Insights into the formulation properties, biocompatibility, and permeability of poorly water-soluble methoxyflavones with PEG400 and propylene glycol

1D. Chen, H. Li, W. Li, S. Feng and D. Deng, Kaempferia parviflora and its methoxyflavones: Chemistry and biological activities, Evid. Based Complement Alternat. Med. 2018 (2018) Article ID 4057456 (16 pages); https://doi.org/10.1155/2018/4057456Search in Google Scholar

2S. Yoshino, R. Awa, Y. Miyake, I. Fukuhara, H. Sato, T. Ashino, S. Tomita and H. Kuwahara, Daily intake of <em>Kaempferia parviflora</em> extract decreases abdominal fat in overweight and pre-obese subjects: a randomized, double-blind, placebo-controlled clinical study, DMSO 11 (2018) 447–458; https://doi.org/10.2147/DMSO.S169925Search in Google Scholar

3C. Mekjaruskul, Y.-T. Yang, M. G. D. Leed, M. P. Sadgrove, M. Jay and B. Sripanidkulchai, Novel formulation strategies for enhancing oral delivery of methoxyflavones in Kaempferia parviflora by SMEDDS or complexation with 2-hydroxypropyl-β-cyclodextrin, Int. J. Pharm. 445(1-2) (2013) 1–11; https://doi.org/10.1016/j.ijpharm.2013.01.052Search in Google Scholar

4P. Chairuk, S. Tubtimsri, C. Jansakul, P. Sriamornsak and Y. Weerapol, Enhancing oral absorption of poorly water-soluble herb (Kaempferia parviflora) extract using self-nanoemulsifying formulation, Pharm. Dev. Technol. 25(3) (2020) 340–350; https://doi.org/10.1080/10837450.2019.1703134Search in Google Scholar

5C. Mekjaruskul and B. Sripanidkulchai, Kaempferia parviflora nanosuspension formulation for scalability and improvement of dissolution profiles and intestinal absorption, AAPS PharmSciTech. 21 (2020) Article ID 52; https://doi.org/10.1208/s12249-019-1588-4Search in Google Scholar

6Y. Weerapol, S. Tubtimsri, C. Jansakul and P. Sriamornsak, Improved dissolution of Kaempferia parviflora extract for oral administration by preparing solid dispersion via solvent evaporation, Asian J. Pharm. Sci. 12(2) (2017) 124–133; https://doi.org/10.1016/j.ajps.2016.09.005Search in Google Scholar

7K. Sutthanut, B. Sripanidkulchai, C. Yenjai and M. Jay, Simultaneous identification and quantitation of 11 flavonoid constituents in Kaempferia parviflora by gas chromatography, J. Chrom. A 1143(1-2) (2007) 227–233; https://doi.org/10.1016/j.chroma.2007.01.033Search in Google Scholar

8N. Koirala, N. H. Thuan, G. P. Ghimire, D. V. Thang and J. K. Sohng, Methylation of flavonoids: Chemical structures, bioactivities, progress and perspectives for biotechnological production, Enzyme Microbial. Tech. 86 (2016) 103–116; https://doi.org/10.1016/j.enzmictec.2016.02.003Search in Google Scholar

9L. Zhang, H. Luan, W. Lu and H. Wang, Preformulation studies and enabling formulation selection for an insoluble compound at preclinical stage – from in vitro, in silico to in vivo, J. Pharm. Sci. 109 (2020) 950–958; https://doi.org/10.1016/j.xphs.2019.10.023Search in Google Scholar

10A. Hussain, M. A. Altamimi, O. Afzal, A. S. A. Altamimi, A. Ali, A. Ali, F. Martinez, M. U. Mohd Siddique, W. E. Acree and A. Jouyban, Preferential solvation study of the synthesized aldose reductase inhibitor (SE415) in the {PEG 400 (1) + water (2)} cosolvent mixture and gastroplus-based prediction, ACS Omega 7(1) (2022) 1197–1210; https://doi.org/10.1021/acsomega.1c05788Search in Google Scholar

11S. Kalepu and V. Nekkanti, Insoluble drug delivery strategies: review of recent advances and business prospects, Acta Pharm. Sin. B 5(5) (2015) 442–453; https://doi.org/10.1016/j.apsb.2015.07.003Search in Google Scholar

12A. A. D’souza and R. Shegokar, Polyethylene glycol (PEG): a versatile polymer for pharmaceutical applications, Expert Opin. Drug Deliv. 13(9) (2016) 1257–1275; https://doi.org/10.1080/17425247.2016.1182485Search in Google Scholar

