title: Cu(I)-assisted click chemistry strategy for conjugation of non-protected cross-bridged macrocyclic chelators to tumour-targeting peptides.
abstract: Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry has inherent challenges for copper-labeled radiopharmaceuticals. An azide-modified phosphonate-based cross-bridged macrocyclic chelator was synthesized for click chemistry conjugation with azide-modified Y3-TATE (a somatostatin analogue) on resin, without the need for protecting the chelator. The (64)Cu-labeled bioconjugate shows favourable in vitro and in vivo behaviour.
authors: Department of Radiology, University of Pittsburgh, Pittsburgh, PA, USA. andersoncj@upmc.edu.
authors: Zhengxin
authors: Z
authors: Cai
authors: Barbara T Y
authors: BT
authors: Li
authors: Edward H
authors: EH
authors: Wong
authors: Gary R
authors: GR
authors: Weisman
authors: Carolyn J
authors: CJ
authors: Anderson
mesh_terms: D000480:Alkynes / Q000737:chemistry* / Q000493:pharmacokinetics; D000818:Animals; D001386:Azides / Q000737:chemistry* / Q000493:pharmacokinetics; D002614:Chelating Agents / Q000737:chemistry* / Q000493:pharmacokinetics; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry* / Q000493:pharmacokinetics; D061565:Cycloaddition Reaction; D045325:HCT116 Cells; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry; D006801:Humans; D051379:Mice; D009369:Neoplasms / Q000378:metabolism; D063065:Organophosphonates / Q000737:chemistry; D013004:Somatostatin / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000493:pharmacokinetics; D014018:Tissue Distribution
chemical_list: C000595578:1,4,8,11-tetraazacyclotetradecane-1-(methanephosphonic acid)-8-(methane carboxylic acid); D000480:Alkynes; D001386:Azides; D002614:Chelating Agents; D006574:Heterocyclic Compounds, 2-Ring; D063065:Organophosphonates; D013004:Somatostatin; D003300:Copper
references: J Am Chem Soc. 2006 Nov 29;128(47):15096-7
references: 17117854
references: Q J Nucl Med Mol Imaging. 2008 Jun;52(2):111-20
references: 18174879
references: Bioconjug Chem. 2012 Jul 18;23(7):1470-7
references: 22663248
references: Curr Pharm Des. 2007;13(1):3-16
references: 17266585
references: Chem Soc Rev. 2011 May;40(5):2848-66
references: 21380414
references: Chem Rev. 2009 Oct;109(10):4760-79
references: 19824702
references: J Med Chem. 2014 Jul 24;57(14):6019-29
references: 24983404
references: J Labelled Comp Radiopharm. 2014 Apr;57(4):224-30
references: 24347474
references: Physiol Rev. 2008 Apr;88(2):451-87
references: 18391170
references: Nucl Med Biol. 1997 Jan;24(1):35-43
references: 9080473
references: Dalton Trans. 2010 Jan 21;39(3):675-96
references: 20066208
references: Dalton Trans. 2012 Feb 21;41(7):1938-50
references: 22170043
references: Bioconjug Chem. 2009 Oct 21;20(10 ):1940-9
references: 19803478
references: Nucl Med Biol. 2003 Jul;30(5):535-9
references: 12831992
references: Regul Pept. 2004 Jun 15;119(1-2):11-20
references: 15093692
references: Acc Chem Res. 2009 Jul 21;42(7):832-41
references: 19530674
references: Chemistry. 2009;15(15):3720-8
references: 19222074
references: Nat Protoc. 2006;1(6):3062-8
references: 17406569
references: Chem Commun (Camb). 2010 Mar 14;46(10):1706-8
references: 20177623
references: Mol Pharm. 2013 Aug 5;10(8):2925-33
references: 23768172
references: J Med Chem. 2004 Mar 11;47(6):1465-74
references: 14998334