Advanced search
Publication Cover
Molecular Simulation Volume 45, 2019 - Issue 17
Submit an article Journal homepage
139
Views
1
CrossRef citations to date
0
Altmetric
Articles

The role of regioselective hydroxylation on toxicity of diclofenac and related derivatives

Ana C. S. P. S. de JesusNúcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém, Brazil
,
Fernanda M. CostaNúcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém, Brazil
,
Paulo A. P. F. G. das NevesNúcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém, Brazil
,
Fernanda P. A. MeloNúcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém, Brazil
,
Antonio S. SilvaNúcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém, Brazil
,
Osmarina P. P. SilvaNúcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém, Brazil
,
Cleydson B. R. SantosLaboratório de Modelagem e Química Computacional, Departamento de Ciências Biológicas e Ciências da Saúde, Universidade Federal do Amapá, Macapá, Brazil
&
Rosivaldo S. BorgesNúcleo de Estudos e Seleção de Moléculas Bioativas, Instituto de Ciências da Saúde, Universidade Federal do Pará, Belém, BrazilCorrespondence[email protected]
[email protected]
 show all
Pages 1454-1458 | Received 09 Mar 2019, Accepted 30 Jul 2019, Published online: 23 Aug 2019

References

  • Krasniqi V, Dimovski A, Domjanović IK, et al. How polymorphisms of the cytochrome P450 genes affect ibuprofen and diclofenac metabolism and toxicity. Arh Hig Rada Toksikol. 2016;67:1–8. doi: 10.1515/aiht-2016-67-2754
  • Bessone F. Non-steroidal anti-inflammatory drugs: WHAT is the actual risk of liver damage? World J Gastroenterol. 2010;16:5651–5661. doi: 10.3748/wjg.v16.i45.5651
  • Palkar MB, Singhai AS, Ronad PM, et al. Synthesis, pharmacological screening and in silico studies of new class of diclofenac analogues as a promising anti-inflammatory agents. Bioorg Med Chem. 2014;22:2855–2866. doi: 10.1016/j.bmc.2014.03.043
  • Manrique-Moreno M, Heinbockelb L, Suwalsky M, et al. Biophysical study of the non-steroidal anti-inflammatory drugs (NSAID) ibuprofen, naproxen and diclofenac with phosphatidylserine bilayer membranes. Biochim Biophys Acta. 2016;1858:2123–2131. doi: 10.1016/j.bbamem.2016.06.009
  • Njoku DB. Drug-induced hepatotoxicity: metabolic, genetic and immunological basis. Int J Mol Sci. 2014;15:6990–7003. doi: 10.3390/ijms15046990
  • Sarda S, Page C, Pickup K, et al. Diclofenac metabolism in the mouse: novel in vivo metabolites identified by high performance liquid chromatography coupled to linear ion trap mass spectrometry. Xenobiotica. 2012;42:179–194. doi: 10.3109/00498254.2011.607865
  • Leeuwen JSV, Vredenburg G, Dragovic S, et al. Metabolism related toxicity of diclofenac in yeast as model system. Toxicol Lett. 2011;200:162–168. doi: 10.1016/j.toxlet.2010.11.010
  • Faber H, Melles D, Brauckmann C, et al. Simulation of the oxidative metabolism of diclofenaco by electrochemistry/(liquid chromatography/)mass spectrometry. Anal Bioanal Chem. 2012;403:345–354. doi: 10.1007/s00216-011-5665-0
  • Llerena A, Alvarez M, Dorado P, et al. Interethnic differences in the relevance of CYP2C9 genotype and environmental factors for diclofenac metabolism in Hispanics from Cuba and Spain. Pharmacogenomics J. 2013;14(3):229–234. doi: 10.1038/tpj.2013.28
  • Daily EB, Aquilante CL. Cytochrome P450 2C8 pharmacogenetics: a review of clinical studies. Pharmacogenomics. 2009;10:1489–1510. doi: 10.2217/pgs.09.82
  • Lonsdale R, Houghton KT, Zurek J, et al. Quantum mechanics/molecular mechanics modeling of regioselectivity of drug metabolism in cytochrome P450 2C9. J Am Chem Soc. 2013;135(21):8001–8015. doi: 10.1021/ja402016p
  • Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 03, Revision C.02. Wallingford (CT): Gaussian, Inc; 2004.
  • Parr RG, Yang W. Density functional theory of atoms and molecules. New York (NY): Oxford University Press; 1989.
  • Stewart JJP. Optimization of parameters for semiempirical methods I. method. J Comput Chem. 1989;10:209. doi: 10.1002/jcc.540100208
  • Becke AD. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A. 1988;38:3098. doi: 10.1103/PhysRevA.38.3098
  • Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B. 1988;37:785. doi: 10.1103/PhysRevB.37.785
  • Hehre WJ, Radom L, Schleyer PVR, et al. Ab Initio molecular orbital theory. New York (NY): Wiley; 1986.
  • Borges RS, Batista Junior J, Viana RB, et al. Understanding the molecular aspects of tetrahydrocannabinol and cannabidiol as antioxidants. Molecules. 2013;18:12663–12674. doi: 10.3390/molecules181012663
  • Savir Y, Tlusty T. Conformational proofreading: the impact of conformational changes on the specificity of molecular recognition. PLoS ONE. 2007;2(5):e468. doi: 10.1371/journal.pone.0000468
  • Attia SM. Deleterious effects of reactive metabolites. Oxid Med Cell Longev. 2010;3:238–253. doi: 10.4161/oxim.3.4.13246
  • Greenslade D, Havler ME, Humphrey MJ, et al. Species differences in the metabolism and excretion of fenclofenac. Xenobiotica. 1980;10:753–760. doi: 10.3109/00498258009033803
  • Prescott LF. Effects of non-narcotic analgesics on the liver. Drugs. 1986;32:129–147. doi: 10.2165/00003495-198600324-00010

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:

Order Reprints Request Corporate Permissions

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:

Request Academic Permissions

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.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.