Photoremovable Protecting Groups

Binkley, Roger W.; Flechtner, Thomas W.

doi:10.1007/978-1-4613-2681-6_7

Cited by 39 publications

(19 citation statements)

References 102 publications

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“…Several recently developed caging chromophores are photolyzed in this range 1 , however these cages are somewhat limited by the photosolvolysis reactions they use 32 . In contrast, the intramolecular photoredox reaction used by BIST can be used for carbon-amine and carbonether photoscission 43 (see Supplementary Fig. 4 where we show that amines and alcohols are uncaged cleanly from BIST).…”

Section: Discussionmentioning

confidence: 97%

Calcium Uncaging with Visible Light

et al. 2016

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We have designed a nitroaromatic photochemical protecting group that absorbs visible light in the violet-blue range. The chromophore is a dinitro derivative of bisstyrylthiophene (or BIST) that absorbs light very effectively (ε440 = 66,000 M−1 cm−1 and two-photon cross section of 350 GM at 775 nm). We developed a “caged calcium” molecule by conjugation of BIST to a Ca2+ chelator that upon laser flash photolysis rapidly releases Ca2+ in less than 0.2 ms. Using the patch-clamp method the optical probe, loaded with Ca2+, was delivered into acutely isolated mouse cardiac myocytes, where either one- and two-photon uncaging of Ca2+ induced highly local or cell-wide physiological Ca2+ signaling events.

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Section: Discussionmentioning

confidence: 97%

Calcium Uncaging with Visible Light

et al. 2016

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“…Chromophores for caged compounds were initially developed by organic chemists for use as photochemical protecting groups in the synthesis of small organic molecules. Thus, the ortho ‐nitrobenzyl (Barltrop et al ., ) and the dimethoxy‐ ortho ‐nitrobenzyl (Patchornik et al ., ) photochemical protecting groups were widely used (Amit et al ., ; Binkley & Flechtner, ). With the invention of caged compounds (Kaplan et al ., ) these chromphores became widely used by physiologists for most important signaling molecules such as IP 3 (Walker et al ., ), cGMP (Nargeot et al ., ), calcium (Tsien & Zucker, ), neurotransmitters (Milburn et al ., ), peptides (Walker et al ., ), lipids (Xia et al ., ), proteins (Marriott, ), RNA (Chaulk & MacMillan, ) and DNA (Monroe et al ., ).…”

Section: Introduction To Caged Compounds and Chromophore Designmentioning

confidence: 99%

Caged compounds for multichromic optical interrogation of neural systems

Amatrudo

Olson

Agarwal

et al. 2014

Eur J of Neuroscience

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Caged compounds have widely used by neurophysiologists to study many aspects of cellular signaling in glia and neurons. Biologically inert before irradiation, they can be loaded into cells via patch pipette or topically applied in situ to a defined concentration, photolysis releases the caged compound in a very rapid and spatially defined way. Since caged compounds are exogenous optical probes, they include not only natural products such neurotransmitters, calcium and IP3, but non-natural products such as fluorophores, drugs and antibodies. In this Technical Spotlight we provide a short introduction to the uncaging technique by discussing the nitroaromatic caging chromophores most widely used in such experiments (e.g. CNB1, DMNB, MNI and CDNI). We show that recently developed caging chromophores (RuBi and DEAC450) that are photolyzed with blue light (ca. 430–480 nm range) can be combined with traditional nitroaromatic caged compounds to enable two-color optical probing of neuronal function. For example, one-photon uncaging of either RuBi-GABA or DEAC450-GABA with a 473-nm laser is facile, and can block non-linear currents (dendritic spikes or action potentials) evoked by two-photon uncaging of CDNI-Glu at 720 nm. We also show that two-photon uncaging of DEAC450-Glu and CDNI-GABA at 900 and 720 nm, respectively, can be used to fire and block action potentials. Our experiments illustrate that recently developed chromophores have taken uncaging out of the “monochrome era”, in which it has existed since 1978, so as to enable multichromic interrogation of neuronal function with single synapse precision.

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“…Photoremovable (photoreleasable, photocleavable, or photoactivatable) protecting groups (PPGs) have been extensively used in different contexts to selectively release chemical entities with light. − Photoactivation of signaling molecules is a powerful technique that enables the study of dynamic physiological processes in cell culture, intact tissues, and whole animals. − A wide variety of PPGs have been developed for the selective protection and release of a variety of functional groups such as alcohols, amines (as carbamates), metal cations, esters, diols, phosphates, and amides.…”

Section: Introductionmentioning

confidence: 99%

Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology

et al. 2017

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Representative tertiary amines were linked to the 8-cyano-7-hydroxyquinolinyl (CyHQ) photoremovable protecting group (PPG) to create photoactivatable forms suitable for use in studying cell physiology. The photoactivation of tamoxifen and 4-hydroxytamoxifen, which can be used to activate Cre recombinase and CRISPR-Cas9 gene editing, demonstrated that highly efficient release of bioactive molecules could be achieved through one- and two-photon excitation (1PE and 2PE). CyHQ-protected anilines underwent a photoaza-Claisen rearrangement instead of releasing amines. Time-resolved spectroscopic studies revealed that photorelease of the tertiary amines was extremely fast, occurring from a singlet excited state of CyHQ on the 70 ps time scale.

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Photoremovable Protecting Groups

Cited by 39 publications

References 102 publications

Calcium Uncaging with Visible Light

Calcium Uncaging with Visible Light

Caged compounds for multichromic optical interrogation of neural systems

Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology

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