Enhancement of the solubility and efficacy of poorly water-soluble drugs by hydrophobically-modified polysaccharide derivatives

Pharmaceutical Research

Volumn 24, Issue 12, 2007, Pages 2317-2326

  Henni Silhadi, Widad ^a   Deyme, Michel ^a   Boissonnade, Marie Martine ^a   Appel, Martine ^a   Le Cerf, Didier ^b   Picton, Luc ^b   Rosilio, Véronique ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b UNIVERSITÉ DE ROUEN   (France)

Author keywords

Cytotoxicity studies; Docetaxel; Hydrophobically modified carboxymethylpullulan; Solubilization; Surface tension

Indexed keywords

ALCOHOL; BENZOPHENONE; CARBOXYMETHYLPULLULAN DERIVATIVE; DOCETAXEL; POLYSACCHARIDE; POLYSORBATE 80; PULLULAN; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; COMPARATIVE STUDY; CYTOTOXICITY; DRUG EFFICACY; DRUG FORMULATION; DRUG SOLUBILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROPHOBICITY; IN VITRO STUDY; PRIORITY JOURNAL; SPECTROFLUOROMETRY; SURFACE TENSION; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BENZOPHENONES; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL SURVIVAL; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG COMPOUNDING; ETHANOL; FEMALE; GLUCANS; HUMANS; HYDROPHOBICITY; MACROPHAGES; MICE; NANOSTRUCTURES; PHOTOSENSITIZING AGENTS; POLYSORBATES; SOLUBILITY; SOLVENTS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; SURFACE TENSION; TAXOIDS; VEHICLES; WATER;

EID: 35848949987     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-007-9461-7     Document Type: Article

References (52)

