New reagents for photoaffinity labeling: synthesis and photolysis of functionalized perfluorophenyl azides

Keana, John F. W.; Cai, Sui Xiong

doi:10.1021/jo00298a048

Cited by 274 publications

(243 citation statements)

References 3 publications

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“…Indeed, the formation of double bonds has been reported during the oxidation of polypropylene. 31 The presence of ethers cannot be confirmed or ruled out with the present data since their expected C-O stretch in the region of 1150-1085 is obscured by a broad signal that extends from 1430 to 700 cm 21 . The broad signal might be due to significant overlap of infrared bands from chemically different ketones, carboxylic acids, etc.…”

Section: Surface Chemistry and Immobilization Of Dna On Poly(cyclic Ocontrasting

confidence: 57%

“…The formation of ketones has been reported previously for the ozone oxidation of other polymeric systems. 25 Closer inspection of the peak at 1708 cm 21 indicates that it has a strong overlapping band (2/3 the height) at 1730 cm 21 which is attributed to the formation of carboxylic acids and esters. The presence of carboxylic acids has also been corroborated by observing the characteristic resonances for carboxylate after reaction with ammonia (data not shown).…”

Section: Surface Chemistry and Immobilization Of Dna On Poly(cyclic Omentioning

confidence: 99%

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Surface modification of thermoplastics—towards the plastic biochip for high throughput screening devices

et al. 2007

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/npsi/ctrl?action=rtdoc&an=3539033&lang=en http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/ctrl?action=rtdoc&an=3539033&lang=frAccess and use of this website and the material on it are subject to the Terms and Conditions set forth at http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/jsp/nparc_cp.jsp?lang=en NRC Publications Archive Archives des publications du CNRCThis publication could be one of several versions: author's original, accepted manuscript or the publisher's version. / La version de cette publication peut être l'une des suivantes : la version prépublication de l'auteur, la version acceptée du manuscrit ou la version de l'éditeur. For the publisher's version, please access the DOI link below./ Pour consulter la version de l'éditeur, utilisez le lien DOI ci-dessous.http://dx.doi.org/10.1039/b700322fLab on Chip, 7, 2007-01-01 Microarrays have become one of the most convenient tools for high throughput screening, supporting major advances in genomics and proteomics. Other important applications can be found in medical diagnostics, detection of biothreats, drug discovery, etc. Integration of microarrays with microfluidic devices can be highly advantageous in terms of portability, shorter analysis time and lower consumption of expensive biological analytes. Since fabrication of microfluidic devices using traditional materials such as glass is rather expensive, there is great interest in employing polymeric materials as a low cost alternative that is suitable for mass production. A number of commercially available plastic materials were reviewed for this purpose and poly(methylmethacrylate) Zeonor 1060R and Zeonex E48R were identified as promising candidates, for which methods for surface modification and covalent immobilization of DNA oligonucleotides were developed. In addition, we present proof-of-concept plastic-based microarrays with and without integration with microfluidics.

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Section: Surface Chemistry and Immobilization Of Dna On Poly(cyclic Ocontrasting

confidence: 57%

Section: Surface Chemistry and Immobilization Of Dna On Poly(cyclic Omentioning

confidence: 99%

Surface modification of thermoplastics—towards the plastic biochip for high throughput screening devices

et al. 2007

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“…4-Azido-2,3,5,6-tetrafluorobenzoic acid 4 (1) (1.00 g, 4.3 mmol) was dissolved in CH 2 Cl 2 (20 mL) at 0 °C. 2,2′-Dithiodiethanol (2) (0.33 g, 2.1 mmol), N,N′-dimethylaminopyridine (DMAP, 0.05 g, 0.43 mmol), and 1,3-dicyclohexylcarbodiimide (DCC, 0.95 g, 4.6 mmol) were added to the solution, and the mixture was allowed to warm to room temperature and stirred for 12 h. After removal of the precipitated dicyclohexylurea by filtration, the reaction mixture was recovered by extraction with CH 2 Cl 2 .…”

Section: 2′-dithioethyl Bis(4-azido-2356-tetrafluorobenzoate) (3)mentioning

confidence: 99%

Photoderivatized Polymer Thin Films at Quartz Crystal Microbalance Surfaces: Sensors for Carbohydrate−Protein Interactions

Pei

et al. 2007

Anal. Chem.

