ChemInform Abstract: Photolabile 1‐(2‐Nitrophenyl)ethyl Phosphate Esters of Adenine Nucleotide Analogues. Synthesis and Mechanism of Photolysis.

Walker, Jeffery W.; Reid, Gordon P.; McCray, James A.; Trentham, David R.

doi:10.1002/chin.198905296

Cited by 56 publications

(134 citation statements)

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“…Normal external solution contained (mM): NaCl, 125; KCl, 2-5; CaCl2, 2; MgSO4, 1; NaHPO4, 1P25; NaHCO3,25;glucose,11; (Raju, Murphy, Levy, Hall & London, 1989) was used with the approach and methods described by Konishi, Hollingworth, Harkins & Baylor (1991 (Llano et al 1991 (Rapp & Guth, 1988 (Walker, Reid, McCray & Trentham, 1988). Full lamp output of 120 mJ in 1 ms at 280-360 nm produced 52 % photolysis of caged ATP and produces equivalent conversion of caged InsP3 ).…”

Section: Methodsmentioning

confidence: 99%

Fast activation and inactivation of inositol trisphosphate‐evoked Ca2+ release in rat cerebellar Purkinje neurones.

Khodakhah¹,

Ogden²

1995

The Journal of Physiology

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Section: Methodsmentioning

confidence: 99%

Fast activation and inactivation of inositol trisphosphate‐evoked Ca2+ release in rat cerebellar Purkinje neurones.

Khodakhah¹,

Ogden²

1995

The Journal of Physiology

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“…The diazo approach has proved very useful for caging phosphates in a wide variety of molecules. ATP and IP 3 have both been caged in one step using diazo chemistry 12 , 14 . There have also been many studies published using NPE-caged ATP and IP 3 by biologists who make these caged compounds 31 , 32 , 33 .…”

Section: Caged Nucleotides Nucleosides and Inositolsmentioning

confidence: 99%

“…The fundamental problem with such rate determinations is that there are few indicators for biomolecules that respond with useful temporal speed. Thus whilst indicators for glutamate, IP 3 , cAMP, cGMP and ATP do exist, only the kinetics of the ATP indicator have been characterized and therefore used to quantify the rate of uncaging 14 . Good indicators for cations (for example, Ca 2+ ) exist, and have been used to characterize some caged calcium compounds.…”

Section: Chemical Considerationsmentioning

confidence: 99%

“…The primary photochemical reaction of ortho-nitrobenzyl, the most widely used and only generically applicable type of caging chromophore, is wellstudied and involves a photochromic aci-nitro intermediate 65 . It was thought that since the appearance of ATP from NPE-caged ATP was concomitant with the decay of its aci-nitro intermediate 14 , that the decay of this species could be used as an indicator of the release of other caged compounds (for example, IP 3 (ref. 12 ) and glutamate 9 ).…”

Section: Chemical Considerationsmentioning

confidence: 99%

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Caged compounds: photorelease technology for control of cellular chemistry and physiology

