Multiple Response Optimization of a HPLC Method for Analyzing Resorcinol and 4-n-Butyl Resorcinol in Lipid Nanoparticles

https://doi.org/10.22146/ijc.58537

Rini Dwiastuti(1*), Dina Christin Ayuning Putri(2), Maywan Hariono(3), Florentinus Dika Octa Riswanto(4)

(1) Department of Pharmaceutical Technology, Faculty of Pharmacy, Sanata Dharma University, Paingan, Maguwoharjo, Depok, Sleman, Yogyakarta 55282, Indonesia
(2) Department of Pharmaceutical Technology, Faculty of Pharmacy, Sanata Dharma University, Paingan, Maguwoharjo, Depok, Sleman, Yogyakarta 55282, Indonesia
(3) Department of Pharmaceutical Analysis and Medicinal Chemistry, Faculty of Pharmacy, Sanata Dharma University, Paingan, Maguwoharjo, Depok, Sleman, Yogyakarta 55282, Indonesia
(4) Department of Pharmaceutical Analysis and Medicinal Chemistry, Faculty of Pharmacy, Sanata Dharma University, Paingan, Maguwoharjo, Depok, Sleman, Yogyakarta 55282, Indonesia
(*) Corresponding Author

Abstract


Resorcinol and 4-n-butyl resorcinol have been used to improve skin health. However, these two compounds were unstable due to the oxidation process. Lipid nanoparticle formulation strategies were reported as the solution to overcome the stability problem for both resorcinol and 4-n-butyl resorcinol. Nevertheless, it is important to determine the content of resorcinol and 4-n-butyl resorcinol in lipid nanoparticle formulation. Aiming to develop the analytical method for resorcinol and 4-n-butyl resorcinol determination, a response surface methodology (RSM) was applied in the HPLC optimization stage. An optimized HPLC condition was obtained by generating a Box-Behnken design followed by multiple response analysis. It was obtained that optimized HPLC conditions due to the predictive multiple response optimization were methanol percentage of 50.0%, acetonitrile percentage of 18.1%, and flow rate of 0.6 mL min–1. This optimized condition was successfully applied and met the requirements of the system suitability test. Quantitative estimation was performed and resulted that the resorcinol and 4-n-butyl resorcinol content in lipid nanoparticles were 70.37 ± 0.47 and 95.07 ± 0.80 µg mL–1, respectively.


Keywords


4-n-butyl resorcinol; Box-Behnken design; HPLC; optimization; resorcinol

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References

[1] Chowdhury, M.A.Z., Banik, S., Uddin, B., Moniruzzaman, M., Karim, N., and Gan, S.H., 2012, Organophosphorus and carbamate pesticide residues detected in water samples collected from paddy and vegetable fields of the Savar and Dhamrai Upazilas in Bangladesh, Int. J. Environ. Res. Public Health, 9 (9), 3318–3329.

[2] Kwon, S.H., Yang, J.H., Shin, J.W., Park, K.C., Huh, C.H., and Na, J.I., 2020, Efficacy of liposome-encapsulated 4-n-butylresorcinol and resveratrol cream in the treatment of melasma, J. Cosmet. Dermatol., 19 (4), 891–895.

[3] Love, A.R., Kerschner, J.L., Barratt, M.J., and Zhou, Y., 2003, Stabilization of resorcinol derivatives in cosmetic compositions, US Patent, US20030180234A1.

[4] Dwiastuti, R., Marchaban, Istyastono, E.P., and Riswanto, F.D.O., 2018, Analytical method validation and determination of free drug content of 4-n-butylresorcinol in complex lipid nanoparticles using RP-HPLC method, Indones. J. Chem., 18 (3), 496–502.

[5] Reverchon, E., and Adami, R., 2006, Nanomaterials and supercritical fluids, J. Supercrit. Fluids, 37 (1), 1–22.

[6] Cooper, D.L., Conder, C.M., and Harirforoosh, S., 2014, Nanoparticles in drug delivery: Mechanism of action, formulation and clinical application towards reduction in drug-associated nephrotoxicity, Expert Opin. Drug Delivery, 11 (10), 1661–1680.

[7] Rahmi, D., 2010, Lemak padat; Sintesis dan aplikasi, JKK, 32 (1), 27.

[8] Glavanović, S., Glavanović, M., and Tomišić, V., 2016, Simultaneous quantitative determination of paracetamol and tramadol in tablet formulation using UV spectrophotometry and chemometric methods, Spectrochim. Acta, Part A, 157, 258–264.

[9] Zielinski, A.A.F., Haminiuk, C.W.I., Alberti, A., Nogueira, A., Demiate, I.M., and Granato, D., 2014, A comparative study of the phenolic compounds and the in vitro antioxidant activity of different Brazilian teas using multivariate statistical techniques, Food Res. Int., 60, 246–254.

[10] Salameh, B.A., Al-Degs, Y.S., Abu Safieh, K.A., and AL-Zghool, A.W., 2019, Novel application of multivariate standard addition method based on net analyte signal for quantification of artificial sweeteners in complex food matrices, J. Food Meas. Charact., 14 (1), 78–87.

