Nifene

Nifene (18F)
Clinical data
ATC code
  • None
Legal status
Legal status
  • Research compound
Identifiers
IUPAC name
  • 3-[(2S)-2,5-Dihydro-1H-pyrrol-2-ylmethoxy]-2-18F-fluoropyridine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H11FN2O
Molar mass194.209 g·mol−1
3D model (JSmol)
SMILES
  • C1C=C[C@H](N1)COC2=C(N=CC=C2)[18F]
InChI
  • InChI=1S/C10H11FN2O/c11-10-9(4-2-6-13-10)14-7-8-3-1-5-12-8/h1-4,6,8,12H,5,7H2/t8-/m0/s1/i11-1
  • Key:GHHQHFNDKOQCRS-IZFLLFDKSA-N

Nifene is a high affinity, selective nicotinic α4β2* receptor partial agonist used in medical research for nicotinic acetylcholine receptors, usually in the form of nifene (18F)[1][2] as a positron emission tomography (PET) radiotracer.[3][4]

Nifene has been used to assess the efficacy of acetylcholinesterase inhibitors in animal models, because the neurotransmitter acetylcholine competes with the binding of nifene at the nicotinic receptor site.[5][6] Learning and behavior studies in animal models using nifene have suggested a potential role of the nicotinic receptors located in distinct white matter tracts.[7] Nifene studies in animal models of lung cancer have suggested an upregulation of the nicotinic receptor in the lung tumors.[8][9] Novel PET and SPECT imaging agents as potential receptor antagonists have been developed based on the structure of nifene; niodene for SPECT,[10] nifrolene for PET [11] and niofene for PET/SPECT.[12] These new derivatives take advantage of the unique in vivo imaging properties of nifene.[13] Human studies with (18F)-nifene make it a promising nicotinic α4β2* receptor PET radiotracer for scientific research and has exhibited reliable test-retest reproducibility.[14] Human white matter thalamic radiations (or tracts) were well demarcated and quantified using (18F)-nifene.[15]

