Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 51, 2021 - Issue 8
824
Views
7
CrossRef citations to date
0
Altmetric
General Xenobiochemistry

Employing in vitro metabolism to guide design of F-labelled PET probes of novel α-synuclein binding bifunctional compounds

, , , , , & show all
Pages 885-900 | Received 03 May 2021, Accepted 11 Jun 2021, Published online: 30 Jun 2021

References

  • Agundez JA, Garcia-Martin E, Alonso-Navarro H, Jimenez-Jimenez FJ. 2013. Anti-Parkinson's disease drugs and pharmacogenetic considerations. Expert Opin Drug Metab Toxicol. 9 (7):859–874.
  • Bar Am O, Amit T, Youdim MB. 2004. Contrasting neuroprotective and neurotoxic actions of respective metabolites of anti-Parkinson drugs rasagiline and selegiline. Neurosci Lett. 355 (3):169–172.
  • Bar-Am O, Weinreb O, Amit T, Youdim MB. 2010. The neuroprotective mechanism of 1-(R)-aminoindan, the major metabolite of the anti-parkinsonian drug rasagiline. J Neurochem. 112 (5):1131–1137.
  • Barreto GE, Iarkov A, Moran VE. 2014. Beneficial effects of nicotine, cotinine and its metabolites as potential agents for Parkinson's disease. Front Aging Neurosci. 6:340.
  • Benowitz NL, Hukkanen J, and Jacob P. 3rd, 2009. Nicotine chemistry, metabolism, kinetics and biomarkers. Handb Exp Pharmacol. 192:29–60.
  • Berthou F, Ratanasavanh D, Alix D, Carlhant D, Riche C, Guillouzo A. 1988. Caffeine and theophylline metabolism in newborn and adult human hepatocytes; comparison with adult rat hepatocytes. Biochem Pharmacol. 37(19):3691–3700.
  • Berthou F, Ratanasavanh D, Riche C, Picart D, Voirin T, Guillouzo A. 1989. Comparison of caffeine metabolism by slices, microsomes and hepatocyte cultures from adult human liver. Xenobiotica. 19(4):401–417.
  • Bianco G, Abate S, Labella C, Cataldi TR. 2009. Identification and fragmentation pathways of caffeine metabolites in urine samples via liquid chromatography with positive electrospray ionization coupled to a hybrid quadrupole linear ion trap(LTQ) and Fourier transform ion cyclotron resonance mass spectrometry and tandem mass spectrometry. Rapid Commun Mass Spectrom. 23 (7):1065–1074.
  • Bier D, Hartmann R, Holschbach M. 2013. Collision-induced dissociation studies of caffeine in positive electrospray ionisation mass spectrometry using six deuterated isotopomers and one N1-ethylated homologue. Rapid Commun Mass Spectrom. 27(8):885–895.
  • Bonomi RE, Laws M, Popov V, Kamal S, Potukutchi S, Shavrin A, Lu X, Turkman N, Liu RS, Mangner T, et al. 2018. A Novel Substrate Radiotracer for Molecular Imaging of SIRT2 Expression and Activity with Positron Emission Tomography. Mol Imaging Biol. 20(4):594–604.
  • Brandange S, Lindblom L. 1979. Enzyme Aldehyde Oxidase Is an Iminium Oxidase - Reaction with Nicotine Delta-1'(5')Iminium Ion. Biochem Biophys Res Commun. 91(3):991–996.
  • Campbell ME, Grant DM, Inaba T, Kalow W. 1987. Biotransformation of caffeine, paraxanthine, theophylline, and theobromine by polycyclic aromatic hydrocarbon-inducible cytochrome(s) P-450 in human liver microsomes. Drug Metab Dispos. 15(2):237–249.
  • Chau KY, Cooper JM, Schapira AH. 2010. Rasagiline protects against alpha-synuclein induced sensitivity to oxidative stress in dopaminergic cells. Neurochem Int. 57(5):525–529.
  • Chen K, Chen X. 2010. Design and development of molecular imaging probes. Curr Top Med Chem. 10(12):1227–1236.
  • Chênevert R, Mohammadi-Ziarani G, Caron D, Dasser M. 1999. Chemoenzymatic enantioselective synthesis of (-)-enterolactone. Can J Chem. 77(2):223–226.