1. F. Petit-Agnely, I. Illiopoulos and R. Zana. Hydrophobically modified sodium polyacrylates in aqueous solutions: association mechanism and characterization of the aggregates by fluorescence probing. Langmuir 16:9921-9927 (2000).
2. C. Lee, C.-P. Huang, and Y.-D. Lee. Preparation of amphiphilic Poly(l-lactide)-graft-Chondroitin Sulfate copolymer self-aggregates and its aggregation behavior. Biomacromolecules 7(4):1179-1186 (2006).
3. J. X. Zhang, L. Y. Qiu, Y. Jin, and K. J. Zhu. Thermally responsive polymeric micelles self-assembled by amphiphilic polyphosphazene with poly(N-isopropylacrylamide) and ethyl glycinate as side groups: polymer synthesis, characterization, and in vitro drug release study. J. Biomed. Mater. Res. A. 76(4):773-780 (2006).
4. C. Caroline, S. Kadi, M. Rinaudo, and R. Auzély-Velty. New associative systems based on alkylated hyaluronic acid. Synthesis and aqueous solution properties. Polymer 47(8):2706-2713 (2006).
5. C. Rouzes, A. Durand, M. Leonard, and E. Dellacherie. Surface activity and emulsification properties of hydrophobically modified dextrans. J. Colloid Interface Sci. 253(1):217-223 (2002).
6. S. Weiping, W. Sufen, C. Guohua, and X. Guiying. Surface and aggregate properties of an amphiphilic derivative of carboxymethylchitosan. Carbohydr. Res. 339:1113-1118 (2004).
7. S. Simon, J. Y. Dugast, D. Le Cerf, L. Picton, and G. Muller. Amphiphilic polysaccharides. Evidence for a competition between intra and intermolecular associations in dilute system. Polymer 44(26):7917-7924 (2003).
8. C. Duval, D. Le Cerf, L. Picton, and G. Muller. Aggregation of amphiphilic pullulan derivatives evidenced by on-line flow field flow fractionation/multi-angle laser light scattering. J. Chrom. B: Biomed. Sci. Appl. 753:115-122 (2001).
9. C. Esquenet, P. Terech, F. Boue, and E. Buhler. Structural and rheological properties of hydrophobically modified polysaccharide associative networks. Langmuir 20(9):3583-3592 (2004).
10. U. P. Strauss and E. G. Jackson. Polysoaps. I. Viscosity and solubilization studies on an n-dodecyl bromide addition compound of poly-2-vinylpyridine. J. Polym. Sci. 6:649-659 (1951).
11. R. Zana (Eds.). Surfactant solutions. New methods of investigation, Marcel Dekker, New York, 1987.
12. J. E. Glass (Ed). Polymers in aqueous media: performance through association. Adv. Chem. Ser. 223, Am. Chem. Soc., Washington, DC, 1989.
13. J. E. Glass (Ed). Associative polymers in aqueous solutions, ACS Symp. Ser. 765, Am. Chem. Soc., Washington, DC, 2000.
14. K. Akiyoshi, J. Sunamoto. In: S. E. Friberg and B. Lindman (eds.), Organized Solutions, Marcel Dekker, New York, 1991.
15. M. Lazzari, C. Rodriguez-Abreu, J. Rivas, and M. A. Lopez-Quintela. Self-assembly: a minimalist route to the fabrication of nanomaterials. J. Nanosci. Nanotechnol. 6:892-905 (2006).
16. I. F. Uchegbu. Pharmaceutical nanotechnology: polymeric vesicles for drug and gene delivery. Expert opin. Drug Deliv. 3(5):629-640 (2006).
17. C. L. McCormick, J. Bock, and D. N. Schultz. Water soluble polymers. In Encyclopedia of Polymer Science and Engineering 17, Wiley, New York, 1989, pp. 780-883.
18. J. E. Glass. Water soluble polymers: beauty and performance. Adv. Chem. Ser. 213, Am. Chem. Soc., Washington, DC, 1986.
19. W. Sui, S. Wang, G. Chen, and G. Xu. Surface and aggregate properties of an amphiphilic derivative of carboxymethylchitosan. Carbohydr. Res. 339(6):1113-1118 (2004).
20. W. Henni, M. Deyme, M. Stchakovsky, D. Le Cerf, L. Picton, and V. Rosilio. Aggregation of hydrophobically modified polysaccharides in solution and at the air water interface. J. Colloid Interface Sci. 281(2):316-324 (2005).
21. L. M. Landoll. Non ionic polymer surfactants. J. Polym. Sci. Polym. Chem. 20(2):443-445 (1982).
22. M. F. Francis, L. Lavoie, F. M. Winnik, and J.-C. Leroux. Solubilization of cyclosporin A in dextran-g-polyethyleneglycolalkyl ether polymeric micelles. Eur. J. Pharm. Biopharm. 56:337-346 (2003).
23. S. Weiping, Y. Changqing, C. Yanjing, Z. Zhiguo, and K. Xiangzheng. Self-assembly of an amphiphilic derivative of chitosan and micellar solubilization of puerarin. Colloids Surf. B Biointerfaces 48(1):13-16 (2006).
24. W. Liu, S. J. Sun, X. Zhang, and K. D. Yao. Self-aggregation behavior of alkylated chitosan and its effect on the release of a hydrophobic drug. J. Biomater. Sci. Polym. Ed. 14(8):851-859 (2003).
25. C. Zhang, P. Qineng, and H. Zhang. Self-assembly and characterization of paclitaxel-loaded N-octyl-O-sulfate chitosan micellar system. Colloids and Surf. B: Biointerfaces 39:69-75 (2004).
26. M. Leonard, M. R. De Boisseson, P. Hubert, F. Dalençon, and E. Dellacherie. Hydrophobically modified alginate hydrogels as protein carriers with specific controlled release. J. Control. Release 98(3):395-405 (2004).
27. K. Akiyoshi, S. Kobayashi, S. Shichibe, D. Mix, M. Baudys, S. Wan Kimb, and J. Sunamoto. Self-assembled hydrogel nanoparticle of cholesterol-bearing pullulan as a carrier of protein drugs: complexation and stabilization of insulin. J. Control. Release 54:313-320 (1998).
