Functionalized Diterpene Parvifloron D-loaded Hybrid Nanoparticles for Targeted Delivery in Melanoma Therapy

References

• Garbe C Peris K Hauschild A et al. Diagnosis and treatment of melanoma. European consensus-based interdisciplinary guideline–Update 2012. Eur. J. Cancer.48 (15), 2375–2390 (2012).
   PubMed Web of Science ®Google Scholar
• Eggermont AMM Spatz A Robert C . Cutaneous melanoma. Lancet383 (9919), 816–827.
   PubMed Web of Science ®Google Scholar
• Wolinsky JB Colson YL Grinstaff MW . Local drug delivery strategies for cancer treatment: gels, nanoparticles, polymeric films, rods, and wafers. J. Control. Rel.159 (1), 14–26 (2012).
   PubMed Web of Science ®Google Scholar
• d'Angelo I Conte C Miro A Quaglia F Ungaro F . Core–shell nanocarriers for cancer therapy. Part I: biologically oriented design rules. Expert Opin. Drug Deliv.11 (2), 283–297 (2014).
   PubMed Web of Science ®Google Scholar
• Dianzani C Zara GP Maina G et al. Drug delivery nanoparticles in skin cancers. Biomed. Res. Int.2014, Article ID 895986 (2014).
   PubMed Web of Science ®Google Scholar
• Simões MCF Sousa JJS Pais A . Skin cancer and new treatment perspectives: a review. Cancer Lett.357 (1), 8–42 (2015).
   PubMed Web of Science ®Google Scholar
• Zhao Q-H Zhang Y Liu Y et al. Anticancer effect of realgar nanoparticles on mouse melanoma skin cancer in vivo via transdermal drug delivery. Med. Oncol.27 (2), 203–212 (2010).
   PubMed Web of Science ®Google Scholar
• Weinberg BD Blanco E Gao J . Polymer implants for intratumoral drug delivery and cancer therapy. J. Pharm. Sci.97 (5), 1681–1702 (2008).
   PubMed Web of Science ®Google Scholar
• Liu R Wolinsky J Walpole J et al. Prevention of local tumor recurrence following surgery using low-dose chemotherapeutic polymer films. Ann. Surg. Oncol.17 (4), 1203–1213 (2010).
   PubMed Web of Science ®Google Scholar
• Micali G Lacarrubba F Nasca MR Ferraro S Schwartz RA . Topical pharmacotherapy for skin cancer: part II. Clinical applications. J. Am. Acad. Dermatol.70 (6), 979.e1–979.e12 (2014).
   PubMedGoogle Scholar
• Ma M Hao Y Liu N et al. A novel lipid-based nanomicelle of docetaxel: evaluation of antitumor activity and biodistribution. Int. J. Nanomedicine7, 3389–3398 (2012).
   PubMed Web of Science ®Google Scholar
• Mangalathillam S Rejinold NS Nair A Lakshmanan V-K Nair SV Jayakumar R . Curcumin loaded chitin nanogels for skin cancer treatment via the transdermal route. Nanoscale4 (1), 239–250 (2012).
   PubMed Web of Science ®Google Scholar
• Zhang L He R Gu H-C . Oleic acid coating on the monodisperse magnetite nanoparticles. Appl. Surf. Sci.253 (5), 2611–2617 (2006).
   Web of Science ®Google Scholar
• Silva CO Rijo P Molpeceres J et al. Polymeric nanoparticles modified with fatty acids encapsulating betamethasone for anti-inflammatory treatment. Int. J. Pharm.493 (1–2), 271–284 (2015).
   PubMed Web of Science ®Google Scholar
• Park J-H Cho H-J Yoon HY et al. Hyaluronic acid derivative-coated nanohybrid liposomes for cancer imaging and drug delivery. J. Control. Rel.174 (0), 98–108 (2014).
   PubMedGoogle Scholar
• Ahrens T Assmann V Fieber C et al. CD44 is the principal mediator of hyaluronic-acid-induced melanoma cell proliferation. J. Invest. Dermatol.116 (1), 93–101 (2001).
   PubMed Web of Science ®Google Scholar
• Kong M Chen XG Kweon DK Park HJ . Investigations on skin permeation of hyaluronic acid based nanoemulsion as transdermal carrier. Carbohydr. Polym.86 (2), 837–843 (2011).
   Web of Science ®Google Scholar
• Yang J-A Kim E-S Kwon JH et al. Transdermal delivery of hyaluronic acid–human growth hormone conjugate. Biomaterials33 (25), 5947–5954 (2012).
