中枢神经系统α7烟碱型乙酰神经胆碱受体显像剂研究进展
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摘要
α7烟碱型乙酰神经胆碱受体(α7-nAChRs)与中枢神经系统多种功能和退行性神经疾病密切相关。正电子发射断层显像(PET)、单光子发射计算机化断层显像(SPECT)技术的发展,在分子水平为退行性神经疾病早期诊断提供了可能。研制出以α7 nAChR为靶点的亲和性高,特异性强,选择性好的显像剂对以老年痴呆为主的退行性神经疾病早期诊断和疗效检测具有重要意义。本文介绍了国内外α7 nAChRs放射性配体近几年发展状况,并简要介绍了各配体优缺点及未来展望。
α7 nicotinic acetylcholine receptors(α7-nAChRs) are closely related to various functions of the central nervous system and degenerative neurological diseases. With the development of positron emission tomography(PET) and single photon emission computerized tomography(SPECT), it is possible to early diagnose neurodegenerative diseases at molecular level. It is of great significance to develop an imaging agent with high affinity, specificity and selectivity targeting α7-nAChR for the early diagnosis and therapeutic effect detection of degenerative neuropathy with Alzheimer's disease as the main target. In this paper, we summarized the development of a7 nAChR radioligands at home and abroad in recent years. The advantages, disadvantages and future prospects of these ligands are briefly introduced.
α7 nicotinic acetylcholine receptors(α7-nAChRs) are closely related to various functions of the central nervous system and degenerative neurological diseases. With the development of positron emission tomography(PET) and single photon emission computerized tomography(SPECT), it is possible to early diagnose neurodegenerative diseases at molecular level. It is of great significance to develop an imaging agent with high affinity, specificity and selectivity targeting α7-nAChR for the early diagnosis and therapeutic effect detection of degenerative neuropathy with Alzheimer's disease as the main target. In this paper, we summarized the development of a7 nAChR radioligands at home and abroad in recent years. The advantages, disadvantages and future prospects of these ligands are briefly introduced.
引文
[1] Dani J A.Overview of nicotinic receptors and their roles in the central nervous system[J].Biol Psychiatry,2001,49(3):66-74.
[2] Dani J A,Bertrand D.Nicotinic acetylcholine receptors and nicotinic cholinergic mechanisms of the central nervous system[J].Annu Rev Pharmacol Toxicol,2007,47:699-729.
[3] Jensen A A.Neuronal nicotinic acetylcholine receptors:structural revelations,target identifications,and therapeutic inspirations[J].J Med Chem,2005,48(15):4 705-4 745.
[4] Dang N,Meng X,Song H.Nicotinic acetylcholine receptors and cancer[J].Biomed Rep,2016,4(5):515-518.
[5] Wang H Y,Lee D H,D’Aandera M R,et al.Beta-amyloid (1-42) binds to alpha 7 nicotinic acetylcholine receptor with high affinity,implications for Alzheimer’s disease pathology[J].J Biol Chem,2000,275:5 626-5 632.
[6] Brust P,Winnie D C.Neuroimaging-clinical applictions[M].Rijeka:In Tech,2014:533-558.
[7] Richer G.α7 Nicotinic acetylcholine receptors and their role in cognition[J].Brain Res Bull,2013,93:86-96.
[8] Burghaus L,Schutz U,Krempel U,et al.Loss of nicotinic acetylholine receptor subunits alpha4 and alpha7 in the cerebral cortex of Parkinson patients[J].Parkinsonism Relat Disord,2003,9(5):243-246.
[9] Wang H,Yu M,Ochani M,et al.Nicotinic acetylcholine receptor α7 subunit is an essential regulator of inflammation[J].Nature,2003,421:384-387.
[10] Hashimoto T,Ichiki T,Watanabe A,et al.Stimulation of α7nicotinic acetylcholine receptor by Ar-R17779 suppresses atherosclerosis and aortic aneurysm formation in apolipoprotein E-deficient mice[J].Vascul Pharmacol,2014,61(2/3):49-55.
