Literature DB >> 21899931

Synthesis and pharmacological evaluation of indole-based sigma receptor ligands.

Christophe Mésangeau1, Emanuele Amata, Walid Alsharif, Michael J Seminerio, Matthew J Robson, Rae R Matsumoto, Jacques H Poupaert, Christopher R McCurdy.   

Abstract

A series of novel indole-based analogs were prepared and their affinities for sigma receptors were determined using in vitro radioligand binding assays. The results of this study identified several compounds with nanomolar sigma-2 affinity and significant selectivity over sigma-1 receptors. In particular, 2-(4-(3-(4-fluorophenyl)indol-1-yl)butyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (9f) was found to display high affinity at sigma-2 receptors with good selectivity (σ-1/σ-2 = 395). The pharmacological binding profile for this compound was established with other relevant non-sigma sites.
Copyright © 2011. Published by Elsevier Masson SAS.

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Year:  2011        PMID： 21899931      PMCID： PMC3272488          DOI： 10.1016/j.ejmech.2011.08.031

Source DB:  PubMed          Journal:  Eur J Med Chem        ISSN： 0223-5234            Impact factor:   6.514


  33 in total

1.  A proposal for the classification of sigma binding sites.

Authors:  R Quirion; W D Bowen; Y Itzhak; J L Junien; J M Musacchio; R B Rothman; T P Su; S W Tam; D P Taylor
Journal:  Trends Pharmacol Sci       Date:  1992-03       Impact factor: 14.819

2.  Cloning and functional characterization of a sigma receptor from rat brain.

Authors:  P Seth; Y J Fei; H W Li; W Huang; F H Leibach; V Ganapathy
Journal:  J Neurochem       Date:  1998-03       Impact factor: 5.372

3.  Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction.

Authors:  Y Cheng; W H Prusoff
Journal:  Biochem Pharmacol       Date:  1973-12-01       Impact factor: 5.858

4.  The selective sigma2-ligand Lu 28-179 has potent anxiolytic-like effects in rodents.

Authors:  C Sánchez; J Arnt; B Costall; M E Kelly; E Meier; R J Naylor; J Perregaard
Journal:  J Pharmacol Exp Ther       Date:  1997-12       Impact factor: 4.030

5.  Sigma 2 receptors as potential biomarkers of proliferation in breast cancer.

Authors:  R H Mach; C R Smith; I al-Nabulsi; B R Whirrett; S R Childers; K T Wheeler
Journal:  Cancer Res       Date:  1997-01-01       Impact factor: 12.701

6.  Purification, molecular cloning, and expression of the mammalian sigma1-binding site.

Authors:  M Hanner; F F Moebius; A Flandorfer; H G Knaus; J Striessnig; E Kempner; H Glossmann
Journal:  Proc Natl Acad Sci U S A       Date:  1996-07-23       Impact factor: 11.205

7.  Characterization of two novel sigma receptor ligands: antidystonic effects in rats suggest sigma receptor antagonism.

Authors:  R R Matsumoto; W D Bowen; M A Tom; V N Vo; D D Truong; B R De Costa
Journal:  Eur J Pharmacol       Date:  1995-07-14       Impact factor: 4.432

8.  Sigma-1 and sigma-2 receptors are expressed in a wide variety of human and rodent tumor cell lines.

Authors:  B J Vilner; C S John; W D Bowen
Journal:  Cancer Res       Date:  1995-01-15       Impact factor: 12.701

9.  Sigma ligands with subnanomolar affinity and preference for the sigma 2 binding site. 1. 3-(omega-aminoalkyl)-1H-indoles.

Authors:  J Perregaard; E K Moltzen; E Meier; C Sánchez
Journal:  J Med Chem       Date:  1995-05-26       Impact factor: 7.446

Review 10.  Clinical trials with sigma ligands.

