Lyotropic Liquid-Crystalline Nanosystems as Drug Delivery Agents for 5-Fluorouracil: Structure and Cytotoxicity

Langmuir

Volumn 33, Issue 43, 2017, Pages 12369-12378

  Astolfi, Paola ^a   Giorgini, Elisabetta ^a   Gambini, Valentina ^b   Rossi, Barbara ^c   Vaccari, Lisa ^c   Vita, Francesco ^a   Francescangeli, Oriano ^a   Marchini, Cristina ^b   Pisani, Michela ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

^b UNIVERSITY OF CAMERINO   (Italy)

^c SINCROTRONE TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; CHLORINE COMPOUNDS; CRYSTALLINE MATERIALS; LIGHT SCATTERING; LIPID BILAYERS; X RAY SCATTERING;

ATTENUATED TOTAL REFLECTION FOURIER TRANSFORM INFRARED; COMPLEMENTARY TECHNIQUES; LIQUID CRYSTALLINE SYSTEM; LYOTROPIC LIQUID CRYSTALLINE; PHYSICO-CHEMICAL CHARACTERIZATION; PHYSICOCHEMICAL PROPERTY; SYNCHROTRON SMALL ANGLE X-RAY SCATTERINGS; UV-RESONANCE RAMAN SPECTROSCOPY;

NANOSYSTEMS;

FATTY ALCOHOL; FLUOROURACIL; LIPID; NANOMATERIAL;

CHEMISTRY; DRUG DELIVERY SYSTEM; LIQUID CRYSTAL; SYNCHROTRON;

DRUG DELIVERY SYSTEMS; FATTY ALCOHOLS; FLUOROURACIL; LIPIDS; LIQUID CRYSTALS; NANOSTRUCTURES; SYNCHROTRONS;

EID: 85032665638     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/acs.langmuir.7b03173     Document Type: Article

References (52)