[11] 沈颖华,殷华.烟碱型乙酰胆碱受体的激动与阿尔茨海默病的治疗[J].解放军药学学报,2008,24(2):159-162.
[12] Goncalves J M.Immunosensor for diagnosis of Alzheimer disease using amyloid-beta 1-40 peptide and silk fibroin thin films[J].Mater Sci Eng C Mater Biol Appl,2016,68:338-342.
[13] Wang H Y,Daniel H S,Michael R,et al.β-Amyloid1-42 binds to alpha 7 nicotinic acetylcholine receptor with high affinity.Implications for Alzheimer’s disease pathology[J].Journal of Biological Chemistry,2000,275(8):5 626-5 632.
[14] Wang H Y,Lee D H S,Davis C B et al.Amyloid peptide Aβ1–42 binds selectively and with picomolar affinity to a7 nicotinic acetylcholine receptors[J].Journal of Neurochemistry,2000,75:1 155-1 161.
[15] Nagele R G,D’Andrea M R,Anderson W J,et al.Intracellular accumulation of β-amyloid 1-42 in neurons is facilitated by the α7 nicotinic acetylcholine receptor in Alzheimer’s disease[J].Neuroscience,2002,110(2):199-211.
[16] Wang H Y,Li Weiwei,Nancy J,et al.Alpha 7 nicotinic acetylcholine receptors mediate beta-amyloid peptide-induced tau protein phosphorylation[J].Journal of Biological Chemistry,2003,278(34):31 547-31 553.
[17] Lee D H S,Wang H Y.Differential physiologic responses of alpha7 nicotinic acetylcholine receptors to beta-amyloid1-40 and beta-amyloid1-42[J].Journal of Neurobiology,2003,55(1):25-30.
[18] Dziewczapolski G,Glogowski C M,Masliah E.et al.Deletion of the alpha 7 nicotinic acetylcholine receptor gene improves cognitive deficits and synaptic pathology in a mouse model of Alzheimer's disease[J].J NEUROSCI,2009 (29):8 805-8 815.
[19] Lu Jiahong,L.C.-z.h,Wang Liang,et al.The accumulation of α7 nAChR and the relationship between α7 nAChR and Aβ1-42 in Alzheimer’s disease[J].Chinese Journal of Neurol,2004,37(5):389-392.
[20] Bodnar A L,Cortes-Burgos L A,Cook K K,et al.Discovery and structure-activity relationship of quinuclidine benzamides as agonists of α7 nicotinic acetylcholine receptors[J].Journal of Medicinal Chemistry,2005,48(4):905-908.
[21] Hajos M,Hurst R S,Hoffmann W E,et al.The selective alpha7 nicotinic acetylcholine receptor agonist PNU-282987 [N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-4-chlorobenzamide hydrochloride] enhances GABAergic synaptic activity in brain slices and restores auditory gating deficits in anesthetized rats[J].Journal of Pharmacology and Experimental Therapeutics,2005,312(3):1 213-1 222.
[22] Wishka D G,Daniel P W,Yates K M,et al.Discovery of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide,an agonist of the α7 nicotinic acetylcholine receptor,for the potential treatment of cognitive deficits in schizophrenia:synthesis and structure-activity relationship[J].Journal of Medicinal Chemistry,2006,49:4 425-4 436.
[23] Biton B,Bergis O E,Galli F,et al.SSR180711,a novel selective alpha7 nicotinic receptor partial agonist:(1) binding and functional profile[J].Neuropsychopharmacology,2007,32(1):1-16.
[24] Bitner R S B,William H,Anderson David J.Broad-spectrum efficacy across cognitive domains by alpha 7 nicotinic acetylcholine receptor agonism correlates with activation of ERK1/2 and CREB phosphorylation pathways[J].Journal of Neuroscience,2007,27(39):10 578-10 587.
[25] Schwieler L,Erhardt S.Inhibitory action of clozapine on rat ventral tegmental area dopamine neurons following increased levels of endogenous kynurenic acid[J].Neuropsychopharmacology,2003,28(10):1 770-1 777.
