title: trans-Cyclooctene--a stable, voracious dienophile for bioorthogonal labeling.
abstract: Discussed herein is the development and advancement of trans-cyclooctene as a tool for facilitating bioorthogonal labeling through reactions with s-tetrazines. While a number of strained alkenes have been shown to combine with tetrazines for applications in bioorthogonal labeling, trans-cyclooctene enables fastest reactivity at low concentration with rate constants in excess of k2=10(6) M(-1) s(-1). In the present article, we describe advances in computation and synthesis that have enabled applications in chemical biology and nuclear medicine.
authors: Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, United States.
authors: Ramajeyam
authors: R
authors: Selvaraj
authors: Joseph M
authors: JM
authors: Fox
mesh_terms: D000818:Animals; D002470:Cell Survival; D034242:Cyclooctanes / Q000032:analysis* / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D009683:Nuclear Medicine; D011506:Proteins / Q000737:chemistry
chemical_list: D034242:Cyclooctanes; D011506:Proteins; C474479:cyclooctane
references: Acc Chem Res. 2011 Sep 20;44(9):816-27
references: 21627112
references: ACS Chem Biol. 2013 May 17;8(5):987-99
references: 23463944
references: J Am Chem Soc. 2004 Nov 24;126(46):15046-7
references: 15547999
references: J Am Chem Soc. 2004 Aug 25;126(33):10256-7
references: 15315433
references: Angew Chem Int Ed Engl. 2010 Apr 26;49(19):3375-8
references: 20391522
references: Angew Chem Int Ed Engl. 2011 Dec 9;50(50):12042-5
references: 21997950
references: Nat Chem. 2012 Feb 05;4(4):298-304
references: 22437715
references: Chem Commun (Camb). 2013 May 8;49(36):3805-7
references: 23535705
references: J Am Chem Soc. 2008 Oct 15;130(41):13518-9
references: 18798613
references: Angew Chem Int Ed Engl. 2010 Dec 3;49(49):9422-5
references: 20857472
references: Bioconjug Chem. 2008 Dec;19(12):2297-9
references: 19053305
references: J Am Chem Soc. 2008 Mar 26;130(12):3760-1
references: 18321114
references: Mol Imaging. 2013 Mar-Apr;12(2):121-8
references: 23415400
references: Angew Chem Int Ed Engl. 2009;48(38):6974-98
references: 19714693
references: J Am Chem Soc. 2010 Jun 16;132(23):7838-9
references: 20481508
references: Angew Chem Int Ed Engl. 2012 Apr 23;51(17):4166-70
references: 22473599
references: Chem Commun (Camb). 2011 Jul 7;47(25):7203-5
references: 21611648
references: Angew Chem Int Ed Engl. 2010 Apr 6;49(16):2869-72
references: 20306505
references: Angew Chem Int Ed Engl. 2012 Jan 23;51(4):920-2
references: 22162316
references: Chem Sci. 2011 Nov;2(11):2162-2165
references: 23125911
references: Org Biomol Chem. 2011 Nov 7;9(21):7303-5
references: 21915395
references: Chem Soc Rev. 2013 Jun 21;42(12):5131-42
references: 23563107
references: J Am Chem Soc. 2012 Nov 14;134(45):18638-43
references: 23072583
references: Angew Chem Int Ed Engl. 2012 May 21;51(21):5222-5
references: 22511586
references: Angew Chem Int Ed Engl. 2013 Apr 8;52(15):4265-8
references: 23468318
references: Angew Chem Int Ed Engl. 2011 Feb 18;50(8):1922-5
references: 21328671
references: Bioconjug Chem. 2011 Nov 16;22(11):2263-70
references: 21950520
references: J Am Chem Soc. 2008 Jul 30;130(30):9654-5
references: 18593155
references: Bioconjug Chem. 2013 Jul 17;24(7):1210-7
references: 23725393
references: J Am Chem Soc. 2012 Oct 31;134(43):17904-7
references: 23061442
references: Acc Chem Res. 2011 Sep 20;44(9):730-41
references: 21563755
references: Bioconjug Chem. 2012 Jul 18;23(7):1382-6
references: 22709568
references: Bioconjug Chem. 2008 Dec;19(12):2543-8
references: 19053314
references: Nat Nanotechnol. 2010 Sep;5(9):660-5
references: 20676091
references: ChemMedChem. 2011 Mar 7;6(3):424-7
references: 21360818
references: J Nucl Med. 2013 Aug;54(8):1389-96
references: 23708196
references: J Am Chem Soc. 2012 Jan 18;134(2):792-5
references: 22176354
references: Chem Commun (Camb). 2010 Feb 14;46(6):931-3
references: 20107654
references: Proc Natl Acad Sci U S A. 2012 Mar 27;109(13):4762-7
references: 22411831
references: J Pept Sci. 2009 Mar;15(3):235-41
references: 19177421
references: Chem Soc Rev. 2010 Apr;39(4):1272-9
references: 20349533
references: J Am Chem Soc. 2012 Feb 15;134(6):2898-901
references: 22283158
references: Angew Chem Int Ed Engl. 2009;48(38):7013-6
references: 19697389
references: J Am Chem Soc. 2005 Aug 3;127(30):10767-70
references: 16045367
references: J Am Chem Soc. 2005 Oct 5;127(39):13490-1
references: 16190700
references: Proc Natl Acad Sci U S A. 2007 Oct 23;104(43):16793-7
references: 17942682
references: Chem Commun (Camb). 2012 Feb 7;48(12):1736-8
references: 22159330
references: J Am Chem Soc. 2009 Apr 15;131(14):5233-43
references: 19301865
references: J Am Chem Soc. 2011 Feb 2;133(4):949-57
references: 21182329
references: J Nucl Med. 2013 Feb;54(2):244-51
references: 23297075
references: J Am Chem Soc. 2012 Jun 27;134(25):10317-20
references: 22694658
references: J Am Chem Soc. 2008 Jul 30;130(30):9642-3
references: 18593118
references: J Am Chem Soc. 2011 Jun 29;133(25):9646-9
references: 21599005
references: Bioorg Med Chem Lett. 2011 Sep 1;21(17):5011-4
references: 21601452
references: J Am Chem Soc. 2011 Nov 9;133(44):17570-3
references: 21962173
references: Angew Chem Int Ed Engl. 2012 Apr 27;51(18):4466-9
references: 22438179
references: Angew Chem Int Ed Engl. 2012 Jul 23;51(30):7476-9
references: 22696426
references: Angew Chem Int Ed Engl. 2013 Jul 1;52(27):6917-20
references: 23712730
references: Chem Commun (Camb). 2010 Nov 14;46(42):8043-5
references: 20862423
references: J Am Chem Soc. 2002 Dec 4;124(48):14322-3
references: 12452703