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Voltammetric study of valsartan–Ni complex: application to valsartan analysis in pharmaceuticals and in vivo human urine profiling

  • Marwa A. A. Ragab
  • Mohamed A. Korany
  • Shereen M. Galal
  • Aya R. Ahmed
Original Paper
  • 36 Downloads

Abstract

Valsartan (VAL) can be analyzed at the mercury electrode in the presence of nickel (II) yielding a sensitive cathodic peak at − 0.7 V which may be attributed to the reduction of the complex formed between nickel and VAL. Low LOD and LOQ were achieved (7.6 and 23 nM, respectively) permitting the analysis of VAL not only in its pharmaceutical formula, but also in human urine. The influence of adding transition metal, Ni(II), to the electrolyte containing VAL, on the voltammetric response was studied. Differential-pulse voltammetry, using working electrode: hanging mercury drop electrode (HMDE), was applied to elucidate and confirm the possible complexation reaction that could occur between VAL and nickel which aids in the determination of VAL in tablets and human urine. A simple cleanup procedure was applied for urine samples that involves the use of solid-phase extraction with the elution of VAL with methanol. The polarographic peak, which corresponds to the reduction of Ni(II) in the formed complex with VAL, was a function of the concentration of VAL, pH of the medium and Ni(II) concentration at the electrode surface. At Britton–Robinson buffer pH 6 and using 800 µM Ni(II), the reduction peak current linearly varied with the VAL concentration over the ranges of 25–150 and 25–200 nM in tablets as well as urinalysis, respectively.

Keywords

Valsartan Ni(II) Complexation Tablets Urine Voltammetry 

Notes

Funding

All authors received no funding

Compliance with ethical standards

Conflict of interest

On behalf of all authors, the corresponding author states that there is no conflict of interest.

Supplementary material

11696_2018_671_MOESM1_ESM.docx (125 kb)
Supplementary material 1 (DOCX 126 kb)