13R. P. Gullapalli and C. L. Mazzitelli, Polyethylene glycols in oral and parenteral formulations – A critical review, Int. J. Pharm. 496(2) (2015) 219–239; https://doi.org/10.1016/j.ijpharm.2015.11.015Search in Google Scholar

14C. Jansakul, K. Tachanaparuksa, M. J. Mulvany and Y. Sukpondma, Relaxant mechanisms of 3,5,7,3’,4’-pentamethoxyflavone on isolated human cavernosum, Eur. J. Pharmacol. 691(1-3) (2012) 235–244; https://doi.org/10.1016/j.ejphar.2012.07.019Search in Google Scholar

15S. Yorsin, K. Kanokwiroon, N. Radenahmad and C. Jansakul, Increased vascular eNOS and cystathionine-γ-lyase protein after 6 weeks oral administration of 3,5,7,3’,4’-pentamethoxyflavone to middle-aged male rats, Naunyn-Schmiedeberg‘s Arch. Pharmacol. 389 (2016) 1183–1194; https://doi.org/10.1007/s00210-016-1280-0Search in Google Scholar

16S. Sawatdee, H. Phetmung and T. Srichana, Sildenafil citrate monohydrate-cyclodextrin nanosus-pension complexes for use in metered-dose inhalers, Int. J. Pharm. 455(1-2) (2013) 248–258; https://doi.org/10.1016/j.ijpharm.2013.07.023Search in Google Scholar

17P. B. Rathi, M. Kale, J. Soleymani and A. Jouyban, Solubility of etoricoxib in aqueous solutions of glycerin, methanol, polyethylene glycols 200, 400, 600, and propylene glycol at 298.2 K, J. Chem. Eng. Data 63(2) (2018) 321–330; https://doi.org/10.1021/acs.jced.7b00709Search in Google Scholar

18B.-L. Ma, Y. Yang, Y. Dai, Q. Li, G. Lin and Y.-M. Ma, Polyethylene glycol 400 (PEG400) affects the systemic exposure of oral drugs based on multiple mechanisms: taking berberine as an example, RSC Adv. 7 (2017) 2435–2442; https://doi.org/10.1039/C6RA26284HSearch in Google Scholar

19International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use, ICH Harmonised Tripartite Guideline, Validation of Analytical Procedures: Text and Methodology Q2(R1), Current Step 4 version, November 2005; https://www.ich.org/fileadmin/Public_Web_Site/ICH_Products/Guidelines/Quality/Q2_R1/Step4/Q2_R1__Guideline.pdf last acess date May 16, 2023.Search in Google Scholar

20F. N. Eze and O. F. Nwabor, Valorization of Pichia spent medium via one-pot synthesis of biocompatible silver nanoparticles with potent antioxidant, antimicrobial, tyrosinase inhibitory and reusable catalytic activities, Mater. Sci. Eng. C 115 (2020) Article ID 111104 (14 pages); https://doi.org/10.1016/j.msec.2020.111104Search in Google Scholar

21Y. Kamiya, S. Otsuka, T. Miura, H. Takaku, R. Yamada, M. Nakazato, H. Nakamura, S. Mizuno, F. Shono, K. Funatsu and H. Yamazaki, Plasma and hepatic concentrations of chemicals after virtual oral administrations extrapolated using rat plasma data and simple physiologically based pharmacokinetic models, Chem. Res. Toxicol. 32(1) (2019) 211–218; https://doi.org/10.1021/acs.chemrestox.8b00307Search in Google Scholar

22R. C. R. Beck, A. R. Pohlmann, C. Hoffmeister, M. R. Gallas, E. Collnot, U. F. Schaefer, S. S. Guterres and C. M. Lehr, Dexamethasone-loaded nanoparticle-coated microparticles: Correlation between in vitro drug release and drug transport across Caco-2 cell monolayers, Eur. J. Pharm. Biopharm. 67(1) (2007) 18–30; https://doi.org/10.1016/j.ejpb.2007.01.007Search in Google Scholar

23G. Kigen and G. Edwards, Drug-transporter mediated interactions between anthelminthic and anti retroviral drugs across the Caco-2 cell monolayers, BMC Pharmacol. Toxicol. 18 (2017) Article ID 20 (18 pages); https://doi.org/10.1186/s40360-017-0129-6Search in Google Scholar

