An oil-free microemulsion for intravenous delivery of diallyl trisulfide: Formulation and evaluation

International Journal of Pharmaceutics

Volumn 407, Issue 1-2, 2011, Pages 158-166

  Li, Xinru ^a   Yue, Yuanting ^a   Zhou, Yanxia ^a   Fan, Yating ^a   Fan, Chao ^a   Huang, Yanqing ^a   Wu, Fei ^a   Liu, Yan ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

Diallyl trisulfide; Microemulsion; Pharmacokinetics; Safety

Indexed keywords

ALCOHOL; CHENTIAN; CREMOPHOR; DIALLYL TRISULFIDE; PROPYLENE GLYCOL; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

ANAPHYLAXIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG EFFICACY; DRUG FORMULATION; DRUG SAFETY; DRUG SCREENING; FEMALE; GUINEA PIG; HEMOLYSIS; LD 50; MALE; MICROEMULSION; MOUSE; NONHUMAN; PLASMA CONCENTRATION-TIME CURVE; PRIORITY JOURNAL; RABBIT; RAT; TOXICITY TESTING;

ALLYL COMPOUNDS; ANAPHYLAXIS; ANIMALS; ANTIOXIDANTS; AREA UNDER CURVE; EMULSIONS; ETHANOL; EXCIPIENTS; FEMALE; GLYCEROL; GUINEA PIGS; INJECTIONS, INTRAVENOUS; LETHAL DOSE 50; MALE; MICE; PARTICLE SIZE; PROPYLENE GLYCOL; RABBITS; RATS; RATS, SPRAGUE-DAWLEY; SODIUM CHLORIDE; SULFIDES; TIME FACTORS; TISSUE DISTRIBUTION;

EID: 79952312739     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2011.01.008     Document Type: Article

References (50)

