Imiquimod-oleic acid prodrug-loaded cream reduced drug crystallinity and induced indistinguishable cytotoxicity and apoptosis in mice melanoma tumour

References

• Amini, S., et al., 2010. Non surgical innovations in the treatment of non melanoma skin cancer. J clin aesthet dermatol, 3(6), 20–34.
   Google Scholar
• Aspord, C., et al., 2014. Imiquimod inhibits melanoma development by promoting pDC cytotoxic functions and impding vascularisation. Journal of investigative dermatology, 134(10), 2551–2561.
   PubMed Web of Science ®Google Scholar
• Barry, B.W., 1987. Mode of action of penetration enhancers in human skin. Journal of controlled release, 6(1), 85–97.
   Google Scholar
• Barry, B.W. and Meyer, M.C., 1975. Assessment of the spreadability of official pharmaceutical creams and ointments using the master curve concept. Journal of Texture Studies, 6(4), 433–444.
   Google Scholar
• Bonde, S., Bonde, C., and Mavani, N., 2018. Formulation, optimization and evaluation of organogel for topical delivery of acyclovir. Current drug delivery, 15(3), 397–405.
   PubMed Web of Science ®Google Scholar
• Bougueon, G., et al., 2016. Formulation and characterization of a 0.1% rapamycin cream for the treatment of tuberous sclerosis complex related angiofibromas. International journal of pharmaceutics, 509, 279–284.
   PubMed Web of Science ®Google Scholar
• Bradshaw, T.D., et al., 1998. 2-(4-Aminophenyl) benzothiazoles: novel agents with selective profiles of in vitro antitumour activity. British journal of cancer, 77(5), 745–752.
   PubMed Web of Science ®Google Scholar
• Bragta, P., et al., 2018. Intratumoural administration of carboplatin bearing poly (ε-caprolactone) nanoparticles amalgamated with in situ gel tendered augmented drug delivery, cytotoxicity, and apoptosis in melanoma tumour. Colloids and surfaces B: biointerfaces, 166, 339–348.
   PubMed Web of Science ®Google Scholar
• Brunngraber, E.G., and Brown, B.D., 1967. Preparation and properties of sialomucopolysaccharides obtained from rat brain. Biochemical journal, 103(1), 65–72.
   PubMed Web of Science ®Google Scholar
• Bubna, A.K., 2015. Imiquimod: Its role in the treatment of cutaneous malignancies. Indian journal of pharmacology, 47(4), 354–359.
   PubMed Web of Science ®Google Scholar
• Chang, R.K., et al., 2013. Generic development of topical dermatologic products: formulation development, process development, and testing of topical dermatologic products. The aaps journal, 15(1), 41–52.
   PubMed Web of Science ®Google Scholar
• Chen, M.X., Alexander, K.S., and Baki, G., 2016. Formulation and evaluation of antibacterial creams and gels containing metal ions for topical application. Journal of pharmaceutics, 2016, 10. Article ID 5754349, pages.
   Google Scholar
• Chen, Y., Wang, M., and Fang, L., 2013. Biomaterials as novel penetration enhancers for transdermal and dermal drug delivery systems. Drug delivery, 20(5), 199–209.
   PubMed Web of Science ®Google Scholar
• Chollet J.L., et al. 1998. Zarraga. AAPS Annual Meeting, abstract 2445. San Francisco.
   Google Scholar
• Coventry, B.J., Baume, D., and Lilly, C., 2015. Long-term survival in advanced melanoma patients using repeated therapies: successive immunomodulation improving the odds. Cancer management and research, 7, 93–103.
   PubMed Web of Science ®Google Scholar
• El-Khattouti, A., et al., 2016. Imiquimod-induced apoptosis of melanoma cells is mediated by ER stress dependent Noxa induction and enhanced by NF-κB inhibition. Journal of cellular and molecular medicine, 20(2), 266–286.
   PubMed Web of Science ®Google Scholar
• Hanna, E., Abadi, R., and Abbas, O., 2016. Imiquimod in dermatology: an overview. International journal of dermatology, 55(8), 831–844.
   PubMed Web of Science ®Google Scholar
• Harrison, L.I., et al., 2009. A pharmaceutical comparison of different commercially available imiquimod 5% cream products. J dermatolog treat, 10, 1–5.
   Google Scholar
• Huang, S.J., et al., 2009. Imiquimod enhances IFN-gamma production and effector function of T cells infiltrating human squamous cell carcinomas of the skin. Journal of investigative dermatology, 129(11), 2676–2685.