24S. Songngam, M. Sukwattanasinitt, K. Siralertmukul and P. Sawasdee, A 5,7-dimethoxyflavone/hydroxypropyl-β-cyclodextrin inclusion complex with anti-butyrylcholinesterase activity, AAPS PharmSciTech. 15 (2014) 1189–1196; https://doi.org/10.1208/s12249-014-0157-0Search in Google Scholar

25R. Paberit, E. Rilby, J. Göhl, J. Swenson, Z. Refaa, P. Johansson and H. Jansson, Cycling stability of poly(ethylene glycol) of six molecular weights: Influence of thermal conditions for energy applications, ACS Appl. Energy Mater. 3 (2020) 10578–10589; https://doi.org/10.1021/acsaem.0c01621Search in Google Scholar

26T. Uemura, N. Yanai, S. Watanabe, H. Tanaka, R. Numaguchi, M. T. Miyahara, Y. Ohta, M. Nagaoka and S. Kitagawa, Unveiling thermal transitions of polymers in subnanometre pores, Nat. Commun. 1 (2010) Article ID 83 (8 pages); https://doi.org/10.1038/ncomms1091Search in Google Scholar

27C. Belingheri, E. Curti, A. Ferrillo and E. Vittadini, Evaluation of porous starch as a flavour carrier, Food Funct. 3 (2012) 255–261; https://doi.org/10.1039/C1FO10184FSearch in Google Scholar

28H. J. Oh, B. D. Freeman, J. E. McGrath, C. H. Lee and D. R. Paul, Thermal analysis of disulfonated poly(arylene ether sulfone) plasticized with poly(ethylene glycol) for membrane formation, Polymer, Special issue: Porous Polymers 55(1) (2014) 235–247; https://doi.org/10.1016/j.polymer.2013.11.041Search in Google Scholar

29J. A. Manthey, Fourier transform infrared spectroscopic analysis of the polymethoxylated flavone content of orange oil residues, J. Agric. Food Chem. 54(9) (2006) 3215–3218; https://doi.org/10.1021/jf053134aSearch in Google Scholar

30I. M. Deygen and Е. V. Kudryashova, New versatile approach for analysis of PEG content in conjugates and complexes with biomacromolecules based on FTIR spectroscopy, Colloids Surfaces B: Bio-interfaces 141 (2016) 36–43; https://doi.org/10.1016/j.colsurfb.2016.01.030Search in Google Scholar

31K. S. Suganthi, N. Anusha and K. S. Rajan, Low viscous ZnO-propylene glycol nanofluid: a potential coolant candidate, J. Nanopart. Res. 15 (2013) Article ID 1986; https://doi.org/10.1007/s11051-013-1986-6Search in Google Scholar

32K. Adhikari, W. Buatong, E. Thawithong, T. Suwandecha and T. Srichana, Factors affecting enhanced permeation of amphotericin B across cell membranes and safety of formulation, AAPS PharmSciTech. 17 (2016) 820–828; https://doi.org/10.1208/s12249-015-0406-xSearch in Google Scholar

33M. Z. Jora, M. V. C. Cardoso and E. Sabadini, Dynamical aspects of water-poly(ethylene glycol) solutions studied by ¹H NMR, J. Mol. Liquids 222 (2016) 94–100; https://doi.org/10.1016/j.molliq.2016.06.101Search in Google Scholar

34L. L. Tshweu, M. A. Shemis, A. Abdelghany, A. Gouda, L. A. Pilcher, N. R. S. Sibuyi, M. Meyer, A. Dube and M. O. Balogun, Synthesis, physicochemical characterization, toxicity and efficacy of a PEG conjugate and a hybrid PEG conjugate nanoparticle formulation of the antibiotic moxifloxacin, RSC Adv. 34 (2020) 19770–19780; https://doi.org/10.1039/C9RA10872FSearch in Google Scholar

35J. Fattori, F. H. S. Rodrigues, J. G. M. Pontes, A. Paula Espíndola and L. Tasic, Chapter 6 – Monitoring Intermolecular and Intramolecular Interactions by NMR Spectroscopy, in Applications of NMR Spectroscopy (Eds. A. ur-Rahman and M. I. Choudhary), Vol. 3, Bentham Science Publishers, Karachi 2015, pp. 180–266; https://doi.org/10.1016/B978-1-68108-063-5.50006-0Search in Google Scholar

36G. Akerlof, Dielectric constants of some organic solvent-water mixtures at various temperatures, J. Am. Chem. Soc. 54(11) (1932) 4125–4139; https://doi.org/10.1021/ja01350a001Search in Google Scholar

