Literature DB >> 25777268

Mild, Pd-catalyzed stannylation of radioiodination targets.

Julie E Pickett1, András Váradi1, Travis C Palmer1, Steven G Grinnell1, Joel M Schrock1, Gavril W Pasternak1, Rashad R Karimov2, Susruta Majumdar3.   

Abstract

Trialkylstannanes are versatile precursors for chemical transformations, including radiolabeling with a variety of halogens, particularly iodine. In the present work a convenient, Pd-mediated stannylation method is presented that can be performed in an open flask. The method is selective for aryl iodides allowing selective stannylations in the presence of other halogen atoms. The reaction conditions are mild, making the method compatible with chemically sensitive bioactive compounds.
Copyright © 2015 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Opioid; Radioiodination; Radioligand binding; Sigma receptor; Stannylation

Mesh：

Substances：

Year:  2015        PMID： 25777268      PMCID： PMC4385467          DOI： 10.1016/j.bmcl.2015.02.055

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


  16 in total

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Authors:  Duane A Burnett; Mary Ann Caplen; Martin S Domalski; Margaret E Browne; Harry R Davis; John W Clader
Journal:  Bioorg Med Chem Lett       Date:  2002-02-11       Impact factor: 2.823

2.  A facile no-carrier-added radioiodination procedure suitable for radiolabeling kits.

Authors:  George W Kabalka; Arjun R Mereddy
Journal:  Nucl Med Biol       Date:  2004-10       Impact factor: 2.408

3.  Syntheses and characterization of polymer-supported organotrifluoroborates: applications in radioiodination reactions.

Authors:  Li Yong; Min-Liang Yao; James F Green; Hall Kelly; George W Kabalka
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4.  Sequential cytoprotective responses to Sigma1 ligand-induced endoplasmic reticulum stress.

Authors:  Joel M Schrock; Christina M Spino; Charles G Longen; Stacy M Stabler; Jacqueline C Marino; Gavril W Pasternak; Felix J Kim
Journal:  Mol Pharmacol       Date:  2013-09-04       Impact factor: 4.436

5.  Generation of novel radiolabeled opiates through site-selective iodination.

Authors:  Susruta Majumdar; Maxim Burgman; Nathan Haselton; Steven Grinnell; Julia Ocampo; Anna Rose Pasternak; Gavril W Pasternak
Journal:  Bioorg Med Chem Lett       Date:  2011-05-08       Impact factor: 2.823

6.  Synthesis of radioiodinated aryl iodides via boronate precursors.

Authors:  George W Kabalka; Murthy R Akula; Jianhua Zhang
Journal:  Nucl Med Biol       Date:  2002-11       Impact factor: 2.408

7.  Binding of the non-classical cannabinoid CP 55,940, and the diarylpyrazole AM251 to rodent brain cannabinoid receptors.

Authors:  S J Gatley; R Lan; B Pyatt; A N Gifford; N D Volkow; A Makriyannis
Journal:  Life Sci       Date:  1997       Impact factor: 5.037

8.  Amine- and ether-chelated aryllithium reagents-structure and dynamics.

Authors:  Hans J Reich; Wayne S Goldenberg; Aaron W Sanders; Kevin L Jantzi; C Christoph Tzschucke
Journal:  J Am Chem Soc       Date:  2003-03-26       Impact factor: 15.419

9.  A facile synthesis of radioiodinated (Z)-vinyl iodides via vinylboronates.

Authors:  George W Kabalka; Murthy R Akula; Jinhua Zhang
Journal:  Nucl Med Biol       Date:  2003-05       Impact factor: 2.408

10.  Radiosynthesis, cerebral distribution, and binding of [125I]-1-(p-iodophenyl)-3-(1-adamantyl)guanidine, a ligand for sigma binding sites.

Authors:  A S Kimes; A A Wilson; U Scheffel; B G Campbell; E D London
Journal:  J Med Chem       Date:  1992-12-11       Impact factor: 7.446
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  9 in total

1.  Imaging Sigma-1 Receptor (S1R) Expression Using Iodine-124-Labeled 1-(4-Iodophenyl)-3-(2-adamantyl)guanidine ([124I]IPAG).