[26] Mullen G,Napier J,Balestra M,et al.(-)-Spiro[1-azabicyclo[2.2.2]octane-3,5′ -oxazolidin-2’-one],a conformationally restricted analogue of acetylcholine,is a highly selective full agonist at the α7 nicotinic acetylcholine receptor[J].Journal of Medicinal Chemistry,2000,43(22):4 045-4 050.
[27] Gundisch D,Andral M,Munoz L,et al.Synthesis and evaluation of phenylcarbamate derivatives as ligands for nicotinic acetylcholine receptors[J].Bioorganic and Medicinal Chemistry,2004,12(18):4 953-62.
[28] Hansen H H,Timmermann D B,Peters D,et al.Alpha-7 nicotinic acetylcholine receptor agonists selectively activate limbic regions of the rat forebrain:An effect similar to antipsychotics[J].Journal of Neuroscience Research,2010,85(8):1 810-1 818.
[29] Walker D P,Wishka D G,Piotrowski D G,et al.Design,synthesis,structure-activity relationship,and in vivo activity of azabicyclic aryl amides as alpha7 nicotinic acetylcholine receptor agonists[J].Bioorganic and Medicinal Chemistry,2006,14(24):8 219-8 248.
[30] Tatsumi R,Seio K,Fujio M,et al.(+)-3-[2-(Benzo[b]thiophen-2-yl)-2-oxoethyl]-1 -azabicyclo[2.2.2]octane as potent agonists for the alpha7 nicotinic acetylcholine receptor[J].Bioorganic and Medicinal Chemistry Letters,2004,14(14):3 781-3 784.
[31] Barak S,Arad M,De Levie A,et al.Pro-cognitive and antipsychotic efficacy of the alpha7 nicotinic partial agonist SSR180711 in pharmacological and neurodevelopmental latent inhibition models of schizophrenia[J].Neuropsychopharmacology,2009,34(7):1 753-1 763.
[32] Pichat P,Bergis O E,Terranova J P,et al.SSR180711,a novel selective alpha7 nicotinic receptor partial agonist:(Ⅱ) efficacy in experimental models predictive of activity against cognitive symptoms of schizophrenia[J].Neuropsychopharmacology,2007,32(1):17-34.
[33] Tietje K R,Anderson D J,Bitner R S,et al.Preclinical characterization of A-582941:a novel alpha7 neuronal nicotinic receptor agonist with broad spectrum cognition-enhancing properties[J].CNS Neuroscience Therapeutics,2008,14(1):65-82.
[34] Acker B A,Jacobsen E J,Rogers B N,et al.Discovery of N-[(3R,5R)-1- azabicyclo [3.2.1]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide as an agonist of the alpha7 nicotinic acetylcholine receptor:in vitro and in vivo activity [J].Bioorganic Medicinal Chemistry Letters,2008,18(12):3 611-3 615.
[35] Hashimoto K.Phencyclidine-induced cognitive deficits in mice are improved by subsequent subchronic administration of the novel selective alpha7 nicotinic receptor agonist SSR180711[J].Biol Psychiatry,2008,63(1):92-97.
[36] Macallan D R E,Wonnacott G G L S .Methyllycaconitine and (+)-anatoxin-a differentiate between nicotinic receptors in vertebrate and invertebrate nervous systems[J].Federation of European Biochemical Societies,1988,226(2):357-363.
[37] Navarro Herna’n A,Philip Abraham D Z.Synthesis and pharmacological characterization of [125I]Iodomethyllycaconitine ([125I]Iodo-MLA).A new ligand for the α7 nicotinic acetylcholine receptor[J].Journal of Medicinal Chemistry,2000,43:142-145.
[38] Davies A R L,Hardick D J,Blagbrough I S,et al.Characterisation of the binding of (3H) methyllycaconitine:a new radioligand for labelling α7-type neuronal nicotinic acetylcholine receptors[J].Neuropharmacology,1999,38(5):679.
[39] Pomper M G,Phillips E,Fan H,et al.Synthesis and Biodistribution of Radiolabeled 7 Nicotinic Acetylcholine Receptor Ligands[J].Journal of Nuclear Medicine Official Publication Society of Nuclear Medicine,2005,46(2):326-34.
