141
Views
0
CrossRef citations to date
0
Altmetric
Research Article

High-Affinity Sigma-1 (σ1) Receptor Ligands Based on the σ1 Antagonist PB212

, , , , , , , & show all
Pages 2547-2562 | Received 19 Feb 2019, Accepted 25 Jul 2019, Published online: 21 Oct 2019

References

  • Hanner M , MoebusFF, FlandorferAet al. Purification, molecular cloning, and expression of the mammalian sigma1-binding site. Proc. Natl Acad. Sci. USA93, 8072–8077 (1996).
  • Schmidt HR , ZhengS, GurpinarE, KoehlA, ManglikA, KruseAC. Crystal structure of the human σ1 receptor. Nature532, 527–530 (2016).
  • Schmidt HR , BetzR, DrorRO, KruseAC. Structural basis for σ1 receptor ligand recognition. Nat. Struct. Mol. Biol.25, 981–987 (2018).
  • Alon A , SchmidtHR, WoodMD, SahnJJ, MartinSF, KruseAC. Identification of the gene that codes for the σ2 receptor. Proc. Natl Acad. Sci. USA114, 7160–7165 (2017).
  • Abate C , NisoM, InfantinoV, MengaA, BerardiF. Elements in support of the ‘non-identity’ of the PGRMC1 protein with the σ2 receptor. Eur. J. Pharmacol.758, 16–23 (2015).
  • Chu UB , MavlyutovT, ChuMLet al. The sigma-2 receptor and progesterone receptor membrane component 1 are different binding sites derived from independent genes. EBioMedicine2, 1806–1813 (2015).
  • Pati ML , GrozaD, RigantiCet al. Sigma-2 receptor and progesterone receptor membrane component 1 (PGRMC1) are two different proteins: proofs by fluorescent labeling and binding of sigma-2 receptor ligands to PGRMC1. Pharmacol. Rep.117, 67–74 (2017).
  • Su TP , SuTC, NakamuraY, TsaiSY. The sigma-1 receptor as a pluripotent modulator in living systems. Trends Pharmacol. Sci.37, 262–278 (2016).
  • Rennekamp AJ , HuangXP, WangYet al. σ1 Receptor ligands control a switch between passive and active threat responses. Nat. Chem. Biol.12, 552–558 (2016).
  • Smith SB , SuTP. Sigma Receptors: Their Role in Disease and as Therapeutic Targets, Volume 964. Springer International Publishing AG, Cham, Switzerland (2017).
  • Berardi F , FerorelliS, AbateCet al. Methyl substitution on the piperidine ring of N-[ω-(6-Methoxynaphthalen-1-yl)alkyl] derivatives as a probe for selective binding and activity at the σ1 receptor. J. Med. Chem.48, 8237–8244 (2005).
  • Skuza G , SadajW, KabińskiMet al. The effects of new sigma (σ) receptor ligands, PB190 and PB212, in the models predictive of antidepressant activity. Pharmacol. Rep.66, 320–324 (2014).
  • Gasparre G , AbateC, BerardiF, CassanoG. The sigma-1 receptor antagonist PB212 reduces the Ca2+-release through the inositol (1, 4, 5)-trisphosphate receptor in SK-N-SH cells. Eur. J. Pharmacol.684, 59–63 (2012).
  • Skuza G , SzymańskaM, BudziszewskaB, AbateC, BerardiF. Effects of PB190 and PB212, new σ receptor ligands, on glucocorticoid receptor-mediated gene transcription in LMCAT cells. Pharmacol. Rep.63, 1564–1568 (2011).
  • Niso M , AbateC, FerorelliSet al. Investigation of σ receptors agonist/antagonist activity through N-(6-methoxytetralin-1-yl)- and N-(6-methoxynaphthalen-1-yl)alkyl derivatives of Polymethylpiperidines. Bioorg. Med. Chem.21, 1865–1869 (2013).
  • Glennon RA . Pharmacophore identification for sigma-1 (σ1) receptor binding: application of the “deconstruction–reconstruction–elaboration” approach. Mini-Rev. Med. Chem.5, 927–940 (2005).
  • Matsumoto RR , BowenWD, TomMA, TruongDD, DeCosta BR. Characterization of two novel sigma receptor ligands: antidystonic effects in rats suggest sigma receptor antagonism. Eur. J. Pharmacol.280, 301–310 (1995).
  • Niso M , RigantiC, PatiML, GhigoD, BerardiF, AbateC. Novel and selective fluorescent σ2 -receptor ligand with a 3,4-dihydroisoquinolin-1-one scaffold: a tool to study σ2 receptors in living Cells. Chembiochem.16, 1078–1083 (2015).
  • Galiano M , GasparreG, LippeC, CassanoG. Calcium response after stimulation by substance P of U373 MG cells: inhibition of store-operated calcium entry by protein kinase C. Cell Calcium35, 123–130 (2004).
  • Gasparre G , AbateC, CarlucciR, BerardiF, CassanoG. The σ1 receptor agonist (+)-pentazocine increases store-operated Ca2+ Entry in MCF7σ1 and SK-N-SH cell lines. Pharmacol. Rep.69, 542–545 (2017).