  • Davie CA. 2008. A review of Parkinson's disease. Br Med Bull. 86:109–127.
  • de Biase S, Merlino G, Lorenzut S, Valente M, Gigli GL. 2014. ADMET considerations when prescribing novel therapeutics to treat restless legs syndrome. Expert Opin Drug Metab Toxicol. 10(10):1365–1380.
  • Deftereos SN, Dodou E, Andronis C, Persidis A. 2012. From depression to neurodegeneration and heart failure: re-examining the potential of MAO inhibitors. Expert Rev Clin Pharmacol. 5(4):413–425.
  • Dimpfel W, Hoffmann JA. 2011. Effects of rasagiline, its metabolite aminoindan and selegiline on glutamate receptor mediated signalling in the rat hippocampus slice in vitro. BMC Pharmacol. 11:2.
  • Ferrero JL, Neims AH. 1983. Metabolism of caffeine by mouse liver microsomes: GSH or cytosol causes a shift in products from 1,3,7-trimethylurate to a substituted diaminouracil. Life Sci. 33(12):1173–1178.
  • Forno LS. 1996. Neuropathology of Parkinson's disease. J Neuropathol Exp Neurol. 55(3):259–272.
  • Grant DM, Campbell ME, Tang BK, Kalow W. 1987. Biotransformation of caffeine by microsomes from human liver. Kinetics and inhibition studies. Biochem Pharmacol. 36(8):1251–1260.
  • Hecht SS, Hochalter JB, Villalta PW, Murphy SE. 2000. 2'-Hydroxylation of nicotine by cytochrome P450 2A6 and human liver microsomes: formation of a lung carcinogen precursor. Proc Natl Acad Sci U S A. 97(23):12493–12497.
  • Hughes AJ, Ben-Shlomo Y, Daniel SE, Lees AJ. 1992. What features improve the accuracy of clinical diagnosis in Parkinson's disease: a clinicopathologic study. Neurology. 42(6):1142–1146.
  • Hughes AJ, Daniel SE, Lees AJ. 2001. Improved accuracy of clinical diagnosis of Lewy body Parkinson's disease. Neurology. 57(8):1497–1499.
  • Jacobson O, Kiesewetter DO, Chen X. 2015. Fluorine-18 radiochemistry, labeling strategies and synthetic routes. Bioconjug Chem. 26(1):1–18.
  • Jia L, Liu X. 2007. The conduct of drug metabolism studies considered good practice (II): in vitro experiments. Curr Drug Metab. 8(8):822–829.
  • Kakish J, Allen KJ, Harkness TA, Krol ES, Lee JS. 2016. Novel Dimer Compounds That Bind α-Synuclein Can Rescue Cell Growth in a Yeast Model Overexpressing α-Synuclein. A Possible Prevention Strategy for Parkinson's Disease . ACS Chem Neurosci. 7(12):1671–1680.
  • Kakish J, Lee D, Lee JS. 2015. Drugs That Bind to α-Synuclein: Neuroprotective or Neurotoxic? ACS Chem Neurosci. 6(12):1930–1940.
  • Litvan I, MacIntyre A, Goetz CG, Wenning GK, Jellinger K, Verny M, Bartko JJ, Jankovic J, McKee A, Brandel JP, et al. 1998. Accuracy of the clinical diagnoses of Lewy body disease, Parkinson disease, and dementia with Lewy bodies: a clinicopathologic study. Arch Neurol. 55(7):969–978.
  • Medana C, Santoro V, Dal Bello F, Sala C, Pazzi M, Sarro M, Calza P. 2016. Mass spectrometric fragmentation and photocatalytic transformation of nicotine and cotinine. Rapid Commun Mass Spectrom. 30(24):2617–2627.
  • Mendes VM, Coelho M, Tome AR, Cunha RA, Manadas B. 2019. Validation of an LC-MS/MS Method for the Quantification of Caffeine and Theobromine Using Non-Matched Matrix Calibration Curve. Molecules. 24(16):2863.
  • Mukai M, Uchimura T, Zhang X, Greene D, Vergeire M, Cantillon M. 2018. Effects of Rifampin on the Pharmacokinetics of a Single Dose of Istradefylline in Healthy Subjects. J Clin Pharmacol. 58(2):193–201.
  • Murphy PJ. 1973. Enzymatic oxidation of nicotine to nicotine 1'(5') iminium ion. A newly discovered intermediate in the metabolism of nicotine. J Biol Chem. 248(8):2796–2800.
