Preparation of the Dexamethasone-incorporated Lipid Nanosphere: Characteristics of Lipid Nanosphere by Varying Species and Ratio of Lipid
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1 Journal of the Korean Chemical Society 2006, Vol. 50, No. 6 Printed in the Republic of Korea k ù : w y ù p x*á Á w Á w yw q ( ) Preparation of the Dexamethasone-incorporated Lipid Nanosphere: Characteristics of Lipid Nanosphere by Varying Species and Ratio of Lipid Suk Hyun Jung*, Jung Eun Lee, Hasoo Seong, Byung Cheol Shin Bioactive Molecules Delivery & Control Team, Korea Research Institute of Chemical Technology, 100 Jang Dong, Yuseong, Deajeon , Korea (Received July 20, 2006). g pg l k z e. ù ù ƒ yƒ. k ƒ yw» w ù k w ün w wš w. ù, g l š w y y w w. ù w w z, j» š t w p sƒw. j» 80~120 nm, z 80% z. ¼ ƒ ¼ z ƒw š, g l w z w. ù x w z ƒw. k ù ù ƒ y w ƒ» w. : ù, y y, ù, k ABSTRACT. Though the coricosteroid drug dexamethasone is an efficacious antiinflammatory drug, it is difficult to formulate in an injectable formulation due to its poor aqueous solubility. A lipid-based nanosphere formulation containing dexamethasone was designed for solubilization of the drug in aqueous solution and sustained release of the drug from the nanosphere. The lipid nanospheres, composed of phospholipid, cholesterol and cationic lipid, were prepared by self emulsification-solvent diffusion method followed by diafiltration. Physicochemical characteristics such as mean particle diameter, zeta potential and drug loading efficiency of the lipid nanospheres were investigated according to the variation of either the kind of lipid or the lipid composition. The lipid nanospheres had a mean diameter nm and dexamethasone loading efficiency of greater than 80%. The drug loading efficiency increased with the increase of the length of aliphatic chain attached to the phospholipid. However, the drug loading efficiency was inversely proportional to the increase of cholesterol content in the lipid composition. The lipid nanosphere could not be prepared without the use of cationic lipid and the drug loading efficiency was proportional to the increase of cationic lipid content. The lipid nanospheres containing dexamethasone are a promising novel drug carrier for an injectable formulation of the poorly water-soluble drugs. Keywords: Lipid Nanosphere, Spontaneous Emulsification-solvent Diffusion, Poorly Water-soluble Drug, Dexamethasone 464
2 2006, Vol. 50, No. 6 k ù : w y ù p 465,, y w š w, s, j ù xk. (droplet) 1 jš e (amphiphilic) y w k ù w z ù û. s (phospholipid) d x j» s (vesicle) s ü w w š x yw w ù s,, s(macrophage) w ƒ š. š j ù w w š w, k q (targeting) wù š s. w û w ù (lipid nanoparticle)ƒ y š. ù š k š yww ³ w wš þƒw š (solid solution) w w. y w ù w j ù w j ƒ š. yù w n y w nw (degenerative arthritis) y ³ w w p (reumatoid arthritis) p w y. ü e ƒ e w z l (cavum articulare) n w ù n w. k (dexamethasone) 2, v e z l. ù k w w z wš w w w ƒ ûš l v» w, ü, w n, ü» w j» ƒ. k š w k wwš, n l k w w z j ƒ w š. 3-5 ù k ƒ y w, g l w ù y y (self emulsification-solvent diffusion) w. ù w ù 6 x, k z ù e w r. Õ (hydrophobic tail) ky ¼ z y w š, ù y w sw g l w yƒ ù p z e w w. w ù p y w ù ù y p š w. x ù w» w 1,2-Dimyristoyl-sn-glycero-3-phosphocholine (DMPC), Dimethyldioctadecyl-ammoniumbromide (DDAB), 1,2- Distearoyl-sn-glycero-3-phosphocholine (DSPC), 1,2-Dioleoylsn-glycero-3-phosphoethanolamine (DOPE), 1,2-Dipalmitoylsn-glycero-3-phosphocholine (DPPC), 1,2-Dioleoyl-3-trimethylammonium-propane(DOTAP), L-α-Phosphatidylcholine (soy-hydrogenated)(hspc) Cholesterol (CHOL) Avanti Polar Lipids (Alabaster, AL, ) w w š, k Tokyo Chemical Industry (Tokyo, ) w w. p w.
