Nifene

Nifene (18F)
Clinical data
Pregnancy
category
  • N/A
ATC code none
Legal status
Legal status
  • Research compound
Identifiers
PubChem (CID) 6917075
ChemSpider 5292349
Chemical and physical data
Formula C10H11FN2O
Molar mass 193.208078 g/mol
3D model (Jmol) Interactive image

Nifene is a high affinity, selective nicotinic α4β2 receptor 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]

References

  1. ↑ Pichika, R; Easwaramoorthy, B; Collins, D; Christian, B. T.; Shi, B; Narayanan, T. K.; Potkin, S. G.; Mukherjee, J (2006). "Nicotinic alpha4beta2 receptor imaging agents: Part II. Synthesis and biological evaluation of 2-18Ffluoro-3-2-((S)-3-pyrrolinyl)methoxypyridine (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.
  3. ↑ Kant, R; Constantinescu, C. C.; Parekh, P; Pandey, S. K.; Pan, M. L.; Easwaramoorthy, B; Mukherjee, J (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 3203019Freely accessible. PMID 22039577.
  4. ↑ Hillmer, A. T.; Wooten, D. W.; Slesarev, M. S.; Ahlers, E. O.; Barnhart, T. E.; Murali, D; Schneider, M. L.; Mukherjee, J; Christian, B. T. (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 3580212Freely accessible. PMID 22851633.
  5. ↑ Easwaramoorthy, B; Pichika, R; Collins, D; Potkin, S. G.; Leslie, F. M.; Mukherjee, J (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.
  6. ↑ Hillmer, A. T.; Wooten, D. W.; Farhoud, M; Higgins, A. T.; Lao, P. J.; Barnhart, T. E.; Mukherjee, J; Christian, B. T. (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 3806056Freely accessible. PMID 23913347.
  7. ↑ Bieszczad, K. M.; Kant, R; Constantinescu, C. C.; Pandey, S. K.; Kawai, H. D.; Metherate, R; Weinberger, N. M.; Mukherjee, J (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 3292694Freely accessible. PMID 22213342.
  8. ↑ V, Galitovskiy; SA, Kuruvilla; E, Sevriokov; A, Corches; ML, Pan; M, Kalantari-Dehaghi; AI, Chernyavsky; J, Mukherjee; SA, Grando (2013). "Development of novel approach to diagnostic imaging of lung cancer with 18F-Nifene PET/CT using A/J Mice treated with NNK". Journal of Cancer Research & Therapy. 1 (4): 128. doi:10.14312/2052-4994.2013-20.
  9. ↑ Tang, W; Kuruvilla, S. A.; Galitovskiy, V; Pan, M. L.; Grando, S. A.; 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 4074498Freely accessible. PMID 24982818.
  10. ↑ Pandey, S. K.; Pan, S; Kant, R; Kuruvilla, S. A.; Pan, M. L.; Mukherjee, J (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 3508149Freely accessible. PMID 23116890.
  11. ↑ Pichika, R; Kuruvilla, S. A.; Patel, N; Vu, K; Sinha, S; Easwaramoorthy, B; Narayanan, T. K.; Shi, B; Christian, B; Mukherjee, J (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 3514651Freely accessible. PMID 23141552.
  12. ↑ Kuruvilla, S. A.; Hillmer, A. T.; Wooten, D. W.; Patel, A; Christian, B. T.; Mukherjee, J (2014). "Synthesis and evaluation of 2-(18)F-fluoro-5-iodo-3-2-(S)-3,4-dehydropyrrolinylmethoxypyridine ((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 4074501Freely accessible. PMID 24982821.
  13. ↑ Hillmer, A. T.; Wooten, D. W.; Slesarev, M. S.; Ahlers, E. O.; Barnhart, T. E.; Schneider, M. L.; Mukherjee, J; Christian, B. T. (2013). "Measuring α4β2* nicotinic acetylcholine receptor density in vivo with (18)Fnifene PET in the nonhuman primate". Journal of Cerebral Blood Flow & Metabolism. 33 (11): 1806–14. doi:10.1038/jcbfm.2013.136. PMC 3824181Freely accessible. PMID 23942367.
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