   PubMed Web of Science ®Google Scholar
• Jyoti, K., et al., 2017. Inhalable bioresponsive chitosan microspheres of doxorubicin and soluble curcumin augmented drug delivery in lung cancer cells. International journal of biological macromolecules, 98, 50–58.
   PubMed Web of Science ®Google Scholar
• Kaur, A., et al., 2018. Self-assembled nanomicelles of amphiphilic clotrimazole glycyl-glycine analogue augmented drug delivery, apoptosis and restrained melanoma tumour progression. Materials science and engineering: c, 89, 75–86.
   PubMed Web of Science ®Google Scholar
• Kiernan, J. A., 2008. Histological and histochemical methods: theory and practice. 4th ed. Bloxham, UK: Scion.
   Google Scholar
• Kim, B.Y., et al., 2005. Ketorolac amide prodrugs for transdermal delivery: stability and in vitro rat skin permeation. International journal of pharmaceutics, 293(1-2), 193–202.
   PubMed Web of Science ®Google Scholar
• Lane, M.E., 2013. Skin penetration enhancers. International journal of pharmaceutics, 447(1-2), 12–21.
   PubMed Web of Science ®Google Scholar
• Lopez-Bergami, P., Fitchman, B., and Ronai, Z., 2008. Understanding signaling cascades in melanoma. Photochemistry and photobiology, 84(2), 289–306.
   PubMed Web of Science ®Google Scholar
• Madan, J., et al., 2014. Enhanced noscapine delivery using estrogen receptor targeted nanoparticles for breast cancer therapy. Anti-cancer drugs, 25, 704–716.
   PubMed Web of Science ®Google Scholar
• Marepally, S., et al., 2013. Design, synthesis of novel lipids as chemical permeation enhancers and development of nano particle system for transdermal drug delivery. PLoS one, 8(12), e82581.
   PubMed Web of Science ®Google Scholar
• Marjukka Suhonen, T., Bouwstra, J.A., and Urtti, A., 1999. Chemical enhancement of percutaneous absorption in relation to stratum corneum structural alterations. Journal of controlled release, 59(2), 149–161.
   PubMed Web of Science ®Google Scholar
• Marples, M. J., 1965. The ecology of the human skin. Springfield, IL: Charles C Thomas Publisher, 03–154.
   Google Scholar
• Matsuzawa, H., et al., 2013. Dynamic molecular behaviour and cluster structure of octanoic acid in its liquid and CCl4 solution. Food and nutrition sciences, 4, 25–32.
   Google Scholar
• Mosmann, T., 1983. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of immunological methods, 65(1–2), 55–63.
   PubMed Web of Science ®Google Scholar
• Naik, A., et al., 1995. Mechanism of oleic acid-induced skin penetration enhancement in vivo in humans. Journal of controlled release, 37(3), 299–306.
   Web of Science ®Google Scholar
• Park, E.K., and Song, K.W., 2010. Rheological evaluation of petroleum jelly as a base material in ointment and cream formulations: steady shear flow behaviour. Archives of pharmacal research, 33(1), 141–150.
   PubMed Web of Science ®Google Scholar
• Pathan, I.B., and Setty, C.M., 2009. Chemical penetration enhancers for transdermal drug delivery systems. Tropical J pharm res, 8, 173–179.
   Web of Science ®Google Scholar
• Paula, D.D., Martins, C.A., and Bentley, M., 2008. Development and validation of HPLC method for imiquimod determination in skin penetration studies. Biomedical chromatography, 22(12), 1416–1423.
   PubMed Web of Science ®Google Scholar
• Raschke, T., et al., 2004. Topical activity of ascorbic acid: from in vitro optimization to in vivo efficacy. Skin pharmacology and physiology, 17(4), 200–206.
   PubMedGoogle Scholar
• Rau, H. and Lessmann, T., 2015. Dipeptide-based prodrug linkers for aliphatic amine-containing drugs. United States Patent US20130053301A1.
   Google Scholar
• Redondo, P., et al., 2007. Imiquimod enhances the systemic immunity attained by local cryosurgery destruction of melanoma lesions. Journal of investigative dermatology, 127(7), 1673–1680.
   PubMed Web of Science ®Google Scholar
• Rehman, K., Mohd Amin, M.C.I., and Zulfakar, M.H., 2014. Development and physical characterization of polymer-fish oil bigel (hydrogel/oleogel) system as a transdermal drug delivery vehicle. Journal of oleo science, 63(10), 961–970.
