Literature DB >> 28806084

Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology.

Naeem Asad1, Davide Deodato1, Xin Lan2, Magnus B Widegren1, David Lee Phillips2, Lili Du2, Timothy M Dore1,3.   

Abstract

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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Year:  2017        PMID: 28806084     DOI: 10.1021/jacs.7b06363

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  8 in total

1.  S,S-Chiral Linker Induced U Shape with a Syn-facial Sensitizer and Photocleavable Ethene Group.

Authors:  Goutam Ghosh; Sarah J Belh; Callistus Chiemezie; Niluksha Walalawela; Ashwini A Ghogare; Mariana Vignoni; Andrés H Thomas; Sherri A McFarland; Edyta M Greer; Alexander Greer
Journal:  Photochem Photobiol       Date:  2018-09-27       Impact factor: 3.421

2.  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

3.  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

4.  Photoactivatable drugs for nicotinic optopharmacology.

Authors:  Sambashiva Banala; Matthew C Arvin; Nicholas M Bannon; Xiao-Tao Jin; John J Macklin; Yong Wang; Can Peng; Guiqing Zhao; John J Marshall; Kyle R Gee; David L Wokosin; Veronica J Kim; J Michael McIntosh; Anis Contractor; Henry A Lester; Yevgenia Kozorovitskiy; Ryan M Drenan; Luke D Lavis
Journal:  Nat Methods       Date:  2018-03-26       Impact factor: 28.547

5.  Practical Synthesis of Quinoline-Protected Morpholino Oligomers for Light-Triggered Regulation of Gene Function.

Authors:  Davide Deodato; Timothy M Dore
Journal:  Molecules       Date:  2020-04-29       Impact factor: 4.411

6.  Photoactivatable Dopamine and Sulpiride to Explore the Function of Dopaminergic Neurons and Circuits.

Authors:  Naeem Asad; Duncan E McLain; Alec F Condon; Sangram Gore; Shahienaz E Hampton; Sauparnika Vijay; John T Williams; Timothy M Dore
Journal:  ACS Chem Neurosci       Date:  2020-03-04       Impact factor: 4.418

7.  Direct Detection of the Photorearrangement Reaction of Quinoline-Protected Dialkylanilines.

Authors:  Runhui Liang; Xin Lan; Naeem Asad; Timothy M Dore; Qidi Zhang; Lili Du; David Lee Phillips
Journal:  Photochem Photobiol       Date:  2021-12-02       Impact factor: 3.521

8.  Bypassing Glutamic Acid Decarboxylase 1 (Gad1) Induced Craniofacial Defects with a Photoactivatable Translation Blocker Morpholino.

Authors:  Matthew J O'Connor; Lindsey L Beebe; Davide Deodato; Rebecca E Ball; A Tyler Page; Ariel J VanLeuven; Kyle T Harris; Sungdae Park; Vani Hariharan; James D Lauderdale; Timothy M Dore
Journal:  ACS Chem Neurosci       Date:  2018-09-24       Impact factor: 4.418

  8 in total

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