Mitotane liposomes for potential treatment of adrenal cortical carcinoma: ex vivo intestinal permeation and in vivo bioavailability

References

• Ali MH, Moghaddam B, Kirby DJ, Mohammed AR, Perrie Y. 2013. The role of lipid geometry in designing liposomes for the solubilisation of poorly water soluble drugs. Int J Pharm. 453:225–232.
   PubMed Web of Science ®Google Scholar
• Alves GP, Santana MH. 2004. Phospholipid dry powders produced by spray drying processing: structural, thermodynamic and physical properties. Powder Technol. 145:139–148.
   Web of Science ®Google Scholar
• Amidon G, Lennernãs H, Shah VP, Crison JR. 1995. A theoretical basis for a biopharmaceutical drug classification: the correlation of in vivo drug product dissolution and in vivo bioavailability. Pharm Res. 12:414–420.
   Web of Science ®Google Scholar
• Asare EA, Wang TS, Winchester DP, Mallin K, Kebebew E, Sturgeon C. 2014. A novel staging system for adrenocortical carcinoma better predicts survival in patients with stage I/II disease. Surgery. 156:1378–1385. discussion 1385–1376.
   PubMed Web of Science ®Google Scholar
• Attivi D, Ajana I, Astier A, Demore B, Gibaud S. 2010. Development of microemulsion of mitotane for improvement of oral bioavailability. Drug Dev Ind Pharm. 36:421–427.
   PubMed Web of Science ®Google Scholar
• Barlaskar FM, Hammer GD. 2007. The molecular genetics of adrenocortical carcinoma. Rev Endocr Metab Disord. 8:343–348.
   PubMed Web of Science ®Google Scholar
• Barthe L, Bessouet M, Woodley J, Houin G. 1998. The improved everted gut sac: a simple method to study intestinal P-glycoprotein. Int J Pharm. 173:255–258.
   Web of Science ®Google Scholar
• Barthe L, Woodley J, Houin G. 1999. Gastrointestinal absorption of drugs: methods and studies. Fundam Clin Pharmacol. 13:154–168.
   PubMed Web of Science ®Google Scholar
• Chen PS, Toribara TY, Warner H. 1956. Microdetermination of phosphorus. Anal Chem. 28:1756–1758.
   Web of Science ®Google Scholar
• Clares B, Calpena AC, Parra A, Abrego G, Alvarado H, Fangueiro JF, Souto EB. 2014. Nanoemulsions (NEs), liposomes (LPs) and solid lipid nanoparticles (SLNs) for retinyl palmitate: effect on skin permeation. Int J Pharm. 473:591–598.
   PubMed Web of Science ®Google Scholar
• Copland MJ, Rades T, Davies NM. 2000. Hydration of lipid films with an aqueous solution of Quil A: a simple method for the preparation of immune-stimulating complexes. Int J Pharm. 196:135–139.
   PubMedGoogle Scholar
• da Silva CF, Severino P, Martins F, Chaud MV, Santana M. 2009. The intestinal permeation of didanosine from granules containing microspheres using the everted gut sac model. J Microencapsulation. 26:523–528.
   PubMed Web of Science ®Google Scholar
• Daeihamed M, Dadashzadeh S, Haeri A, Akhlaghi MF. 2017. Potential of liposomes for enhancement of oral drug absorption. Curr Drug Deliv. 14:289–303.
   PubMed Web of Science ®Google Scholar
• Daghastanli KR, Ferreira RB, Thedei G Jr, Maggio B, Ciancaglini P. 2004. Lipid composition-dependent incorporation of multiple membrane proteins into liposomes. Colloids Surf B Biointerfaces. 36:127–137.
   PubMed Web of Science ®Google Scholar
• de Paula Rigoletto T, Silva CL, Santana MHA, Rosada RS, de la Torre LG. 2012. Effects of extrusion, lipid concentration and purity on physico-chemical and biological properties of cationic liposomes for gene vaccine applications. J Microencapsulation. 29:759–769.
   PubMed Web of Science ®Google Scholar
• Desai MP, Labhasetwar V, Amidon GL, Levy RJ. 1996. Gastrointestinal uptake of biodegradable microparticles: effect of particle size. Pharm Res. 13:1838–1845.
   PubMed Web of Science ®Google Scholar
• Diez C, Traag W, Zommer P, Marinero P, Atienza J. 2006. Comparison of an acetonitrile extraction/partitioning and “dispersive solid-phase extraction” method with classical multi-residue methods for the extraction of herbicide residues in barley samples. J Chromatogr A. 1131:11–23.
   PubMed Web of Science ®Google Scholar
• Edwards KA, Baeumner AJ. 2006. Analysis of liposomes. Talanta. 68:1432–1441.