References

  1. Abdel-Megied A, Gaber A, Abdelmageed H, Omar OM (2014) Determination of Losartan in tablet dosage form and some biological body fluids via complexation with Cu (II) using cathodic adsorptive stripping voltammetry. Sci J 2:8–13Google Scholar
  2. Ayman AG, Fahim S (2009) Spectroscopic and thermal studies on copper(II) and cobalt(II)-losartan complexes. ICAIJ 4:6–9Google Scholar
  3. Belicky S, Tkac J (2015) Can glycoprofiling be helpful in detecting prostate cancer? Chem Pap 69:90–111.  https://doi.org/10.1515/chempap-2015-0052 CrossRefGoogle Scholar
  4. Bhandari D, Bowman BA, Patel AB, Chambers DM, De Jesús VR, Blount BC (2018) UPLC-ESI-MS/MS method for the quantitative measurement of aliphatic diamines, trimethylamine N-oxide, and β-methylamino-l-alanine in human urine. J Chromatogr B 1083:86–92.  https://doi.org/10.1016/j.jchromb.2018.02.043 CrossRefGoogle Scholar
  5. Cagigal E, González L, Alonso R, Jiménez R (2001) Experimental design methodologies to optimise the spectrofluorimetric determination of Losartan and Valsartan in human urine. Talanta 54:1121–1133.  https://doi.org/10.1016/S0039-9140(01)00379-4 CrossRefGoogle Scholar
  6. Correia dos Santos MM, Famila V, Simões Gonçalves ML (2002) Copper-psychoactive drug complexes: a voltammetric approach to complexation by 1,4-benzodiazepines. Anal Biochem 303:111–119.  https://doi.org/10.1006/abio.2002.5580 CrossRefGoogle Scholar
  7. Del Rosario Brunetto M et al (2009) Determination of losartan, telmisartan, and valsartan by direct injection of human urine into a column-switching liquid chromatographic system with fluorescence detection. J Pharm Biomed Anal 50:194–199.  https://doi.org/10.1016/j.jpba.2009.04.015 CrossRefGoogle Scholar
  8. Denadai AM et al (2013) Control of size in losartan/copper(II) coordination complex hydrophobic precipitate. Mater Sci Eng C Mater Biol Appl 33:3916–3922.  https://doi.org/10.1016/j.msec.2013.05.033 CrossRefGoogle Scholar
  9. El-Kosasy AM, Tawakkol SM, Ayad MF, Sheta AI (2015) New methods for amlodipine and valsartan native spectrofluorimetric determination, with factors optimization study. Talanta 143:402–413.  https://doi.org/10.1016/j.talanta.2015.05.012 CrossRefGoogle Scholar
  10. Ensafi AA, Hajian R (2008) Determination of losartan and triamterene in pharmaceutical compounds and urine using cathodic adsorptive stripping voltammetry. Anal Sci 24:1449–1454CrossRefGoogle Scholar
  11. Etcheverry SB, Di Virgilio AL, Nascimento OR, Williams PA (2012) Dinuclear copper(II) complexes with valsartan. Synthesis, characterization and cytotoxicity. J Inorg Biochem 107:25–33.  https://doi.org/10.1016/j.jinorgbio.2011.10.005 CrossRefGoogle Scholar
  12. Ferreira VS, Zanoni MVB, Furlan M, Fogg AG (1997) Differential pulse polarographic determination of ceftazidime in urine samples with and without prior extraction. Anal Chim Acta 351:105–114.  https://doi.org/10.1016/S0003-2670(97)00347-4 CrossRefGoogle Scholar
  13. Guidance for Industry-Bioanalytical Method Validation, US Department of Health and Human Services Food and Drug Administration, Center for Drug Evaluation and Research (CDER), Center for Veterinary Medicine (CVM) (2001).Google Scholar
  14. Gunduz SB, Ahmet D (2014) Investigation of the metal bonding properties of some ARA-II compounds using spectrofluorimetric method. Current Drug Therapy 9:285–293.  https://doi.org/10.2174/1574885510999150505165817 CrossRefGoogle Scholar
  15. Gürler N, Eskiköy Bayraktepe D, Yazan Z, Dinç E (2013) Electrochemical characterization and voltammetric anodic stripping methods for the determination of valsartan. Rev Chim Buchar Original Ed 64:1211–1217Google Scholar
  16. Habib I, Weshahy A, Toubar SS, El-Alamin M (2008) Stripping voltammetric determination of valsartan in bulk and pharmaceutical products. Pharmazie 63:337–341.  https://doi.org/10.1691/ph.2008.7352 Google Scholar
  17. Hafez HM, Elshanawane AA, Abdelaziz LM, Kamal MM (2013) Quantitative determination of three angiotensin-II-receptor antagonists in presence of hydrochlorothiazide by RP-HPLC in their tablet preparations. Iran J Pharm Res 12:635–643Google Scholar
