Abstract
A surface-enhanced Raman scattering (SERS) method is described for the determination of prazosin (PRH) and losartan (LOS). Silver nanoparticles modified with β-cyclodextrin (CD-S-Ag NPs) were prepared and serve as a sensitive SERS substrate. β-CD is both a reductant for silver ions and a host molecule that binds the analytes which leads to strong SERS enhancement. The method has distinct features: (a) The linear response extends from 0.1 to 60 μM for PRH, and from 1.0 to 100 μM for LOS; (b) the respective limits of detection are as low as 15 nM and 0.92 μM; and (c) the specific SERS bands of PRH and LOS are located at 703 and 1298 cm−1 respectively. The method was successfully applied to the determination of PRH and LOS illegally added to healthcare products. The recovery of PRH and LOS from spiked samples ranges between 91.3 and 109.3%, and from 87.4 to 105.2%, respectively, both with relative standard deviation of <5%.
Similar content being viewed by others
References
Wang Y, Peng X, Nie X, Chen L, Weldon R, Zhang W et al (2016) Burden of hypertension in China over the past decades: systematic analysis of prevalence, treatment and control of hypertension. Eur J Prev Cardiol 23(8):792–800. https://doi.org/10.1177/2047487315617105
Wang Y, Peng X, Nie X, Chen L, Weldon R, Zhang W, ... Cai J (2016) Burden of hypertension in China over the past decades: systematic analysis of prevalence, treatment and control of hypertension. Eur J Prev Cardiol 23(8): 792–800. https://doi.org/10.1016/S0140-6736(02)11403-6
Wankhede SB, Raka KC, Wadkar SB, Chitlange SS (2010) Spectrophotometric and HPLC methods for simultaneous estimation of amlodipine besilate, losartan potassium and hydrochlorothiazide in tablets. Indian J Pharm Sci 72(1):136. https://doi.org/10.4103/0250-474X.62239
Stolarczyk M, Maslanka A, Apola A, Krzek J (2013) Determination of losartan potassium, quinapril hydrochloride and hydrochlorothiazide in pharmaceutical preparations using derivative spectrophotometry and chromatographic-densitometric method. Acta Pol Pharm 70(6):967–976
Shah SN, Sultana N, Hasan N, Arayne MS (2015) Novel RP-HPLC method for simultaneous determination of prazosin and NSAIDs in bulk, pharmaceutical formulations and human serum. World J Pharm Res 4:333–350
Sivakumar T, Venkatesan P, Manavalan R, Valliappan K (2007) Development of a HPLC method for the simultaneous determination of losartan potassium and atenolol in tablets. Indian J Pharm Sci 69(1):154. https://doi.org/10.4103/0250-474X.32137
Erceg M, Cindric M, Frketic LP, Vertzoni M, Cetina-Cižmek B, Reppas C (2010) A LC-MS-MS method for determination of low doxazosin concentrations in plasma after oral administration to dogs. J Chromatogr Sci 48(2):114–119. https://doi.org/10.1093/chromsci/48.2.114
Salvadori MC, Moreira RF, Borges BC, Andraus MH, Azevedo CP, Moreno RA, Borges NC (2009) Simultaneous determination of losartan and hydrochlorothiazide in human plasma by LC/MS/MS with electrospray ionization and its application to pharmacokinetics. Clin Exp Hypertens 31(5):415–427. https://doi.org/10.1080/10641960802668714
Cagigal E, Gonzalez L, Alonso RM, Jimenez RM (2001) Experimental design methodologies to optimise the spectrofluorimetric determination of losartan and valsartan in human urine. Talanta 54(6):1121–1133. https://doi.org/10.1016/S0039-9140(01)00379-4
Li Y, Deng Y, Zhou X, Hu J (2018) A label-free turn-on-off fluorescent sensor for the sensitive detection of cysteine via blocking the Ag+-enhancing glutathione-capped gold nanoclusters. Talanta 179:742–752. https://doi.org/10.1016/j.talanta.2017.11.057
Ma P, Liang F, Yang Q, Wang D, Sun Y, Wang X et al (2014) Highly sensitive SERS probe for mercury (II) using cyclodextrin-protected silver nanoparticles functionalized with methimazole. Microchim Acta 181(9–10):975–981. https://doi.org/10.1007/s00604-014-1196-7
Ouyang L, Zhu L, Ruan Y, Tang H (2015) Preparation of a native β-cyclodextrin modified plasmonic hydrogel substrate and its use as a surface-enhanced Raman scattering scaffold for antibiotics identification. J Mater Chem C 3(29):7575–7582. https://doi.org/10.1039/c5tc01368b
West MJ, Went MJ (2011) Detection of drugs of abuse by Raman spectroscopy. Drug Test Anal 3(9):532–538. https://doi.org/10.1002/dta.217
Rodriguez JD, Westenberger BJ, Buhse LF, Kauffman JF (2011) Quantitative evaluation of the sensitivity of library-based Raman spectral correlation methods. Anal Chem 83(11):4061–4067. https://doi.org/10.1021/ac200040b
Bate R, Mooney L, Milligan J (2012) The danger of substandard drugs in emerging markets: an assessment of basic product quality. Pharmacologia 3(2):46–51. https://doi.org/10.5567/pharmacologia.2012.46.51
