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Research Articles

Ion-pair compounds of diacerein for enhancing skin permeability in vitro: the compatibility–permeability relationship of counter ion and diacerein

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Pages 499-505 | Received 26 Dec 2021, Accepted 17 Jan 2022, Published online: 11 Feb 2022

References

  • Arunan E, Desiraju GR, Klein RA, et al. (2011). Defining the hydrogen bond: an account (IUPAC technical report). Pure Appl Chem 83:1619–36.
  • Aziz D, Abdelbary A, Elassasy AI. (2018a). Investigating superiority of novel bilosomes over niosomes in the transdermal delivery of diacerein: in vitro characterization, ex vivo permeation and in vivo skin deposition study. J Liposome Res 29:73–85.
  • Aziz D, Abdelbary A, Elassasy A. (2018b). Fabrication of novel elastosomes for boosting the transdermal delivery of diacerein: statistical optimization, ex-vivo permeation, in-vivo skin deposition and pharmacokinetic assessment compared to oral formulation. Drug Deliv 25:815–26.
  • Cavallari C, Passerini N, Fini A, et al. (1998). Partition of diclofenac salts as ion-pairs. Eur J Pharm Sci 6:S63.
  • Chattopadhyay H, Datta S. (2018). Transdermal delivery of diacerein with homing carrier glucosamine sulphate laden in oil-in-water nanoemulsion. Mater Today Proc 5:9690–7.
  • Cristofoli M, Kung CP, Hadgraft J, et al. (2021). Ion pairs for transdermal and dermal drug delivery: a review. Pharmaceutics 13:909.
  • Cui H, Quan P, Zhao H, et al. (2015). Mechanism of ion-pair strategy in modulating skin permeability of zaltoprofen: insight from molecular-level resolution based on molecular modeling and confocal laser scanning microscopy. J Pharm Sci 104:3395–403.
  • Delgado-Charro MB, Guy RH. (2014). Effective use of transdermal drug delivery in children. Adv Drug Deliv Rev 73:63–82.
  • Dhaneshwar S, Patel V, Patil D, et al. (2013). Studies on synthesis, stability, release and pharmacodynamic profile of a novel diacerein-thymol prodrug. Bioorg Med Chem Lett 23:55–61.
  • Domagala F, Martin G, Bogdanowicz P, et al. (2006) Inhibition of interleukin-1beta-induced activation of MEK/ERK pathway and DNA binding of NF-kappaB and AP-1: potential mechanism for diacerein effects in osteoarthritis. Biorheology 43:577–87.
  • El-Say KM, Abd-Allah FI, Lila AE, et al. (2016) Diacerein niosomal gel for topical delivery: development, in vitro and in vivo assessment. J Liposome Res 26:57–68.
  • Felisaz N, Boumediene K, Ghayor C, et al. (1999). Stimulating effect of diacerein on TGF-beta1 and beta2 expression in articular chondrocytes cultured with and without interleukin-1. Osteoarthritis Cartilage 7:255–64.
  • Fini A, Fazio G, Gonzalez-Rodriguez M, et al. (1999). Formation of ion-pairs in aqueous solutions of diclofenac salts. Int J Pharm 187:163–73.
  • Gary PM, Simon CW, Sun Y. (2012). Mathematical modelling of percutaneous absorption. Curr Opin Colloid Interface Sci 17:72–166.
  • Hadgraft J. (2001). Skin, the final frontier. Int J Pharm 224:1–18.
  • Higaki K, Nakayama K, Suyama T, et al. (2005). Enhancement of topical delivery of drugs via direct penetration by reducing blood flow rate in skin. Int J Pharm 288:227–33.
  • Kitadai HK, Takahashi HK, Straus AH, et al. (2006). Effect of oral diacerein (DAR) in an experimental hip chondrolysis model. J Orthop Res 24:1240–8.
  • Mahajan A, Singh K, Tandon VR, et al. (2006). Diacerein: a new symptomatic slow acting drug for osteoarthritis. J Med Educ Res 8:173–5.
  • McNaught AD, Wilkinson A. (1997). Compendium of chemical terminology. 2nd ed. Oxford (UK): Blackwell Scientific Publications.
  • Ogiso T, Shintani M. (1990). Mechanism for the enhancement effect of fatty acids on the percutaneous absorption of propranolol. J Pharm Sci 79:1065–71.
  • Rehman M, Madni A, Ihsan A, et al. (2015). Solid and liquid lipid-based binary solid lipid nanoparticles of diacerein: in vitro evaluation of sustained release, simultaneous loading of gold nanoparticles, and potential thermoresponsive behavior. Int J Nanomedicine 10:2805–14.
  • Shinkai N, Korenaga K, Mizu H, et al. (2008). Intra-articular penetration of ketoprofen and analgesic effects after topical patch application in rats. J Control Release 131:107–12.
  • Silverstein RM, Webster FX, Kiemle DJ, et al. (2014). Spectrometric identification of organic compounds. 8th ed, New Jersey: Willey.
  • Song T, Quan P, Xiang R, et al. (2016). Regulating the skin permeation rate of escitalopram by ion-pair formation with organic acids. AAPS PharmSciTech 17:1267–73.
  • Song W, Cun D, Xi H, et al. (2012). The control of skin-permeating rate of bisoprolol by ion-pair strategy for long-acting transdermal patches. AAPS PharmSciTech 13:811–5.
  • Spencer CM, Wilde MI. (1997). Diacerein. Drugs 53:98.
  • Tang HB, Yan M, Li HD, et al. (2014). Dynamic detection of non-protein-bound strychnine and brucine in rabbit muscle and synovial fluid after topical application of total Strychnos alkaloid patches. Drug Test Anal 6:357–62.
  • Walke PS, Khairna PS, Narkhede MR, et al. (2011). Solubility enhancement of diacerein by mannitol solid dispersions. Int J Pharm Sci 3:261–4.
  • Wang Y, Ren J, Zhang C, et al. (2016). Compatibility studies between amphiphilic pH-sensitive polymer and hydrophobic drug using multiscale simulations. RSC Adv 6:101323–33.
  • Wu P, Liang Q, Feng P, et al. (2017). Novel brucine gel transdermal delivery system designed for anti-inflammatory and analgesic activities. Int J Mol Sci 18:757.
  • Xi H, Cun D, Wang Z, et al. (2012a). Effect of the stability of hydrogen-bonded ion pairs with organic amines on transdermal penetration of teriflunomide. Int J Pharm 436:857–61.
  • Xi H, Wang Z, Chen Y, et al. (2012b). The relationship between hydrogen-bonded ion-pair stability and transdermal penetration of lornoxicam with organic amines. Eur J Pharm Sci 47:325–30.
  • Xu L, Yang ZY, Tang HB, et al. (2011). Effect of chemical enhancers on the permeation of strychnine across pig skin in vitro. Central South Pharm 9:761–3.
  • Zhao H, Liu C, Quan P, et al. (2017). Mechanism study on ion-pair complexes controlling skin permeability: effect of ion-pair dissociation in the viable epidermis on transdermal permeation of bisoprolol. Int J Pharm 532:29–36.