  18. Ibrahim MM, Hegazy MA, El-Bayoumi AE-A, Abdel-Gawad FM, Abd El-Ghani MA (2013) Evaluating the reducing properties of some antihypertensive and antibacterial drugs, through their reaction with iron (III) ions. ACAIJ 12:141–149Google Scholar
  19. Islas MS et al (2013) Improvement of the antihypertensive capacity of candesartan and trityl candesartan by their SOD mimetic copper(II) complexes. J Inorg Biochem 123:23–33.  https://doi.org/10.1016/j.jinorgbio.2013.02.005 CrossRefGoogle Scholar
  20. Kadam BR, Bari SB (2007) Quantitative analysis of valsartan and hydrochlorothiazide in tablets by high performance thin-layer chromatography with ultraviolet absorption densitometry. Acta Chromatographica 18:260–269Google Scholar
  21. Khashaba YP, Refat H, Ali H, El-Wekil M (2016) Complexation Based Voltammetric Determination of Pantoprazole Sodium in Pharmaceutical Formulations and Rabbit Plasma. Electroanalysis 29:890–897.  https://doi.org/10.1002/elan.201600639 CrossRefGoogle Scholar
  22. Khashaba YP, Refat H, Ali H, El-Wekil M (2017) Highly sensitive and selective complexation based voltammetric methods for the analysis of rabeprazole sodium in real samples. RSC Adv 7:3043–3050.  https://doi.org/10.1039/C6RA25565E CrossRefGoogle Scholar
  23. Korany MA, Mahgoub H, Haggag RS, Ragab MAA, Elmallah OA (2018a) Chemometrics-assisted spectrophotometric green method for correcting interferences in biowaiver studies: application to assay and dissolution profiling study of donepezil hydrochloride tablets. Spectrochim Acta Part A Mol Biomol Spectrosc 199:328–339.  https://doi.org/10.1016/j.saa.2018.03.059 CrossRefGoogle Scholar
  24. Korany MA, Mahgoub H, Haggag RS, Ragab MAA, Elmallah OA (2018b) Green gas chromatographic stability-indicating method for the determination of Lacosamide in tablets. Application to in vivo human urine profiling. J Chromatogr B 1083:75–85.  https://doi.org/10.1016/j.jchromb.2018.02.033 CrossRefGoogle Scholar
  25. Lachowicz JI et al (2017) Complex formation equilibria of Cu(2 +) and Zn(2 +) with irbesartan and losartan. Eur J Pharm Sci 97:158–169.  https://doi.org/10.1016/j.ejps.2016.11.010 CrossRefGoogle Scholar
  26. Levi M, Wuerzner G, Ezan E, Pruvost A (2009) Direct analysis of valsartan or candesartan in human plasma and urines by on-line solid phase extraction coupled to electrospray tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 877:919–926.  https://doi.org/10.1016/j.jchromb.2009.02.030 CrossRefGoogle Scholar
  27. Lotfy HM, Hegazy MA, Mowaka S, Mohamed EH (2015) Novel spectrophotometric methods for simultaneous determination of amlodipine, valsartan and hydrochlorothiazide in their ternary mixture. Spectrochim Acta A Mol Biomol Spectrosc 140:495–508.  https://doi.org/10.1016/j.saa.2014.12.096 CrossRefGoogle Scholar
  28. Mansano GR, Pires Eisele AP, Dall’Antonia LH, Afonso S, Sartori ER (2015) Electroanalytical application of a boron-doped diamond electrode: improving the simultaneous voltammetric determination of amlodipine and valsartan in urine and combined dosage forms. Anal Methods 738:188–194.  https://doi.org/10.1039/C4AY02511C Google Scholar
  29. Martin BK (1967) Drug urinary excretion data–some aspects concerning the interpretation. Br J Pharm Chemother 29:181–193CrossRefGoogle Scholar
  30. Miller JN, Miller JC (2005) Statistics and chemometrics for analytical chemistry. Newyork, Pearson Prentice HallGoogle Scholar
  31. Parambi DGT, Mathew M, Ganesan V (2011) Quantitative analysis of valsartan in tablets formulations by high performance thin-layer chromatography. J Appl Pharm Sci 01:76–78Google Scholar
  32. Parashar HM, Jabali JV (2014) Synthesis, spectral, thermal, anti microbial and catalytic activity of zn2+ and cd2+ chelates with valsartan. Int J Pharm Bio Sci 5:383–389Google Scholar
  33. Pınar EE, İbrahim HT, Ceren K, Esma K (2014) Simultaneous determination of valsartan and amlodipine besylate in human serum and pharmaceutical dosage forms by voltammetry. Int J Electrochem 9:2208–2220Google Scholar