Authors:  H-P Volz; K D Stoll
Journal:  Pharmacopsychiatry       Date:  2004-11       Impact factor: 5.788
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  9 in total

1.  Multifunctional thiosemicarbazones and deconstructed analogues as a strategy to study the involvement of metal chelation, Sigma-2 (σ2) receptor and P-gp protein in the cytotoxic action: In vitro and in vivo activity in pancreatic tumors.

Authors:  Maria Laura Pati; Mauro Niso; Dirk Spitzer; Francesco Berardi; Marialessandra Contino; Chiara Riganti; William G Hawkins; Carmen Abate
Journal:  Eur J Med Chem       Date:  2017-12-08       Impact factor: 6.514

2.  Transition-Metal-Free C3 Arylation of Indoles with Aryl Halides.

Authors:  Ji Chen; Jimmy Wu
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-03       Impact factor: 15.336

3.  Discovery and development of brain-penetrant 18F-labeled radioligands for neuroimaging of the sigma-2 receptors.

Authors:  Ying Zhang; Tao Wang; Xiaojun Zhang; Winnie Deuther-Conrad; Hualong Fu; Mengchao Cui; Jinming Zhang; Peter Brust; Yiyun Huang; Hongmei Jia
Journal:  Acta Pharm Sin B       Date:  2021-09-04       Impact factor: 14.903

4.  Benzimidazolone-based selective σ2 receptor ligands: Synthesis and pharmacological evaluation.

Authors:  Sebastiano Intagliata; Walid F Alsharif; Christophe Mesangeau; Nicola Fazio; Michael Seminerio; Yan-Tong Xu; Rae R Matsumoto; Christopher R McCurdy
Journal:  Eur J Med Chem       Date:  2019-01-09       Impact factor: 6.514

5.  Sigma-1 and Sigma-2 receptor ligands induce apoptosis and autophagy but have opposite effect on cell proliferation in uveal melanoma.

Authors:  Lucia Longhitano; Carlo Castruccio Castracani; Daniele Tibullo; Roberto Avola; Maria Viola; Giuliano Russo; Orazio Prezzavento; Agostino Marrazzo; Emanuele Amata; Michele Reibaldi; Antonio Longo; Andrea Russo; Nunziatina Laura Parrinello; Giovanni Li Volti
Journal:  Oncotarget       Date:  2017-07-25

6.  A Structure- and Ligand-Based Virtual Screening of a Database of "Small" Marine Natural Products for the Identification of "Blue" Sigma-2 Receptor Ligands.

Authors:  Giuseppe Floresta; Emanuele Amata; Carla Barbaraci; Davide Gentile; Rita Turnaturi; Agostino Marrazzo; Antonio Rescifina
Journal:  Mar Drugs       Date:  2018-10-14       Impact factor: 5.118

Review 7.  PB28, the Sigma-1 and Sigma-2 Receptors Modulator With Potent Anti-SARS-CoV-2 Activity: A Review About Its Pharmacological Properties and Structure Affinity Relationships.

Authors:  Carmen Abate; Mauro Niso; Francesca Serena Abatematteo; Marialessandra Contino; Nicola Antonio Colabufo; Francesco Berardi
Journal:  Front Pharmacol       Date:  2020-12-07       Impact factor: 5.810

8.  Exploration of Diazaspiro Cores as Piperazine Bioisosteres in the Development of σ2 Receptor Ligands.

Authors:  Kuiying Xu; Chia-Ju Hsieh; Ji Youn Lee; Aladdin Riad; Nicholas J Izzo; Gary Look; Susan Catalano; Robert H Mach
Journal:  Int J Mol Sci       Date:  2022-07-27       Impact factor: 6.208

9.  Catalyst-Controlled Regioselectivity in Pd-Catalyzed Aerobic Oxidative Arylation of Indoles.

Authors:  Dian Wang; Chase A Salazar; Shannon S Stahl
Journal:  Organometallics       Date:  2021-04-08       Impact factor: 3.837
  9 in total

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