Cyclodextrin-mediated gold nanoparticles as multisensing probe for the selective detection of hydroxychloroquine drug

Jaise Mariya George; Beena Mathew

Korean Journal of Chemical Engineering, Vol.38, No.3, 624-634, March, 2021

DOI10.1007/s11814-020-0719-7 Export Citation

Cyclodextrin-mediated gold nanoparticles as multisensing probe for the selective detection of hydroxychloroquine drug

Jaise Mariya George, and Beena Mathew^†

School of Chemical Sciences, Mahatma Gandhi University, Kottayam-686560, Kerala, India

E-mail:

β-Cyclodextrin (β-CD) modified gold nanoparticles (AuNP) were rapidly synthesized using microwave assisted procedure. Parameters, such as time, pH and concentrations of β-CD and gold, were optimized for the synthesis of β-CD-AuNP. The addition of enantiomers and racemic mixture of hydroxychloroquine (R-HCQ, S-HCQ and RS-HCQ) drugs and their interaction with β-CD led to a red shift in the surface plasmon resonance of β-CD-AuNP. The changes associated with the introduction of HCQ in β-CD-AuNP were studied using various characterization techniques such as UV-vis, FT-IR, XRD, dynamic light scattering, zeta potential, transmission electron microscopy, fluorescence spectroscopy and electrochemical techniques. The host-guest interaction of β-cyclodextrin with S-HCQ, RHCQ and RS-HCQ resulted in the aggregation of gold nanoparticles. The surface plasmon resonance at 521 nm for β- CD-AuNP was shifted to 600, 620 and 670 nm on the addition of S-HCQ, R-HCQ and RS-HCQ, respectively, with a color change from pink to blue. The selectivity and sensitivity of the developed system for RS-HCQ were investigated and the limit of detection (LOD=3 s/m) was found to be 2.61, 0.15, and 0.85nM for optical, fluorescence and electrochemical methods, respectively. The successful monitoring of RS-HCQ drug in pharmaceutical samples is possible with these techniques.

Keywords:Gold Nanoparticles;β-Cyclodextrin;Hydroxy Chloroquine;Enantiomeric;Sensing

[References]

