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Fmoc solid-phase synthesis of RF9 optimization with mass spectrometry verification Cover

Fmoc solid-phase synthesis of RF9 optimization with mass spectrometry verification

Open Access
|Jul 2022

References

  1. 1. Wojciechowski P, Andrzejewski K, Kaczyńska K. Intracerebroventricular neuropeptide FF diminishes the number of apneas and cardiovascular effects produced by opioid receptors’ activation. Int J Mol Sci. 2020;21:8931.10.3390/ijms21238931772809733255594
  2. 2. Elhabazi K, Trigo JM, Mollereau C, Moulédous L, Zajac JM, Bihel F, et al. Involvement of neuropeptide FF receptors in neuroadaptive responses to acute and chronic opiate treatments. Br J Pharmacol. 2012;165(2):424-35.10.1111/j.1476-5381.2011.01563.x326819621718302
  3. 3. Hartman K, Mielczarek P, Smoluch M, Silberring J. Inhibitors of neuropeptide peptidases engaged in pain and drug dependence. Neuropharmacology. 2020;175:108137.10.1016/j.neuropharm.2020.10813732526240
  4. 4. Simonin F, Schmitt M, Laulin JP, Laboureyras E, Jhamandas JH, MacTavish D, et al. RF9, a potent and selective neuropeptide FF receptor antagonist, prevents opioid-induced tolerance associated with hyperalgesia. Proc Natl Acad Sci USA. 2006;103(2):466-71.10.1073/pnas.0502090103132615016407169
  5. 5. Grasso G, Mielczarek P, Niedziolka M, Silberring J. Metabolism of cryptic peptides derived from neuropeptide FF precursors: the involvement of insulin-degrading enzyme. Int J Mol Sci. 2014;15(9):16787-99.10.3390/ijms150916787420085225247577
  6. 6. Fang Q, Wang YQ, He F, Guo J, Guo J, Chen Q, Wang R. Inhibition of neuropeptide FF (NPFF)-induced hypothermia and anti-morphine analgesia by RF9, a new selective NPFF receptors antagonist. Regul Pept. 2008;147(1-3):45-51.10.1016/j.regpep.2007.12.007
  7. 7. Zhang T, Han Z, Shi X, Zhao W, Wang Z, Zhang R, et al. Discovery of two novel branched peptidomimetics containing endomorphin-2 and RF9 pharmacophores: Synthesis and neuropharmacological evaluation. Bioorg Med Chem. 2019;27(4):630-43.10.1016/j.bmc.2019.01.00330626554
  8. 8. Hammoud H, Elhabazi K, Quillet R, Bertin I, Utard V, Laboureyras E, et al. Aminoguanidine ydrazone derhivatives as nonpeptide NPFF1 receptor antagonists reverse opioid induced hyperalgesia. ACS Chem Neurosci. 2018;9(11):2599-609.10.1021/acschemneuro.8b0009929727163
  9. 9. Kotlinska JH, Gibula-Bruzda E, Koltunowska D, Raoof H, Suder P, Silberring J. Modulation of neuropeptide FF (NPFF) receptors influences the expression of amphetamine-induced conditioned place preference and amphetamine withdrawal anxiety-like behavior in rats. Peptides. 2012, 33(1):156-63.10.1016/j.peptides.2011.12.00222197492
  10. 10. Wang ZL, Pan JX, Song JJ, Tang HH, Yu HP, Li XH, et al. Structure-based optimization of multifunctional agonists for opioid and neuropeptide FF receptors with potent nontolerance forming analgesic activities. J Med Chem. 2016;59(22):10198-208.10.1021/acs.jmedchem.6b0118127798836
  11. 11. Wang YQ, Guo J, Wang SB, Fang Q, He F, Wang R. Neuropeptide FF receptors antagonist, RF9, attenuates opioid-evoked hypothermia in mice. Peptides. 2008;29(7):1183-90.10.1016/j.peptides.2008.02.01618406009
  12. 12. El-Faham A, Albericio F. COMU: a third generation of uronium-type coupling reagents. J Pept Sci. 2010;16(1):6-9.10.1002/psc.120419950108
  13. 13. El-Faham A, Subirós-Funosas RS, Prohens R, Albericio F. COMU: A safer and more effective replacement for benzotriazole-based uranium coupling reagents. Chem A Eur J. 2009;15:9404-16.10.1002/chem.20090061519621394
  14. 14. Hartman K, Mielczarek P, Silberring J. Synthesis of the novel covalent cysteine proteases inhibitor with iodoacetic functional group. Molecules. 2020;25(4):813.10.3390/molecules25040813707052132069913
  15. 15. Christensen T. Qualitative test for monitoring coupling completeness in solid phase peptide synthesis using chloranil. Acta Chem Scand B. 1979;33:763-6.10.3891/acta.chem.scand.33b-0763
  16. 16. Mielczarek P, Raoof H, Kotlinska JH, Stefanowicz P, Szewczuk Z, Suder P, et al. Electrochemical simulation of cocaine metabolism-a step toward predictive toxicology for drugs of abuse. Eur J Mass Spectrom (Chichester). 2014;20(4):279-85.10.1255/ejms.128425420340
  17. 17. Mielczarek P, Silberring J, Smoluch M. Technical note: Air compared to nitrogen as nebulizing and drying gases for electrospray ionization mass spectrometry. Eur J Mass Spectrom (Chichester). 2016;22(5):213-6.10.1255/ejms.143527882886
DOI: https://doi.org/10.2478/cipms-2022-0003 | Journal eISSN: 2300-6676 | Journal ISSN: 2084-980X
Language: English
Page range: 11 - 15
Submitted on: Sep 7, 2021
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Accepted on: Jun 6, 2022
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Published on: Jul 28, 2022
Published by: Sciendo
In partnership with: Paradigm Publishing Services
Publication frequency: 4 issues per year

© 2022 Marta Orocz, Kinga Hartman, Marek Smoluch, Jerzy Silberring, Przemyslaw Mielczarek, published by Sciendo
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.