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Literature DB >> 30835125

Sulfonamides Are an Overlooked Class of Electron Donors in Luminogenic Luciferins and Fluorescent Dyes.

Deepak K Sharma¹, Spencer T Adams¹, Kate L Liebmann¹, Adam Choi¹, Stephen C Miller¹.

Abstract

Many fluorophores, and all bright light-emitting substrates for firefly luciferase, contain hydroxyl or amine electron donors. Sulfonamides were found to be capable of serving as replacements for these canonical groups. Unlike "caged" carboxamides, sulfonamide donors enable bioluminescence, and sulfonamidyl luciferins, coumarins, rhodols, and rhodamines are fluorescent in water.

Entities: Chemical Disease Gene Species

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Year: 2019 PMID： 30835125 PMCID： PMC6474412 DOI： 10.1021/acs.orglett.9b00173

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

29 in total

1. Rhodamine-based fluorogenic probe for imaging biological thiol.

Authors: Aya Shibata; Kazuhiro Furukawa; Hiroshi Abe; Satoshi Tsuneda; Yoshihiro Ito
Journal: Bioorg Med Chem Lett Date: 2008-03-10 Impact factor: 2.823

2. Latent luciferase activity in the fruit fly revealed by a synthetic luciferin.

Authors: David M Mofford; Gadarla Randheer Reddy; Stephen C Miller
Journal: Proc Natl Acad Sci U S A Date: 2014-03-10 Impact factor: 11.205

3. Rapid Access to a Broad Range of 6'-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors.

Authors: Deepak K Sharma; Spencer T Adams; Kate L Liebmann; Stephen C Miller
Journal: Org Lett Date: 2017-11-03 Impact factor: 6.005

4. Sulfone-Rhodamines: A New Class of Near-Infrared Fluorescent Dyes for Bioimaging.

Authors: Jing Liu; Yuan-Qiang Sun; Hongxing Zhang; Heping Shi; Yawei Shi; Wei Guo
Journal: ACS Appl Mater Interfaces Date: 2016-08-26 Impact factor: 9.229

5. Synthesis of rhodamines from fluoresceins using Pd-catalyzed C-N cross-coupling.

Authors: Jonathan B Grimm; Luke D Lavis
Journal: Org Lett Date: 2011-11-17 Impact factor: 6.005

6. Luciferin Amides Enable in Vivo Bioluminescence Detection of Endogenous Fatty Acid Amide Hydrolase Activity.

Authors: David M Mofford; Spencer T Adams; G S Kiran Kumar Reddy; Gadarla Randheer Reddy; Stephen C Miller
Journal: J Am Chem Soc Date: 2015-07-02 Impact factor: 15.419

7. A general method to improve fluorophores for live-cell and single-molecule microscopy.

Authors: Jonathan B Grimm; Brian P English; Jiji Chen; Joel P Slaughter; Zhengjian Zhang; Andrey Revyakin; Ronak Patel; John J Macklin; Davide Normanno; Robert H Singer; Timothée Lionnet; Luke D Lavis
Journal: Nat Methods Date: 2015-01-19 Impact factor: 28.547

8. Click beetle luciferase mutant and near infrared naphthyl-luciferins for improved bioluminescence imaging.

Authors: Mary P Hall; Carolyn C Woodroofe; Monika G Wood; Ivo Que; Moniek Van't Root; Yanto Ridwan; Ce Shi; Thomas A Kirkland; Lance P Encell; Keith V Wood; Clemens Löwik; Laura Mezzanotte
Journal: Nat Commun Date: 2018-01-09 Impact factor: 14.919

9. Tuning the Color Palette of Fluorescent Copper Sensors through Systematic Heteroatom Substitution at Rhodol Cores.

Authors: Shang Jia; Karla M Ramos-Torres; Safacan Kolemen; Cheri M Ackerman; Christopher J Chang
Journal: ACS Chem Biol Date: 2017-11-07 Impact factor: 5.100

10. Aminoluciferins extend firefly luciferase bioluminescence into the near-infrared and can be preferred substrates over D-luciferin.

Authors: David M Mofford; Gadarla Randheer Reddy; Stephen C Miller
Journal: J Am Chem Soc Date: 2014-09-11 Impact factor: 15.419

3 in total