Formulation and evaluation of itraconazole liposomes for Hedgehog pathway inhibition

References

• Aghaloo, T.L., et al., 2007. Oxysterols enhance osteoblast differentiation in vitro and bone healing in vivo. Journal of orthopaedic research, 25(11), 1488–1497.
   PubMed Web of Science ®Google Scholar
• Amakye, D., Jagani, Z., and Dorsch, M., 2013. Unraveling the therapeutic potential of the Hedgehog pathway in cancer. Nature medicine, 19(11), 1410–1422.
   PubMed Web of Science ®Google Scholar
• Atwood, S.X., et al., 2015. Smoothened variants explain the majority of drug resistance in basal cell carcinoma. Cancer cell, 27(3), 342–353.
   PubMed Web of Science ®Google Scholar
• Briscoe, J., and Thérond, P.P., 2013. The mechanisms of Hedgehog signalling and its roles in development and disease. Nature reviews molecular cell biology, 14(7), 416–429.
   PubMed Web of Science ®Google Scholar
• Bulbake, U., et al., 2017. Liposomal formulations in clinical use: an updated review. Pharmaceutics, 9(4), 12.
   PubMed Web of Science ®Google Scholar
• Conte, P.L., et al., 1994. In vitro and in vivo antifungal activity of liposomal and free itraconazole against Candida albicans. Current therapeutic research, 55(8), 938–943.
   Web of Science ®Google Scholar
• Corcoran, R.B., and Scott, M.P., 2006. Oxysterols stimulate Sonic hedgehog signal transduction and proliferation of medulloblastoma cells. Proceedings of the national academy of sciences, 103(22), 8408–8413.
   PubMed Web of Science ®Google Scholar
• Costa, A.P., et al., 2016. Liposome formation using a coaxial turbulent jet in co-flow. Pharmaceutical research, 33(2), 404–416.
   PubMed Web of Science ®Google Scholar
• Ćurić, A., et al., 2013. Formulation optimization of itraconazole loaded PEGylated liposomes for parenteral administration by using design of experiments. International journal of pharmaceutics, 448(1), 189–197.
   PubMed Web of Science ®Google Scholar
• Das, S., Samant, R.S., and Shevde, L.A., 2013. Nonclassical activation of Hedgehog signaling enhances multidrug resistance and makes cancer cells refractory to smoothened-targeting hedgehog inhibition. Journal of biological chemistry, 288(17), 11824–11833.
   PubMed Web of Science ®Google Scholar
• Dijkgraaf, G.J.P., et al., 2011. Small molecule inhibition of GDC-0449 refractory smoothened mutants and downstream mechanisms of drug resistance. Cancer research, 71(2), 435–444.
   PubMed Web of Science ®Google Scholar
• Domínguez-Gil Hurlé, A., Sánchez Navarro, A., and García Sánchez, M.J., 2006. Therapeutic drug monitoring of itraconazole and the relevance of pharmacokinetic interactions. Clinical microbiology and infection, 12(Supplement 7), 97–106.
   PubMedGoogle Scholar
• Dwyer, J.R., et al., 2007. Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells. Journal of biological chemistry, 282(12), 8959–8968.
   PubMed Web of Science ®Google Scholar
• Federman, N., and Denny, C.T., 2010. Targeting liposomes toward novel pediatric anticancer therapeutics. Pediatric research, 67(5), 514–519.
   PubMed Web of Science ®Google Scholar
• Gibson, P., et al., 2010. Subtypes of medulloblastoma have distinct developmental origins. Nature, 468(7327), 1095–1099.
   PubMed Web of Science ®Google Scholar
• Gupta, A.K., Cooper, E.A., and Ginter, G., 2003. Efficacy and safety of itraconazole use in children. Dermatologic clinics, 21(3), 521–535.
   PubMed Web of Science ®Google Scholar
• Hadden, M.K., 2014. Hedgehog pathway agonism: therapeutic potential and small-molecule development. ChemMedChem, 9(1), 27–37.
   PubMed Web of Science ®Google Scholar
• Home - ClinicalTrials.gov [online], 2017. Available from: https://clinicaltrials.gov/ [Accessed 10 October 2017].
   Google Scholar
• Jacoby, E., et al., 2006. The 7 TM G-protein-coupled receptor target family. ChemMedChem, 1(8), 760–782.
   Web of Science ®Google Scholar
• Johnson, J.S., et al., 2011. Novel oxysterols have pro-osteogenic and anti-adipogenic effects in vitro and induce spinal fusion in vivo. Journal of cellular biochemistry, 112(6), 1673–1684.