1. Angelova, A.; Angelov, B.; Mutafchieva, R.; Lesieur, S.; Couvreur, P. Self-Assembled Multiconmpartment Liquid Crystalline Lipid Carriers for Protein, Peptide, and Nucleic Acid Drug Delivery Acc. Chem. Res. 2011, 44 (2) 147-156 10.1021/ar100120v
2. Angelova, A.; Garamus, V. M.; Angelov, B.; Tian, Z.; Li, Y.; Zou, A. Advances in structural design of lipid-based nanocarriers for delivery of macromolecular drugs, phytochemicals and anti-tumor agents. Adv. Colloid Interface Sci. 2017, DOI: 10.1016/j.cis.2017.04.006.
3. Conn, C. E.; Drummond, C. J. Nanostructured bicontinuos cubic lipid self-assembly materials as matrices for protein encapsulation Soft Matter 2013, 9, 3449-3464 10.1039/c3sm27743g
4. Barauskas, J.; Landh, T. Phase Behavior of the Phytantriol/Water System Langmuir 2003, 19, 9562-9565 10.1021/la0350812
5. Dong, Y.-D.; Larson, I.; Hanley, T.; Boyd, B. J. Bulk and Dispersed Aqueous Phase Behavior of Phytantriol: Effect of Vitamin E Acetate and F127 Polymer on Liquid Crystal Nanostructure Langmuir 2006, 22, 9512-9518 10.1021/la061706v
6. Dong, Y.-D; Dong, A. W.; Larson, I.; Rappolt, M.; Amenitsch, H.; Hanley, T.; Boyd, B. J. Impurities in Commercial phytantriol Significantly Alter Its Lyotropic Liquid Crystalline Phase Behavior Langmuir 2008, 24, 6998-7003 10.1021/la8005579
7. Guo, C.; Wang, J.; Cao, F.; Lee, R. J.; Zhai, G. Lyotropic liquid crystal systems in drug delivery Drug Discovery Today 2010, 15 (23/24) 1032-1040 10.1016/j.drudis.2010.09.006
8. Salonen, A.; Guillot, S.; Glatter, O. Determination of water content in internally self-assembled monoglyceride-based dispersions from the bulk phase Langmuir 2007, 23, 9151-9154 10.1021/la7015319
9. Swarnakar, N. K.; Thanki, K.; Jain, S. Bicontinuous Cubic Liquid Crystalline Nanoparticles for Oral Delivery of Doxorubicin: Implications on Bioavailability, Therapeutic Efficacy, and Cardiotoxicity Pharm. Res. 2014, 31, 1219-1238 10.1007/s11095-013-1244-8
10. Nazaruk, E.; Majkowska-Pilip, A.; Bilewicz, R. Lipidic Cubic-Phase Nanoparticles-Cubosomes for Efficient Drug Delivery to Cancer Cells ChemPlusChem 2017, 82 (4) 570-575 10.1002/cplu.201600534
11. Jain, S.; Bhankur, N.; Swarnakar, N. K.; Thanki, K. Phytantriol Based "Stealth" Lyotropic Liquid Crystalline Nanoparticles for Improved Antitumor Efficacy and Reduced Toxicity of Docetaxel Pharm. Res. 2015, 32, 3282-3292 10.1007/s11095-015-1706-2
12. Aleandri, S.; Bandera, D.; Mezzenga, R.; Landau, E. M. Biotinylated Cubosomes: A Versatile Tool for Active Targeting and Codelivery of Paclitaxel and a Fluorescein-Based Lipid Dye Langmuir 2015, 31, 12770-12776 10.1021/acs.langmuir.5b03469
13. Chen, Y.; Angelova, A.; Angelov, B.; Drechsler, M.; Garamus, V. M.; Willumeit-Romer, R.; Zou, A. Sterically stabilized spongosomes for multi-drug delivery of anticancer medicines J. Mater. Chem. B 2015, 3, 7734-7744 10.1039/C5TB01193K
14. Toft, D. J.; Cryns, V. L. Minireview: Basal-Like Breast Cancer: From Moleculr Prifiles To Targeted Therapies Mol. Endocrinol. 2011, 25 (2) 199-211 10.1210/me.2010-0164
15. Heggie, G. D.; Sommadossi, J.-P.; Cross, D. S.; Huster, W. J.; Diasio, R. B. Clinical Pharmacokinetics of 5-Fluorouracil and Its Metabolites in Plasma, Urine, and Bile Cancer Res. 1987, 47, 2203-2206
16. Di Paolo, A.; Danesi, R.; Falcone, A.; Cionini, L.; Vannozzi, F.; Masi, G.; Allegrini, G.; Mini, E.; Bocci, G.; Conte, P. F.; Del Tacca, M. Relationship between 5-fluorouracil disposition, toxicity and dihydropyrimidine dehydrogenase activity in cancer patients Ann. Oncol 2001, 12, 1301-1306 10.1023/A:1012294617392
17. Arias, J. L. Novel Strategies to Improve the Anticancer Action of 5-Fluorouracil by Using Drug Delivery Systems Molecules 2008, 13, 2340-2369 10.3390/molecules13102340
18. Masloub, S. M.; Elmalahy, M. H.; Sabry, D.; Mohamed, W. S.; Ahmed, S. H. Comparative evaluation of PLGA nanoparticle delivery system for 5-fluorouracil and curcumin on squamous cell carcinoma Arch. Oral Biol. 2016, 64, 1-10 10.1016/j.archoralbio.2015.12.003
