Lamellar liquid crystalline phases for cutaneous delivery of paclitaxel: Impact of the monoglyceride

Pharmaceutical Research

Volumn 30, Issue 3, 2013, Pages 694-706

  Hosmer, Jaclyn M ^a   Steiner, Alexandre A ^a,b   Lopes, Luciana B ^a  

^a ALBANY COLLEGE OF PHARMACY AND HEALTH SCIENCES   (United States)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

cutaneous delivery; lamellar phase; monoglycerides; paclitaxel; skin

Indexed keywords

GLYCEROL OLEATE; INTERLEUKIN 1ALPHA; MONOACYLGLYCEROL; MONOMYRISTOLEIN; OCTANOIN; PACLITAXEL; POLYMER; POLYOXYTHELENE 10 OLEOYL ETHER; TRITON X 100; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHEMICAL PARAMETERS; CONTROLLED STUDY; CYTOKINE RELEASE; DRUG DELIVERY SYSTEM; DRUG DISTRIBUTION; DRUG DOSAGE FORM COMPARISON; DRUG FORMULATION; DRUG PENETRATION; DRUG RELEASE; DRUG SOLUBILITY; DRUG TOLERABILITY; ELECTRIC RESISTANCE; IN VITRO STUDY; IN VIVO STUDY; LAMELLAR LIQUID CRYSTALLINE PHASE; MALE; MONOGLYCERIDE ACYL CHAIN LENGTH; NONHUMAN; PHYSICAL PHASE; PRIORITY JOURNAL; RAT; SKIN IRRITATION; SKIN PENETRATION; SWINE;

ADMINISTRATION, CUTANEOUS; ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CAPRYLATES; DRUG CARRIERS; GLYCERIDES; LIQUID CRYSTALS; MALE; MONOGLYCERIDES; PACLITAXEL; PHASE TRANSITION; RATS; SKIN; SKIN ABSORPTION; SKIN IRRITANCY TESTS; SWINE;

EID: 84878875488     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-012-0908-0     Document Type: Article

References (64)

