Formulation and evaluation of novel glycyrrhizic acid micelles for transdermal delivery of podophyllotoxin

References

• Agren A, Elofsson R. (1967). Complex formation between macromolecules and drugs. I. Dialysis studies of phenol and polyethylene glycol (PEG). Acta Pharm Suec 4:281–92
   PubMedGoogle Scholar
• Alvarez-Roman R, Naik A, Kalia YN, et al. (2004). Skin penetration and distribution of polymeric nanoparticles. J Control Release 99:53–62
   PubMed Web of Science ®Google Scholar
• Asl MN, Hosseinzadeh H. (2008). Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds. Phytother Res 22:709–24
   PubMed Web of Science ®Google Scholar
• Bi X, Zhu G, Han Z, et al. (2009). Protective effect of glycyrrhizin on nephrotic syndrome induced by adriamycin in rats. Clin Invest Med 32:E229–38
   PubMed Web of Science ®Google Scholar
• Burd EM. (2003). Human papillomavirus and cervical cancer. Clin Microbiol Rev 16:1–17
   PubMed Web of Science ®Google Scholar
• Chen H, Chang X, Du D, et al. (2006). Podophyllotoxin-loaded solid lipid nanoparticles for epidermal targeting. J Control Release 110:296–306
   PubMed Web of Science ®Google Scholar
• Cohen DE, Heidary N. (2004). Treatment of irritant and allergic contact dermatitis. Dermatol Ther 17:334–40
   PubMedGoogle Scholar
• Cosmetic Ingredient Review Expert Panel. (2007). Final report on the safety assessment of Glycyrrhetinic Acid, Potassium Glycyrrhetinate, Disodium Succinoyl Glycyrrhetinate, Glyceryl Glycyrrhetinate, Glycyrrhetinyl Stearate, Stearyl Glycyrrhetinate, Glycyrrhizic Acid, Ammonium Glycyrrhizate, Dipotassium Glycyrrhizate, Disodium Glycyrrhizate, Trisodium Glycyrrhizate, Methyl Glycyrrhizate, and Potassium Glycyrrhizinate. Int J Toxicol 26:79–112
   Web of Science ®Google Scholar
• Dahmani FZ, Yang H, Zhou J, et al. (2012). Enhanced oral bioavailability of paclitaxel in pluronic/LHR mixed polymeric micelles: preparation, in vitro and in vivo evaluation. Eur J Pharm Sci 47:179–89
   PubMed Web of Science ®Google Scholar
• del Rio C, Hall G, Holmes K, et al. (2012). Update to CDC's sexually transmitted diseases treatment guidelines, 2010: oral cephalosporins no longer a recommended treatment for gonococcal infections (Reprinted from MMWR, vol 61, pg 590, 2012). J Am Med Assoc 308:1850–3
   Web of Science ®Google Scholar
• Fomina MK, Avgustinovich DF, Tolstikova TG. (2014). Effects of buspirone complex with glycyrrhizic acid on behavior of mice with anxious-depressive state. Ross Fiziol Zh Im I M Sechenova 100:808–19
   PubMedGoogle Scholar
• Fukai T, Satoh K, Nomura T, Sakagami H. (2003). Preliminary evaluation of antinephritis and radical scavenging activities of glabridin from Glycyrrhiza glabra. Fitoterapia 74:624–9
   PubMed Web of Science ®Google Scholar
• Gordaliza M, Garcia PA, del Corral JM, et al. (2004). Podophyllotoxin: distribution, sources, applications and new cytotoxic derivatives. Toxicon 44:441–59
   PubMed Web of Science ®Google Scholar
• Hazzah HA, Farid RM, Nasra MM, et al. (2015). A new approach for treatment of precancerous lesions with curcumin solid-lipid nanoparticle-loaded gels: in vitro and clinical evaluation. Drug Deliv. [Epub ahead of print]. doi: 10.3109/10717544.2015.1065524
   PubMed Web of Science ®Google Scholar
• Hermanns-Le T, Arrese JE, Goffin V, Pierard GE. (1998). Podophyllotoxin-induced acantholysis and cytolysis in a skin equivalent model. Eur J Morphol 36:183–7
   PubMedGoogle Scholar