[40] Ogawa M,Tatsumi R,Fujio M,et al.Synthesis and evaluation of [125I]I-TSA as a brain nicotinic acetylcholine receptor alpha7 subtype imaging agent[J].Nuclear Medicine and Biology,2006,33(3):311-316.
[41] Kim S W,Ding Y S,Alexoff D,et al.Synthesis and positron emission tomography studies of C-11-labeled isotopomers and metabolites of GTS-21,a partial alpha7 nicotinic cholinergic agonist drug[J].Nuclear Medicine and Biology,2007,34(5):541-551.
[42] Kenji H,Shingo N ,Hiroyuki O ,et al.[11C]CHIBA-1001 as a novel PET ligand for α7 nicotinic receptors in the brain:a PET study in conscious monkeys[J].PLoS ONE,2008,3(9):e3231.
[43] Toyohara J,Sakata M,Wu J,et al.Preclinical and the first clinical studies on [11C]CHIBA-1001 for mapping alpha7 nicotinic receptors by positron emission tomography[J].Annals of Nuclear Medicine,2009,23(3):301-309.
[44] Masatomo Ishikawa M S,Toyohara J,Keiichi Oda,et al.Occupancy of α 7 nicotinic acetylcholine receptors in the brain by tropisetron:a positron emission tomography study using [11C]CHIBA-1001 in healthy human subjects[J].Clinical Psychopharmacology and Neuroscience,2011,9(3):111-116.
[45] Toyohara J,Ishiwata K,Sakata M,et al.In vivo evaluation of alpha7 nicotinic acetylcholine receptor agonists [11C]A-582941 and [11C]A-844606 in mice and conscious monkeys[J].PLOS ONE,2010,5(2):e8961.
[46] Ogawa M,Nishiyama M,Tsukada H,et al.Synthesis and evaluation of new imaging agent for central nicotinic acetylcholine receptor alpha7 subtype[J].Nuclear Medicine and Biology,2010,37(3):347-355.
[47] Ettrup A,Mikkelsen J D,Lehel S,et al.11C-NS14492 as a novel PET radioligand for imaging cerebral alpha7 nicotinic acetylcholine receptors:in vivo evaluation and drug occupancy measurements[J].Journal of Nuclear Medicine,2011,52(9):1 449-1 456.
[48] Briggs C A,Gronlien J H,Curzon P,et al.Role of channel activation in cognitive enhancement mediated by alpha7 nicotinic acetylcholine receptors[J].British Journal of Pharmacology,2009,158(6):1 486-1 494.
[49] Deuther-Conrad W,Fisher S,Hiller A,et al.Assessment of alpha7 nicotinic acetylcholine receptor availability in juvenile pig brain with [18F]NS10743[J].European Journal of Nuclear Medicine and Molecular Imaging,2011,38(8):1 541-1 519.
[50] Rotering S,Deuther-Conrad W,Cumming P,et al.Imaging of alpha7 nicotinic acetylcholine receptors in brain and cerebral vasculature of juvenile pigs with [18F]NS14490[J].EJNMMI Research,2014,4:43.
[51] Gao Y,Ravert H T,Scheffel U,et al.5-(5-(6-[11C]methyl-3,6-diazabicyclo [3.2.0]heptan-3-yl)pyridin-2-yl)-1H-indole as a potential PET radioligand for imaging cerebral alpha7-nAChR in mice[J].Bioorganic and Medicinal Chemistry,2012,20(12):3698-702.
[52] Horti A G,Ravert H T,Gao Y,et al.Synthesis and evaluation of new radioligands [11C]A-833834 and [11C]A-752274 for positron-emission tomography of alpha7-nicotinic acetylcholine receptors[J].Nuclear Medicine and Biology,2013,40(3):395-402.
[53] Ravert H T,Dorff P,Foss C A,et al.Radiochemical synthesis and in vivo evaluation of [18F]AZ11637326:an agonist probe for the alpha7 nicotinic acetylcholine receptor[J].Nuclear Medicine and Biology,2013,40(6):731-739.