   PubMed Web of Science ®Google Scholar
• Carlson JA Linette GP Aplin A Ng B Slominski A . Melanocyte receptors: clinical implications and therapeutic relevance. Dermatol. Clin.25 (4), 541–557 (2007).
   PubMed Web of Science ®Google Scholar
• Abdel-Mottaleb MMA Neumann D Lamprecht A . Lipid nanocapsules for dermal application: a comparative study of lipid-based versus polymer-based nanocarriers. Eur. J. Pharm. Biopharm.79 (1), 36–42 (2010).
   Web of Science ®Google Scholar
• Bombelli FB Webster CA Moncrieff M Sherwood V . The scope of nanoparticle therapies for future metastatic melanoma treatment. Lancet Oncol.15 (1), e22–e32 (2014).
   PubMed Web of Science ®Google Scholar
• Gonçalves AS Macedo AS Souto EB . Therapeutic nanosystems for oncology nanomedicine. Clin. Transl. Oncol.14 (12), 883–890 (2012).
   PubMed Web of Science ®Google Scholar
• Madhunapantula SV Robertson GP . Chapter twelve–chemoprevention of melanoma. In : Advances in Pharmacology. KeiranSMS ( Ed.). Academic Press, Cambridge, USA, 361–398 (2012).
   Google Scholar
• Simões MF Rijo P Duarte A Matias D Rodríguez B . An easy and stereoselective rearrangement of an abietane diterpenoid into a bioactive microstegiol derivative. Phytochem. Lett.3 (4), 234–237 (2010).
   Web of Science ®Google Scholar
• Burmistrova O Simões MF Rijo P Quintana J Bermejo J Estévez F . Antiproliferative activity of abietane diterpenoids against human tumor cells. J. Nat. Prod.76 (8), 1413–1423 (2013).
   PubMed Web of Science ®Google Scholar
• Burmistrova O Perdomo J Simões MF Rijo P Quintana J Estévez F . The abietane diterpenoid parvifloron D from Plectranthus ecklonii is a potent apoptotic inducer in human leukemia cells. Phytomedicine22 (11), 1009–16 (2015).
   PubMed Web of Science ®Google Scholar
• Scodeller P Catalano PN Salguero N Duran H Wolosiuk A Soler-Illia GJAA . Hyaluronan degrading silica nanoparticles for skin cancer therapy. Nanoscale.5 (20), 9690–9698 (2013).
   PubMed Web of Science ®Google Scholar
• Chung H Lee J Jeong D Han I-O Oh E-S . Melanocortin 1 receptor regulates melanoma cell migration by controlling syndecan-2 expression. J. Biol. Chem.287 (23), 19326–19335 (2012).
   PubMed Web of Science ®Google Scholar
• Dou J Pan M Wen P et al. Isolation and identification of cancer stem-like cells from murine melanoma cell lines. Cell. Mol. Immunol.4 (6), 467–472 (2007).
   PubMed Web of Science ®Google Scholar
• Nicoletti I Migliorati G Pagliacci MC Grignani F Riccardi C . A rapid and simple method for measuring thymocyte apoptosis by propidium iodide staining and flow cytometry. J. Immunol. Methods139 (2), 271–279 (1991).
   PubMed Web of Science ®Google Scholar
• Froidevaux S Calame-Christe M Schuhmacher J et al. A gallium-labeled DOTA-α-melanocyte-stimulating hormone analog for PET imaging of melanoma metastases. J. Nucl. Med.45 (1), 116–123 (2004).
   PubMed Web of Science ®Google Scholar
• Rijo P Matias D Fernandes A Simões M Nicolai M Reis C . Antimicrobial plant extracts encapsulated into polymeric beads for potential application on the skin. Polymers (Basel)6 (2), 479–490 (2014).
   Web of Science ®Google Scholar
• de Oliveira CA Peres DD Graziola F et al. Cutaneous biocompatible rutin-loaded gelatin-based nanoparticles increase the SPF of the association of UVA and UVB filters. Eur. J. Pharm. Sci.81, 1–9 (2015).
   PubMed Web of Science ®Google Scholar
• Knor T Meholjić-Fetahović A Mehmedagić A . Stratum corneum hydration and skin surface pH in patients with atopic dermatitis. Acta Dermatovenerol. Croat.19 (4), 242–247 (2011).
   PubMed Web of Science ®Google Scholar
• Markovic BD Vladimirov SM Cudina OA Odovic JV Karljikovic-Rajic KD . A PAMPA assay as fast predictive model of passive human skin permeability of new synthesized corticosteroid C-21 esters. Molecules17 (1), 480–491 (2012).