[11] Wang, P., Zhang, H., Yang, H., Nie, L., and Zang, H., 2015, Rapid determination of major bioactive isoflavonoid compounds during the extraction process of kudzu (Pueraria lobata) by near-infrared transmission spectroscopy, Spectrochim. Acta, Part A, 137, 1403–1408.

[12] Gómez, J.D., Vital, C.E., Oliveira, M.G.A., and Ramos, H.J.O., 2018, Broad range flavonoid profiling by LC/MS of soybean genotypes contrasting for resistance to Anticarsia gemmatalis (Lepidoptera: Noctuidae), PLoS One, 13 (10), e0205010.

[13] Riswanto, F.D.O., Rohman, A., Pramono, S., and Martono, S., 2021, Soybean (Glycine max L.) isoflavones: Chemical composition and its chemometrics-assisted extraction and authentication, J. Appl. Pharm. Sci., 11 (1), 12–20.

[14] Kayesh, R., Jahan, M.S., and Sultan, M.Z., 2017, Development using response surface methodology and validation of a stability-indicating RP-HPLC method for simultaneous estimation of azilsartan medoxomil and chlorthalidone in solid dosage form, Chromatographia, 80 (4), 593–603.

[15] Yusof, N.A.A., Mat Hadzir, N., Ashari, S.E., Mohamad Hanapi, N.S., and Dol Hamid, R., 2019, Optimization of enzymatic synthesis of betulinic acid amide in organic solvent by response surface methodology (RSM), Indones. J. Chem., 19 (4), 849–857.

[16] Cheung, Y., Meenu, M., Yu, X., and Xu, B., 2019, Phenolic acids and flavonoids profiles of commercial honey from different floral sources and geographic sources, Int. J. Food Prop., 22 (1), 290–308.

[17] Soto-Zarazúa, M.G., Rodrigues, F., Pimentel, F.B., Bah, M.M., and Oliveira, M.B.P.P., 2016, The isoflavone content of two new alfalfa-derived products for instant beverage preparation, Food Funct., 7 (1), 364–371.

[18] Gliszczyńska-Świgło, A., and Rybicka, I., 2015, Simultaneous determination of caffeine and water-soluble vitamins in energy drinks by HPLC with photodiode array and fluorescence detection, Food Anal. Methods, 8 (1), 139–146.

[19] Danezis, G.P., Tsagkaris, A.S., Camin, F., Brusic, V., and Georgiou, C.A., 2016, Food authentication: Techniques, trends & emerging approaches, TrAC, Trends Anal. Chem., 85, 123–132.

[20] Çelik, B., 2017, Risperidone mucoadhesive buccal tablets: Formulation design, optimization and evaluation, Drug Des. Dev. Ther., 11, 3355–3365.

[21] Razzaq, S.N., Ashfaq, M., Mariam, I., Khan, I.U., and Razzaq, S.S., 2013, Simultaneous RP-HPLC determination of sparfloxacin and dexamethasone in pharmaceutical formulations, Braz. J. Pharm. Sci., 49 (2), 301–309.

[22] Alzoman, N.Z., 2016, A validated stability-indicating and stereoselective HPLC method for the determination of lenalidomide enantiomers in bulk form and capsules, J. Chromatogr. Sci., 54 (5), 730–735.

[23] Syukri, Y., Martien, R., Lukitaningsih, E., and Nugroho, A.E., 2016, Quantification of andrographolide isolated from Andrographis paniculata Nees obtained from traditional market in Yogyakarta using validated HPLC, Indones. J. Chem., 16 (2), 190–197.

[24] Kadam, P.V., Yadav, K.N., Bhingare, C.L., and Patil, M.J., 2018, Standardization and quantification of curcumin from Curcuma longa extract using UV visible spectroscopy and HPLC, J. Pharmacogn. Phytochem., 7 (5), 1913–1918.

[25] Zhu, J., Fan, X., Cheng, Y., Agarwal, R., Moore, C.M.V., Chen, S.T., and Tong, W., 2014, Chemometric analysis for identification of botanical raw materials for pharmaceutical use: A case study using Panax notoginseng, PLoS One, 9 (1), e87462.

[26] Shailajan, S., Hande, H., Singh, D., and Tiwari, B., 2014, Estimation of ursolic acid from Urtica dioica L. using validated HPTLC method, J. Appl. Pharm. Sci., 4 (5), 92–95.

[27] Cinier, R., and Guilment, J., 1996, Quantitative analysis of resorcinol in aqueous solution by near-infrared spectroscopy, Vib. Spectrosc., 11 (1), 51–59.

[28] Wu, H.W., Chen, M.L., Shou, D., and Zhu, Y., 2012, Determination of resorcinol and phloroglucinol in environmental water samples using ion chromatography with chemiluminescence detection, Chin. J. Anal. Chem., 40 (11), 1747–1751.