2007

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Caged compounds are light-sensitive probes that functionally encapsulate biomolecules in an inactive form. Irradiation liberates the trapped molecule, permitting targeted perturbation of a biological process. Uncaging technology and fluorescence microscopy are 'optically orthogonal': the former allows control, and the latter, observation of cellular function. Used in conjunction with other technologies (for example, patch clamp and/or genetics), the light beam becomes a uniquely powerful tool to stimulate a selected biological target in space or time. Here I describe important examples of widely used caged compounds, their design features and synthesis, as well as practical details of how to use them with living cells.The idea behind the caging technique is that a molecule of interest can be rendered biologically inert (or caged) by chemical modification with a photoremovable protecting group (Fig. 1). Illumination results in a concentration jump of the biologically active molecule that can bind to its cellular receptor, switching on (or off) the targeted process. Virtually every kind of signaling molecule or second messenger, of every size| [mdash]|from protons to proteins| [mdash]|has been caged 1 .Why are caged compounds so useful? A single component of cellular chemistry can control the function of a cell, and such cellular regulation can be temporally or spatially defined, intracellular or extracellular, and amplitude-or frequency-modulated 2 . Photomanipulation of cellular chemistry using caged compounds provides a uniquely powerful means to interact with such cellular dynamics, as it can touch upon any one of the above dimensions. Thus, since light passes through cell membranes, uncaging can rapidly release a biomolecule in an intracellular compartment. This space is not readily accessible to many second messengers (for example, inositol-1,4,5-trisphosphate (IP 3 ), ATP, Ca 2+ , cAMP, cGMP) when they are applied to cells externally, as their charge makes them impermeable to the plasma membrane. Furthermore, uniform illumination results in release throughout the cytosol, or the release can be localized by focusing the uncaging beam on one part of a cell. Likewise, extracellular uncaging of neurotransmitters and hormones is tunable, allowing stimulation of many neurons simultaneously or of single synapses| [mdash]|by global or focused illumination, respectively. Light cannot only be directed, but also modulated in time andCorrespondence should be addressed to Graham C R Ellis-Davies (cagedca@hotmail.com). (Fig. 2) has been widely used to study many Ca 2+ -controlled processes. In particular, secretory processes in neuronal and non-neuronal cells have been extensively studied with caged calcium 22 . Rapid uncaging of glutamate using two-photon photolysis is particularly useful for the rational stimulation of visually identified synapses in complex tissue preparations such as acutely isolated brain slices from the hippocampus 23 (Fig. 2b). Finally, uncaging of mRNA in vivo in zebrafish is an excellen...

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“…Photolabile protecting groups function by rendering a molecule of interest inert until photolysis, and have been used extensively since their introduction in 1962 (1) for controlled release and kinetic studies (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13). For biological systems, this approach allows control of concentration, location, and timing of the compound's release into a system.…”

Section: Introductionmentioning

confidence: 99%

Biotinylated Photocleavable Polyethylenimine: Capture and Triggered Release of Nucleic Acids from Solid Supports

Handwerger

Diamond

2007

Bioconjugate Chem.

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A biotinylated photocleavable polyethylenimine (B-PC-PEI) was designed and synthesized for the capture and controlled release of nucleic acids from solid supports. B-PC-PEI was synthesized via a 3-step reaction process and verified by 1 H NMR and mass spectrometry. In aqueous solution, the o-nitrobenzyl group within B-PC-PEI was efficiently cleaved by 5 min of 365 nm light exposure from a distance of 20 cm (9 mW/cm 2 ). When coupled to streptavidin-coated beads, the PEI domain of Cy5-labeled B-PC-PEI was released by 365 nm light exposure. In contrast, a Cy5-labeled biotinylated PEI (B-PEI) was used as a control and negligible fluorescence loss was observed. Cy5-labeled siRNA was electrostatically captured to streptavidin-coated beads preabsorbed with B-PC-PEI or B-PEI, and flow cytometry demonstrated significant loss of fluorescence from the bead surface after 5 min of light exposure only for B-PC-PEI, demonstrating controlled release of siRNA from the bead surface. Finally, the release of the Cy5-labeled siRNA into the supernatant was quantified. The release of Cy5-siRNA into the supernatant was significantly greater after 5 min of light exposure for B-PC-PEI/streptavidin beads compared to 0 min exposure and remained unchanged for B-PEI/streptavidin beads. B-PC-PEI facilitates capture and triggered release of surface-tethered nucleic acids with light exposure and is fully compatible with streptavidin-based applications.

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ChemInform Abstract: Photolabile 1‐(2‐Nitrophenyl)ethyl Phosphate Esters of Adenine Nucleotide Analogues. Synthesis and Mechanism of Photolysis.

Abstract: Photolabile precursors of ATP are needed to investigate mechanisms of muscle contraction and its regulation and ion conductance in sensory neurons within intact biological systems.

Cited by 56 publications

References 1 publication

Fast activation and inactivation of inositol trisphosphate‐evoked Ca2+ release in rat cerebellar Purkinje neurones.

Fast activation and inactivation of inositol trisphosphate‐evoked Ca2+ release in rat cerebellar Purkinje neurones.

Caged compounds: photorelease technology for control of cellular chemistry and physiology

Biotinylated Photocleavable Polyethylenimine: Capture and Triggered Release of Nucleic Acids from Solid Supports

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