19. Mathew, M. E.; Mohan, J. C.; Manzoor, K.; Nair, S. V.; Tamura, H.; Jayakumar, R. Folate conjugated carboxymethyl chitosan-manganese doped zinc sulphide nanoparticles for targeted drug delivery and imaging of cancer cells Carbohydr. Polym. 2010, 80, 442-448 10.1016/j.carbpol.2009.11.047
20. Khallaf, R. A.; Salem, H. F.; Abdelbary, A. 5-Fluorouracil Shell-enriched Solid Lipid Nanoparticles (SLN) for Effective Skin Carcinoma Treatment Drug Delivery 2016, 23 (9) 3452-3460 10.1080/10717544.2016.1194498
21. Nasr, M.; Ghorab, M. K.; Abdelazem, A. In vitro and in vivo evaluation of cubosomes containing 5-fluorouracil for liver targeting Acta Pharm. Sin. B 2015, 5 (1) 79-88 10.1016/j.apsb.2014.12.001
22. D'Amico, F.; Saito, M.; Bencivenga, F.; Marsi, M.; Gessini, A.; Camisasca, G.; Principi, E.; Cucini, R.; Di Fonzo, S.; Battistoni, A.; Giangrisostomi, E.; Masciovecchio, C. UV resonant Raman scattering facility at Elettra Nucl. Instrum. Methods Phys. Res., Sect. A 2013, 703, 33-37 10.1016/j.nima.2012.11.037
23. Kalogris, C.; Garulli, C.; Pietrella, L.; Gambini, V.; Pucciarelli, S.; Lucci, C.; Tilio, M.; Elexpuru Zabaleta, M.; Bartolacci, C.; Andreani, C.; Giangrossi, M.; Iezzi, M.; Belletti, B.; Marchini, C.; Amici, A. Sanguinarine suppresses basal-like breast cancer growth through Dihydrofolate Reductase inhibition Biochem. Pharmacol. 2014, 90 (3) 226-234 10.1016/j.bcp.2014.05.014
24. Angelov, B.; Garamus, V. M.; Drechsler, M.; Angelova, A. Structural analysis of nanoparticulate carriers for encapsulation of macromolecular drugs J. Mol. Liq. 2017, 235, 83-89 10.1016/j.molliq.2016.11.064
25. Nazaruk, E.; Miszta, P.; Filipek, S.; Górecka, E.; Landau, E. M.; Bilewicz, R. Lyotropic Cubic Phases for Drug Delivery: Diffusion and Sustained Release from the Mesophase Evaluated by Electrochemical Methods Langmuir 2015, 31, 12753-12761 10.1021/acs.langmuir.5b03247
26. Squires, A. M.; Templer, R. H.; Seddon, J. M.; Woenkhaus, J.; Winter, R.; Narayanan, T.; Finet, S. Kinetics and mechanism of the interconversion of inverse bicontinuous cubic mesophases Phys. Rev. E 2005, 72, 011502/1-011502/16 10.1103/PhysRevE.72.011502
27. Ranneh, A.-H.; Iwao, Y.; Noguchi, S.; Oka, T.; Itai, S. The use of surfactants to enhance the solubility and stability of the water-insoluble anticancer drug SN38 into liquid crystalline phase nanoparticles Int. J. Pharm. 2016, 515, 501-505 10.1016/j.ijpharm.2016.10.058
28. Dobrowolski, J. Cz.; Rode, J. E.; Kołos, R.; Jamróz, M. H.; Bajdor, K.; Mazurek, A. P. Ar-Matrix IR Spectra of 5-Halouracils Interpreted by Means of DFT Calculations J. Phys. Chem. A 2005, 109, 2167-2182 10.1021/jp045213f
29. Rastogi, V. K.; Palafox, M. A. Vibrational spectra, tautomerism and thermodynamics of anticarcinogenic drug: 5-Fluorouracil Spectrochim. Acta, Part A 2011, 79, 970-977 10.1016/j.saa.2011.04.008
30. Alcolea Palafox, M.; Tardajos, G.; Guerrero-Martinez, A.; Vats, J. K.; Joe, H.; Rastogi, V. K. Relationships observed in the structure and spectra of uracil and its 5-substituted derivatives Spectrochim. Acta, Part A 2010, 75, 1261-1269 10.1016/j.saa.2009.12.042
31. Datt, A.; Burns, E. A.; Dhuna, N. A.; Larsen, S. C. Loading and release of 5-fluorouracil from HY zeolites with varying SiO2/Al2O3 ratios Microporous Mesoporous Mater. 2013, 167, 182-187 10.1016/j.micromeso.2012.09.011
32. Egodawatte, S.; Dominguez, S., Jr.; Larsen, S. Solvent effects in the development of a drug delivery system for 5-fluorouracil using magnetic mesopourous silica nanoparticles Microporous Mesoporous Mater. 2017, 237, 108-116 10.1016/j.micromeso.2016.09.024
33. Misiunas, A.; Niaura, G.; Talaikytè, Z.; Eicher-Lorka, O.; Razumas, V. Infrared and Raman bands of phytantriol as markers of hydrogen bonding and interchain interaction Spectrochim. Acta, Part A 2005, 62, 945-957 10.1016/j.saa.2005.03.024