  • Nwabufo CK, El-Aneed A, Krol ES. 2019. Tandem mass spectrometric analysis of novel caffeine scaffold-based bifunctional compounds for Parkinson's disease. Rapid Commun Mass Spectrom. 33(23):1792–1803.
  • Park BK, Kitteringham NR. 1994. Effects of fluorine substitution on drug metabolism: pharmacological and toxicological implications. Drug Metab Rev. 26(3):605–643.
  • Patil SP, Jain PD, Ghumatkar PJ, Tambe R, Sathaye S. 2014. Neuroprotective effect of metformin in MPTP-induced Parkinson's disease in mice. Neuroscience. 277:747–754.
  • Peterson LA, Trevor A, Castagnoli N. Jr., 1987. Stereochemical studies on the cytochrome P-450 catalyzed oxidation of (S)-nicotine to the (S)-nicotine delta 1'(5')-iminium species. J Med Chem. 30(2):249–254.
  • Postuma RB, Lang AE, Munhoz RP, Charland K, Pelletier A, Moscovich M, Filla L, Zanatta D, Rios Romenets S, Altman R, et al. 2012. Caffeine for treatment of Parkinson disease: a randomized controlled trial. Neurology. 79(7):651–658.
  • Prediger RD. 2010. Effects of caffeine in Parkinson's disease: from neuroprotection to the management of motor and non-motor symptoms. J Alzheimers Dis. 20 Suppl 1(Suppl 1):S205–S220.
  • Quik M. 2004. Smoking, nicotine and Parkinson's disease. Trends Neurosci. 27(9):561–568.
  • Quik M, Perez XA, Bordia T. 2012. Nicotine as a potential neuroprotective agent for Parkinson's disease. Mov Disord. 27(8):947–957.
  • Rajput AH, Rozdilsky B, Rajput A. 1991. Accuracy of clinical diagnosis in parkinsonism-a prospective study. Can J Neurol Sci. 18(3):275–278.
  • Rizzo G, Copetti M, Arcuti S, Martino D, Fontana A, Logroscino G. 2016. Accuracy of clinical diagnosis of Parkinson disease: A systematic review and meta-analysis. Neurology. 86(6):566–576.
  • Ross GW, Petrovitch H. 2001. Current evidence for neuroprotective effects of nicotine and caffeine against Parkinson's disease. Drugs Aging. 18(11):797–806.
  • Samii A, Nutt JG, Ransom BR. 2004. Parkinson's disease. Lancet. 363(9423):1783–1793.
  • Schrag A, Ben-Shlomo Y, Quinn N. 2002. How valid is the clinical diagnosis of Parkinson's disease in the community? J Neurol Neurosurg Psychiatry. 73(5):529–534.
  • Sterling J, Veinberg A, Lerner D, Goldenberg W, Levy R, Youdim M, Finberg J. 1998. N-propargyl-1-aminoindan (rasagiline) and derivatives: highly selective and potent inhibitors of monoamine oxidase B. Journal of Neural Transmission. Supplementa. 52:301–305.
  • Temporal KH, Scott KS, Mohr ALA, Logan BK. 2017. Metabolic Profile Determination of NBOMe Compounds Using Human Liver Microsomes and Comparison with Findings in Authentic Human Blood and Urine. J Anal Toxicol. 41(7):646–657.
  • Tolosa E, Gaig C, Santamaría J, Compta Y. 2009. Diagnosis and the premotor phase of Parkinson disease. Neurology. 72(7 Suppl):S12–S20.
  • Uversky VN. 2008. Alpha-synuclein misfolding and neurodegenerative diseases. Curr Protein Pept Sci. 9(5):507–540.
  • Wahlqvist ML, Lee MS, Hsu CC, Chuang SY, Lee JT, Tsai HN. 2012. Metformin-inclusive sulfonylurea therapy reduces the risk of Parkinson's disease occurring with Type 2 diabetes in a Taiwanese population cohort. Parkinsonism Relat Disord. 18(6):753–758.
  • Wang T, Yang L, Hua J, Xie H, Jiang X, Wang L. 2016. Simultaneous bioanalysis of rasagiline and its major metabolites in human plasma by LC-MS/MS: Application to a clinical pharmacokinetic study. J Pharm Biomed Anal. 125:280–285.

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.