• Imai T, Sakai M, Ohtake H, et al. (1999). In vitro and in vivo evaluation of the enhancing activity of glycyrrhizin on the intestinal absorption of drugs. Pharm Res 16:80–6
   PubMed Web of Science ®Google Scholar
• Kao TC, Shyu MH, Yen GC. (2009). Neuroprotective effects of glycyrrhizic acid and 18beta-glycyrrhetinic acid in PC12 cells via modulation of the PI3K/Akt pathway. J Agric Food Chem 57:754–61
   PubMed Web of Science ®Google Scholar
• Kao TC, Shyu MH, Yen GC. (2010). Glycyrrhizic acid and 18beta-glycyrrhetinic acid inhibit inflammation via PI3K/Akt/GSK3beta signaling and glucocorticoid receptor activation. J Agric Food Chem 58:8623–9
   PubMed Web of Science ®Google Scholar
• Lacey CJ, Goodall RL, Tennvall GR, et al. (2003). Randomised controlled trial and economic evaluation of podophyllotoxin solution, podophyllotoxin cream, and podophyllin in the treatment of genital warts. Sex Transm Infect 79:270–5
   PubMed Web of Science ®Google Scholar
• Lacey CJ, Woodhall SC, Wikstrom A, Ross J. (2013). 2012 European guideline for the management of anogenital warts. J Eur Acad Dermatol Venereol 27:e263–70
   PubMed Web of Science ®Google Scholar
• Lee EG, Mickle-Kawar BM, Gallucci RM. (2013). IL-6 deficiency exacerbates skin inflammation in a murine model of irritant dermatitis. J Immunotoxicol 10:192–200
   PubMed Web of Science ®Google Scholar
• Longstaff E, von Krogh G. (2001). Condyloma eradication: self-therapy with 0.15–0.5% podophyllotoxin versus 20–25% podophyllin preparations–an integrated safety assessment. Regul Toxicol Pharmacol 33:117–37
   PubMed Web of Science ®Google Scholar
• Lu Y, Meng Q, Zhang G, Bei X. (2008). Clozapine-induced hepatotoxicity in rat hepatocytes by gel entrapment and monolayer culture. Toxicol In Vitro 22:1754–60
   PubMed Web of Science ®Google Scholar
• Megrab NA, Williams AC, Barry BW. (1995). Oestradiol permeation across human skin, silastic and snake skin membranes: the effects of ethanol/water co-solvent systems. Int J Pharm 116:101–12
   Web of Science ®Google Scholar
• Oxholm A, Oxholm P, Staberg B, Bendtzen K. (1988). Immunohistological detection of interleukin I-like molecules and tumour necrosis factor in human epidermis before and after UVB-irradiation in vivo. Br J Dermatol 118:369–76
   PubMed Web of Science ®Google Scholar
• Park HY, Park SH, Yoon HK, et al. (2004). Anti-allergic activity of 18beta-glycyrrhetinic acid-3-O-beta-D-glucuronide. Arch Pharm Res 27:57–60
   PubMed Web of Science ®Google Scholar
• Polyakov NE, Khan VK, Taraban MB, et al. (2005). Complexation of lappaconitine with glycyrrhizic acid: stability and reactivity studies. J Phys Chem B 109:24526–30
   PubMed Web of Science ®Google Scholar
• Polyakov NE, Leshina TV, Salakhutdinov NF, Kispert LD. (2006). Host-guest complexes of carotenoids with beta-glycyrrhizic acid. J Phys Chem B 110:6991–8
   PubMed Web of Science ®Google Scholar
• Qin L, Xue M, Wang W, et al. (2010). The in vitro and in vivo anti-tumor effect of layered double hydroxides nanoparticles as delivery for podophyllotoxin. Int J Pharm 388:223–30
   PubMed Web of Science ®Google Scholar
• Rossi T, Benassi L, Magnoni C, et al. (2005). Effects of glycyrrhizin on UVB-irradiated melanoma cells. In Vivo 19:319–22
   PubMed Web of Science ®Google Scholar
• Roy A, Ernsting MJ, Undzys E, Li SD. (2015). A highly tumor-targeted nanoparticle of podophyllotoxin penetrated tumor core and regressed multidrug resistant tumors. Biomaterials 52:335–46
   PubMed Web of Science ®Google Scholar
