Literature DB >> 26758021

3-Trifluoromethyl-3-aryldiazirine photolabels with enhanced ambient light stability.

Arun Babu Kumar1, Jeremiah D Tipton2, Roman Manetsch1.   

Abstract

Ambient light stable 3-trifluoromethyl-3-aryldiazirine photolabels are developed via stabilization of the strained three membered diazirine ring by replacing the phenyl ring with electron withdrawing heterocyclic rings. Photolabeling studies reveal that these ambient light stable photolabels are equally efficient in photolabeling target proteins as the traditional 3-trifluoromethyl-3-phenyldiazirine and found to significantly increase the aqueous solubility of the photoaffinity labels.

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Year:  2016        PMID： 26758021      PMCID： PMC9233740          DOI： 10.1039/c5cc09518b

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.065


  23 in total

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Journal:  Curr Top Med Chem       Date:  2002-03       Impact factor: 3.295

2.  Electronegativities from core-ionization energies: electronegativities of SF5 and CF3.

Authors:  Jan E True; T Darrah Thomas; Rolf W Winter; Gary L Gard
Journal:  Inorg Chem       Date:  2003-07-14       Impact factor: 5.165

Review 3.  Photoaffinity ligands in the study of cytochrome p450 active site structure.

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Journal:  Curr Med Chem       Date:  2003-04       Impact factor: 4.530

4.  Synthesis of trifluoromethylaryl diazirine and benzophenone derivatives of etomidate that are potent general anesthetics and effective photolabels for probing sites on ligand-gated ion channels.

Authors:  S Shaukat Husain; Selvanayagam Nirthanan; Dirk Ruesch; Ken Solt; Qi Cheng; Guo-Dong Li; Enrique Arevalo; Richard W Olsen; Douglas E Raines; Stuart A Forman; Jonathan B Cohen; Keith W Miller
Journal:  J Med Chem       Date:  2006-08-10       Impact factor: 7.446

5.  Survey of four different photoreactive moieties for DNA photoaffinity labeling of yeast RNA polymerase III transcription complexes.

Authors:  J J Tate; J Persinger; B Bartholomew
Journal:  Nucleic Acids Res       Date:  1998-03-15       Impact factor: 16.971

6.  Design, synthesis and photoactivation studies of fluorous photolabels.

Authors:  Arun Babu Kumar; Jordan Micheal Anderson; Roman Manetsch
Journal:  Org Biomol Chem       Date:  2011-07-25       Impact factor: 3.876

7.  A nonspectroscopic method to determine the photolytic decomposition pathways of 3-chloro-3-alkyldiazirine: carbene, diazo and rearrangement in excited state.

Authors:  Takatsugu Wakahara; Yasuyuki Niino; Takashi Kato; Yutaka Maeda; Takeshi Akasaka; Michael T H Liu; K Kobayashi; S Nagase
Journal:  J Am Chem Soc       Date:  2002-08-14       Impact factor: 15.419

8.  A remarkable [2.2.2]propellane.

Authors:  Yigang He; Christopher P Junk; John J Cawley; David M Lemal
Journal:  J Am Chem Soc       Date:  2003-05-14       Impact factor: 15.419

9.  3-Trifluoromethyl-3-phenyldiazirine. A new carbene generating group for photolabeling reagents.

Authors:  J Brunner; H Senn; F M Richards
Journal:  J Biol Chem       Date:  1980-04-25       Impact factor: 5.157

10.  Orally bioavailable 6-chloro-7-methoxy-4(1H)-quinolones efficacious against multiple stages of Plasmodium.

Authors:  R Matthew Cross; David L Flanigan; Andrii Monastyrskyi; Alexis N LaCrue; Fabián E Sáenz; Jordany R Maignan; Tina S Mutka; Karen L White; David M Shackleford; Ian Bathurst; Frank R Fronczek; Lukasz Wojtas; Wayne C Guida; Susan A Charman; Jeremy N Burrows; Dennis E Kyle; Roman Manetsch
Journal:  J Med Chem       Date:  2014-10-22       Impact factor: 7.446
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  1 in total

1.  Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH.

Authors:  Femke Beiroth; Tomas Koudelka; Thorsten Overath; Stefan D Knight; Andreas Tholey; Thisbe K Lindhorst
Journal:  Beilstein J Org Chem       Date:  2018-07-24       Impact factor: 2.883
  1 in total

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