Chemistry:Nifene

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Short description: Chemical compound
Nifene (18F)
Nifene 18F.svg
Clinical data
ATC code
  • None
Legal status
Legal status
  • Research compound
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC10H11FN2O
Molar mass194.209 g·mol−1
3D model (JSmol)

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. ↑ "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. April 2006. doi:10.1016/j.nucmedbio.2005.12.017. PMID 16631077. 
  2. ↑ 2-18FFluoro-3-2-((S)-3-pyrrolinyl)methoxypyridine. 2004. PMID 20641387. 
  3. ↑ "Evaluation of F-nifene binding to α4β2 nicotinic receptors in the rat brain using microPET imaging". EJNMMI Research 1: 6. June 2011. doi:10.1186/2191-219X-1-6. PMID 22039577. 
  4. ↑ "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. September 2012. doi:10.2967/jnumed.112.103846. PMID 22851633. 
  5. ↑ "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. January 2007. doi:10.1002/syn.20338. PMID 17068780. 
  6. ↑ "PET imaging of acetylcholinesterase inhibitor-induced effects on α4β2 nicotinic acetylcholine receptor binding". Synapse 67 (12): 882–6. December 2013. doi:10.1002/syn.21698. PMID 23913347. 
  7. ↑ "Nicotinic acetylcholine receptors in rat forebrain that bind 18F-nifene: relating PET imaging, autoradiography, and behavior". Synapse 66 (5): 418–34. May 2012. doi:10.1002/syn.21530. PMID 22213342. 
  8. ↑ "18F-Nifene PET/CT using A/J mice treated with NNK". Journal of Cancer Research & Therapy 1 (4): 128–137. June 2013. doi:10.14312/2052-4994.2013-20. PMID 28553544. 
  9. ↑ "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. 2014. PMID 24982818. 
  10. ↑ "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. December 2012. doi:10.1016/j.bmcl.2012.10.012. PMID 23116890. 
  11. ↑ "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. January 2013. doi:10.1016/j.nucmedbio.2012.09.009. PMID 23141552. 
  12. ↑ "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. 2014. PMID 24982821. 
  13. ↑ "Measuring α4β2* nicotinic acetylcholine receptor density in vivo with [(18)Fnifene PET in the nonhuman primate"]. Journal of Cerebral Blood Flow and Metabolism 33 (11): 1806–14. November 2013. doi:10.1038/jcbfm.2013.136. PMID 23942367. 
  14. ↑ "[18 FNifene test-retest reproducibility in first-in-human imaging of α4β2* nicotinic acetylcholine receptors"]. Synapse (New York, N.Y.) 71 (8): e21981. August 2017. doi:10.1002/syn.21981. PMID 28420041. 
  15. ↑ "Human brain imaging of nicotinic acetylcholine α4β2* receptors using [18 FNifene: Selectivity, functional activity, toxicity, aging effects, gender effects, and extrathalamic pathways"]. The Journal of Comparative Neurology 526 (1): 80–95. January 2018. doi:10.1002/cne.24320. PMID 28875553. 

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