   PubMed Web of Science ®Google Scholar
• FDA. 2008. [accessed 2015 Sep 23]. http://www.fda.gov/ohrms/dockets/ac/01/slides/3763s2_10_KUMI.PPT
   Google Scholar
• Frohlich E, Roblegg E. 2012. Models for oral uptake of nanoparticles in consumer products. Toxicology. 291:10–17.
   PubMed Web of Science ®Google Scholar
• Grando CRC, Guimarães CA, Mercuri LP, Matos JR, Santana M. 2013. Preparation and characterization of solid lipid nanoparticles loaded with racemic mitotane. J Coll Sci Biotechnol. 2:140–145.
   Google Scholar
• Hantel C, Jung S, Mussack T, Reincke M, Beuschlein F. 2014. Liposomal polychemotherapy improves adrenocortical carcinoma treatment in a preclinical rodent model. Endocr Relat Cancer. 21:383–394.
   PubMed Web of Science ®Google Scholar
• He P, Davis SS, Illum L. 1998. In vitro evaluation of the mucoadhesive properties of chitosan microspheres. Int J Pharm. 166:75–88.
   Web of Science ®Google Scholar
• Hermansson V, Cantillana T, Hovander L, Bergman A, Ljungvall K, Magnusson U, Törneke K, Brandt I. 2008. Pharmacokinetics of the adrenocorticolytic compounds 3-methylsulphonyl-DDE and o,p’-DDD (mitotane) in Minipigs. Cancer Chemother Pharmacol. 61:267–274.
   PubMed Web of Science ®Google Scholar
• Jung S, Nagy Z, Fassnacht M, Zambetti G, Weiss M, Reincke M, Igaz P, Beuschlein F, Hantel C. 2016. Preclinical progress and first translational steps for a liposomal chemotherapy protocol against adrenocortical carcinoma. Endocr Relat Cancer. 23:825–837.
   PubMed Web of Science ®Google Scholar
• Kukuchi H, Yamauchi H, Hirota S. 1991. A spray-drying method for mass production of liposomes. Chem Pharm Bull. 39:1522–1527.
   Web of Science ®Google Scholar
• Lee D, Yanamadala V, Shankar GM, Shin JH. 2016. Metastatic adrenal cortical carcinoma to T12 vertebrae. J Clin Neurosci. 27:166–169.
   PubMed Web of Science ®Google Scholar
• Li SS, Tang XY, Zhang SG, Ni SL, Yang NB, Lu MQ. 2016. Voriconazole combined with low-dose amphotericin B liposome for treatment of cryptococcal meningitis. Infect Dis. 48:563–563.
   PubMed Web of Science ®Google Scholar
• Lin YH, Chen YS, Wu TC, Chen LJ. 2011. Enhancement of dissolution rate of mitotane and warfarin prepared by using microemulsion systems. Colloids Surf B Biointerfaces. 85:366–372.
   PubMed Web of Science ®Google Scholar
• Maiter D, Bex M, Vroonen L, T'Sjoen G, Gil T, Banh C, Chadarevian R. 2016. Efficacy and safety of mitotane in the treatment of adrenocortical carcinoma: a retrospective study in 34 Belgian patients. Ann Endocrinol (Paris). 77:578–585.
   PubMed Web of Science ®Google Scholar
• Makwana K, Tandel H. 2012. Design and characterization of anionic PEGylated liposomal formulation loaded with paclitax for ovarian cancer. J Pharm Bioall Sci. 4:17–18.
   Google Scholar
• Manirakiza P, Covaci A, Schepens P. 2000. Single step clean-up and GC-MS quantification of organochlorine pesticide residues in spice powder. Chromatographia. 52:787–790.
   Web of Science ®Google Scholar
• Misra A, Jinturkar K, Patel D, Lalani J, Chougule M. 2009. Recent advances in liposomal dry powder formulations: preparation and evaluation. Expert Opinion on Drug Delivery. 6:71–89.
   PubMed Web of Science ®Google Scholar
• Moolenaar A, Van Slooten H, Van Seters A, Smeenk D. 1981. Blood levels of o, p′-DDD following administration in various vehicles after a single dose and during long-term treatment. Cancer Chemother Pharmacol. 7:51–54.
   PubMed Web of Science ®Google Scholar
• Nguyen XT, Pabarue HA, Geyer RR, Shroyer LA, Estey LA, Parilo MS, Wilson KS, Prochaska LJ. 2002. Biochemical and biophysical properties of purified phospholipid vesicles containing bovine heart cytochrome c oxidase. Protein Expr Purif. 26:122–130.
   PubMed Web of Science ®Google Scholar
• Ohashi K, Hayashi T, Sakamoto M, Iuchi H, Suzuki H, Ebisawa T, Tojo K, Sasano H, Utsunomiya K. 2016. Aldosterone-producing adrenocortical carcinoma with prominent hepatic metastasis diagnosed by liver biopsy: a case report. BMC Endocr Disord. 16:3.