1. Bjerregaard, S., Wulf-Andersen, L., Stephens, R.W., Lund, L.R., Vermehren, C., Söderberg, I., Frokjaer, S., 2001. Sustained elevated plasma aprotinin concentration in mice following intraperitoneal injections of w/o emulsions incorporating aprotinin. J. Control. Release 71, 87-98. (Pubitemid 32195443)
2. Chan, K.C., Hsu, C.C., Yin, M.C., 2003. Protective effect of three diallyl sulfides against glucose induced erythrocyte and platelet oxidation, and ADP-induced platelet aggregation. Thromb. Res. 108, 317-322.
3. Chiang, Y.H., Jen, L.N., Su, H.Y., Lii, C.K., Sheen, L.Y., Liu, C.T., 2006. Effects of garlic oil and two of its major organosulfur compounds, diallyl disulfide and diallyl trisulfide, on intestinal damage in rats injected with endotoxin. Toxicol. Appl. Pharmacol. 213, 46-54.
4. Darole, P.S., Hegde, D.D., Nair, H.A., 2008. Formulation and evaluation of microemulsion based delivery system for amphotericin B. AAPS PharmSciTech 9, 122-128.
5. Davis, S.R., 2005. An overview of the antifungal properties of allicin and its breakdown products-the possibility of a safe and effective antifungal prophylactic. Mycoses 48, 95-100. (Pubitemid 40395476)
6. Eisenhauer, E.A., ten Bokkel Huinink, W.W., Swenerton, K.D., 1994. European-Canadian randomized trial of paclitaxel in relapsed ovarian cancer: high dose versus low-dose and long versus short infusion. J. Clin. Oncol. 12, 2654-2666.
7. El Maghraby, G.M., 2010. Self-microemulsifying and microemulsion systems for transdermal delivery of indomethacin: effect of phase transition. Colloids Surf. B: Biointerfaces 75, 595-600.
8. Gan, L., Gan, Y., Zhu, C., Zhang, X., Zhu, J., 2009. Novel microemulsion in situ electrolyte-triggered gelling system for ophthalmic delivery of lipophilic cyclosporine A: in vitro and in vivo results. Int. J. Pharm. 365, 143-149.
9. Gelderblom, H., Verweij, J., Nooter, K., Sparreboom, A., 2001. Cremophor EL: the drawbacks and advantages of vehicle selection for drug formulation. Eur. J. Cancer 37, 1590-1598. (Pubitemid 32778603)
10. Gradzielski, M., 1998. Effect of the cosurfactant structure on the bending elasticity in nonionic oil-in-water microemulsions. Langmuir 14, 6037-6044. (Pubitemid 128612926)
11. Guo, T., Chu, X.Q., He, J., Sun, X.H., Song, H.T., Deng, Y.H., 2005. Investigation on stabilities of garlic oil submicron emulsions. Pharm. J. Chin. PLA 21, 81-85.
12. Herman-Antosiewicz, A., Stan, S.D., Hahm, E.R., Xiao, D., Singh, S.V., 2007. Activation of a novel ataxia-telangiectasia mutated and Rad3 related/checkpoint kinase 1-dependent prometaphase checkpoint in cancer cells by diallyl trisulfide, a promising cancer chemopreventive constituent of processed garlic. Mol. Cancer Ther. 6, 1249-1261.
13. Hirunpanich, V., Sato, H., 2009. Improvement of cyclosporine A bioavailability by incorporating ethyl docosahexaenoate in the microemulsion as an oil excipient. Eur. J. Pharm. Biopharm. 73, 247-252.
14. Hong, Y.S., Ham, Y.A., Choi, J.H., Kim, J., 2000. Effects of allyl sulfur compounds and garlic extract on the expression of Bcl-2, Bax, and p53 in non small cell lung cancer cell lines. Exp. Mol. Med. 32, 127-134.
15. Kawakami, K., Yoshikawa, T., Moroto, Y., Kanaoka, E., Takahashi, K., Nishihara, Y., Masuda, K., 2002. Microemulsion formulation for enhanced absorption of poorly soluble drugs: I. Prescription design. J. Control. Release 81, 65-74. (Pubitemid 34454850)
16. Kiepert, S., 1989. Microemulsions and the potential pharmaceutical use. Die Pharmazie 44, 433-444.
17. Kim, Y.A., Xiao, D., Xiao, H., Powolny, A.A., Lew, K.L., Reilly, M.L., Zeng, Y., Wang, Z., Singh, S.V., 2007. Mitochondria mediated apoptosis by diallyl trisulfide in human prostate cancer cells is associated with generation of reactive oxygen species and regulated by Bax/Bak. Mol. Cancer Ther. 6, 1599-1609.
18. Lawrence, M.J., Rees, G.D., 2000. Microemulsion-based media as novel drug delivery systems. Adv. Drug Deliv. Rev. 45, 89-121.
19. Li, L., Nandi, I., Kim, K.H., 2002. Development of an ethyl laurate-based microemulsion for rapid-onset intranasal delivery of diazepam. Int. J. Pharm. 237, 77-85.
20. Liu, C.T., Hse, H., Lii, C.K., Chen, P.S., Sheen, L.Y., 2005. Effects of garlic oil and diallyl trisulfide on glycemic control in diabetic rats. Eur. J. Pharmacol. 516, 165-173.
21. Lovell, M.W., Johnson, H.W., Hui, H.W., Cannon, J.B., Gupta, P.K., Hsu, C.C., 1994. Less-painful emulsion formulations for intravenous administration of clarithromycin. Int. J. Pharm. 109, 45-57.
22. Lu, Y., Wang, Y.J., Tang, X., 2008. Formulation and thermal sterile stability of a less painful intravenous clarithromycin emulsion containing vitamin E. Int. J. Pharm. 346, 47-56.
23. Milner, J.A., 2001. Mechanisms by which garlic and allyl sulfur compounds suppress carcinogen bioactivation. Garlic and carcinogenesis. Adv. Exp. Med. Biol. 492, 69-81.
24. Mousa, A.S., Mousa, S.A., 2007. Cellular effects of garlic supplements and antioxidant vitamins in lowering marginally high blood pressure in humans: pilot study. Nutr. Res. 27, 119-123.
25. Nornoo, A.O., Osborne, D.W., Chow, D.S.L., 2008. Cremophor-free intravenous microemulsions for paclitaxel. I. Formulation, cytotoxicity and hemolysis. Int. J. Pharm. 349, 108-116.