   PubMed Web of Science ®Google Scholar
• Rowat, A.C., Kitson, N., and Thewalt, J.L., 2006. Interactions of oleic acid and model stratum corneum membranes as seen by 2H NMR. International journal of pharmaceutics, 307(2), 225–231.
   PubMed Web of Science ®Google Scholar
• Schon, M.P., et al., 2004. Death receptor independent apoptosis in malignant melanoma induced bythe small-molecule immune response modifier imiquimod. Journal of investigative dermatology, 122, 1266–1276.
   PubMed Web of Science ®Google Scholar
• Shah, V.P., Elkins, J.S., and Williams, R.L., 1999. Evaluation of the test system used for in vitro release of drugs for topical dermatological drug products. Pharmaceutical development and technology, 4(3), 377–385.
   PubMed Web of Science ®Google Scholar
• Shah, K., et al., 2017. Prodrugs of NSAIDs: A review. The open medicinal chemistry journal, 11(1), 146–195.
   PubMedGoogle Scholar
• Shojaei, H., et al., 2009. Toll-like receptors 3 and 7 agonists enhance tumour cell lysis by human gamma delta T cells. Cancer research, 69(22), 8710–8717.
   PubMed Web of Science ®Google Scholar
• Siewert, M., et al., 2003. FIP/AAPS guidelines to dissolution/in vitro release testing of novel/special dosage forms. AAPS pharmscitech, 4(1), 43.
   Google Scholar
• Singh, L., et al., 2015. Expression of pro-apoptotic Bax and anti-apoptotic Bcl-2 proteins in human retinoblastoma. Clinical & experimental ophthalmology, 43(3), 259–267.
   PubMed Web of Science ®Google Scholar
• Singh, T.P., et al., 2016. Monocyte derived inflammatory langerhans cells and dermal dendritic cells mediate psoriasis like inflammation. Nature communications, 7(1), 13581.
   PubMed Web of Science ®Google Scholar
• Sioud, M., 2006. Single-stranded small interfering RNAs are more immunostimulatory than their double-stranded counterparts: a central role for 2'-hydroxyl uridines in immune responses. European journal of immunology, 36(5), 1222–1230.
   PubMed Web of Science ®Google Scholar
• Smith, P.K., et al., 1985. Measurement of protein using bicinchoninic acid. Analytical biochemistry, 150(1), 76–85.
   PubMed Web of Science ®Google Scholar
• Soni, N., et al., 2017. Noscapinoids bearing silver nanocrystals augmented drug delivery, cytotoxicity, apoptosis and cellular uptake in B16F1, mouse melanoma skin cancer cells. Biomedicine & pharmacotherapy, 90, 906–913.
   PubMed Web of Science ®Google Scholar
• Statham, A.S. and Nelson, R.J. 2011a. Pharmaceutical cream with reduced imiquimod impurities at four months using refined oleic acid. United States Patent US 7,902,213 B2.
   Google Scholar
• Statham, A.S. and Nelson, R.J. 2011b. Method of stabilizing imiquimod. United States Patent 7902242 B2.
   Google Scholar
• Statham, A.S. and Nelson, R.J. 2011c. Reduction of imiquimod impurities using refined oleic acid. United States Patent US20100130530 A1.
   Google Scholar
• Takeuchi, Y., et al., 1998. Skin penetration enhancing action of cis-unsaturated fatty acids with -9, and -12 chain lengths. Biological & pharmaceutical bulletin, 21(5), 484–491.
   PubMed Web of Science ®Google Scholar
• Varma, S.R., et al., 2017. Imiquimod-induced psoriasis-like inflammation in differentiated Human keratinocytes: Its evaluation using curcumin. European journal of pharmacology, 813, 33–41.
   PubMed Web of Science ®Google Scholar
• Yan, Y.D., et al., 2011. Evaluation of physicochemical properties, skin permeation and accumulation profiles of salicylic acid amide prodrugs as sunscreen agent. International journal of pharmaceutics, 419(1–2), 154–160.
   PubMed Web of Science ®Google Scholar
• Yang, Y., et al., 2012. Effect of size, surface charge, and hydrophobicity of poly (amidoamine) dendrimers on their skin penetration. Biomacromolecules, 13(7), 2154–2162.
   PubMed Web of Science ®Google Scholar
• Yatvin, M.B., Stowell, M.H.B. 2002. Covalent polar lipid-conjugates with biologically active compounds for use in salves. United States Patent US6, 387, 876.
   Google Scholar