   PubMed Web of Science ®Google Scholar
• Pashirova TN, Zueva IV, Petrov KA, Lukashenko SS, Nizameev IR, Kulik NV, Voloshina AD, Almasy L, Kadirov MK, Masson P, et al. 2018. Mixed cationic liposomes for brain delivery of drugs by the intranasal route: the acetylcholinesterase reactivator 2-PAM as encapsulated drug model. Colloids Surf B Biointerfaces. 171:358–367.
   PubMed Web of Science ®Google Scholar
• Petersen GH, Alzghari SK, Chee W, Sankari SS, La-Beck NM. 2016. Meta-analysis of clinical and preclinical studies comparing the anticancer efficacy of liposomal versus conventional non-liposomal doxorubicin. J Controlled Release. 232:255–264.
   PubMed Web of Science ®Google Scholar
• Pianovski MA, Maluf EM, de Carvalho DS, Ribeiro RC, Rodriguez-Galindo C, Boffetta P, Zancanella P, Figueiredo BC. 2006. Mortality rate of adrenocortical tumors in children under 15 years of age in Curitiba. Pediatr Blood Cancer. 47:56–60.
   PubMed Web of Science ®Google Scholar
• Pudipeddi M, Serajuddin AT. 2005. Trends in solubility of polymorphs. J Pharm Sci. 94:929–939.
   PubMed Web of Science ®Google Scholar
• Rodrigues MV, Reyes FG, Magalhães PM, Rath S. 2007. GC-MS determination of organochlorine pesticides in medicinal plants harvested in Brazil. J Braz Chem Soc. 18:135–142.
   Web of Science ®Google Scholar
• Severino P, Moraes LF, Zanchetta B, Souto EB, Santana MH. 2012. Elastic liposomes containing benzophenone-3 for sun protection factor enhancement. Pharm Dev Technolo. 17:661–665.
   PubMed Web of Science ®Google Scholar
• Severino P, Pinho SC, Souto EB, Santana MH. 2011. Polymorphism, crystallinity and hydrophilic-lipophilic balance of stearic acid and stearic acid-capric/caprylic triglyceride matrices for production of stable nanoparticles. Colloids Surf B Biointerfaces. 86:125–130.
   PubMed Web of Science ®Google Scholar
• Severino P, Souto EB, Pinho SC, Santana MH. 2013. Hydrophilic coating of mitotane-loaded lipid nanoparticles: preliminary studies for mucosal adhesion. Pharm Dev Technol. 18:577–581.
   PubMed Web of Science ®Google Scholar
• Souto EB. 2009. A special issue on lipid-based delivery systems (liposomes, lipid nanoparticles, lipid matrices and medicines). J Biomed Nanotechnol. 5:315–316.
   PubMed Web of Science ®Google Scholar
• Souto EB, Souto SB, Campos JR, Severino P, Pashirova TN, Zakharova LY, Silva AM, Durazzo A, Lucarini M, Izzo AA, et al. 2019. Nanoparticle delivery systems in the treatment of diabetes complications. Molecules. 24:4209.
   PubMed Web of Science ®Google Scholar
• Stigliano A, Cerquetti L, Lardo P, Petrangeli E, Toscano V. 2017. New insights and future perspectives in the therapeutic strategy of adrenocortical carcinoma. Oncol Rep. 37:1301–1311.
   PubMed Web of Science ®Google Scholar
• Teixeira MC, Carbone C, Souto EB. 2017. Beyond liposomes: recent advances on lipid based nanostructures for poorly soluble/poorly permeable drug delivery. Prog Lipid Res. 68:1–11.
   PubMed Web of Science ®Google Scholar
• Westover EJ, Lin X, Riehl TE, Ma L, Stenson WF, Covey DF, Ostlund RE. 2006. Rapid transient absorption and biliary secretion of enantiomeric cholesterol in hamsters. J Lipid Res. 47:2374–2381.
   PubMed Web of Science ®Google Scholar
• Xu YZ, Zhu Y. 2013. Conventional chemotherapy and emerging targeted therapy for advanced adrenocortical carcinoma. Anticancer Agents Med Chem. 13:248–253.
   PubMed Web of Science ®Google Scholar
• Yin F, Guo S, Gan Y, Zhang X. 2014. Preparation of redispersible liposomal dry powder using an ultrasonic spray freeze-drying technique for transdermal delivery of human epithelial growth factor. Int J Nanomedicine. 9:1665–1676.
   PubMed Web of Science ®Google Scholar
• Zancanella P, Pianovski MAD, Oliveira BH, Ferman S, Piovezan GC, Lichtvan LL, Voss SZ, Stinghen ST, Callefe LG, Parise GA, et al. 2006. Mitotane associated with cisplatin, etoposide, and doxorubicin in advanced childhood adrenocortical carcinoma: mitotane monitoring and tumor regression. J Pediatr Hematol Oncol. 28:513–524.
   PubMed Web of Science ®Google Scholar