Highly Efficient and Ultrafast Phototriggers for cAMP and cGMP by Using Long-Wavelength UV/Vis-Activation

Hagen, Volker; Bendig, J.; Frings, Stephan; Eckardt, Torsten; Helm, S.; Reuter, D.; Kaupp, U. Benjamin

doi:10.1002/1521-3773(20010316)40:6<1045::aid-anie10450>3.0.co;2-f

Cited by 160 publications

(151 citation statements)

References 16 publications

Supporting

Mentioning

141

Contrasting

Unclassified

Order By: Relevance

“…NPE-IP 3 has a low two-photon crosssection (|[sim]| 0.001 GM), so a caged IP 3 with larger cross-section (0.035 GM) has been synthesized in seven synthetic steps, permitting localized two-photon uncaging of IP 3 in living cells 37 . Finally, membrane-permeant ester derivatives of caged cAMP and IP 3 probes have been made using multistep syntheses that permit loading of these second messengers into intact cells 38 , 39 , 40 .…”

Section: Caged Nucleotides Nucleosides and Inositolsmentioning

confidence: 99%

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

2007

View full text Add to dashboard Cite

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...

show abstract

Section: Caged Nucleotides Nucleosides and Inositolsmentioning

confidence: 99%

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

2007

View full text Add to dashboard Cite

show abstract

“…The caged BCMCM-cAMP (Hagen et al 2001) and BCMCM-8-Br-cAMP (Boccaccio et al 2006) were dissolved in DMSO at 10 or 50 mM and stored at Ϫ20°C for up to 3 mo. The final concentration of 50 M was obtained by diluting an aliquot of the stock solution into the pipette solution, kept refrigerated in the dark during the experimental session, and stored for a few days at Ϫ20°C.…”

Section: Solutionsmentioning

confidence: 99%

Temporal Development of Cyclic Nucleotide-Gated and Ca²⁺-Activated Cl⁻ Currents in Isolated Mouse Olfactory Sensory Neurons

Boccaccio

Menini²

2007

Journal of Neurophysiology

View full text Add to dashboard Cite

“…18 A long wavelength absorber is 25 aminocoumarinylmethyl λ max 402 nm (ε 18,600). 19 Likewise, certain brominated hydroxycoumarinylmethyl groups have wavelength maxima ranging from 325-397 nm (ε ca.1.2-2.0 x 10 4 ). 20 Hydroxyquinolinylmethyl protecting groups have maxima at wavelengths as long as 386 nm (ε 3,300).…”

mentioning

confidence: 99%

Photochemical electrocyclic ring closure and leaving group expulsion from N-(9-oxothioxanthenyl)benzothiophene carboxamides

Sarker

Shahrin

Steinmetz

et al. 2013

Photochem Photobiol Sci

View full text Add to dashboard Cite

Highly Efficient and Ultrafast Phototriggers for cAMP and cGMP by Using Long-Wavelength UV/Vis-Activation

Cited by 160 publications

References 16 publications

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

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

Temporal Development of Cyclic Nucleotide-Gated and Ca²⁺-Activated Cl⁻ Currents in Isolated Mouse Olfactory Sensory Neurons

Photochemical electrocyclic ring closure and leaving group expulsion from N-(9-oxothioxanthenyl)benzothiophene carboxamides

Contact Info

Product

Resources

About

Highly Efficient and Ultrafast Phototriggers for cAMP and cGMP by Using Long-Wavelength UV/Vis-Activation

Cited by 160 publications

References 16 publications

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

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

Temporal Development of Cyclic Nucleotide-Gated and Ca2+-Activated Cl− Currents in Isolated Mouse Olfactory Sensory Neurons

Photochemical electrocyclic ring closure and leaving group expulsion from N-(9-oxothioxanthenyl)benzothiophene carboxamides

Contact Info

Product

Resources

About

Temporal Development of Cyclic Nucleotide-Gated and Ca²⁺-Activated Cl⁻ Currents in Isolated Mouse Olfactory Sensory Neurons