  • Eswar N , WebbB, Marti-RenomMAet al. Comparative protein structure modeling using MODELLER. Curr. Protoc. Protein Sci. (Suppl. 50), 2.9.1–2.9.31 (2007).
  • Jones G , WillettP, GlenRC, LeachAR, TaylorR. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol.267, 727–748 (1997).
  • Alix K , KhatriS, MosierPDet al. Superagonist, full agonist, partial agonist, and antagonist actions of arylguanidines at 5-hydroxytryptamine-3 (h5-HT3) Subunit A Receptors. ACS Chem. Neurosci.7, 1565–1574 (2016).
  • Barré B , GonnardL, CampagneRet al. Iron- and cobalt-catalyzed arylation of azetidines, pyrrolidines, and piperidines with grignard reagents. Org. Lett.16, 6160–6163 (2014).
  • Macchia M , CervettoL, DemontisGCet al. New N-n-propyl-substituted 3-aryl- and 3-cyclohexylpiperidines as partial agonists at the D4 dopamine receptor. J. Med. Chem.46, 161–168 (2003).
  • Lindsay Smith JR , NormanROC, RowleyAG. Amine oxidation. Part VI. Metal-ion induced dehydrative cyclisation, reduction, and reductive fragmentation of arylethyldimethylamine N-oxides. J. Chem. Soc. Perkin Trans.1, 228–234 (1972).
  • Sari O , BoucleS, CoxBDet al. Synthesis of sulfamoylbenzamide derivatives as HBV capsid assembly effector. Eur. J. Med. Chem.138, 407–421 (2017).
  • Audouze K , NielsenEØ, OlsenGMet al. New ligands with affinity for the α4β2 subtype of nicotinic acetylcholine receptors. synthesis, receptor binding, and 3D-QSAR modeling. J. Med. Chem.49, 3159–3171 (2006).
  • Abate C , PatiML, ContinoMet al. From mixed sigma-2 receptor/p-glycoprotein targeting agents to selective p-glycoprotein modulators: small structural changes address the mechanism of interaction at the efflux pump. Eur. J. Med. Chem.89, 606–615 (2015).
  • Abate C , SelivanovaSV, MüllerAet al. Development of 3,4-dihydroisoquinolin-1(2H)-one derivatives for the positron emission tomography (PET) imaging of σ2 receptors. Eur. J. Med. Chem.69, 920–930 (2013).
  • Niso M , AbateC, ContinoM, FerorelliSet al. Sigma-2 receptor agonists as possible antitumor agents in resistant tumors: hints for collateral sensitivity. ChemMedChem8, 2026–2035 (2013).
  • Niso M , PatiML, BerardiF, AbateC. Rigid versus flexible anilines or anilides confirm the bicyclic ring as the hydrophobic portion for optimal σ2 receptor binding and provide novel tools for the development of future σ2 receptor PET radiotracers. RSC Adv.6, 88508–88518 (2016).
  • Wu Z , BowenWD. Role of sigma-1 receptor C-terminal segment in inositol 1,4,5-trisphosphate receptor activation: constitutive enhancement of calcium signaling in MCF-7 tumor cells. J. Biol. Chem.283, 28198–28215 (2008).
  • Vilner BJ , BowenWD. Modulation of cellular calcium by sigma-2 receptors: release from intracellular stores in human SK-N-SH neuroblastoma cells. J. Pharmacol. Exp. Ther.292, 900–911 (2000).
  • Abate C , NisoM, LacivitaE, MosierPD, ToscanoA, PerroneR. Analogues of σ receptor ligand 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-propyl]piperazine (PB28) with added polar functionality and reduced lipophilicity for potential use as positron emission tomography radiotracers. J. Med. Chem.54, 1022–1032 (2011).
  • Kim FJ , PasternakGW. σ1 receptor ligand binding: an an open-and-shut case. Nat. Struct. Mol. Biol.25, 992–993 (2018).
  • Sguazzini E , SchmidtHR, IyerKA, KruseAC, DukatM. Reevaluation of fenpropimorph as a σ receptor ligand: structure–affinity relationship studies at human σ1 receptors. Bioorg. Med. Chem. Lett.27, 2912–2919 (2017).
  • Singh SK , DasA. The n→π* interaction: a rapidly emerging non-covalent interaction. Phys. Chem. Chem. Phys.17, 9596–9612 (2015).
  • Gris G , Portillo-SalidoE, AubelB, DarbakyYet al. The selective sigma-1 receptor antagonist E-52862 attenuates neuropathic pain of different aetiology in rats. Sci. Rep.6, 24591 (2016).
  • Clinical trials database . NCT02753101. https://clinicaltrials.gov/ct2/show/NCT02753101
  • Clinical trials database . NCT03790709. https://clinicaltrials.gov/ct2/show/NCT03790709
  • Clinical trials database . NCT03019289. https://clinicaltrials.gov/ct2/show/NCT03019289

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.