Arylethynyl receptors for neutral molecules and anions: emerging applications in cellular imaging.
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).
Carroll
Calden N
CN
Department of Chemistry and the Materials Science Institute, 1253 University of Oregon, Eugene, OR 97403-1253, USA.
Naleway
John J
JJ
Haley
Michael M
MM
Johnson
Darren W
DW
D000114:Acetylene / Q000031:analogs & derivatives / Q000737:chemistry; D000818:Animals; D000838:Anions / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000737:chemistry; D051379:Mice; D008856:Microscopy, Fluorescence; D008968:Molecular Conformation; D041681:NIH 3T3 Cells; D049268:Positron-Emission Tomography
D000838:Anions; D005456:Fluorescent Dyes; C044736:phenylacetylene; D000114:Acetylene
Am J Physiol Cell Physiol. 2006 Feb;290(2):C499-514
16403948
J Org Chem. 2005 Jun 24;70(13):4935-53
15960491
Chemistry. 2010 Mar 1;16(9):2714-8
20131345
Chem Commun (Camb). 2009 May 14;(18):2520-2
19532876
J Hazard Mater. 2008 Mar 1;151(2-3):811-20
17658682
J Am Chem Soc. 2002 Aug 7;124(31):9014-5
12148981
Angew Chem Int Ed Engl. 2007;46(35):6629-33
17665407
Cytometry. 1997 Aug 1;28(4):316-22
9266752
Org Lett. 2010 Mar 5;12(5):940-3
20131818
Environ Sci Technol. 2006 Nov 15;40(22):6928-33
17153996
Chemistry. 2002 Nov 15;8(22):5250-64
12613044
Plant Physiol. 1990 Jul;93(3):841-5
16667590
J Am Chem Soc. 2004 Feb 25;126(7):2022-7
14971935
Angew Chem Int Ed Engl. 2005 Dec 9;44(48):7926-9
16281317
J Am Chem Soc. 2008 Mar 26;130(12):4105-13
18314990
Cell Calcium. 1990 Feb-Mar;11(2-3):57-62
2191781
Chem Commun (Camb). 2005 Aug 14;(30):3761-72
16041411
Biochem Biophys Res Commun. 1991 May 31;177(1):184-91
2043105
Chem Commun (Camb). 2005 Aug 14;(30):3805-7
16041423
Chem Commun (Camb). 2006 Nov 28;(44):4578-80
17082848
Methods Cell Biol. 1998;56:237-51
9500141
J Org Chem. 2007 Aug 31;72(18):6692-9
17685654
J Am Chem Soc. 2008 Nov 26;130(47):15950-6
18980309
J Pharmacol Exp Ther. 2001 Feb;296(2):359-63
11160618
Org Lett. 2002 Mar 21;4(6):881-4
11893176
J Biol Chem. 2005 Jan 14;280(2):1241-7
15504734
Org Biomol Chem. 2010 Mar 7;8(5):1010-6
20165790
J Org Chem. 2007 Apr 13;72(8):2785-93
17367190
J Org Chem. 2003 Dec 26;68(26):9907-15
14682682
Nature. 2002 Jan 17;415(6869):287-94
11796999
Proc Natl Acad Sci U S A. 2004 Nov 30;101(48):16756-61
15548616
Am J Physiol. 1992 Jan;262(1):C242-50
1370743
Ann Med Interne (Paris). 2000 Mar;151(2):97-106
10855362
Neuropharmacology. 1999 Oct;38(10):1493-503
10530811
Plant Mol Biol. 1995 Jun;28(3):353-61
7543302
Chem Commun (Camb). 2007 Aug 28;(32):3401-3
18019511
Science. 1991 Jul 12;253(5016):202-5
1712984
J Biol Chem. 1985 Mar 25;260(6):3440-50
3838314
Environ Sci Technol. 2010 Apr 15;44(8):3073-8
20345133
J Org Chem. 2007 Feb 2;72(3):687-99
17253783
Org Lett. 2010 Mar 19;12(6):1160-3
20148571
Proc Natl Acad Sci U S A. 2006 Aug 15;103(33):12296-300
16894154
Nucl Med Biol. 2005 Aug;32(6):631-40
16026710
Angew Chem Int Ed Engl. 2005 Nov 4;44(43):7040-4
16217822
Cell. 2001 Jan 26;104(2):205-15
11207362
J Membr Biol. 2001 Feb 1;179(3):165-83
11246418
Curr Pharm Des. 2004;10(30):3835-52
15579074
Bioorg Med Chem Lett. 2002 Feb 11;12(3):407-9
11814808
Cell Calcium. 1996 Apr;19(4):337-49
8983854
Org Lett. 2002 Sep 5;4(18):3107-10
12201728
Biotechniques. 2002 Aug;33(2):358-64
12188188
J Org Chem. 1999 Oct 29;64(22):8170-8176
11674733
Cryst Growth Des. 2015 Mar 4;15(3):1502-1511
26405435
J Am Chem Soc. 2004 Mar 24;126(11):3559-66
15025485
J Gen Physiol. 2004 Nov;124(5):513-26
15477379
Bioorg Med Chem Lett. 2008 Sep 1;18(17):4823-7
18707879
J Biol Chem. 1987 Jun 25;262(18):8884-8
3597398
Anal Chem. 1999 Nov 1;71(21):4837-43
10565275
Chemistry. 2006 Mar 1;12(8):2263-9
16363007
Neuroreport. 1995 Apr 19;6(6):929-32
7612885
Angew Chem Int Ed Engl. 2007;46(46):8890-4
17935104
Chem Rev. 1997 Oct 1;97(6):2267-2340
11848901
Chem Rev. 2003 Nov;103(11):4419-76
14611267
Phys Chem Chem Phys. 2005 Feb 21;7(4):600-6
19787875
Bioorg Med Chem Lett. 2004 Aug 2;14(15):3893-6
15225692
Methods Cell Biol. 1989;30:157-92
2648109
Chem Soc Rev. 2009 Feb;38(2):506-19
19169464
Chem Commun (Camb). 2005 Nov 14;(42):5355-7
16244753
Angew Chem Int Ed Engl. 1998 Mar 16;37(5):649-652
29711073
Chem Soc Rev. 2009 Jun;38(6):1572-86
19587953
Angew Chem Int Ed Engl. 2005 Sep 5;44(35):5679-82
16086350
Angew Chem Int Ed Engl. 2008;47(1):117-20
17992675
Nature. 1981 Apr 9;290(5806):527-8
7219539
Angew Chem Int Ed Engl. 2000 Mar;39(5):945-947
10760902
J Biol Chem. 2002 Feb 15;277(7):5506-13
11741919
Chem Rev. 2000 Mar 8;100(3):853-908
11749254