1. Barcelo R, Viteri A, Munoz A, Gil-Negrete A, Rubio I, Lopez-Vivanco G. Paclitaxel for progressive basal cell carcinoma. J Am Acad Dermatol. 2006;54(2 Suppl):S50-2.
2. Cheung MC, Pantanowitz L, Dezube BJ. AIDS-related malignancies: emerging challenges in the era of highly active antiretroviral therapy. Oncologist. 2005;10(6):412-26.
3. Antman K, Chang Y. Kaposi's sarcoma. N Engl J Med. 2000;342(14):1027-38.
4. Ganesh T. Improved biochemical strategies for targeted delivery of taxoids. Bioorg Med Chem. 2007;15(11):3597-623.
5. Ferguson T, Wilcken N, Vagg R, Ghersi D, Nowak AK. Taxanes for adjuvant treatment of early breast cancer. Cochrane Database Syst Rev. 2007;4:CD004421.
6. Utreja P, Jain S, Tiwary AK. Localized delivery of paclitaxel using elastic liposomes: formulation development and evaluation. Drug Deliv. 2011;18(5):367-76.
7. Khandavilli S, Panchagnula R. Nanoemulsions as versatile formulations for paclitaxel delivery: peroral and dermal delivery studies in rats. J Invest Dermatol. 2007;127(1):154-62.
8. Panchagnula R, Desu H, Jain A, Khandavilli S. Feasibility studies of dermal delivery of paclitaxel with binary combinations of ethanol and isopropyl myristate: role of solubility, partitioning and lipid bilayer perturbation. Farmaco. 2005;60(11-12):894-9.
9. Paolino D, Celia C, Trapasso E, Cilurzo F, Fresta M. Paclitaxel-loaded ethosomes(R): potential treatment of squamous cell carcinoma, a malignant transformation of actinic keratoses. Eur J Pharm Biopharm. 2012;81(1):102-12.
10. Hosmer JM, Shin SH, Nornoo A, Zheng H, Lopes LB. Influence of internal structure and composition of liquid crystalline phases on topical delivery of paclitaxel. J Pharm Sci. 2011;100(4):1444-55.
11. Nesseem DI. Formulation and evaluation of itraconazole via liquid crystal for topical delivery system. J Pharm Biomed Anal. 2001;26(3):387-99.
12. Ganem-Quintanar A, Quintanar-Guerrero D, Buri P. Monoolein: a review of the pharmaceutical applications. Drug Dev Ind Pharm. 2000;26(8):809-20.
13. Sadhale Y, Shah JC. Stabilization of insulin against agitation-induced aggregation by the GMO cubic phase gel. Int J Pharm. 1999;191(1):51-64.
14. Muller-Goymann CC. Physicochemical characterization of colloidal drug delivery systems such as reverse micelles, vesicles, liquid crystals and nanoparticles for topical administration. Eur J Pharm Biopharm. 2004;58(2):343-56.
15. Savic S, Weber C, Savic MM, Muller-Goymann C. Natural surfactant-based topical vehicles for two model drugs: influence of different lipophilic excipients on in vitro/in vivo skin performance. Int J Pharm. 2009;381(2):220-30.
16. Lopes LB, VanDeWall H, Li HT, Venugopal V, Li HK, Naydin S, Hosmer J, Levendusky M, Zheng H, Bentley MV, Levin R, Hass MA. Topical delivery of lycopene using microemulsions: enhanced skin penetration and tissue antioxidant activity. J Pharm Sci. 2010;99(3):1346-57.
17. Furuishi T, Oda S, Saito H, Fukami T, Suzuki T, Tomono K. Effect of permeation enhancers on the in vitro percutaneous absorption of pentazocine. Biol Pharm Bull. 2007;30(7):1350-3.
18. Shah JC, Sadhale Y, Chilukuri DM. Cubic phase gels as drug delivery systems. Adv Drug Deliv Rev. 2001;47(2-3):229-50.
19. Makai M, Csanyi E, Nemeth Z, Palinkas J, Eros I. Structure and drug release of lamellar liquid crystals containing glycerol. Int J Pharm. 2003;256(1-2):95-107.
20. Lopes LB, Murphy N, Nornoo A. Enhancement of transdermal delivery of progesterone using medium-chain mono and diglycerides as skin penetration enhancers. Pharm Dev Technol. 2009;14(5):524-9.
21. Ivens UI, Steinkjer B, Serup J, Tetens V. Ointment is evenly spread on the skin, in contrast to creams and solutions. Br J Dermatol. 2001;145(2):264-7.
22. Mahdi ES, Noor AM, Sakeena MH, Abdullah GZ, Abdulkarim MF, Sattar MA. Formulation and in vitro release evaluation of newly synthesized palm kernel oil esters-based nanoemulsion delivery system for 30% ethanolic dried extract derived from local Phyllanthus urinaria for skin antiaging. Int J Nanomedicine. 2011;6:2499-512.