[29] Pistonesi, M.F., Di Nezio, M.S., Centurión, M.E., Palomeque, M.E., Lista, A.G., and Band, B.S.F., 2006, Determination of phenol, resorcinol and hydroquinone in air samples by synchronous fluorescence using partial least-squares (PLS), Talanta, 69 (5), 1265–1268.

[30] Boer, J., and Jemec, G.B.E., 2009, Resorcinol peels as a possible self-treatment of painful nodules in hidradenitis suppurativa, Clin. Exp. Dermatol., 35 (1), 36–40.

[31] Narita, M., Murakami, K., and Kauffmann, J.M., 2007, Determination of dye precursors in hair coloring products by liquid chromatography with electrochemical detection, Anal. Chim. Acta, 588 (2), 316–320.

[32] Riswanto, F.D.O., Desra, A., Sari, R.M., Thomas, V., Rohman, A., Pramono, S., and Martono, S., 2020, Employing an R software package rsm for optimizing of genistein, daidzein, and glycitein separation and its application for soy milk analysis by HPLC method, Indones. J. Chem., 20 (5), 1184–1198.

[33] Sahoo, D.K., and Sahu, P.K., 2015, Chemometric approach for RP-HPLC determination of azithromycin, secnidazole, and fluconazole using response surface methodology, J. Liq. Chromatogr. Relat. Technol., 38 (6), 750–758.

[34] Bae, H., Jung, H.S., and Jung, J.Y., 2018, Optimization of HPLC-tandem mass spectrometry for chlortetracycline using response surface analysis, Environ. Eng. Res., 23 (3), 309–315.

[35] Hibbert, D.B., 2012, Experimental design in chromatography: A tutorial review, J. Chromatogr. B, 910, 2–13.

[36] Giles, H.F., Wagner, J.R., and Mount, E.M., 2014, Extrusion: The Definitive Processing Guide and Handbook, 2nd Ed., William Andrew, Inc., Norwich, New York.

[37] Das, A.K., and Dewanjee, S., 2018, "Chapter 3 - Optimization of extraction using mathematical models and computation", in Computational Phytochemistry, Eds. Sarker, S.D., and Nahar, L., Elsevier, Inc., Amsterdam, 75–106.

[38] Myers, R.H., Montgomery, D.C., and Anderson-Cook, C.M., 2016, Response Surface Methodology: Process and Product Optimization Using Designed Experiments, 4th Ed., John Wiley & Sons, Inc., Hoboken, New Jersey.

[39] Ferreira, S.L.C., Bruns, R.E., Ferreira, H.S., Matos, G.D., David, J.M., Brandão, G.C., da Silva, E.G.P., Portugal, L.A., dos Reis, P.S., Souza, A.S., and dos Santos, W.N.L., 2007, Box-Behnken design: An alternative for the optimization of analytical methods, Anal. Chim. Acta, 597 (2), 179–186.

[40] Chaudhari, S.R., and Shirkhedkar, A.A., 2019, Design of experiment avenue for development and validation of RP-HPLC-PDA method for determination of apremilast in bulk and in in-house tablet formulation, J. Anal. Sci. Technol., 10 (1), 10.

[41] Vera-Candioti, L., De Zan, M. M., Cámara, M. S., and Goicoechea, H. C., 2014, Experimental design and multiple response optimization. Using the desirability function in analytical methods development, Talanta, 124, 123–138.

[42] Çankaya, N., Bulduk, İ., and Çolak, A.M., 2019, Extraction, development and validation of HPLC-UV method for rapid and sensitive determination of colchicine from Colchicum autumnale L. bulbs, Saudi J. Biol. Sci., 26 (2), 345–351.

[43] Dwiastuti, R., Noegrohati, S., Istyastono, E.P., and Marchaban, 2016, Formulation and physical properties observations of soy lecithin liposome containing 4-n-butylresorcinol, AIP Conf. Proc., 1755, 160005.

[44] Amdoun, R., Khelifi, L., Khelifi-Slaoui, M., Amroune, S., Asch, M., Assaf-Ducrocq, C., and Gontier, E., 2018, The desirability optimization methodology; A tool to predict two antagonist responses in biotechnological systems: Case of biomass growth and hyoscyamine content in elicited Datura stramonium hairy roots, Iran. J. Biotechnol., 16 (1), e1339.

[45] Kannappan, V., and Mannemala, S.S., 2014, Multiple response optimization of a HPLC method for the determination of enantiomeric purity of S-Ofloxacin, Chromatographia, 77 (17), 1203–1211.

[46] Snyder, L.R., Kirkland, J.J., and Dolan, J.W., 2010, Introduction to Modern Liquid Chromatography, 3rd Ed., John Wiley & Sons, Inc., New Jersey.

[47] Munawar, T.M., Prakash, D.V.S., and Vangalapati, M., 2019, Development of response surface methodology for optimization of parameters and quantitative analysis of chebulinic acid from composition of medicinal herbs by HPLC, Saudi J. Biol. Sci., 26 (7), 1809–1814.



DOI: https://doi.org/10.22146/ijc.58537

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