   PubMed Web of Science ®Google Scholar
• Yoshida H Nagaoka A Kusaka-Kikushima A et al. KIAA1199, a deafness gene of unknown function, is a new hyaluronan binding protein involved in hyaluronan depolymerization. Proc. Natl Acad. Sci.110 (14), 5612–5617 (2013).
   PubMed Web of Science ®Google Scholar
• Jonsson AL Granqvist A Elvin J Johansson ME Haraldsson B Nyström J . Effects of melanocortin 1 receptor agonists in experimental nephropathies. PLoS One9 (1), e87816 (2014).
   PubMed Web of Science ®Google Scholar
• Cassard L Cohen-Solal JFG Galinha A et al. Modulation of tumor growth by inhibitory Fcγ receptor expressed by human melanoma cells. J. Clin. Invest.110 (10), 1549–1557 (2002).
   PubMed Web of Science ®Google Scholar
• Nam K Nam HY Kim P-H Kim SW . Paclitaxel-conjugated PEG and arginine-grafted bioreducible poly (disulfide amine) micelles for co-delivery of drug and gene. Biomaterials33 (32), 8122–8130 (2012).
   PubMed Web of Science ®Google Scholar
• Muhl S Méndez JM . A review of the preparation of carbon nitride films. Diam. Relat. Mater.8 (10), 1809–1830 (1999).
   Web of Science ®Google Scholar
• Oliveira CS de Bock CE Molloy TJ et al. Macrophage migration inhibitory factor engages PI3K/Akt signalling and is a prognostic factor in metastatic melanoma. BMC Cancer14 (1), 1–14 (2014).
   PubMedGoogle Scholar
• Clawson GA Matters GL Xin P et al. Macrophage-tumor cell fusions from peripheral blood of melanoma patients. PLoS One10 (8), e0134320 (2015).
   PubMed Web of Science ®Google Scholar
• Haycock JW Wagner M Morandini R Ghanem G Rennie IG Mac Neil S . α-Melanocyte-stimulating hormone inhibits NF-κB activation in human melanocytes and melanoma cells. J. Invest. Dermatol.113 (4), 560–566 (1999).
   PubMed Web of Science ®Google Scholar
• Bichakjian CK Halpern AC Johnson TM et al. Guidelines of care for the management of primary cutaneous melanoma. J. Am. Acad. Dermatol.65 (5), 1032–1047 (2011).
   PubMed Web of Science ®Google Scholar
• Antony J Saikia M Vinod V et al. DW-F5: A novel formulation against malignant melanoma from Wrightia tinctoria. Sci. Rep.5, 11107 (2015).
   PubMed Web of Science ®Google Scholar
• Calvo P Remunan-Lopez C Vila-Jato JL Alonso MJ . Chitosan and chitosan/ethylene oxide-propylene oxide block copolymer nanoparticles as novel carriers for proteins and vaccines. Pharm. Res. [Internet]14 (10), 1431–1436 (1997).
   PubMed Web of Science ®Google Scholar
• Bennet D Marimuthu M Kim S An J . Dual drug-loaded nanoparticles on self-integrated scaffold for controlled delivery. Int. J. Nanomedicine7 (3399–3419), (2012).
   PubMedGoogle Scholar
• Mizrahy S Raz SR Hasgaard M et al. Hyaluronan-coated nanoparticles: the influence of the molecular weight on CD44-hyaluronan interactions and on the immune response. J. Control. Release156 (2), 231–238 (2011).
   PubMed Web of Science ®Google Scholar
• Liu Y Sun J Cao W et al. Dual targeting folate-conjugated hyaluronic acid polymeric micelles for paclitaxel delivery. Int. J. Pharm.421 (1), 160–169 (2011).
   PubMed Web of Science ®Google Scholar
• Song S Chen F Qi H et al. Multifunctional tumor-targeting nanocarriers based on hyaluronic acid-mediated and pH-sensitive properties for efficient delivery of docetaxel. Pharm. Res.31 (4), 1032–1045 (2014).
   PubMed Web of Science ®Google Scholar
• Honary S Zahir F . Effect of zeta potential on the properties of nano-drug delivery systems-a review (Part 2). Trop. J. Pharm. Res.12 (2), 265–273 (2013).
   Google Scholar
• Yang X Li Y Li M Zhang L Feng L Zhang N . Hyaluronic acid-coated nanostructured lipid carriers for targeting paclitaxel to cancer. Cancer Lett.334 (2), 338–345 (2013).
