Literature DB >> 22344608

Applications of p-hydroxyphenacyl (pHP) and coumarin-4-ylmethyl photoremovable protecting groups.

Richard S Givens1, Marina Rubina, Jakob Wirz.   

Abstract

Most applications of photoremovable protecting groups have used o-nitrobenzyl compounds and their (often commercially available) derivatives that, however, have several disadvantages. The focus of this review is on applications of the more recently developed title compounds, which are especially well suited for time-resolved biochemical and physiological investigations, because they release the caged substrates in high yield within a few nanoseconds or less. Together, these two chromophores cover the action spectrum for photorelease from >700 nm to 250 nm.

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Year:  2012        PMID: 22344608      PMCID: PMC3422890          DOI: 10.1039/c2pp05399c

Source DB:  PubMed          Journal:  Photochem Photobiol Sci        ISSN: 1474-905X            Impact factor:   3.982


  71 in total

Review 1.  Using photolabile ligands in drug discovery and development.

Authors:  G Dormán; G D Prestwich
Journal:  Trends Biotechnol       Date:  2000-02       Impact factor: 19.536

2.  Rapid photolytic release of cytidine 5'-diphosphate from a coumarin derivative: a new tool for the investigation of ribonucleotide reductases.

Authors:  Ralph O Schönleber; Jürgen Bendig; Volker Hagen; Bernd Giese
Journal:  Bioorg Med Chem       Date:  2002-01       Impact factor: 3.641

3.  Label-free screening of drug-protein interactions by time-resolved Fourier transform infrared spectroscopic assays exemplified by Ras interactions.

Authors:  Carsten Kötting; Yan Suveyzdis; Ravi S Bojja; Nils Metzler-Nolte; Klaus Gerwert
Journal:  Appl Spectrosc       Date:  2010-09       Impact factor: 2.388

4.  Coumarinylmethyl esters for ultrafast release of high concentrations of cyclic nucleotides upon one- and two-photon photolysis.

Authors:  Volker Hagen; Brigitte Dekowski; Vasilica Nache; Reinhard Schmidt; Daniel Geissler; Dorothea Lorenz; Jenny Eichhorst; Sandro Keller; Hiroshi Kaneko; Klaus Benndorf; Burkhard Wiesner
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-09       Impact factor: 15.336

5.  Fluorescent caged compounds of 2,4-dichlorophenoxyacetic acid (2,4-d): photorelease technology for controlled release of 2,4-D.

Authors:  Sanghamitra Atta; Avijit Jana; Rajakumar Ananthakirshnan; Pradeep Singh Narayana Dhuleep
Journal:  J Agric Food Chem       Date:  2010-10-25       Impact factor: 5.279

6.  Synthesis, photophysical, photochemical and biological properties of caged GABA, 4-[[(2H-1-benzopyran-2-one-7-amino-4-methoxy) carbonyl] amino] butanoic acid.

Authors:  Beate Cürten; Paul H M Kullmann; Mark E Bier; Karl Kandler; Brigitte F Schmidt
Journal:  Photochem Photobiol       Date:  2005 May-Jun       Impact factor: 3.421

7.  Synthesis of carbamate-type caged derivatives of a novel glutamate transporter blocker.

Authors:  Kiyo Takaoka; Yoshiro Tatsu; Noboru Yumoto; Terumi Nakajima; Keiko Shimamoto
Journal:  Bioorg Med Chem       Date:  2004-07-01       Impact factor: 3.641

8.  {7-[Bis(carboxymethyl)amino]coumarin-4-yl}methoxycarbonyl derivatives for photorelease of carboxylic acids, alcohols/phenols, thioalcohols/thiophenols, and amines.