[54] Gao Y,Kellar K J,Yasuda R P,et al.Derivatives of dibenzothiophene for positron emission tomography imaging of alpha7-nicotinic acetylcholine receptors[J].Journal of Medicinal Chemistry,2013,56(19):7 574-7 589.
[55] Horti A G,Gao Y,Kuwabara H,et al.18F-ASEM,a radiolabeled antagonist for imaging the alpha7-nicotinic acetylcholine receptor with PET[J].Journal of Nuclear Medicine,2014,55(4):672-627.
[56] Wang Huan,Zhang Huabei.Radiosynthesis and in-vivo evaluation of [125I]IBT :a single-photon emission computed tomography radiotracer for α7-nicotinic acetylcholine receptor imaging[J].Nuclear Medicine Communications,2017,38(8):683-693.
[57] Wang Shuxia,Zhang Huabe.Design,synthesis and biological evaluation of 1,4-Diazobicylco[3.2.2]nonane derivatives as a7-Nicotinic acetylcholine receptor PET/CT imaging agents and agonists for Alzheimer's disease[J].European Journal of Medicinal Chemistry,2018,159:255-266.
[2] Dani J A,Bertrand D.Nicotinic acetylcholine receptors and nicotinic cholinergic mechanisms of the central nervous system[J].Annu Rev Pharmacol Toxicol,2007,47:699-729.
[3] Jensen A A.Neuronal nicotinic acetylcholine receptors:structural revelations,target identifications,and therapeutic inspirations[J].J Med Chem,2005,48(15):4 705-4 745.
[4] Dang N,Meng X,Song H.Nicotinic acetylcholine receptors and cancer[J].Biomed Rep,2016,4(5):515-518.
[5] Wang H Y,Lee D H,D’Aandera M R,et al.Beta-amyloid (1-42) binds to alpha 7 nicotinic acetylcholine receptor with high affinity,implications for Alzheimer’s disease pathology[J].J Biol Chem,2000,275:5 626-5 632.
[6] Brust P,Winnie D C.Neuroimaging-clinical applictions[M].Rijeka:In Tech,2014:533-558.
[7] Richer G.α7 Nicotinic acetylcholine receptors and their role in cognition[J].Brain Res Bull,2013,93:86-96.
[8] Burghaus L,Schutz U,Krempel U,et al.Loss of nicotinic acetylholine receptor subunits alpha4 and alpha7 in the cerebral cortex of Parkinson patients[J].Parkinsonism Relat Disord,2003,9(5):243-246.
[9] Wang H,Yu M,Ochani M,et al.Nicotinic acetylcholine receptor α7 subunit is an essential regulator of inflammation[J].Nature,2003,421:384-387.
[10] Hashimoto T,Ichiki T,Watanabe A,et al.Stimulation of α7nicotinic acetylcholine receptor by Ar-R17779 suppresses atherosclerosis and aortic aneurysm formation in apolipoprotein E-deficient mice[J].Vascul Pharmacol,2014,61(2/3):49-55.
[11] 沈颖华,殷华.烟碱型乙酰胆碱受体的激动与阿尔茨海默病的治疗[J].解放军药学学报,2008,24(2):159-162.
[12] Goncalves J M.Immunosensor for diagnosis of Alzheimer disease using amyloid-beta 1-40 peptide and silk fibroin thin films[J].Mater Sci Eng C Mater Biol Appl,2016,68:338-342.
[13] Wang H Y,Daniel H S,Michael R,et al.β-Amyloid1-42 binds to alpha 7 nicotinic acetylcholine receptor with high affinity.Implications for Alzheimer’s disease pathology[J].Journal of Biological Chemistry,2000,275(8):5 626-5 632.
[14] Wang H Y,Lee D H S,Davis C B et al.Amyloid peptide Aβ1–42 binds selectively and with picomolar affinity to a7 nicotinic acetylcholine receptors[J].Journal of Neurochemistry,2000,75:1 155-1 161.
[15] Nagele R G,D’Andrea M R,Anderson W J,et al.Intracellular accumulation of β-amyloid 1-42 in neurons is facilitated by the α7 nicotinic acetylcholine receptor in Alzheimer’s disease[J].Neuroscience,2002,110(2):199-211.