23. Liang L, Lin SW, Dai W, Lu JK, Yang TY, Xiang Y, Zhang Y, Li RT, Zhang Q. Novel cathepsin B-sensitive paclitaxel conjugate: higher water solubility, better efficacy and lower toxicity. J Contr Release. 2012;160(3):618-29.
24. Rachakonda VK, Yerramsetty KM, Madihally SV, Robinson Jr RL, Gasem KA. Screening of chemical penetration enhancers for transdermal drug delivery using electrical resistance of skin. Pharm Res. 2008;25(11):2697-704.
25. Davies DJ, Ward RJ, Heylings JR. Multi-species assessment of electrical resistance as a skin integrity marker for in vitro percutaneous absorption studies. Toxicol In Vitro. 2004;18(3):351-8.
26. Heylings JR, Clowes HM, Hughes L. Comparison of tissue sources for the skin integrity function test (SIFT). Toxicol In Vitro. 2001;15(4-5):597-600.
27. Pollack, GH. Cells, gels and the engines of life: a new, unifying approach to cell biology. Ebner and Sons; 2001.
28. Serban MA, Liu Y, Prestwich GD. Effects of extracellular matrix analogues on primary human fibroblast behavior. Acta Biomater. 2008;4(1):67-75.
29. Lee CM, Maibach HI. Deep percutaneous penetration into muscles and joints. J Pharm Sci. 2006;95(7):1405-13.
30. Nornoo AO, Zheng H, Lopes LB, Johnson-Restrepo B, Kannan K, Reed R. Oral microemulsions of paclitaxel: in situ and pharmacokinetic studies. Eur J Pharm Biopharm. 2009;71(2):310-7.
31. Verhulst C, Coiffard C, Coiffard LJ, Rivalland P, De Roeck-Holtzhauer Y. In vitro correlation between two colorimetric assays and the pyruvic acid consumption by fibroblasts cultured to determine the sodium laurylsulfate cytotoxicity. J Pharmacol Toxicol Methods. 1998;39(3):143-6.
32. Bagley DM, Gardner JR, Holland G, Lewis RW, Vrijhof H, Walker AP. Eye irritation: updated reference chemicals data bank. Toxicol In Vitro. 1999;13(3):505-10.
33. Kandárová, H, Hayden, P, Klausner, M, Kubilus, J, Sheasgreen, J. An in vitro Skin Irritation Test (SIT) using the EpiDerm Reconstructed Human Epidermal (RHE) Model. JoVE. 2009;29. http://www.jove.com/ index/Details.stp?ID=1366, doi: 10.3791/1366.
34. Roguet R. Use of skin cell cultures for in vitro assessment of corrosion and cutaneous irritancy. Cell Biol Toxicol. 1999;15(1):63-75.
35. Welss T, Basketter DA, Schroder KR. In vitro skin irritation: facts and future. State of the art review of mechanisms and models. Toxicol In Vitro. 2004;18(3):231-43.
36. Carvalho FC, Sarmento VH, Chiavacci LA, Barbi MS, Gremiao MP. Development and in vitro evaluation of surfactant systems for controlled release of zidovudine. J Pharm Sci. 2010;99(5):2367-74.
37. Diat O, Roux D, Nallet F. Effect of shear on a lyotropic lamellar phase. J Phys II. 1993;3:1427-52.
38. de Silva JP, Poulos AS, Pansu B, Davidson P, Kasmi B, Petermann D, Asnacios S, Meneau F, Imperor M. Rheological behaviour of polyoxometalate-doped lyotropic lamellar phases. Eur Phys J E Soft Matter. 2011;34(1):1-9.
39. Venuganti VVK, Perumal OP. Poly(amidoamine) dendrimers as skin penetration enhancers: influence of charge, generation, and concentration. J Pharm Sci. 2009;98(7):2345-56.
40. Wang Z, Diao Z, Liu F, Li G, Zhang G. Microstructure and rheological properties of liquid crystallines formed in Brij 97/water/IPM system. J Colloid Interface Sci. 2006;297(2):813-8.
41. Caboi F, Amico GS, Pitzalis P, Monduzzi M, Nylander T, Larsson K. Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior. Chem Phys Lipids. 2001;109(1):47-62.
42. Otto A, du Plessis J, Wiechers JW. Formulation effects of topical emulsions on transdermal and dermal delivery. Int J Cosmet Sci. 2009;31(1):1-19.
43. Amar-Yuli I, Garti N. Transitions induced by solubilized fat into reverse hexagonal mesophases. Colloids Surf B Biointerfaces. 2005;43(2):72-82.
44. Briggs J, Caffrey M. The temperature-composition phase diagram of monomyristolein in water: equilibrium and metastability aspects. Biophys J. 1994;66(3 Pt 1):573-87.
