Competition between cleavage and decarboxylation in photolysis of α-carboxy-2-nitrobenzyl protected cysteine derivatives

Kotzur, Nico; Briand, Benoît; Beyermann, Michael; Hagen, Volker

doi:10.1039/b900865a

Cited by 12 publications

(8 citation statements)

References 13 publications

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“…The photolabile agarose is modified with α-carboxy-2-nitrobenzyl cysteine, similar to S-2-nitrobenzyl cysteine previously reported to afford photolabile functionality to agarose (Luo and Shoichet 2004). However, the α-carboxy-2-nitrobenzyl leaving group used in the present study has been shown to be less cytotoxic and more water soluble than that of the 2-nitrobenzyl moiety (Pan and Bayley 1997; Walker et al 1998; Kotzur et al 2009). A digital micromirror device (DMD) in our photolithography apparatus served as a dynamic mask for irradiating both PEG and the photolabile agarose.…”

Section: Introductionmentioning

confidence: 75%

“…Figure 1 outlines the synthesis pathway for the photolabile cysteine grafted to agarose. First, the photolabile moiety tert -butyl 2-bromo-2-(2-nitrophenyl)acetate ( t Bu-BNPA) was synthesized according to a modified protocol (Kotzur et al 2009). Briefly, 2-(2-nitrophenyl)acetic acid (5.0 g, 27.6 mmol), 4-dimethylaminopyridine (1.85 g, 15.1 mmol), and N , N ’diisopropylcarbodiimide (5.2 ml, 33.2 mmol) were dissolved in 50 ml dichloromethane (DCM) and cooled to 0°C.…”

Section: Methodsmentioning

confidence: 99%

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Structural and molecular micropatterning of dual hydrogel constructs for neural growth models using photochemical strategies

Horn-Ranney

Curley

Catig

et al. 2012

Biomed Microdevices

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Chemotactic and haptotactic cues guide neurite growth toward appropriate targets by eliciting attractive or repulsive responses from the neurite growth cones. Here we present an integrated system allowing both structural and molecular micropatterning in dual hydrogel 3D tissue culture constructs for directing in vitro neuronal growth via structural, immobilized, and soluble guidance cues. These tissue culture constructs were fabricated into specifiable geometries using UV light reflected from a digital micromirror device acting as a dynamic photomask, resulting in dual hydrogel constructs consisting of a cell growth-restrictive polyethylene glycol (PEG) boundary with a cell growth-permissive interior of photolabile α-carboxy-2-nitrobenzyl cysteine agarose (CNBC-A). This CNBC-A was irradiated in discrete areas and subsequently tagged with maleimide-conjugated biomolecules. Fluorescent microscopy showed biomolecule binding only at the sites of irradiation in CNBC-A, and confocal microscopy confirmed 3D binding through the depth of the construct. Neurite outgrowth studies showed contained growth throughout CNBC-A. The diffusion rate of soluble fluorescein-bovine serum albumin through the dual hydrogel construct was controlled by PEG concentration and the distance between the protein source and the agarose interior; the timescale for a transient protein gradient changed with these parameters. These findings suggest the dual hydrogel system is a usefulplatform for manipulating a 3D in vitro microenvironment with patterned structural and molecular guidance cues for modeling neural growth and guidance.

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Section: Introductionmentioning

confidence: 75%

Section: Methodsmentioning

confidence: 99%

Structural and molecular micropatterning of dual hydrogel constructs for neural growth models using photochemical strategies

Horn-Ranney

Curley

Catig

et al. 2012

Biomed Microdevices

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“…16 After illumination, the PG is cleaved and the caged biomolecule is released irreversibly, thus revealing the active species. Photocaged Cys has been site-specifically incorporated to study thiol function and targeted covalent labeling in small molecules, 17 peptides, 18 and proteins. 19 Photocaged selenocysteine has also been reported.…”

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confidence: 99%

Light-Mediated Sulfenic Acid Generation from Photocaged Cysteine Sulfoxide

Pan

Carroll

2015

Org. Lett.

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S-Sulfenylation is a post-translational modification with crucial role in regulating protein function. However, its analysis has remained challenging due to the lack of facile sulfenic acid models. We report the first photocaged cysteine sulfenic acid with efficient photodeprotection, and demonstrate its utility by generating sulfenic acid in a thiol peroxidase after illumination in vitro. These caged sulfoxides should be promising for site-specific incorporation of Cys sulfenic acid in living cells via genetic code expansion.

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“…[1] Such orthogonal and mild photolytic cleavage is particularly attractive for solid-supported organic synthesis, [2] in the field of combinatorial library screening, [3] and for the tracking of molecular dynamics in biological systems. [4] Of the myriad of photocleavable protecting groups which have been studied, the o-nitrobenzyl group is certainly the predominant one since it enables the caging of a wide range of functionalities, such as carboxy, [5] amine, [6] hydroxy, [7] and thiol. [8] In addition, the use of light as a trigger provides a straightforward means to obtain spatial and temporal control over a desired molecular cleavage, [9] which has found significant attention in constructing patterns of multiple cell lines, [10] the production of 3D structured materials for tissue scaffolds, [11] and the photo-caging of active compounds [12] for instance.…”

mentioning

confidence: 99%