[16] Wang H Y,Li Weiwei,Nancy J,et al.Alpha 7 nicotinic acetylcholine receptors mediate beta-amyloid peptide-induced tau protein phosphorylation[J].Journal of Biological Chemistry,2003,278(34):31 547-31 553.
[17] Lee D H S,Wang H Y.Differential physiologic responses of alpha7 nicotinic acetylcholine receptors to beta-amyloid1-40 and beta-amyloid1-42[J].Journal of Neurobiology,2003,55(1):25-30.
[18] Dziewczapolski G,Glogowski C M,Masliah E.et al.Deletion of the alpha 7 nicotinic acetylcholine receptor gene improves cognitive deficits and synaptic pathology in a mouse model of Alzheimer's disease[J].J NEUROSCI,2009 (29):8 805-8 815.
[19] Lu Jiahong,L.C.-z.h,Wang Liang,et al.The accumulation of α7 nAChR and the relationship between α7 nAChR and Aβ1-42 in Alzheimer’s disease[J].Chinese Journal of Neurol,2004,37(5):389-392.
[20] Bodnar A L,Cortes-Burgos L A,Cook K K,et al.Discovery and structure-activity relationship of quinuclidine benzamides as agonists of α7 nicotinic acetylcholine receptors[J].Journal of Medicinal Chemistry,2005,48(4):905-908.
[21] Hajos M,Hurst R S,Hoffmann W E,et al.The selective alpha7 nicotinic acetylcholine receptor agonist PNU-282987 [N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-4-chlorobenzamide hydrochloride] enhances GABAergic synaptic activity in brain slices and restores auditory gating deficits in anesthetized rats[J].Journal of Pharmacology and Experimental Therapeutics,2005,312(3):1 213-1 222.
[22] Wishka D G,Daniel P W,Yates K M,et al.Discovery of N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide,an agonist of the α7 nicotinic acetylcholine receptor,for the potential treatment of cognitive deficits in schizophrenia:synthesis and structure-activity relationship[J].Journal of Medicinal Chemistry,2006,49:4 425-4 436.
[23] Biton B,Bergis O E,Galli F,et al.SSR180711,a novel selective alpha7 nicotinic receptor partial agonist:(1) binding and functional profile[J].Neuropsychopharmacology,2007,32(1):1-16.
[24] Bitner R S B,William H,Anderson David J.Broad-spectrum efficacy across cognitive domains by alpha 7 nicotinic acetylcholine receptor agonism correlates with activation of ERK1/2 and CREB phosphorylation pathways[J].Journal of Neuroscience,2007,27(39):10 578-10 587.
[25] Schwieler L,Erhardt S.Inhibitory action of clozapine on rat ventral tegmental area dopamine neurons following increased levels of endogenous kynurenic acid[J].Neuropsychopharmacology,2003,28(10):1 770-1 777.
[26] Mullen G,Napier J,Balestra M,et al.(-)-Spiro[1-azabicyclo[2.2.2]octane-3,5′ -oxazolidin-2’-one],a conformationally restricted analogue of acetylcholine,is a highly selective full agonist at the α7 nicotinic acetylcholine receptor[J].Journal of Medicinal Chemistry,2000,43(22):4 045-4 050.
[27] Gundisch D,Andral M,Munoz L,et al.Synthesis and evaluation of phenylcarbamate derivatives as ligands for nicotinic acetylcholine receptors[J].Bioorganic and Medicinal Chemistry,2004,12(18):4 953-62.
[28] Hansen H H,Timmermann D B,Peters D,et al.Alpha-7 nicotinic acetylcholine receptor agonists selectively activate limbic regions of the rat forebrain:An effect similar to antipsychotics[J].Journal of Neuroscience Research,2010,85(8):1 810-1 818.
[29] Walker D P,Wishka D G,Piotrowski D G,et al.Design,synthesis,structure-activity relationship,and in vivo activity of azabicyclic aryl amides as alpha7 nicotinic acetylcholine receptor agonists[J].Bioorganic and Medicinal Chemistry,2006,14(24):8 219-8 248.
