Literature DB >> 18037291

Functionalization of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) core.

Lingling Li1, Binh Nguyen, Kevin Burgess.   

Abstract

The new BODIPY systems 1 and 2 were prepared and then used as substrates to explore S(N)Ar and F-B displacement reactions. Chloride was easily displaced from 1 by a piperidine/ester, methylmagnesium bromide selectively displaced fluoride, and cyanide could attack both sites. System 2 readily added soft nucleophiles to the electrophilic carbon atoms, providing a new method for bioconjugation of BODIPYs to proteins while also introducing a (19)F probe.

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Year:  2007        PMID： 18037291      PMCID： PMC2430868          DOI： 10.1016/j.bmcl.2007.10.103

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  9 in total

1.  A highly potassium-selective ratiometric fluorescent indicator based on BODIPY azacrown ether excitable with visible light.

Authors:  Mukulesh Baruah; Wenwu Qin; Renaud A L Vallée; David Beljonne; Taoufik Rohand; Wim Dehaen; Noël Boens
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

2.  Functionalisation of fluorescent BODIPY dyes by nucleophilic substitution.

Authors:  Taoufik Rohand; Mukulesh Baruah; Wenwu Qin; Noël Boens; Wim Dehaen
Journal:  Chem Commun (Camb)       Date:  2005-11-22       Impact factor: 6.222

3.  BODIPY dyes and their derivatives: syntheses and spectroscopic properties.

Authors:  Aurore Loudet; Kevin Burgess
Journal:  Chem Rev       Date:  2007-10-09       Impact factor: 60.622

4.  Convenient method to access new 4,4-dialkoxy- and 4,4-diaryloxy-diaza-s-indacene dyes: Synthesis and spectroscopic evaluation.

Authors:  Chouaib Tahtaoui; Cécile Thomas; François Rohmer; Philippe Klotz; Guy Duportail; Yves Mély; Dominique Bonnet; Marcel Hibert
Journal:  J Org Chem       Date:  2007-01-05       Impact factor: 4.354

5.  Synthesis and photophysical properties of borondipyrromethene dyes bearing aryl substituents at the boron center.

Authors:  Christine Goze; Gilles Ulrich; Laura J Mallon; Ben D Allen; Anthony Harriman; Raymond Ziessel
Journal:  J Am Chem Soc       Date:  2006-08-09       Impact factor: 15.419

6.  Unusual fluorescent monomeric and dimeric dialkynyl dipyrromethene-borane complexes.

Authors:  Christine Goze; Gilles Ulrich; Raymond Ziessel
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

7.  Tunable design strategy for fluorescence probes based on 4-substituted BODIPY chromophore: improvement of highly sensitive fluorescence probe for nitric oxide.

Authors:  Yu Gabe; Tasuku Ueno; Yasuteru Urano; Hirotatsu Kojima; Tetsuo Nagano
Journal:  Anal Bioanal Chem       Date:  2006-08-02       Impact factor: 4.142

8.  BODIPY-based hydroxyaryl derivatives as fluorescent pH probes.

Authors:  Mukulesh Baruah; Wenwu Qin; Nikola Basarić; Wim M De Borggraeve; Noël Boens
Journal:  J Org Chem       Date:  2005-05-13       Impact factor: 4.354

9.  Cyanine dye labeling reagents: sulfoindocyanine succinimidyl esters.

Authors:  R B Mujumdar; L A Ernst; S R Mujumdar; C J Lewis; A S Waggoner
Journal:  Bioconjug Chem       Date:  1993 Mar-Apr       Impact factor: 4.774
  9 in total
  14 in total

1.  Synthesis and transformations of 5-chloro-2,2'-dipyrrins and their boron complexes, 8-chloro-BODIPYs.

Authors:  Haijun Wang; M Graça H Vicente; Frank R Fronczek; Kevin M Smith
Journal:  Chemistry       Date:  2014-03-11       Impact factor: 5.236

2.  Synthesis and spectroscopic properties of β,β'-dibenzo-3,5,8-triaryl-BODIPYs.

Authors:  Qianli Meng; Frank R Fronczek; M Graça H Vicente
Journal:  New J Chem       Date:  2016-02-08       Impact factor: 3.591

3.  Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.

Authors:  Ning Zhao; Sunting Xuan; Frank R Fronczek; Kevin M Smith; M Graça H Vicente
Journal:  J Org Chem       Date:  2015-07-28       Impact factor: 4.354

4.  Synthesis, spectroscopic properties and protein labeling of water soluble 3,5-disubstituted boron dipyrromethenes.

Authors:  Ozlem Dilek; Susan L Bane
Journal:  Bioorg Med Chem Lett       Date:  2009-10-22       Impact factor: 2.823

5.  Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives.

Authors:  Andrea Savoldelli; Qianli Meng; Roberto Paolesse; Frank R Fronczek; Kevin M Smith; M Graça H Vicente
Journal:  J Org Chem       Date:  2018-05-29       Impact factor: 4.354

6.  Synthesis and regioselective functionalization of perhalogenated BODIPYs.

Authors:  Ning Zhao; Sunting Xuan; Brandon Byrd; Frank R Fronczek; Kevin M Smith; M Graça H Vicente
Journal:  Org Biomol Chem       Date:  2016-06-02       Impact factor: 3.876

7.  Functionalization of 3,5,8-trichlorinated BODIPY dyes.

Authors:  Haijun Wang; Frank R Fronczek; M Graça H Vicente; Kevin M Smith
Journal:  J Org Chem       Date:  2014-10-14       Impact factor: 4.354

8.  Stability of a Series of BODIPYs in Acidic Conditions: An Experimental and Computational Study into the Role of the Substituents at Boron.

Authors:  Maodie Wang; M Graça H Vicente; Deanna Mason; Petia Bobadova-Parvanova
Journal:  ACS Omega       Date:  2018-05-21

9.  Fluorinated Boron-Dipyrromethene (BODIPY) Dyes: Bright and Versatile Probes for Surface Analysis.

Authors:  Mandy Hecht; Tobias Fischer; Paul Dietrich; Werner Kraus; Ana B Descalzo; Wolfgang E S Unger; Knut Rurack
Journal:  ChemistryOpen       Date:  2013-01-09       Impact factor: 2.911

10.  BODIPY-Based Fluorescent Probes for Sensing Protein Surface-Hydrophobicity.

Authors:  Nethaniah Dorh; Shilei Zhu; Kamal B Dhungana; Ranjit Pati; Fen-Tair Luo; Haiying Liu; Ashutosh Tiwari
Journal:  Sci Rep       Date:  2015-12-18       Impact factor: 4.379
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