Xu J, Du J, Jing C, Zhang Y, Cui J (2014) Facile detection of polycyclic aromatic hydrocarbons by a surface-enhanced Raman scattering sensor based on the au coffee ring effect. ACS Appl Mater Interfaces 6(9):6891–6897. https://doi.org/10.1021/am500705a
Liu L, Zhu S (2007) A study on the supramolecular structure of inclusion complex of β-cyclodextrin with prazosin hydrochloride. Carbohyd Polym 68(3):472–476. https://doi.org/10.1016/j.carbpol.2006.11.007
Yang L, Chen Y, Li H, Luo L, Zhao Y, Zhang H, Tian Y (2015) Application of silver nanoparticles decorated with β-cyclodextrin in determination of 6-mercaptopurine by surface-enhanced Raman spectroscopy. Anal Methods 7(16):6520–6527. https://doi.org/10.1039/C5AY01212K
Ouyang L, Li D, Zhu L, Yang W, Tang H (2016) A new plasmonic Pickering emulsion based SERS sensor for in situ reaction monitoring and kinetic study. J Mater Chem C 4(4):736–744. https://doi.org/10.1039/c5tc03831f
Yu Z, Grasso MF, Sorensen HH, Zhang P (2019) Ratiometric SERS detection of polycyclic aromatic hydrocarbons assisted by β-cyclodextrin-modified gold nanoparticles. Microchimica Acta 186(6):391. https://doi.org/10.1007/s00604-019-3511-9
Mizera M, Lewadowska K, Talaczyńska A, Cielecka-Piontek J (2015) Computational study of influence of diffuse basis functions on geometry optimization and spectroscopic properties of losartan potassium. Spectrochim Acta A Mol Biomol Spectrosc 137:1029–1038. https://doi.org/10.1016/j.saa.2014.09.036
Cavalli A (2010) Computational drug design: a guide for computational and medicinal chemists. By DC Young. ChemMedChem 5(2):305–306. https://doi.org/10.1002/cmdc.200900460
Karakaya, M., Kürekçi, M., Eskiyurt, B., Sert, Y., & Çırak, Ç. (2015). Experimental and computational study on molecular structure and vibrational analysis of an antihyperglycemic biomolecule: Gliclazide. Spectrochim Acta A 135:137–146. https://doi.org/10.1016/j.saa.2014.06.152
Lee PC, Meisel D (1982) Adsorption and surface-enhanced Raman of dyes on silver and gold sols. J Phys Chem 86(17):3391–3395. https://doi.org/10.1021/j100214a025
Garcia-Rio L, Godoy A, Leis JR (2005) Spectroscopic characterisation of crystal violet inclusion complexes in β-cyclodextrin. Chem Phys Lett 401(1–3):302–306. https://doi.org/10.1016/j.cplett.2004.11.063
Wu J, Zhang L, Bu X, Li P, Zhao B, Tian Y (2018) Determination of the illegal adulteration of natural healthcare products with chemical drugs using surface-enhanced Raman scattering. Analyst 143(21):5202–5209. https://doi.org/10.1039/c8an01286e
Gebhardt J, Kleist C, Jakobtorweihen S, Hansen N (2018) Validation and comparison of force fields for native cyclodextrins in aqueous solution. J Phys Chem B 122(5):1608–1626. https://doi.org/10.1021/acs.jpcb.7b11808
Villaverde J, Morillo E, Pérez-Martínez JI, Ginés JM, Maqueda C (2004) Preparation and characterization of inclusion complex of norflurazon and β-cyclodextrin to improve herbicide formulations. J Agric Food Chem 52(4):864–869. https://doi.org/10.1021/jf0350358
Liu H, Cai X, Wang Y, Chen J (2011) Adsorption mechanism-based screening of cyclodextrin polymers for adsorption and separation of pesticides from water. Water Res 45(11):3499–3511. https://doi.org/10.1016/j.watres.2011.04.004
Lezcano M, Al-Soufi W, Novo M, Rodríguez-Núñez E, Tato JV (2002) Complexation of several benzimidazole-type fungicides with α-and β-cyclodextrins. J Agric Food Chem 50(1):108–112. https://doi.org/10.1021/jf0350358
Szejtli J (1998) Introduction and general overview of cyclodextrin chemistry. Chem Rev 98(5):1743–1754. https://doi.org/10.1021/cr970022c
De Paula WX, Denadai ÂM, Santoro MM, Braga AN, Santos RA, Sinisterra RD (2011) Supramolecular interactions between losartan and hydroxypropyl-β-CD: ESI mass-spectrometry, NMR techniques, phase solubility, isothermal titration calorimetry and anti-hypertensive studies. Int J Pharm 404(1-2):116–123. https://doi.org/10.1016/j.ijpharm.2010.11.008
Acknowledgements
We appreciate financial support from the Science-Technology Development Project of Jilin Province of China (Grant No. 20170101174JC) and the National Natural Science Foundation (Grant No. 21327803, 21773080, 21711540292) of the People’s Republic of China.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no conflicts of interest.
Additional information
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
ESM 1
(DOCX 480 kb)
Rights and permissions
About this article
Cite this article
Wu, J., Ma, H., Bu, X. et al. SERS determination of the antihypertensive drugs prazosin and losartan by using silver nanoparticles coated with β-cyclodextrin. Microchim Acta 186, 801 (2019). https://doi.org/10.1007/s00604-019-3946-z
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s00604-019-3946-z