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Photoderivatized polymer-coated gold surfaces have been developed following a perfluorophenylazide-based double ligation strategy. Gold-plated quartz crystal microbalance (QCM) crystals were initially covalently functionalized with a monolayer of poly(ethylene glycol) (PEG), using photo-or thermolytic nitrene formation and insertion. The polymer surfaces were subsequently used as substrates for photoinsertion of carbohydrate-derivatized photoprobes, yielding different recognition motifs for selective protein binding. The resulting robust and biocompatible sensor surfaces were applied to a flow-through QCM instrument for monitoring lectin-carbohydrate interactions in real time. The results clearly show the predicted lectin selectivity, demonstrating the applicability of the approach.Selective surface generation and functionalization form the basis for intense research in a number of diverse areas such as chemical sensors, interface engineering, and nanotechnology. A versatile method to covalent derivatization is based on the specific chemistry of arylazides. Upon thermal activation or light irradiation, the azide functionality in these structures becomes converted to a highly reactive nitrene species that readily inserts into CH and NH bonds. 1 Especially perfluorophenylazides (PFPAs), 2 which produce markedly enhanced insertion yields, have thus been used to thermo-and photochemically introduce functional groups in a range of entities, including proteins, nanostructures, and synthetic polymers. [3][4][5][6][7][8][9] The versatility of the PFPA chemistry makes it an attractive choice for surface modification. Surfaces can either be globally modified by the technique, or discrete areas can be addressed by arraying techniques such as photomasking and conventional printing devices. HHS Public Access Author Manuscript Author ManuscriptAuthor Manuscript Author ManuscriptThe surface presentation of recognition motifs based on bioactive compounds is central for many applications in bioanalytical and biomaterials science, and carbohydrates and glycomimetic structures are in this context attracting increasing interest. [10][11][12][13][14] Interactions between cellular glycans and proteins have been found to be of special importance in many biological processes, being involved in cell-cell interactions, cell communication, cell proliferation, and cell death. This emerging significance prompts for new means to analytically study these interactions. To date, various methods have been developed to analyze interactions of carbohydrates and proteins, including biosensors, enzyme-linked lectin assays (ELLAs) and cell assays, nuclear magnetic resonance, calorimetric techniques, and, more recently, microarray technologies. [15][16][17][18][19][20][21][22][23] Among these methods, the quartz crystal microbalance (QCM) biosensor format is being increasingly adopted due to its convenient means of operation coupled with high performance. [24][25][26][27][28][29][30][31][32][33] Measurements can also be performed in real tim...

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“…[34,35] The pathway for the adduct formation is therefore favored and insertion reaction yields are greatly enhanced. [36][37][38] Fluorinated phenylazides have gained increasing popularity in photoaffinity labeling, a technique in which a natural ligand modified with a photosensitive moiety is used to probe the binding site structure of the biological receptor. [39,40] We began applying perfluorophenylazides (PFPAs) in surface modifications and have since demonstrated that these compounds are highly efficient for the covalent immobilization of a variety of polymers.…”

Section: Immobilization Of Single Polymer Moleculesmentioning

confidence: 99%

Photochemically Initiated Single Polymer Immobilization

Yan

2007

Chemistry A European J

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New reagents for photoaffinity labeling: synthesis and photolysis of functionalized perfluorophenyl azides

Cited by 274 publications

References 3 publications

Surface modification of thermoplastics—towards the plastic biochip for high throughput screening devices

Surface modification of thermoplastics—towards the plastic biochip for high throughput screening devices

Photoderivatized Polymer Thin Films at Quartz Crystal Microbalance Surfaces: Sensors for Carbohydrate−Protein Interactions

Photochemically Initiated Single Polymer Immobilization

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