28. K. Akiyoshi, S. Deguchi, N. Moriguchi, S. Yamaguchi, and J. Sunamoto. Self-aggregates of hydrophobized polysaccharides in water. Formation and characteristics of nanoparticles. Macromolecules 26:3062-3068 (1993).
29. M. L. Immordino, P. Brusa, S. Arpicco, B. Stella, F. Dosio, and L. Cattel. Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing docetaxel. J. Control. Release 91(3):417-429 (2003).
30. R. Vasu Dev, J. Moses Babu, K. Vyas, P. Sai Ram, P. Ramachandra, N. M. Sekhar, D. N. Mohan Reddy, and N. Srinivasa Rao. Isolation and characterization of impurities in docetaxel. J. Pharm. Biomed. Anal. 40(3):614-622 (2006).
31. K. Kalyanansundaram and J. K. Thomas. Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J. Am. Chem. Soc. 99:2039-2044 (1977).
32. T. Mosmann. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65:55-63 (1983).
33. M. B. Hansen, S. E. Nielsen, and K. Berg. Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill. J. Immunol. Methods 119(2):203-210 (1989).
34. Sanofi Aventis. Taxotere® (docetaxel). http://www.taxotere.com/ professional/about/preparation.do (accessed 02/20/07).
35. A. Neide, B. Vieira, J. Ruggiero Neto, and M. J. Tiera. Synthesis, characterization and solution properties of amphiphilic N-isopropylacrylamide- poly(ethylene glycol)-dodecyl methacrylate thermosensitive polymers. Colloids Surf. A: Physicochem. and Engineering Aspects 262(1-3):251-259 (2005).
36. S. Gautier, M. Boustta, and M. Vert. Alkylated poly (l-lysine citramide) as models to investigate the ability of amphiphilic macromolecular drug carriers to physically entrap lipophilic compounds in aqueous media. J. Control. Release 60(2-3):235-245 (1999).
37. F. Baßmann-Schnitzler and J. M. Séquaris. Sorption properties of hydrophobically modified poly(acrylic acids) as natural organic matter model substances to pyrene. Colloids Surf. A: Physicochem. and Engineering Aspects 260(1-3):119-128 (2005).
38. L. Jongpaiboonkit, Z. Zhou, X. Ni, Y. Z. Wang, and J. Li. Self association and micelle formation of biodegradable poly(ethylene glycol)-poly(l-lactic acid) amphiphilic block co-polymers. J. Biomater. Sci. Polym. Ed. 17(7):747-763 (2006).
39. S. Daoud-Mahammed, C. Ringard-Lefebvre, N. Razzouq, V. Rosilio, B. Gillet, P. Couvreur, C. Amiel, and R. Gref. Spontaneous association of hydrophobized dextran and poly-β-cyclodextrin into nanoassemblies. Formation and interaction with a hydrophobic drug. J. Colloid and Interface Sci. 307(1):83-93 (2007).
40. W. J. Lin, L.-W. Juang, and C.-C. Lin. Stability and release performance of a series of pegylated copolymeric micelles. Pharm. Res. 20:668-673 (2003).
41. R. S. Herbst and R. F. Khuri. Mode of action of docetaxel a basis for combination with novel anticancer agents. Cancer Treat. Rev. 29(5):407-415 (2003).
42. H. Gelderblom, J. Verweij, K. Nooter, and A. Sparreboom. Cremophor EL: the drawbacks and advantages of vehicle selection for drug formulation. Eur. J. Cancer. 37:1590-1598 (2001).
43. S. D. Baker, M. Zhao, P. He, M. A. Carducci, J. Verweij, and A. Sparreboom. Simultaneous analysis of docetaxel and the formulation vehicle polysorbate 80 in human plasma by liquid chromatography/tandem mass spectrometry. Anal. Biochem. 324:276-284 (2004).
44. R. M. Straubinger and S. V. Balasubramanian. Preparation and characterization of taxane-containing liposomes. Methods in Enzymol. 391:97-117 (2005).
45. T. Musumeci, C. A. Ventura, I. Giannone, B. Ruozi, L. Montenegro, R. Pignatello, and G. Puglisi. PLA/PLGA nanoparticles for sustained release of docetaxel. Intern. J. Pharmaceutics 325(1-2):172-179 (2006).
46. A. Benahmed, M. Ranger, and J. C. Leroux. Novel polymeric micelles based on the amphiphilic diblock copolymer poly(N-vinyl-2-pyrrolidone)-block-poly(d,l- lactide). Pharm. Res. 18(3):323-328 (2001).
47. V. C. F. Mosqueira, P. Legrand, R. Gref, B. Heurtault, M. Appel, and G. Barrat. Interactions between a macrophage cell line (J774.A1) and surface-modified poly (d,l-lactide) nanocapsules bearing poly(ethylene glycol). J. Drug Targeting 7(1):65-78 (1999).
48. F. Chellat, Y. Merhi, A. Moreau, and L.Yahia. Therapeutic potential of nanoparticulate systems for macrophage targeting. Biomaterials 26(35):7260-7275 (2005).
49. C. Lemarchand, R. Gref, C. Passirani, E. Garcion, B. Petri, R. Müller, D. Costantini, and P. Couvreur. Influence of polysaccharide coating on the interactions of nanoparticles with biological systems. Biomaterials 27:1108-118 (2006).
50. S. Cheon Lee, C. Kim, I. Chan Kwon, H. Chung, and S. Young Jeong. Polymeric micelles of poly(2-ethyl-2-oxazoline)-block-poly(ε-caprolactone) copolymer as a carrier for paclitaxel. J. Control. Release 89(3):437-446 (2003).
51. S. Drori, G. D. Eytan, and Y. G. Assaraf. Potentiation of anticancer drug cytotoxicity by multidrug-resistance chemosensitizers involves alterations in membrane fluidity leading to increased membrane permeability. Eur. J. Biochem. 228:1020-1029 (1995).
52. C. G. Crispens and J. R. Sorenson. Treatment of reticulum cell sarcoma in SJL/J mice with Tween 80®. Anticancer Res. 8:1341-1343 (1988).