26. Predmore, B.L., Grinsfelder, D.B., Aragon, J.P., Elston, M., Calvert, J.W., Lefer, D.J., 2010. The stable hydrogen sulfide donor, diallyl trisulfide, protects against acute myocardial infarction in mice. J. Am. Coll. Cardiol. 55, A116.E1089.
27. Qi, M.L., Gao, J., Shao, Q.L., 2004. Preparation of allic in-β-cyclodextrin inclusion complex and determination of allicin by gas chromatography. Trans. Beijing Inst. Technol. 24, 650-652.
28. Rowinsky, E.K., Eisenhauer, E.A., Chaudhry, V., Chaudrhy, V., Arbuck, S.G., 1993. Clinical toxicities encountered with paclitaxel (Taxol). Semin Oncol. 20, 1-15. (Pubitemid 23239390)
29. Shi, S., Chen, H., Lin, X., Tang, X., 2010. Pharmacokinetics, tissue distribution and safety of cinnarizine delivered in lipid emulsion. Int. J. Pharm. 383, 264-270.
30. Shukla, Y., Kalra, N., 2007. Cancer chemoprevention with garlic and its constituents. Cancer Lett. 247, 167-181. (Pubitemid 46240620)
31. Singh, S.V., Powolny, A.A., Stan, S.D., Xiao, D., Arlotti, J.A., Warin, R., Hahm, E.R., Marynowski, S.W., Bommareddy, A., Potter, D.M., Dhir, R., 2008. Garlic constituent diallyl trisulfide prevents development of poorly differentiated prostate cancer and pulmonary metastasis multiplicity in TRAMP mice. Cancer Res. 68, 9503-9511.
32. Steiner, M., Khan, A.H., Holbert, D., Lin, R.I.S., 1996. A double-blind crossover study in moderately hypercholesterolemic men that compared the effect of aged garlic extract and placebo administration on blood lipids.Am.J. Clin. Nutr. 64, 866-870.
33. Stoll, A., Seebeck, E., 1951. Chemical investigation on alliin, the specific principle of garlic. Adv. Enzymol. 11, 377-400.
34. Sun, P., Yu, W.P., Duan, Y.X., 2005. Advance of antitumer of extraction of Allium sativum. Qilu Pharm. Affairs 24, 159-161.
35. Sun, P., Deng, S.H., Yu, W.P., 2006. Preparation of long circulation allitridin PEG-liposomes and its pharmacokinetics. Pract. J. Card. Cerebral Pneumal Vasc. Dis. 14, 454-456.
36. Tsai, Y.H., Lee, K.F., Huang, Y.B., Huang, C.T., Wu, P.C., 2010. In vitro permeation and in vivo whitening effect of topical hesperetin microemulsion delivery system. Int. J. Pharm. 388, 257-262.
37. van Zuylen, L., Gianni, L., Verweij, J., 2000. Interrelationships of paclitaxel disposition, infusion duration and Cremophor EL kinetics in cancer patients. Anticancer Drugs 11, 331-337. (Pubitemid 30459468)
38. Wang, Y., Mesfin, G.M., Rodriguez, C.A., Slatter, J.G., Schuette, M.R., Cory, A.L., Higgins, M.J., 1999. Venous irritation, pharmacokinetics, and tissue distribution of tirilazad in rats following intravenous administration of a novel supersaturated submicron lipid emulsion. Pharm. Res. 16, 930-938.
39. Wang, Y., Liu, Y., Shi, Z.X., Hu, X., 2005. Preparation of allitridum liposome and its quality evaluation. J. China-Japan Friendship Hosp. 19, 161-163.
40. Wang, Z.H., 1988. Determination of plasma concentration, biodistribution and bioavailability of Allicin in rabbits by gas chromatographic method. Chin. Tradit. Herbal Drugs 19, 12-14.
41. Weiss, R.B., Donehower, R.C., Wiernik, P.H., 1990. Hypersensitivity reactions from Taxol. J. Clin. Oncol. 8, 1263-1268.
42. Wu, C.C., Sheen, L.Y., Chen, H.W., Tsai, S.J., Lii, C.K., 2001. Effects of organosulfur compounds from garlic oil on the antioxidation system in rat liver and red blood cells. Food Chem. Toxicol. 39, 563-569.
43. Xiao, D., Choi, S., Johnson, D.E., Vogel, V.G., Johnson, C.S., Trump, D.L., Lee, Y.J., Singh, S.V., 2004. Diallyl trisulfide-induced apoptosis in human prostate cancer cells involves c-Jun N terminal kinase and extracellular-signal regulated kinase mediated phosphorylation of Bcl-2. Oncogene 23, 5594-5606. (Pubitemid 39093037)
44. Xiao, D., Li, M., Herman-Antosiewicz, A., Antosiewicz, J., Xiao, H., Lew, K.L., Zeng, Y., Marynowski, S.W., Singh, S.V., 2006. Diallyl trisulfide inhibits angiogenic features of human umbilical vein endothelial cells by causing Akt inactivation and down-regulation of VEGF and VEGF-R2. Nutr. Cancer 55, 94-107. (Pubitemid 44477050)
45. Xiao, D., Zeng, Y., Hahm, E.R., Kim, Y.A., Ramalingam, S., Singh, S.V., 2009. Diallyl trisulfide selectively causes Bax- and Bak-mediated apoptosis in human lung cancer cells. Environ. Mol. Mutagen. 50, 201-212.
46. Yin, Y.M., Cui, F.D., Mu, C.F., Choi, M.K., Kim, J.S., Chung, S.J., Shim, C.K., Kim, D.D., 2009. Docetaxel microemulsion for enhanced oral bioavailability: preparation and in vitro and in vivo evaluation. J. Control. Release 140, 86-94.
47. Zeng, T., Zhang, C.L., Zhu, Z.P., Yu, L.H., Zhao, X.L., Xie, K.Q., 2008. Diallyl trisulfide (DATS) effectively attenuated oxidative stress-mediated liver injury and hepatic mitochondrial dysfunction in acute ethanol-exposed mice. Toxicology 252, 86-91.
48. Zhang, Q.Z., Jiang, X.G., Jiang, W.M., Lu, W., Su, L.N., Shi, Z.Q., 2004. Preparation of nimodipine-loaded microemulsion for intranasal delivery and evaluation on the targeting efficiency to the brain. Int. J. Pharm. 275, 85-96.
49. Zhen, H., Fang, F., Ye, D.Y., Shu, S.N., Zhou, Y.F., Dong, Y.S., Nie, X.C., Li, G., 2006. Experimental study on the action of allitridin against human cytomegalovirus in vitro: inhibitory effects on immediate-early genes. Antiviral Res. 72, 68-74. (Pubitemid 44308445)
50. Zhu, S.Y., Qian, F., Zhang, Y., Tang, C., Yin, C.H., 2007. Synthesis and characterization of PEG modified N-trimethylaminoethylmethacrylate chitosan nanoparticles. Eur. Polym. J. 43, 2244-2253.