   PubMed Web of Science ®Google Scholar
• Kim, J., et al., 2013. Itraconazole and arsenic trioxide inhibit Hedgehog pathway activation and tumor growth associated with acquired resistance to smoothened antagonists. Cancer cell, 23(1), 23–34.
   PubMed Web of Science ®Google Scholar
• Kim, J., et al., 2010. Itraconazole, a commonly used anti-fungal that inhibits Hedgehog pathway activity and cancer growth. Cancer cell, 17(4), 388–399.
   PubMed Web of Science ®Google Scholar
• Kumar, S., et al., 2015. In vitro and in vivo performance of different sized spray-dried crystalline itraconazole. Journal of pharmaceutical sciences, 104(9), 3018–3028.
   PubMed Web of Science ®Google Scholar
• Kumar, S., Shen, J., and Burgess, D.J., 2014. Nano-amorphous spray dried powder to improve oral bioavailability of itraconazole. Journal of controlled release, 192, (Supplement C), 95–102.
   PubMedGoogle Scholar
• Lankalapalli, S., Tenneti, V.S.V.K., and Adama, R., 2017. Preparation and evaluation of liposome formulations for poorly soluble drug itraconazole by complexation. Der Pharmacia Lettre, 7(8), 1–17.
   Google Scholar
• Le Conte, P., et al., 1992. Tissue distribution and antifungal effect of liposomal itraconazole in experimental cryptococcosis and pulmonary aspergillosis. American review of respiratory disease, 145(2_pt_1), 424–429.
   PubMedGoogle Scholar
• Leal, A.F.G., et al., 2015. Antifungal activity of a liposomal itraconazole formulation in experimental Aspergillus flavus keratitis with Endophthalmitis. Mycopathologia, 179(3–4), 225–229.
   PubMed Web of Science ®Google Scholar
• Li, J., et al., 2015. A review on phospholipids and their main applications in drug delivery systems. Asian journal of pharmaceutical sciences, 10(2), 81–98.
   Web of Science ®Google Scholar
• Lin, J.H., and Yamazaki, M., 2003. Role of P-glycoprotein in pharmacokinetics: clinical implications. Clinical pharmacokinetics, 42(1), 59–98.
   PubMed Web of Science ®Google Scholar
• Ling, G., et al., 2001. PATCHED and p53 gene alterations in sporadic and hereditary basal cell cancer. Oncogene, 20(53), 7770.
   PubMed Web of Science ®Google Scholar
• Maschinot, C.A., Pace, J.R., and Hadden, M.K., 2015. Synthetic small molecule inhibitors of Hh signaling as anti-cancer chemotherapeutics. Current medicinal chemistry, 22(35), 4033–4057.
   PubMed Web of Science ®Google Scholar
• Medulloblastoma [online], 2017. Available from: https://www.stjude.org/disease/medulloblastoma.html [Accessed 9 October 2017].
   Google Scholar
• Medulloblastoma | American Brain Tumor Association [online], 2017. Available from: http://www.abta.org/brain-tumor-information/types-of-tumors/medulloblastoma.html [Accessed 11 October 2017].
   Google Scholar
• Munchhof, M.J., et al., 2012. Discovery of PF-04449913, a potent and orally bioavailable inhibitor of smoothened. ACS medicinal chemistry letters, 3(2), 106–111.
   PubMed Web of Science ®Google Scholar
• Oberoi, R.K., et al., 2016. Strategies to improve delivery of anticancer drugs across the blood-brain barrier to treat glioblastoma. Neuro-oncology, 18(1), 27–36.
   PubMed Web of Science ®Google Scholar
• Ogu, C.C., and Maxa, J.L., 2000. Drug interactions due to cytochrome P450. Baylor University Medical Center proceedings), 13(4), 421–423.
   PubMedGoogle Scholar
• Olkkonen, V.M., Béaslas, O., and Nissilä, E., 2012. Oxysterols and their cellular effectors. Biomolecules, 2(1), 76–103.
   PubMedGoogle Scholar
• Pace, J.R., et al., 2016. Repurposing the clinically efficacious antifungal agent itraconazole as an anticancer chemotherapeutic. Journal of medicinal chemistry, 59(8), 3635–3649.
   PubMed Web of Science ®Google Scholar
• Pace, J.R., et al., 2019. Structure-activity relationships for itraconazole-based triazolone analogues as hedgehog pathway inhibitors. Journal of medicinal chemistry, 62(8), 3873–3885.
   PubMed Web of Science ®Google Scholar
• Pan, S., et al., 2010. Discovery of NVP-LDE225, a potent and selective smoothened antagonist. ACS medicinal chemistry letters, 1(3), 130–134.