[30] Tatsumi R,Seio K,Fujio M,et al.(+)-3-[2-(Benzo[b]thiophen-2-yl)-2-oxoethyl]-1 -azabicyclo[2.2.2]octane as potent agonists for the alpha7 nicotinic acetylcholine receptor[J].Bioorganic and Medicinal Chemistry Letters,2004,14(14):3 781-3 784.
[31] Barak S,Arad M,De Levie A,et al.Pro-cognitive and antipsychotic efficacy of the alpha7 nicotinic partial agonist SSR180711 in pharmacological and neurodevelopmental latent inhibition models of schizophrenia[J].Neuropsychopharmacology,2009,34(7):1 753-1 763.
[32] Pichat P,Bergis O E,Terranova J P,et al.SSR180711,a novel selective alpha7 nicotinic receptor partial agonist:(Ⅱ) efficacy in experimental models predictive of activity against cognitive symptoms of schizophrenia[J].Neuropsychopharmacology,2007,32(1):17-34.
[33] Tietje K R,Anderson D J,Bitner R S,et al.Preclinical characterization of A-582941:a novel alpha7 neuronal nicotinic receptor agonist with broad spectrum cognition-enhancing properties[J].CNS Neuroscience Therapeutics,2008,14(1):65-82.
[34] Acker B A,Jacobsen E J,Rogers B N,et al.Discovery of N-[(3R,5R)-1- azabicyclo [3.2.1]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide as an agonist of the alpha7 nicotinic acetylcholine receptor:in vitro and in vivo activity [J].Bioorganic Medicinal Chemistry Letters,2008,18(12):3 611-3 615.
[35] Hashimoto K.Phencyclidine-induced cognitive deficits in mice are improved by subsequent subchronic administration of the novel selective alpha7 nicotinic receptor agonist SSR180711[J].Biol Psychiatry,2008,63(1):92-97.
[36] Macallan D R E,Wonnacott G G L S .Methyllycaconitine and (+)-anatoxin-a differentiate between nicotinic receptors in vertebrate and invertebrate nervous systems[J].Federation of European Biochemical Societies,1988,226(2):357-363.
[37] Navarro Herna’n A,Philip Abraham D Z.Synthesis and pharmacological characterization of [125I]Iodomethyllycaconitine ([125I]Iodo-MLA).A new ligand for the α7 nicotinic acetylcholine receptor[J].Journal of Medicinal Chemistry,2000,43:142-145.
[38] Davies A R L,Hardick D J,Blagbrough I S,et al.Characterisation of the binding of (3H) methyllycaconitine:a new radioligand for labelling α7-type neuronal nicotinic acetylcholine receptors[J].Neuropharmacology,1999,38(5):679.
[39] Pomper M G,Phillips E,Fan H,et al.Synthesis and Biodistribution of Radiolabeled 7 Nicotinic Acetylcholine Receptor Ligands[J].Journal of Nuclear Medicine Official Publication Society of Nuclear Medicine,2005,46(2):326-34.
[40] Ogawa M,Tatsumi R,Fujio M,et al.Synthesis and evaluation of [125I]I-TSA as a brain nicotinic acetylcholine receptor alpha7 subtype imaging agent[J].Nuclear Medicine and Biology,2006,33(3):311-316.
[41] Kim S W,Ding Y S,Alexoff D,et al.Synthesis and positron emission tomography studies of C-11-labeled isotopomers and metabolites of GTS-21,a partial alpha7 nicotinic cholinergic agonist drug[J].Nuclear Medicine and Biology,2007,34(5):541-551.
[42] Kenji H,Shingo N ,Hiroyuki O ,et al.[11C]CHIBA-1001 as a novel PET ligand for α7 nicotinic receptors in the brain:a PET study in conscious monkeys[J].PLoS ONE,2008,3(9):e3231.
[43] Toyohara J,Sakata M,Wu J,et al.Preclinical and the first clinical studies on [11C]CHIBA-1001 for mapping alpha7 nicotinic receptors by positron emission tomography[J].Annals of Nuclear Medicine,2009,23(3):301-309.