34. Dovbeshko, G. I.; Gridina, N. Y.; Kruglova, E. B.; Pashchuk, O. P. FTIR spectroscopy studies of nucleic acid damage Talanta 2000, 53 (1) 233-246 10.1016/S0039-9140(00)00462-8
35. Chong, J. Y. T.; Mulet, X.; Boyd, B. J.; Drummond, C. J. Steric Stabilizers for Cubic Phase Lyotropic Liquid Crystal Nanodispersions (Cubosomes) Adv. Planar Lipid Bilayers Liposomes 2015, 21, 131-187 10.1016/bs.adplan.2014.11.001
36. Svensson, O.; Thuresson, K.; Arnebrant, T. Interaction between Drug Delivery Particles and Mucin in Solution and at Interfaces Langmuir 2008, 24, 2573-2579 10.1021/la702680x
37. Marinova, K. G.; Alargova, R. G.; Denkov, N. D.; Velev, O. D.; Petsev, D. N.; Ivanov, I. B.; Borwankar, R. P. Charging of Oil-Water Interfaces Due to Spontaneous Adsorption of Hydroxyl Ions Langmuir 1996, 12, 2045-2051 10.1021/la950928i
38. Mutalik, S.; Shetty, P. K.; Kumar, A.; Kalra, R.; Parekh, H. S. Enhancemnt in deposition and permeation of 5-fluorouracil through human epidermis assisted by peptide denrimers Drug Delivery 2014, 21 (1) 44-54 10.3109/10717544.2013.845861
39. Boyd, B. J. Characterization of drug release from the cubosomes using the pressure ultrafiltration method Int. J. Pharm. 2003, 260, 239-247 10.1016/S0378-5173(03)00262-X
40. Privat, E. J.; Sowers, L. C. A proposed mechanism for the mutagenicity of 5-formyluracils Mutat. Res., Fundam. Mol. Mech. Mutagen. 1996, 354, 151-156 10.1016/0027-5107(96)00005-X
41. She, X.; Chen, L.; Li, C.; He, C.; He, L.; Kong, L. Functionalization of Hollow Mesopourous Silica Nanoparticles for Improved 5-FU Loading J. Nanomater. 2015, 2015, 1 10.1155/2015/872035
42. Lynch, M. L.; Ofori-Boateng, A.; Hippe, A.; Kochvar, K.; Spicer, P. T. Enhanced loading of water-soluble actives into bicontinuous cubuc phase J. Colloid Interface Sci. 2003, 260, 404-413 10.1016/S0021-9797(02)00016-4
43. Liu, Q.; Dong, Y.-D.; Hanley, T. L.; Boyd, B. J. Sensitivity of Nanostructure in Charged Cubosomes to Phase Changes Triggered by Ionic Species in Solution Langmuir 2013, 29, 14265-14273 10.1021/la402426y
44. Muir, B. W.; Zhen, G.; Gunatillake, P.; Hartley, P. G. Salt Induced Lamellar to Bicontinuous Cubic Phase Transitions in Cationic Nanoparticles J. Phys. Chem. B 2012, 116, 3551-3556 10.1021/jp300239g
45. Wang, N.; Hsu, C.; Zhu, L.; Tseng, S.; Hsu, J. P. Influence of metal oxide nanoparticles concentration on their zeta potential J. Colloid Interface Sci. 2013, 407, 22-28 10.1016/j.jcis.2013.05.058
46. Hinton, T. M.; Grusche, F.; Acharya, D.; Shukla, R.; Bansal, V.; Waddington, L. J.; Monaghan, P.; Muir, B. W. Bicontinuous cubic phase nanoparticle lipid chemistry affacts toxicity in cultured cells Toxicol. Res. 2014, 3, 11-22 10.1039/C3TX50075F
47. Kabanov, A. V.; Alakhov, V. Y. Micelles of Amphiphilic Block Copolymers As Vehicles for Drug Delivery. In Amphiphilic Block Copolymers: Self-Assembly and Applications; Alexandris, P. L., Ed.; Elsevier: New York, 2000.
48. Melik-Nubarov, N. S.; Pomaz, O. O.; Dorodnych, T. Y.; Badun, G. A.; Ksenofontov, A. L.; Schemchukova, O. B.; Arzhakov, S. A. Interaction of tumor and normal blood cells with ethylene oxide and propylene oxide block polymers FEBS Lett. 1999, 446, 194-198 10.1016/S0014-5793(99)00208-2
49. Liu, F.; Yang, J. P.; Huang, L.; Liu, D. X. Effect of non-ionic surfactants on the formation of DNA/emulsion complexes and emulsion-mediated gene transfer Pharm. Res. 1996, 13, 1642-1646 10.1023/A:1016480421204
50. Lv, H.; Zhang, S.; Wang, B.; Cui, S.; Yan, J. Toxicity of cationic lipids and cationic polymers in gene delivery J. Controlled Release 2006, 114, 100-109 10.1016/j.jconrel.2006.04.014
51. Xue, H. X.; Liu, S.; Wong, H. L. Nanotoxicity: a key obstacle to clinical translation of siRNA-based nanomedicine Nanomedicine 2014, 9 (2) 295-312 10.2217/nnm.13.204
52. Li, X.; Kong, X.; Kong, X.; Wang, Y.; Yan, S.; Yang, Q. 53BP1 Sensitizes Breast cancer Cells to 5-Fluorouracil PLoS One 2013, 8 (9) e74928 10.1371/journal.pone.0074928