   PubMed Web of Science ®Google Scholar
• Panwar, P., et al., 2010. Preparation, characterization, and in vitro release study of albendazole-encapsulated nanosize liposomes. International journal of nanomedicine, 5, 101–108.
   PubMed Web of Science ®Google Scholar
• Pardridge, W.M., 2003. Blood-brain barrier drug targeting: the future of brain drug development. Molecular interventions, 3(2), 90–105.
   PubMedGoogle Scholar
• Piacentini, E., 2016. Encapsulation efficiency. In: E. Drioli and L. Giorno, eds. Encyclopedia of membranes. Berlin Heidelberg: Springer, 706–707.
   Google Scholar
• Pubchem, 2017. itraconazole [online]. Available from: https://pubchem.ncbi.nlm.nih.gov/compound/55283 [Accessed 10 October 2017].
   Google Scholar
• Reifenberger, J., et al., 2005. Somatic mutations in the PTCH, SMOH, SUFUH and TP53 genes in sporadic basal cell carcinomas. British journal of dermatology, 152(1), 43–51.
   PubMed Web of Science ®Google Scholar
• Robarge, K.D., et al., 2009. GDC-0449-a potent inhibitor of the hedgehog pathway. Bioorganic & medicinal chemistry letters, 19(19), 5576–5581.
   PubMed Web of Science ®Google Scholar
• Rudin, C.M., et al., 2009. Treatment of medulloblastoma with hedgehog pathway inhibitor GDC-0449. New England journal of medicine, 361(12), 1173–1178.
   PubMed Web of Science ®Google Scholar
• Saraiva, C., et al., 2016. Nanoparticle-mediated brain drug delivery: overcoming blood–brain barrier to treat neurodegenerative diseases. Journal of controlled release, 235(Supplement C), 34–47.
   PubMedGoogle Scholar
• Savjani, K.T., Gajjar, A.K., and Savjani, J.K., 2012. Drug solubility: importance and enhancement techniques. ISRN pharmaceutics, 2012, 195727
   PubMedGoogle Scholar
• Sharpe, H.J., et al., 2015. Genomic analysis of smoothened inhibitor resistance in basal cell carcinoma. Cancer cell, 27(3), 327–341.
   PubMed Web of Science ®Google Scholar
• Soema, P.C., et al., 2015. Predicting the influence of liposomal lipid composition on liposome size, zeta potential and liposome-induced dendritic cell maturation using a design of experiments approach. European journal of pharmaceutics and biopharmaceutics, 94(Supplement C), 427–435.
   PubMedGoogle Scholar
• Staud, F., and Pavek, P., 2005. Breast cancer resistance protein (BCRP/ABCG2). The international journal of biochemistry & cell biology, 37(4), 720–725.
   PubMed Web of Science ®Google Scholar
• Strittmatter, S.M., 2014. Overcoming drug development bottlenecks with repurposing: old drugs learn new tricks. Nature medicine, 20(6), 590–591.
   PubMedGoogle Scholar
• Tang, J., et al., 2010. Pharmacokinetics and biodistribution of itraconazole in rats and mice following intravenous administration in a novel liposome formulation. Drug delivery, 17(4), 223–230.
   PubMed Web of Science ®Google Scholar
• Torchilin, V., and Weissig, V., 2003. Liposomes: a practical approach. New York: Oxford University Press Inc.
   Google Scholar
• van Hoogevest, P., and Wendel, A., 2014. The use of natural and synthetic phospholipids as pharmaceutical excipients. European journal of lipid science and technology, 116(9), 1088–1107.
   PubMed Web of Science ®Google Scholar
• Vasiliou, V., Vasiliou, K., and Nebert, D.W., 2008. Human ATP-binding cassette (ABC) transporter family. Human genomics, 3(3), 281–290.
   Google Scholar
• Wang, J., and Huang, G., 2011. Preparation of itraconazole-loaded liposomes coated by carboxymethyl chitosan and its pharmacokinetics and tissue distribution. Drug delivery, 18(8), 631–638.
   PubMed Web of Science ®Google Scholar
• Wei, X., et al., 2014. Brain tumor-targeted drug delivery strategies. Acta pharmaceutica sinica B, 4(3), 193–201.
   PubMed Web of Science ®Google Scholar
• Yauch, R.L., et al., 2009. Smoothened mutation confers resistance to a Hedgehog pathway inhibitor in medulloblastoma. Science (New York, N.Y.), 326(5952), 572–574.
   PubMed Web of Science ®Google Scholar