[44] Masatomo Ishikawa M S,Toyohara J,Keiichi Oda,et al.Occupancy of α 7 nicotinic acetylcholine receptors in the brain by tropisetron:a positron emission tomography study using [11C]CHIBA-1001 in healthy human subjects[J].Clinical Psychopharmacology and Neuroscience,2011,9(3):111-116.
[45] Toyohara J,Ishiwata K,Sakata M,et al.In vivo evaluation of alpha7 nicotinic acetylcholine receptor agonists [11C]A-582941 and [11C]A-844606 in mice and conscious monkeys[J].PLOS ONE,2010,5(2):e8961.
[46] Ogawa M,Nishiyama M,Tsukada H,et al.Synthesis and evaluation of new imaging agent for central nicotinic acetylcholine receptor alpha7 subtype[J].Nuclear Medicine and Biology,2010,37(3):347-355.
[47] Ettrup A,Mikkelsen J D,Lehel S,et al.11C-NS14492 as a novel PET radioligand for imaging cerebral alpha7 nicotinic acetylcholine receptors:in vivo evaluation and drug occupancy measurements[J].Journal of Nuclear Medicine,2011,52(9):1 449-1 456.
[48] Briggs C A,Gronlien J H,Curzon P,et al.Role of channel activation in cognitive enhancement mediated by alpha7 nicotinic acetylcholine receptors[J].British Journal of Pharmacology,2009,158(6):1 486-1 494.
[49] Deuther-Conrad W,Fisher S,Hiller A,et al.Assessment of alpha7 nicotinic acetylcholine receptor availability in juvenile pig brain with [18F]NS10743[J].European Journal of Nuclear Medicine and Molecular Imaging,2011,38(8):1 541-1 519.
[50] Rotering S,Deuther-Conrad W,Cumming P,et al.Imaging of alpha7 nicotinic acetylcholine receptors in brain and cerebral vasculature of juvenile pigs with [18F]NS14490[J].EJNMMI Research,2014,4:43.
[51] Gao Y,Ravert H T,Scheffel U,et al.5-(5-(6-[11C]methyl-3,6-diazabicyclo [3.2.0]heptan-3-yl)pyridin-2-yl)-1H-indole as a potential PET radioligand for imaging cerebral alpha7-nAChR in mice[J].Bioorganic and Medicinal Chemistry,2012,20(12):3698-702.
[52] Horti A G,Ravert H T,Gao Y,et al.Synthesis and evaluation of new radioligands [11C]A-833834 and [11C]A-752274 for positron-emission tomography of alpha7-nicotinic acetylcholine receptors[J].Nuclear Medicine and Biology,2013,40(3):395-402.
[53] Ravert H T,Dorff P,Foss C A,et al.Radiochemical synthesis and in vivo evaluation of [18F]AZ11637326:an agonist probe for the alpha7 nicotinic acetylcholine receptor[J].Nuclear Medicine and Biology,2013,40(6):731-739.
[54] Gao Y,Kellar K J,Yasuda R P,et al.Derivatives of dibenzothiophene for positron emission tomography imaging of alpha7-nicotinic acetylcholine receptors[J].Journal of Medicinal Chemistry,2013,56(19):7 574-7 589.
[55] Horti A G,Gao Y,Kuwabara H,et al.18F-ASEM,a radiolabeled antagonist for imaging the alpha7-nicotinic acetylcholine receptor with PET[J].Journal of Nuclear Medicine,2014,55(4):672-627.
[56] Wang Huan,Zhang Huabei.Radiosynthesis and in-vivo evaluation of [125I]IBT :a single-photon emission computed tomography radiotracer for α7-nicotinic acetylcholine receptor imaging[J].Nuclear Medicine Communications,2017,38(8):683-693.
[57] Wang Shuxia,Zhang Huabe.Design,synthesis and biological evaluation of 1,4-Diazobicylco[3.2.2]nonane derivatives as a7-Nicotinic acetylcholine receptor PET/CT imaging agents and agonists for Alzheimer's disease[J].European Journal of Medicinal Chemistry,2018,159:255-266.