References

  1. ↑ Pichika R, Easwaramoorthy B, Collins D, Christian BT, Shi B, Narayanan TK, et al. (April 2006). "Nicotinic alpha4beta2 receptor imaging agents: part II. Synthesis and biological evaluation of 2-[18F]fluoro-3-[2-((S)-3-pyrrolinyl)methoxy]pyridine (18F-nifene) in rodents and imaging by PET in nonhuman primate". Nuclear Medicine and Biology. 33 (3): 295–304. doi:10.1016/j.nucmedbio.2005.12.017. PMID 16631077.
  2. ↑ Leung K (2004). "2-18FFluoro-3-2-((S)-3-pyrrolinyl)methoxypyridine". PMID 20641387. {{cite journal}}: Cite journal requires |journal= (help)
  3. ↑ Kant R, Constantinescu CC, Parekh P, Pandey SK, Pan ML, Easwaramoorthy B, Mukherjee J (June 2011). "Evaluation of F-nifene binding to α4β2 nicotinic receptors in the rat brain using microPET imaging". EJNMMI Research. 1: 6. doi:10.1186/2191-219X-1-6. PMC 3203019. PMID 22039577.
  4. ↑ Hillmer AT, Wooten DW, Slesarev MS, Ahlers EO, Barnhart TE, Murali D, et al. (September 2012). "PET imaging of α4β2* nicotinic acetylcholine receptors: quantitative analysis of 18F-nifene kinetics in the nonhuman primate". Journal of Nuclear Medicine. 53 (9): 1471–80. doi:10.2967/jnumed.112.103846. PMC 3580212. PMID 22851633.
  5. ↑ Easwaramoorthy B, Pichika R, Collins D, Potkin SG, Leslie FM, Mukherjee J (January 2007). "Effect of acetylcholinesterase inhibitors on the binding of nicotinic alpha4beta2 receptor PET radiotracer, (18)F-nifene: A measure of acetylcholine competition". Synapse. 61 (1): 29–36. doi:10.1002/syn.20338. PMID 17068780. S2CID 85303757.
  6. ↑ Hillmer AT, Wooten DW, Farhoud M, Higgins AT, Lao PJ, Barnhart TE, et al. (December 2013). "PET imaging of acetylcholinesterase inhibitor-induced effects on α4β2 nicotinic acetylcholine receptor binding". Synapse. 67 (12): 882–6. doi:10.1002/syn.21698. PMC 3806056. PMID 23913347.
  7. ↑ Bieszczad KM, Kant R, Constantinescu CC, Pandey SK, Kawai HD, Metherate R, et al. (May 2012). "Nicotinic acetylcholine receptors in rat forebrain that bind 18F-nifene: relating PET imaging, autoradiography, and behavior". Synapse. 66 (5): 418–34. doi:10.1002/syn.21530. PMC 3292694. PMID 22213342.
  8. ↑ Galitovskiy V, Kuruvilla SA, Sevriokov E, Corches A, Pan ML, Kalantari-Dehaghi M, et al. (June 2013). "18F-Nifene PET/CT using A/J mice treated with NNK". Journal of Cancer Research & Therapy. 1 (4): 128–137. doi:10.14312/2052-4994.2013-20. PMC 5443253. PMID 28553544.
  9. ↑ Tang W, Kuruvilla SA, Galitovskiy V, Pan ML, Grando SA, Mukherjee J (2014). "Targeting histone deacetylase in lung cancer for early diagnosis: (18)F-FAHA PET/CT imaging of NNK-treated A/J mice model". American Journal of Nuclear Medicine and Molecular Imaging. 4 (4): 324–32. PMC 4074498. PMID 24982818.
  10. ↑ Pandey SK, Pan S, Kant R, Kuruvilla SA, Pan ML, Mukherjee J (December 2012). "Synthesis and evaluation of 3-123I-iodo-5-[2-(S)-3-pyrrolinylmethoxy]-pyridine (niodene) as a potential nicotinic α4β2 receptor imaging agent". Bioorganic & Medicinal Chemistry Letters. 22 (24): 7610–4. doi:10.1016/j.bmcl.2012.10.012. PMC 3508149. PMID 23116890.
  11. ↑ Pichika R, Kuruvilla SA, Patel N, Vu K, Sinha S, Easwaramoorthy B, et al. (January 2013). "Nicotinic α4β2 receptor imaging agents. Part IV. Synthesis and biological evaluation of 3-(2-(S)-3,4-dehydropyrrolinyl methoxy)-5-(3'-18F-fluoropropyl)pyridine (18F-Nifrolene) using PET". Nuclear Medicine and Biology. 40 (1): 117–25. doi:10.1016/j.nucmedbio.2012.09.009. PMC 3514651. PMID 23141552.
  12. ↑ Kuruvilla SA, Hillmer AT, Wooten DW, Patel A, Christian BT, Mukherjee J (2014). "Synthesis and evaluation of 2-(18)F-fluoro-5-iodo-3-[2-(S)-3,4-dehydropyrrolinylmethoxy]pyridine ((18)F-Niofene) as a potential imaging agent for nicotinic α4β2 receptors". American Journal of Nuclear Medicine and Molecular Imaging. 4 (4): 354–64. PMC 4074501. PMID 24982821.
  13. ↑ Hillmer AT, Wooten DW, Slesarev MS, Ahlers EO, Barnhart TE, Schneider ML, et al. (November 2013). "Measuring α4β2* nicotinic acetylcholine receptor density in vivo with [(18)F]nifene PET in the nonhuman primate". Journal of Cerebral Blood Flow and Metabolism. 33 (11): 1806–14. doi:10.1038/jcbfm.2013.136. PMC 3824181. PMID 23942367.
  14. ↑ Lao PJ, Betthauser TJ, Tudorascu DL, Barnhart TE, Hillmer AT, Stone CK, Mukherjee J, Christian BT (August 2017). "[18 F]Nifene test-retest reproducibility in first-in-human imaging of α4β2* nicotinic acetylcholine receptors". Synapse. New York, N.Y. 71 (8): e21981. doi:10.1002/syn.21981. PMC 5541262. PMID 28420041.
  15. ↑ Mukherjee J, Lao PJ, Betthauser TJ, Samra GK, Pan ML, Patel IH, Liang C, Metherate R, Christian BT (January 2018). "Human brain imaging of nicotinic acetylcholine α4β2* receptors using [18 F]Nifene: Selectivity, functional activity, toxicity, aging effects, gender effects, and extrathalamic pathways". The Journal of Comparative Neurology. 526 (1): 80–95. doi:10.1002/cne.24320. PMC 5788574. PMID 28875553.
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