   PubMed Web of Science ®Google Scholar
• Ramasamy T Tran TH Choi JY et al. Layer-by-layer coated lipid–polymer hybrid nanoparticles designed for use in anticancer drug delivery. Carbohydr. Polym.102 (0), 653–661 (2014).
   PubMedGoogle Scholar
• Hu F-Q Jiang S-P Du Y-Z Yuan H Ye Y-Q Zeng S . Preparation and characterization of stearic acid nanostructured lipid carriers by solvent diffusion method in an aqueous system. Colloids Surf. B Biointerfaces45 (0), 167–173 (2005).
   PubMedGoogle Scholar
• Shen H Shi S Zhang Z Gong T Sun X . Coating Solid lipid nanoparticles with hyaluronic acid enhances antitumor activity against melanoma stem-like cells. Theranostics5 (7), 755 (2015).
   PubMed Web of Science ®Google Scholar
• Jeong Y-I Kim DH Chung C-W et al. Self-assembled nanoparticles of hyaluronic acid/poly(dl-lactide-co-glycolide) block copolymer. Coll. Surf. B Biointerfaces90 (0), 28–35 (2012).
   PubMedGoogle Scholar
• Pohlmann AR Fonseca FN Paese K et al. Poly(ε-caprolactone) microcapsules and nanocapsules in drug delivery. Expert Opin. Drug Deliv.10 (5), 623–638 (2013).
   PubMed Web of Science ®Google Scholar
• Coffin MD McGinity JW . Biodegradable pseudolatexes: the chemical stability of poly(D,L-Lactide) and poly (∊-caprolactone) nanoparticles in aqueous media. Pharm. Res.9 (2), 200–205.
   PubMed Web of Science ®Google Scholar
• Simulescu V Kalina M Mondek J Pekař M . Long-term degradation study of hyaluronic acid in aqueous solutions without protection against microorganisms. Carbohydr. Polym.137, 664–668 (2016).
   PubMed Web of Science ®Google Scholar
• Morris GA Castile J Smith A Adams GG Harding SE . The effect of prolonged storage at different temperatures on the particle size distribution of tripolyphosphate (TPP)–chitosan nanoparticles. Carbohydr. Polym.84 (4), 1430–1434 (2011).
   Web of Science ®Google Scholar
• das Neves J Amiji M Bahia MF Sarmento B . Assessing the physical–chemical properties and stability of dapivirine-loaded polymeric nanoparticles. Int. J. Pharm.456 (2), 307–314 (2013).
   PubMedGoogle Scholar
• Jain A Jain SK Ganesh N Barve J Beg AM . Design and development of ligand-appended polysaccharidic nanoparticles for the delivery of oxaliplatin in colorectal cancer. Nanomedicine6 (0), 179–190 (2010).
   PubMedGoogle Scholar
• de la Fuente M Seijo B Alonso MJ . Novel hyaluronan-based nanocarriers for transmucosal delivery of macromolecules. Macromol. Biosci.8 (5), 441–450 (2008).
   PubMed Web of Science ®Google Scholar
• Li Y-Y Li L Dong H-Q Cai X-J Ren T-B . Pluronic F127 nanomicelles engineered with nuclear localized functionality for targeted drug delivery. Mater. Sci. Eng. C33 (5), 2698–2707 (2013).
   PubMed Web of Science ®Google Scholar
• Natarajan V Krithica N Madhan B Sehgal PK . Formulation and evaluation of quercetin polycaprolactone microspheres for the treatment of rheumatoid arthritis. J. Pharm. Sci.100 (1), 195–205 (2011).
   PubMed Web of Science ®Google Scholar
• Go DP Hung A Gras SL O'Connor AJ . Use of a short peptide as a building block in the layer-by-layer assembly of biomolecules on polymeric surfaces. J. Phys. Chem. B116 (3), 1120–1133 (2012).
   PubMed Web of Science ®Google Scholar
• Contreras LM de Almeida RFM Villalaín J Fedorov A Prieto M . Interaction of α-melanocyte stimulating hormone with binary phospholipid membranes: structural changes and relevance of phase behavior. Biophys. J.80 (5), 2273–2283 (2001).
   PubMed Web of Science ®Google Scholar
• Tan CP Che Man YB . Differential scanning calorimetric analysis of palm oil, palm oil based products and coconut oil: effects of scanning rate variation. Food Chem.76 (1), 89–102 (2002).
