Literature DB >> 20820467

Arylethynyl receptors for neutral molecules and anions: emerging applications in cellular imaging.

Calden N Carroll1, John J Naleway, Michael M Haley, Darren W Johnson.   

Abstract

This critical review will focus on the application of shape-persistent receptors for anions that derive their rigidity and optoelectronic properties from the inclusion of arylethynyl linkages. It will highlight a few of the design strategies involved in engineering selective and sensitive fluorescent probes and how arylacetylenes can offer a design pathway to some of the more desirable properties of a selective sensor. Additionally, knowledge gained in the study of these receptors in organic media often leads to improved receptor design and the production of chromogenic and fluorogenic probes capable of detecting specific substrates among the multitude of ions present in biological systems. In this ocean of potential targets exists a large number of geometrically distinct anions, which present their own problems to the design of receptors with complementary binding for each preferred coordination geometry. Our interest in targeting charged substrates, specifically how previous work on receptors for cations or neutral guests can be adapted to anions, will be addressed. Additionally, we will focus on the design and development of supramolecular arylethynyl systems, their shape-persistence and fluorogenic or chromogenic optoelectronic responses to complexation. We will also examine briefly how the "chemistry in the cuvet" translates into biological media (125 references).

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Year:  2010        PMID: 20820467      PMCID: PMC3062433          DOI: 10.1039/b926231h

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  75 in total

1.  Expanded Porphyrins and Their Heterologs.

Authors:  Ayub Jasat; David Dolphin
Journal:  Chem Rev       Date:  1997-10-01       Impact factor: 60.622

2.  A colorimetric sensing ensemble for heparin.

Authors:  Zhenlin Zhong; Eric V Anslyn
Journal:  J Am Chem Soc       Date:  2002-08-07       Impact factor: 15.419

3.  Indole-based macrocycles as a class of receptors for anions.

Authors:  Kyoung-Jin Chang; Dohyun Moon; Myoung Soo Lah; Kyu-Sung Jeong
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-09       Impact factor: 15.336

Review 4.  Ratio imaging: practical considerations for measuring intracellular calcium and pH in living tissue.

Authors:  R B Silver
Journal:  Methods Cell Biol       Date:  1998       Impact factor: 1.441

5.  Amidopyrroles: from anion receptors to membrane transport agents.

Authors:  Philip A Gale
Journal:  Chem Commun (Camb)       Date:  2005-05-25       Impact factor: 6.222

6.  Loss of the ClC-7 chloride channel leads to osteopetrosis in mice and man.

Authors:  U Kornak; D Kasper; M R Bösl; E Kaiser; M Schweizer; A Schulz; W Friedrich; G Delling; T J Jentsch
Journal:  Cell       Date:  2001-01-26       Impact factor: 41.582

7.  Synthesis and evaluation of indolinyl- and indolylphenylacetylenes as PET imaging agents for beta-amyloid plaques.

Authors:  Wenchao Qu; Seok-Rye Choi; Catherine Hou; Zhiping Zhuang; Shunichi Oya; Wei Zhang; Mei-Ping Kung; Rajesh Manchandra; Daniel M Skovronsky; Hank F Kung
Journal:  Bioorg Med Chem Lett       Date:  2008-07-24       Impact factor: 2.823

8.  Synthesis of symmetrical bis-alkynyl or alkyl pyridine and thiophene derivatives and their antiangiogenic activities.

Authors:  Chan Mug Ahn; Woon-Seob Shin; Ho Bum Woo; Seokjoon Lee; Hyean-Woo Lee
Journal:  Bioorg Med Chem Lett       Date:  2004-08-02       Impact factor: 2.823

9.  Arsenic removal from real-life groundwater by adsorption on laterite soil.

Authors:  Sanjoy Kumar Maji; Anjali Pal; Tarasankar Pal
Journal:  J Hazard Mater       Date:  2007-06-20       Impact factor: 10.588

10.  Fluorescent and circular dichroic detection of monosaccharides by molecular sensors: bis[(pyrrolyl)ethynyl]naphthyridine and bis[(indolyl)ethynyl]naphthyridine.

Authors:  Jim-Min Fang; Srinivasan Selvi; Jen-Hai Liao; Zdenek Slanina; Chao-Tsen Chen; Pi-Tai Chou
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419

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  16 in total

1.  Ion-π interactions in ligand design for anions and main group cations.

Authors:  Michelle M Watt; Mary S Collins; Darren W Johnson
Journal:  Acc Chem Res       Date:  2012-06-22       Impact factor: 22.384

2.  Do CH-Anion and Anion-π Interactions Alter the Mechanism of 2:1 Host-Guest Complexation in Arylethynyl Monourea Anion Receptors?

Authors:  Lisa M Eytel; Annie K Gilbert; Paul Görner; Lev N Zakharov; Darren W Johnson; Michael M Haley
Journal:  Chemistry       Date:  2017-03-06       Impact factor: 5.236

Review 3.  Ion and molecular recognition using aryl-ethynyl scaffolding.

Authors:  Chris L Vonnegut; Blakely W Tresca; Darren W Johnson; Michael M Haley
Journal:  Chem Asian J       Date:  2015-01-13

4.  A deep cavitand with a fluorescent wall functions as an ion sensor.

Authors:  Orion B Berryman; Aaron C Sather; Julius Rebek
Journal:  Org Lett       Date:  2011-09-13       Impact factor: 6.005

5.  Binding Studies of Cucurbit[7]uril with Gold Nanoparticles Bearing Different Surface Functionalities.

Authors:  Gulen Yesilbag Tonga; Tsukasa Mizuhara; Krishnendu Saha; Ziwen Jiang; Singyuk Hou; Riddha Das; Vincent M Rotello
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

6.  Spermine detection via metal-mediated ethynylarene 'turn-on' fluorescence signaling.

Authors:  James T Fletcher; Brent S Bruck
Journal:  Sens Actuators B Chem       Date:  2015-02-01       Impact factor: 7.460

7.  Solid-State Examination of Conformationally Diverse Sulfonamide Receptors Based on Bis(2-anilinoethynyl)pyridine, -Bipyridine, and -Thiophene.

Authors:  Orion B Berryman; Charles A Johnson; Chris L Vonnegut; Kevin A Fajardo; Lev N Zakharov; Darren W Johnson; Michael M Haley
Journal:  Cryst Growth Des       Date:  2015-03-04       Impact factor: 4.076

8.  Selective nitrate binding in competitive hydrogen bonding solvents: do anion-π interactions facilitate nitrate selectivity?

Authors:  Michelle M Watt; Lev N Zakharov; Michael M Haley; Darren W Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2013-08-12       Impact factor: 15.336

9.  Dicarboxylated ethynylarenes as buffer-dependent chemosensors for Cd(II), Pb(II) and Zn(II).

Authors:  James T Fletcher; Brent S Bruck; Douglas E Deever
Journal:  Tetrahedron Lett       Date:  2013-09-25       Impact factor: 2.415

10.  Harnessing solid-state packing for selective detection of chloride in a macrocyclic anionophore.

Authors:  Chris L Vonnegut; Airlia M Shonkwiler; Lev N Zakharov; Michael M Haley; Darren W Johnson
Journal:  Chem Commun (Camb)       Date:  2016-07-21       Impact factor: 6.222

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