Aravind A, Sebastian M, Mathew B, New J. Chem., 42, 1502 (2018)
Kailasa SK, Mehta VN, Wu HF, RSC Adv., 4, 16188 (2014)
Sebastian M, Aravind A, Mathew B, Mater. Res. Express, 5, 085015 (2018)
Vilela D, Gonzalez MC, Escarpa A, Anal. Chim. Acta, 751, 24 (2012)
Saha K, Agasti SS, Kim C, Li XN, Rotello VM, Chem. Rev., 112(5), 2739 (2012)
Khodaveisi J, Dadfarnia S, Shabani AMH, Saberi D, Sens. Actuators B-Chem., 239, 1300 (2017)
Kang J, Zhang Y, Li X, Miao L, Wu A, ACS Appl. Mater. Interfaces, 8, 1 (2015)
Fang C, Dharmarajan R, Megharaj M, Naidu R, TrAC-Trends Anal. Chem., 86, 143 (2017)
Hu M, Chen J, Li ZY, Au L, Hartland GV, Li X, Marquez M, Xia Y, Chem. Soc. Rev., 35, 1084 (2006)
Daniel MC, Astruc D, Chem. Rev., 104(1), 293 (2004)
Fan C, Wang S, Hong JW, Bazan GC, Plaxco KW, Heeger AJ, Proc. Natl. Acad. Sci. USA, 100, 6297 (2003)
Pikkel J, Chassid O, Sharabi-Nov A, Beiran I, Graefes Arch. Clin. Exp. Ophthalmol., 251, 1687 (2013)
Stelton CR, Connors DV, Walia SS, Walia HS, Clin. Rheumatol., 32, 895 (2013)
Chen JJ, Tarantola RM, Kay CN, Mahajan VB, Eye Rounds. Org. (2011).
Gouveia EV, de A. Morales MS, Gouveia GB, Lourenzi VPM, Arq. Bras. Oftalmol., 70, 1046 (2007)
Shearer RV, Dubois EL, Am. J. Ophthalmol., 64, 245 (1967)
Singh AK, Singh A, Shaikh A, Singh R, Misra A, Diabetes Metab. Syndr., 14, 241 (2020)
Percy LA, Fang MA, Rheum. Dis. Clin. North Am., 26, 433 (2000)
Brocks DR, Pasutto FM, Jamali F, J. Chromatogr. B, 581, 83 (1992)
Volin P, J. Chromatogr. B, 666, 347 (1995)
Wei Y, Nygard GA, Khalil SKW, J. Liq. Chromatogr., 17, 3479 (1994)
Williams SB, Patchen LC, Churchill FC, J. Chromatogr., 433, 197 (1988)
Morris RG, J. Chromatogr. B, 338, 422 (1985)
Wang LZ, Ong RYL, Chin TM, Thuya WL, Wan SC, Wong ALA, Chan SY, Ho PC, Goh BC, J. Pharm. Biomed. Anal., 61, 86 (2012)
Deroco PB, Vicentini FC, Oliveira GG, Rocha RC, Fatibello O, J. Electroanal. Chem., 719, 19 (2014)
Arguelho MLPM, Andrade JF, Stradiotto NR, J. Pharm. Biomed. Anal., 32, 269 (2003)
Khalil MM, El-aziz GMA, Ashry A, J. Iran. Chem. Soc., 15, 2411 (2018)
Crini G, Chem. Rev., 114(21), 10940 (2014)
Sharma N, Baldi A, Drug Deliv., 23, 739 (2016)
Connors KA, Chem. Rev., 97(5), 1325 (1997)
Liu L, Guo QX, J. Inclusion Phenom. Macrocyclic Chem., 42, 1 (2002)
Chatziefthimiou SD, Inclan M, Giastas P, Papakyriakou A, Yannakopoulou K, Mavridis IM, Beilstein J. Org. Chem., 13, 1572 (2017)
Shpigun A, Ananieva IA, Budanova NY, Shapovalova EN, Russ. Chem. Rev., 72, 1035 (2003)
Joseph S, Mathew B, Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 136, 1371 (2015)
Huang T, Meng F, Qi L, J. Phys. Chem. C, 113, 13636 (2009)
Vijayan R, Joseph S, Mathew B, Artif. Cell Nanomed. B, 46, 861 (2017)
George JM, Priyanka RN, Mathew B, Microchem. J., 155, 104686 (2020)
Vijayan R, Joseph S, Mathew B, IET Nanobiotechnol., 12, 850 (2018)
Nguyen TN, Do TH, Nguyen DH, Vu D, Do QH, Tran HN, Nghiem THL, Appl. Phys. Express, 9, 022001 (2016)
George JM, Mathew B, J. Iran. Chem. Soc., 17, 2613 (2020)
Lam K, Van Wyck SJ, Geiger WE, J. Electroanal. Chem., 799, 531 (2017)
Srivastava M, Tiwari P, Mall VK, Srivastava SK, Prakash R, Microchim. Acta, 186, 415 (2019)
Arguelho ML, Andrade JF, Stradiotto NR, J. Pharm. Biomed. Anal., 32, 269 (2003)
Fox RI, Semin Arthritis Rheum., 2, 82 (1993)
Khoobi A, Ghoreishi SM, Behpour M, Analyst, 139, 4064 (2014)
Khoobi A, Ghoreishi SM, Behpour M, Shaterian M, Salavati-Niasari M, Colloids Surf. B: Biointerfaces, 123, 648 (2014)

[1] Aravind A, Sebastian M, Mathew B, New J. Chem., 42, 1502 (2018)

[2] Kailasa SK, Mehta VN, Wu HF, RSC Adv., 4, 16188 (2014)

[3] Sebastian M, Aravind A, Mathew B, Mater. Res. Express, 5, 085015 (2018)

[4] Vilela D, Gonzalez MC, Escarpa A, Anal. Chim. Acta, 751, 24 (2012)

[5] Saha K, Agasti SS, Kim C, Li XN, Rotello VM, Chem. Rev., 112(5), 2739 (2012)

[6] Khodaveisi J, Dadfarnia S, Shabani AMH, Saberi D, Sens. Actuators B-Chem., 239, 1300 (2017)

[7] Kang J, Zhang Y, Li X, Miao L, Wu A, ACS Appl. Mater. Interfaces, 8, 1 (2015)

[8] Fang C, Dharmarajan R, Megharaj M, Naidu R, TrAC-Trends Anal. Chem., 86, 143 (2017)

[9] Hu M, Chen J, Li ZY, Au L, Hartland GV, Li X, Marquez M, Xia Y, Chem. Soc. Rev., 35, 1084 (2006)

[10] Daniel MC, Astruc D, Chem. Rev., 104(1), 293 (2004)

[11] Fan C, Wang S, Hong JW, Bazan GC, Plaxco KW, Heeger AJ, Proc. Natl. Acad. Sci. USA, 100, 6297 (2003)

[12] Pikkel J, Chassid O, Sharabi-Nov A, Beiran I, Graefes Arch. Clin. Exp. Ophthalmol., 251, 1687 (2013)

[13] Stelton CR, Connors DV, Walia SS, Walia HS, Clin. Rheumatol., 32, 895 (2013)

[14] Chen JJ, Tarantola RM, Kay CN, Mahajan VB, Eye Rounds. Org. (2011).