  34. Ragab MAA, Galal SM, Korany MA, Ahmed AR (2017) First derivative emission spectrofluorimetric method for the determination of LCZ696, a newly approved FDA supramolecular complex of valsartan and sacubitril in tablets. Luminescence 32:1417–1425.  https://doi.org/10.1002/bio.3339 CrossRefGoogle Scholar
  35. Ragab MAA, Galal SM, Korany MA, Ahmed AR (2018a) High performance thin-layer and high performance liquid chromatography coupled with photodiode array and fluorescence detectors for analysis of valsartan and sacubitril in their supramolecular complex with quantitation of sacubitril-related substance in raw material and tablets. J Chromatogr Sci 56:498–509.  https://doi.org/10.1093/chromsci/bmy021 CrossRefGoogle Scholar
  36. Ragab MAA, Korany MA, Galal SM, Ahmed AR (2018b) Diode array detection for stability assessment and evaluation of degradation kinetics of newly introduced sacubitril in its supramolecular complex (LCZ696) with valsartan. J Liq Chromatogr Relat Technol 41:1–10.  https://doi.org/10.1080/10826076.2017.1415213 CrossRefGoogle Scholar
  37. Samya ME, Osama HA, Mahmoud AO, Sayed MD, Ahmed MA (2012) Development and validation of HPLC method for simultaneous determination of amlodipine, valsartan, hydrochlorothiazide in dosage form and spiked human plasma. Am J Anal Chem 3:422–430.  https://doi.org/10.4236/ajac.2012.36055 CrossRefGoogle Scholar
  38. Shaalan RA, Belal TS (2010) Simultaneous spectrofluorimetric determination of amlodipine besylate and valsartan in their combined tablets. Drug Testing Anal 2:489–493CrossRefGoogle Scholar
  39. Shah NJ, Suhagia BN, Shah RR, Patel NM (2009) HPTLC method for the simultaneous estimation of valsartan and hydrochlorothiazide in tablet dosage form. Indian J Pharm Sci 71:72–74CrossRefGoogle Scholar
  40. Shah JV, Parekh JM, Shah PA, Shah PV, Sanyal M, Shrivastav PS (2017) Application of an LC–MS/MS method for the analysis of amlodipine, valsartan and hydrochlorothiazide in polypill for a bioequivalence study. J Pharm Anal 7:309–316.  https://doi.org/10.1016/j.jpha.2017.06.001 CrossRefGoogle Scholar
  41. Skibiński R, Komsta Ł, Grech-Baran M, Gumieniczek A (2010) A proposal of reference values for relative uncertainty increase in spectrophotometric analysis of pharmaceutical formulations. Chem Pap 64:273–277.  https://doi.org/10.2478/s11696-009-0093-8 Google Scholar
  42. Sweetman SC (2007) Martindale: the complete drug reference, 35th edn. Pharmaceutical Press, LondonGoogle Scholar
  43. Tian D, Tian X, Tian T, Wang Z, Mo F (2008) Simultaneous determination of valsartan and hydrochlorothiazide in tablets by RP-HPLC. Indian J Pharm Sci 70:372–374CrossRefGoogle Scholar
  44. VALIDATION OF ANALYTICAL PROCEDURES: TEXT AND METHODOLOGY Q2(R1) International Conference on Harmonization, Geneva,. (November 2005). https://www.ich.org/fileadmin/Public_Web_Site/ICH_Products/Guidelines/Quality/Q2_R1/Step4/Q2_R1__Guideline.pdf. Accessed (Last accessed June 2018)
  45. Waldmeier F, Flesch G, Muller P, Winkler T, Kriemler HP, Buhlmayer P, De Gasparo M (1997) Pharmacokinetics, disposition and biotransformation of [14C]-radiolabelled valsartan in healthy male volunteers after a single oral dose. Xenobiotica 27:59–71.  https://doi.org/10.1080/004982597240767 CrossRefGoogle Scholar
  46. Yan J, Wang W, Chen L, Chen S (2008) Electrochemical behavior of valsartan and its determination in capsules. Colloids Surf, B 67:205–209.  https://doi.org/10.1016/j.colsurfb.2008.08.015 CrossRefGoogle Scholar
  47. Zanoni MVB, Fogg AG (1993) Cathodic stripping voltammetric determination of pentamidine isethionate at a hanging mercury drop electrode. Analyst 118:1163–1166.  https://doi.org/10.1039/AN9931801163 CrossRefGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2019

Authors and Affiliations

  1. 1.Department of Pharmaceutical Analytical Chemistry, Faculty of PharmacyUniversity of AlexandriaAlexandriaEgypt

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