Authors:  Volker Hagen; Brigitte Dekowski; Nico Kotzur; Ralf Lechler; Burkhard Wiesner; Benoît Briand; Michael Beyermann
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

9.  Controlled production of amyloid beta peptide from a photo-triggered, water-soluble precursor "click peptide".

Authors:  Atsuhiko Taniguchi; Mariusz Skwarczynski; Youhei Sohma; Takuma Okada; Keisuke Ikeda; Halan Prakash; Hidehito Mukai; Yoshio Hayashi; Tooru Kimura; Shun Hirota; Katsumi Matsuzaki; Yoshiaki Kiso
Journal:  Chembiochem       Date:  2008-12-15       Impact factor: 3.164

10.  New photoprotecting groups: desyl and p-hydroxyphenacyl phosphate and carboxylate esters.

Authors:  R S Givens; J F Weber; A H Jung; C H Park
Journal:  Methods Enzymol       Date:  1998       Impact factor: 1.600

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  31 in total

Review 1.  Development of photolabile protecting groups and their application to the optochemical control of cell signaling.

Authors:  Anirban Bardhan; Alexander Deiters
Journal:  Curr Opin Struct Biol       Date:  2019-05-25       Impact factor: 6.809

2.  Visible photorelease of liquid biopsy markers following microfluidic affinity-enrichment.

Authors:  Thilanga N Pahattuge; J Matt Jackson; Rane Digamber; Harshani Wijerathne; Virginia Brown; Malgorzata A Witek; Chamani Perera; Richard S Givens; Blake R Peterson; Steven A Soper
Journal:  Chem Commun (Camb)       Date:  2020-03-12       Impact factor: 6.222

3.  Dynamic Structural Biology Experiments at XFEL or Synchrotron Sources.

Authors:  Pierre Aller; Allen M Orville
Journal:  Methods Mol Biol       Date:  2021

4.  Development and Biological Evaluation of a Photoactivatable Small Molecule Microtubule-Targeting Agent.

Authors:  Alexander Döbber; Athena F Phoa; Ramzi H Abbassi; Brett W Stringer; Bryan W Day; Terrance G Johns; Mohammed Abadleh; Christian Peifer; Lenka Munoz
Journal:  ACS Med Chem Lett       Date:  2017-03-15       Impact factor: 4.345

Review 5.  Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy.

Authors:  Petr Klán; Tomáš Šolomek; Christian G Bochet; Aurélien Blanc; Richard Givens; Marina Rubina; Vladimir Popik; Alexey Kostikov; Jakob Wirz
Journal:  Chem Rev       Date:  2012-12-21       Impact factor: 60.622

6.  Spectral evolution of a photochemical protecting group for orthogonal two-color uncaging with visible light.

Authors:  Jeremy P Olson; Matthew R Banghart; Bernardo L Sabatini; Graham C R Ellis-Davies
Journal:  J Am Chem Soc       Date:  2013-10-11       Impact factor: 15.419

7.  Spacer-Mediated Control of Coumarin Uncaging for Photocaged Thymidine.

Authors:  Shengzhuang Tang; Jayme Cannon; Kelly Yang; Matthew F Krummel; James R Baker; Seok Ki Choi
Journal:  J Org Chem       Date:  2020-02-05       Impact factor: 4.354

8.  Simultaneous measurement and quantitation of 4-hydroxyphenylacetic acid and dopamine with fast-scan cyclic voltammetry.

Authors:  Mimi Shin; Sam V Kaplan; Kayla D Raider; Michael A Johnson
Journal:  Analyst       Date:  2015-03-18       Impact factor: 4.616

9.  Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.

Authors:  Roy Weinstain; Tomáš Slanina; Dnyaneshwar Kand; Petr Klán
Journal:  Chem Rev       Date:  2020-10-30       Impact factor: 60.622

10.  Stereochemically probing the photo-Favorskii rearrangement: a mechanistic investigation.

Authors:  Richard S Givens; Marina Rubina; Kenneth F Stensrud
Journal:  J Org Chem       Date:  2012-10-24       Impact factor: 4.354

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