Authors:  Kishore K Gangangari; András Váradi; Susruta Majumdar; Steven M Larson; Gavril W Pasternak; NagaVara Kishore Pillarsetty
Journal:  Mol Imaging Biol       Date:  2020-04       Impact factor: 3.488

2.  Mitragynine/Corynantheidine Pseudoindoxyls As Opioid Analgesics with Mu Agonism and Delta Antagonism, Which Do Not Recruit β-Arrestin-2.

Authors:  András Váradi; Gina F Marrone; Travis C Palmer; Ankita Narayan; Márton R Szabó; Valerie Le Rouzic; Steven G Grinnell; Joan J Subrath; Evelyn Warner; Sanjay Kalra; Amanda Hunkele; Jeremy Pagirsky; Shainnel O Eans; Jessica M Medina; Jin Xu; Ying-Xian Pan; Attila Borics; Gavril W Pasternak; Jay P McLaughlin; Susruta Majumdar
Journal:  J Med Chem       Date:  2016-09-02       Impact factor: 7.446

Review 3.  Inorganometallics (Transition Metal-Metalloid Complexes) and Catalysis.

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Journal:  Chem Rev       Date:  2021-12-30       Impact factor: 60.622

4.  Novel Radioiodinated and Radiofluorinated Analogues of FT-2102 for SPECT or PET Imaging of mIDH1 Mutant Tumours.

Authors:  Valérie Weber; Lucie Arnaud; Sladjana Dukic-Stefanovic; Barbara Wenzel; Valérie Roux; Jean-Michel Chezal; Thu-Hang Lai; Rodrigo Teodoro; Klaus Kopka; Elisabeth Miot-Noirault; Winnie Deuther-Conrad; Aurélie Maisonial-Besset
Journal:  Molecules       Date:  2022-06-11       Impact factor: 4.927

5.  Synthesis and characterization of a dual kappa-delta opioid receptor agonist analgesic blocking cocaine reward behavior.

Authors:  András Váradi; Gina F Marrone; Shainnel O Eans; Michelle L Ganno; Joan J Subrath; Valerie Le Rouzic; Amanda Hunkele; Gavril W Pasternak; Jay P McLaughlin; Susruta Majumdar
Journal:  ACS Chem Neurosci       Date:  2015-09-14       Impact factor: 4.418

6.  Controlling opioid receptor functional selectivity by targeting distinct subpockets of the orthosteric site.

Authors:  Rajendra Uprety; Tao Che; Saheem A Zaidi; Steven G Grinnell; Balázs R Varga; Abdelfattah Faouzi; Samuel T Slocum; Abdullah Allaoa; András Varadi; Melissa Nelson; Sarah M Bernhard; Elizaveta Kulko; Valerie Le Rouzic; Shainnel O Eans; Chloe A Simons; Amanda Hunkele; Joan Subrath; Ying Xian Pan; Jonathan A Javitch; Jay P McLaughlin; Bryan L Roth; Gavril W Pasternak; Vsevolod Katritch; Susruta Majumdar
Journal:  Elife       Date:  2021-02-08       Impact factor: 8.140

7.  Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride.

Authors:  Jialin Ming; Qi Shi; Tamio Hayashi
Journal:  Chem Sci       Date:  2018-08-17       Impact factor: 9.825

Review 8.  Alternative Pre-mRNA Splicing of the Mu Opioid Receptor Gene, OPRM1: Insight into Complex Mu Opioid Actions.

Authors:  Shan Liu; Wen-Jia Kang; Anna Abrimian; Jin Xu; Luca Cartegni; Susruta Majumdar; Patrick Hesketh; Alex Bekker; Ying-Xian Pan
Journal:  Biomolecules       Date:  2021-10-15

9.  Kratom Alkaloids as Probes for Opioid Receptor Function: Pharmacological Characterization of Minor Indole and Oxindole Alkaloids from Kratom.

Authors:  Soumen Chakraborty; Rajendra Uprety; Amal E Daibani; Valerie L Rouzic; Amanda Hunkele; Kevin Appourchaux; Shainnel O Eans; Nitin Nuthikattu; Rahul Jilakara; Lisa Thammavong; Gavril W Pasternak; Ying-Xian Pan; Jay P McLaughlin; Tao Che; Susruta Majumdar
Journal:  ACS Chem Neurosci       Date:  2021-07-02       Impact factor: 5.780
  9 in total

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