molecular level targeting with nano-platforms. Targeted delivery reduces generalized distribution by localizing diagnostic and/or therapeutic (theranostic) molecules to an intended target site. The first section of this thesis proposes Hepatitis E Virus (HEV) nanocapsids as a vector to stabilize and target theranostic delivery. Derived from the capsid protein of HEV, a feco-orally transmitted virus, HEV-like particles self-assemble in to non-infectious, nanocapsids that can withstand harsh protease and pH conditions in the mucosal system. The flexible nanocapsid surface protrusion domain is amenable to substantial modi…