45. Larsson K. Cubic lipid-water phases: structures and biomembrane aspects. J Phys Chem. 1989;93(21):7304-14.
46. Pepe D, Phelps J, Lewis K, Dujack J, Scarlett K, Jahan S, Bonnier E, Milic-Pasetto T, Hass MA, Lopes LB. Decylglucoside-based microemulsions for cutaneous localization of lycopene and ascorbic acid. Int J Pharm. 2012;434(1-2):420-8.
47. Kaushik D, Costache A, Michniak-Kohn B. Percutaneous penetration modifiers and formulation effects. Int J Pharm. 2010;386(1-2):42-51.
48. Lopes LB, Lopes JL, Oliveira DC, Thomazini JA, Garcia MT, Fantini MC, Collett JH, Bentley MV. Liquid crystalline phases of monoolein and water for topical delivery of cyclosporin A: characterization and study of in vitro and in vivo delivery. Eur J Pharm Biopharm. 2006;63(2):146-55.
49. Kilfoyle, BE, Sheihet, L, Zhang, Z, Laohoo, M, Kohn, J, Michniak-Kohn, BB. Development of paclitaxel-TyroSpheres for topical skin treatment. J Contr Release. 2012;163(1):18-24.
50. Jensen LB, Magnussson E, Gunnarsson L, Vermehren C, Nielsen HM, Petersson K. Corticosteroid solubility and lipid polarity control release from solid lipid nanoparticles. Int J Pharm. 2010;390(1):53-60.
51. Peh KK, Wong CF, Yuen KH. Possible mechanism for drug retardation from glyceryl monostearate matrix system. Drug Dev Ind Pharm. 2000;26(4):447-50.
52. Hosmer J, Reed R, Bentley MV, Nornoo A, Lopes LB. Microemulsions containing medium-chain glycerides as transdermal delivery systems for hydrophilic and hydrophobic drugs. AAPS PharmSciTech. 2009;10(2):589-96.
53. Holler S, Valenta C. Effect of selected fluorinated drugs in a "ringing" gel on rheological behaviour and skin permeation. Eur J Pharm Biopharm. 2007;66(1):120-6.
54. Aytekin M, Gursoy RN, Ide S, Soylu EH, Hekimoglu S. Formulation and characterization of liquid crystal systems containing azelaic acid for topical delivery. Drug Dev Ind Pharm. 2012. doi: 10.3109/03639045.2012.671829.
55. Moser K, Kriwet K, Naik A, Kalia YN, Guy RH. Passive skin penetration enhancement and its quantification in vitro. Eur J Pharm Biopharm. 2001;52(2):103-12.
56. Reifenrath WG, Hawkins GS, Kurtz MS. Percutaneous penetration and skin retention of topically applied compounds: an in vitro-in vivo study. J Pharm Sci. 1991;80(6):526-32.
57. Matsuda S, Hisama M, Shibayama H, Itou N, Iwaki M. In vitro eye irritancy test of lauryl derivatives and polyoxyethylene alkyl derivatives with the reconstructed rabbit corneal epithelium model. J Oleo Sci. 2009;58(8):437-42.
58. Faller C, Bracher M, Dami N, Roguet R. Predictive ability of reconstructed human epidermis equivalents for the assessment of skin irritation of cosmetics. Toxicol In Vitro. 2002;16(5):557-72.
59. Vian L, Vincent J, Maurin J, Fabre I, Giroux J, Cano JP. Comparison of three in vitro cytotoxicity assays for estimating surfactant ocular irritation. Toxicol In Vitro. 1995;9(2):185-90.
60. Kapoor Y, Howell BA, Chauhan A. Liposome assay for evaluating ocular toxicity of surfactants. Invest Ophthalmol Vis Sci. 2009;50(6):2727-35.
61. Hait SK, Moulik SP. Determination of critical micelle concentration (CMC) of nonionic surfactants by donor-acceptor interaction with lodine and correlation of CMC with hydrophile-lipophile balance and other parameters of the surfactants. J Surfactants Deterg. 2001;4(3):303-9.
62. Ayehunie S, Cannon C, Lamore S, Kubilus J, Anderson DJ, Pudney J, Klausner M. Organotypic human vaginal-ectocervical tissue model for irritation studies of spermicides, microbicides, and feminine-care products. Toxicol In Vitro. 2006;20(5):689-98.
63. Yeh PY, Smith PL, Ellens H. Effect of medium-chain glycerides on physiological properties of rabbit intestinal epithelium in vitro. Pharm Res. 1994;11(8):1148-54.
64. Constantinides PP, Scalart JP, Lancaster C, Marcello J, Marks G, Ellens H, Smith PL. Formulation and intestinal absorption enhancement evaluation of water-in-oil microemulsions incorporating medium-chain glycerides. Pharm Res. 1994;11(10):1385-90.