37M.-J. Ko, H.-H. Nam and M.-S. Chung, Subcritical water extraction of bioactive compounds from Orostachys japonicus A. Berger (Crassulaceae), Sci. Rep. 10 (2020) Article ID 10890 (10 pages); https://doi.org/10.1038/s41598-020-67508-2Search in Google Scholar

38M.-J. Ko, C.-I. Cheigh and M.-S. Chung, Relationship analysis between flavonoids structure and subcritical water extraction (SWE), Food Chem. 143 (2014) 147–155; https://doi.org/10.1016/j.food-chem.2013.07.104Search in Google Scholar

39Z. Zhou, Y. Qu, J. Wang, S. Wang, J. Liu and M. Wu, Measurement and correlation of solubilities of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid in different pure solvents and binary mixtures of water + (ethanol, methanol, or glycol), J. Chem. Eng. Data 56(4) (2011) 1622–1628; https://doi.org/10.1021/je101351wSearch in Google Scholar

40C. MacDonald, W. Lyzenga, D. Shao and R. U. Agu, Water-soluble organic solubilizers for in vitro drug delivery studies with respiratory epithelial cells: selection based on various toxicity indicators, Drug Deliv. 17 (2010) 434–442; https://doi.org/10.3109/10717541003777548Search in Google Scholar

41L. Le Hegarat, S. Huet, E. Pasquier and S. Charles, Impact of solvents on the in vitro genotoxicity of TMPTA in human HepG2 cells, Toxicol. In Vitro 69 (2020) Article ID 105003; https://doi.org/10.1016/j.tiv.2020.105003Search in Google Scholar

42H. Li, X. Zhang and W. Wang, Antiancer activity of 5,7-dimethoxyflavone against liver cancer cell line HEPG2 involves apoptosis, ROS generation and cell cycle arrest, Afr. J. Tradit. Complement Altern. Med. 14(4) (2017) 213–220; https://doi.org/10.21010/ajtcam.v14i4.24Search in Google Scholar

43Y. Miyata, J. Tatsuzaki, J. Yang and H. Kosano, Potential therapeutic agents, polymethoxylated flavones isolated from Kaempferia parviflora for cataract prevention through inhibition of matrix metal-loproteinase-9 in lens epithelial cells, Biol. Pharm. Bull. 42(10) (2019) 1658–1664; https://doi.org/10.1248/bpb.b19-00244Search in Google Scholar

44P. Tep-areenan, P. Sawasdee and M. Randall, Possible mechanisms of vasorelaxation for 5,7-dime-thoxyflavone from Kaempferia parviflora in the rat aorta, Phytother. Res. 24(10) (2010) 1520–1525; https://doi.org/https://doi.org/10.1002/ptr.3164Search in Google Scholar

45H. F. Smyth, C. P. Carpenter and C. S. Weil, The chronic oral toxicology of the polyethylene glycols, J. Am. Pharm. Assoc. 44(1) (1955) 27–30; https://doi.org/10.1002/jps.3030440111Search in Google Scholar

46J. D. R. Schulze, W. A. Waddington, P. J. Eli, G. E. Parsons, M. D. Coffin and A. W. Basit, Concentration-dependent effects of polyethylene glycol 400 on gastrointestinal transit and drug absorption, Pharm. Res. 20 (2003) 1984–1988; https://doi.org/10.1023/b:pham.0000008046.64409.bdSearch in Google Scholar

47G. L. Amidon, H. Lennernäs, V. P. Shah and J. R. Crison, A theoretical basis for a biopharmaceutic drug classification: The correlation of in vitro drug product dissolution and in vivo bioavailability, Pharm. Res. 12 (1995) 413–420; https://doi.org/10.1023/A:1016212804288Search in Google Scholar

48D. A. Volpe, P. J. Faustino, A. B. Ciavarella, E. B. Asafu-Adjaye, C. D. Ellison, L. X. Yu and A. S. Hussain, Classification of drug permeability with a Caco-2 cell monolayer assay, Clin. Res. Regul. Affairs 24(1) (2007) 39–47; https://doi.org/10.1080/10601330701273669Search in Google Scholar

49X.-L. Liang, J. Zhang, G.-W. Zhao, Z. Li, Y. Luo, Z.-G. Liao and D.-M. Yan, Mechanisms of improvement of intestinal transport of baicalin and puerarin by extracts of Radix Angelicae dahuricae, Phytother. Res. 29(2) (2015) 220–227; https://doi.org/10.1002/ptr.5242Search in Google Scholar