• Sapra B, Jain S, Tiwary AK. (2008). Transdermal delivery of carvedilol containing glycyrrhizin and chitosan as permeation enhancers: biochemical, biophysical, microscopic and pharmacodynamic evaluation. Drug Deliv 15:443–54
   PubMed Web of Science ®Google Scholar
• Selyutina OY, Polyakov NE, Korneev DV, Zaitsev BN. (2015). Influence of glycyrrhizin on permeability and elasticity of cell membrane: perspectives for drugs delivery. Drug Deliv. [Epub ahead of print]. doi: 10.3109/10717544.2014.919544
   PubMed Web of Science ®Google Scholar
• Syed TA, Cheema KM, Khayyami M, et al. (1995). Human leukocyte interferon-alpha versus podophyllotoxin in cream for the treatment of genital warts in males. A placebo-controlled, double-blind, comparative study. Dermatology 191:129–32
   PubMed Web of Science ®Google Scholar
• Tamaya T, Sato S, Okada HH. (1986). Possible mechanism of steroid action of the plant herb extracts glycyrrhizin, glycyrrhetinic acid, and paeoniflorin: inhibition by plant herb extracts of steroid protein binding in the rabbit. Am J Obstet Gynecol 155:1134–9
   PubMed Web of Science ®Google Scholar
• Tolstikova TG, Khvostov MV, Bryzgalov AO. (2009). The complexes of drugs with carbohydrate-containing plant metabolites as pharmacologically promising agents. Mini Rev Med Chem 9:1317–28
   PubMed Web of Science ®Google Scholar
• Tolstikova TG, Khvostov MV, Bryzgalov AO, et al. (2010). Improvement of the pharmacological activity of nifedipine by mechanochemical complexation with glycyrrhizic acid. Biomed Khim 56:187–94
   PubMedGoogle Scholar
• Tu JH, Hu DL, Dai LL, et al. (2010). Effect of glycyrrhizin on CYP2C19 and CYP3A4 activity in healthy volunteers with different CYP2C19 genotypes. Xenobiotica 40:393–9
   PubMed Web of Science ®Google Scholar
• Vavilin VA, Salakhutdinov NF, Ragino Iu I, et al. (2008). Cholesterol lowering properties of a complex compound simvastatin with glycyrrhizic acid (simvaglyzin) in experimental models. Biomed Khim 54:301–13
   PubMedGoogle Scholar
• Wang CY, Kao TC, Lo WH, Yen GC. (2011). Glycyrrhizic acid and 18beta-glycyrrhetinic acid modulate lipopolysaccharide-induced inflammatory response by suppression of NF-kappaB through PI3K p110delta and p110gamma inhibitions. J Agric Food Chem 59:7726–33
   PubMed Web of Science ®Google Scholar
• Wang SQ, Liu ST, Zhao BX, et al. (2015). Afatinib reverses multidrug resistance in ovarian cancer via dually inhibiting ATP binding cassette subfamily B member 1. Oncotarget 6:26142–60
   PubMed Web of Science ®Google Scholar
• Williams AC, Barry BW. (2004). Penetration enhancers. Adv Drug Deliv Rev 56:603–18
   PubMed Web of Science ®Google Scholar
• Xie FM, Zeng K, Li GF, et al. (2005). Preparation of stearic acid solid lipid nanoparticles containing podophyllotoxin. Di Yi Jun Yi Da Xue Xue Bao 25:99–101
   PubMedGoogle Scholar
• Xie Y, Ruan B, Chen Y, et al. (2011). Kaposi's sarcoma-associated herpesvirus infection in Chinese patients with chronic hepatitis B. J Med Virol 83:879–83
   PubMed Web of Science ®Google Scholar
• Yadav R, Kumar D, Kumari A, Yadav SK. (2014). Encapsulation of podophyllotoxin and etoposide in biodegradable poly-D,L-lactide nanoparticles improved their anticancer activity. J Microencapsul 31:211–19
   PubMed Web of Science ®Google Scholar
• Yang FH, Zhang Q, Liang QY, et al. (2015). Bioavailability enhancement of paclitaxel via a novel oral drug delivery system: paclitaxel-loaded glycyrrhizic acid micelles. Molecules 20:4337–56
   PubMed Web of Science ®Google Scholar