   Web of Science ®Google Scholar
• Giron D . Thermal analysis and calorimetric methods in the characterisation of polymorphs and solvates. Thermochim. Acta248, 1–59 (1995).
   Web of Science ®Google Scholar
• de la Ossa DHP Ligresti A Gil-Alegre ME et al. Poly-∊-caprolactone microspheres as a drug delivery system for cannabinoid administration: development, characterization and in vitro evaluation of their antitumoral efficacy. J. Control. Release161 (3), 927–932 (2012).
   PubMed Web of Science ®Google Scholar
• Šmejkalová D Nešporová K Hermannová M et al. Paclitaxel isomerisation in polymeric micelles based on hydrophobized hyaluronic acid. Int. J. Pharm.466 (1–2), 147–155 (2014).
   PubMedGoogle Scholar
• Liu F Park J-Y Zhang Y et al. Targeted cancer therapy with novel high drug-loading nanocrystals. J. Pharm. Sci.99 (8), 3542–3551 (2010).
   PubMed Web of Science ®Google Scholar
• Gao Q Liang Q Yu F Xu J Zhao Q Sun B . Synthesis and characterization of novel amphiphilic copolymer stearic acid-coupled F127 nanoparticles for nano-technology based drug delivery system. Coll. Surf. B Bioint.88 (2), 741–748 (2011).
   PubMed Web of Science ®Google Scholar
• Shi S Guo Q Kan B et al. A novel poly(epsilon-caprolactone)-pluronic-poly(epsilon-caprolactone) grafted polyethyleneimine(PCFC-g-PEI), Part 1, synthesis, cytotoxicity, and in vitro transfection study. BMC Biotechnol.9 (1), 65 (2009).
   PubMedGoogle Scholar
• Patrícia Dias de Mendonça Rijo . Phytochemical study and biological activities of Diterpenes and derivatives from Plectranthus species. PhD Thesis. University of Lisbon, Portugal (2010).
   Google Scholar
• Chang MC Tanaka J . XPS study for the microstructure development of hydroxyapatite–collagen nanocomposites cross-linked using glutaraldehyde. Biomaterials.23 (18), 3879–3885 (2002).
   PubMed Web of Science ®Google Scholar
• Selzer D Abdel-Mottaleb MMA Hahn T Schaefer UF Neumann D . Finite and infinite dosing: difficulties in measurements, evaluations and predictions. Adv. Drug Deliv. Rev.65 (2), 278–294 (2013).
   PubMed Web of Science ®Google Scholar
• Delehanty JB Boeneman K Bradburne CE Robertson K Bongard JE Medintz IL . Peptides for specific intracellular delivery and targeting of nanoparticles: implications for developing nanoparticle-mediated drug delivery. Ther. Deliv.1 (3), 411–433 (2010).
   PubMedGoogle Scholar
• Lu W Xiong C Zhang R et al. Receptor-mediated transcytosis: a mechanism for active extravascular transport of nanoparticles in solid tumors. J. Control. Rel. doi:10.1016/j.jconrel.2012.05.014 (2012) ( Epub ahead of print).
   Web of Science ®Google Scholar
• Roberts DW Newton RA Beaumont KA Helen Leonard J Sturm RA . Quantitative analysis of MC1R gene expression in human skin cell cultures. Pigment Cell Res.19 (1), 76–89 (2006).
   PubMedGoogle Scholar
• Tedja R Lim M Amal R Marquis C . Effects of serum adsorption on cellular uptake profile and consequent impact of titanium dioxide nanoparticles on human lung cell lines. ACS Nano6 (5), 4083–4093 (2012).
   PubMed Web of Science ®Google Scholar
• Arias JL Reddy LH Couvreur P . Polymeric nanoparticulate system augmented the anticancer therapeutic efficacy of gemcitabine. J. Drug Target17 (8), 586–598 (2009).
   PubMed Web of Science ®Google Scholar
• Jeevitha D Amarnath K . Chitosan/PLA nanoparticles as a novel carrier for the delivery of anthraquinone: synthesis, characterization and in vitro cytotoxicity evaluation. Colloids Surf. B Biointerfaces101, 126–134 (2013).
   PubMed Web of Science ®Google Scholar
• de Mattos AC Altmeyer C Tominaga T Khalil NM Mainardes RM . Polymeric nanoparticles for oral delivery of 5-fluorouracil: formulation optimization, cytotoxicity assay and pre-clinical pharmacokinetics study. Eur. J. Pharm. Sci.84, 83–91 (2016).
   PubMed Web of Science ®Google Scholar