[15] Gouveia EV, de A. Morales MS, Gouveia GB, Lourenzi VPM, Arq. Bras. Oftalmol., 70, 1046 (2007)

[16] Shearer RV, Dubois EL, Am. J. Ophthalmol., 64, 245 (1967)

[17] Singh AK, Singh A, Shaikh A, Singh R, Misra A, Diabetes Metab. Syndr., 14, 241 (2020)

[18] Percy LA, Fang MA, Rheum. Dis. Clin. North Am., 26, 433 (2000)

[19] Brocks DR, Pasutto FM, Jamali F, J. Chromatogr. B, 581, 83 (1992)

[20] Volin P, J. Chromatogr. B, 666, 347 (1995)

[21] Wei Y, Nygard GA, Khalil SKW, J. Liq. Chromatogr., 17, 3479 (1994)

[22] Williams SB, Patchen LC, Churchill FC, J. Chromatogr., 433, 197 (1988)

[23] Morris RG, J. Chromatogr. B, 338, 422 (1985)

[24] Wang LZ, Ong RYL, Chin TM, Thuya WL, Wan SC, Wong ALA, Chan SY, Ho PC, Goh BC, J. Pharm. Biomed. Anal., 61, 86 (2012)

[25] Deroco PB, Vicentini FC, Oliveira GG, Rocha RC, Fatibello O, J. Electroanal. Chem., 719, 19 (2014)

[26] Arguelho MLPM, Andrade JF, Stradiotto NR, J. Pharm. Biomed. Anal., 32, 269 (2003)

[27] Khalil MM, El-aziz GMA, Ashry A, J. Iran. Chem. Soc., 15, 2411 (2018)

[28] Crini G, Chem. Rev., 114(21), 10940 (2014)

[29] Sharma N, Baldi A, Drug Deliv., 23, 739 (2016)

[30] Connors KA, Chem. Rev., 97(5), 1325 (1997)

[31] Liu L, Guo QX, J. Inclusion Phenom. Macrocyclic Chem., 42, 1 (2002)

[32] Chatziefthimiou SD, Inclan M, Giastas P, Papakyriakou A, Yannakopoulou K, Mavridis IM, Beilstein J. Org. Chem., 13, 1572 (2017)

[33] Shpigun A, Ananieva IA, Budanova NY, Shapovalova EN, Russ. Chem. Rev., 72, 1035 (2003)

[34] Joseph S, Mathew B, Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 136, 1371 (2015)

[35] Huang T, Meng F, Qi L, J. Phys. Chem. C, 113, 13636 (2009)

[36] Vijayan R, Joseph S, Mathew B, Artif. Cell Nanomed. B, 46, 861 (2017)

[37] George JM, Priyanka RN, Mathew B, Microchem. J., 155, 104686 (2020)

[38] Vijayan R, Joseph S, Mathew B, IET Nanobiotechnol., 12, 850 (2018)

[39] Nguyen TN, Do TH, Nguyen DH, Vu D, Do QH, Tran HN, Nghiem THL, Appl. Phys. Express, 9, 022001 (2016)

[40] George JM, Mathew B, J. Iran. Chem. Soc., 17, 2613 (2020)

[41] Lam K, Van Wyck SJ, Geiger WE, J. Electroanal. Chem., 799, 531 (2017)

[42] Srivastava M, Tiwari P, Mall VK, Srivastava SK, Prakash R, Microchim. Acta, 186, 415 (2019)

[43] Arguelho ML, Andrade JF, Stradiotto NR, J. Pharm. Biomed. Anal., 32, 269 (2003)

[44] Fox RI, Semin Arthritis Rheum., 2, 82 (1993)

[45] Khoobi A, Ghoreishi SM, Behpour M, Analyst, 139, 4064 (2014)

[46] Khoobi A, Ghoreishi SM, Behpour M, Shaterian M, Salavati-Niasari M, Colloids Surf. B: Biointerfaces, 123, 648 (2014)