3 466 xá Á w Á ù k ù y- y w. 7-9, g l 7:3:5 š wš ƒƒ y g w. k ƒ ƒƒ 14, DMPC, DPPC HSPC w. DDAB, DOTAP DOPE w g l w 0, 1, 3, 5 7 xw. k 40 mg 8 ml k w g k wš,, g l 2 ml j s ww w z k g l w yww 10 ml w. k yw j» w š q»(ultrasonicator, Model 500, Fisher scientific, ) w 20 ml q w yw 2 23» m w 5 ml/min ƒw g z w š ice-bath w 4 o C wƒ w. 25 ml z» w» w š» w vƒ 10 mlƒ ¾, w k ù ƒ. ù ƒ 0.2 µm» w ù x w w, g l k w. ù j» t w d w ù j» t w» Ÿ d» (Electrophoretic light scattering spectropho- tometer, ELS-8000, Otuska Electronics, ) w d w. j» w ù 0.5 ml w 2.5 ml w o 60 ƒ 25 C w o d w. t w ù 1 ml w z 9 ml w 25 o C, ph 7 d w. ù z d ù k z r k k z Ÿ /ƒ Ÿ ŸŸ»(Shimadzu UV mini 1240, ) d w. r ml y 170 ml yww 250 ml 100 ml w r 65 mg ww w. k 1 mg k 10 ml ww w š 2 ml w r 10 ml ƒw w z 60 C 20 o g. ¾ þ ƒ k z Ÿ d w w. ù k ù ƒ œ w w z r ƒw w g. Ÿ q 423 nm d wš w w k y w. ù k z w w. ù k z (%) = 100 ù w k š ù p ù x x ù y» w k ƒ w ù wš p w., g l 7 : 3 : 5 wš yw ù j», w k z d w Table 1 ùkü. DMPC w ƒ x š HSPC w ù j» 122 nm, k z 76.1% ƒ. HSPC, DPPC Journal of the Korean Chemical Society
4 k ù : w y ù p 467 Table 1. Mean particle diameter, loading efficiency and zeta potential values of the lipid nanospheres 1) Lipid Mean particle diameter (nm) Loading efficiency of dexamethasone(%) Zeta potential (mv) HSPC 122± DPPC 120± ) DMPC ) Mole ratio of lipid : CHOL : DDAB was set to 7 : 3 : 5. 2) Physical properties could not be characterized because of formation of lipid aggregates. DMPC s kp g (phosphatidyl choline) ƒ w k ƒ DMPC 14, DPPC 16 š HSPC 18 k w w. ƒ ù ƒ x DMPC ƒ k. k z k ƒ k ƒ w. ù e ü x w d x d (multi lamella) ƒ k ƒ ƒw ù x w w ƒ. w k d x w ù ƒ k ƒ ƒw z ƒw w w w. wr, ù w x ù ƒ zww w z w ƒ. ù zw w w x» wš w. ƒ ƒ DDAB, DOTAP DOPE w ù wš p w Table 2 Fig. 1 w.» DOPEƒ ù x w w ùkü ƒ DOTAP Table 2. Mean particle diameter, loading efficiency and zeta potential values of the lipid nanospheres 1) Cationic lipid Mean particle diameter (nm) Loading efficiency of dexamethasone(%) Zeta potential (mv) DDAB 122± DOTAP 151± ) DOPE ) Mole ratio of HSPC : CHOL : cationic lipid was set to 7 : 3 : 5. 2) Physical properties could not be characterized because of formation of lipid aggregates. Fig. 1. Particle size distribution of the lipid nanospheres. (a) Mole ratio of HSPC : CHOL : DDAB was set to 7 : 3 : 5. (b) Mole ratio of HSPC : CHOL : DOTAP was set to 7 : 3 : , Vol. 50, No. 6
5 468 xá Á w Á w 151 nm s³ j» ù ƒ x š DDAB w 122 nm s³ j» ù x w. ù x w, ƒ ù w, ù x w d ƒ sw ù» w w ù ƒ (Van der Waals) w j l j» ƒ x w ƒ w ù w w y» ƒ. wr, k z DOPE w ƒ DDAB DOTAP w 76% 63% z k ü (electron)ƒ t w 2 fm», k w»ƒ w» x» w. k z j» š w k ƒ HSPC, ƒ j DDAB w w : g l : 7 : 3 : 5 š w j» 122 nm, z 76.1% ù ƒ ƒ w. z g l w ù g l d w yw yw. wr, Scheme 1 w k g l w yw ƒ š. g l ù x w k g l x w w š g l w k z d w Fig. 2 ùkü. g l w k z 80.3% š g l w ƒ w k z w Scheme 1. Chemical structure of dexamethasone and cholesterol. Fig. 2. Loading efficiency of dexamethasone into lipid nanosphere according to the mole ratio of cholesterol in total lipid composition. g l w 19 7 k z 29.3% g l w k z w. g l w k z g l ù ü w ù ƒ ù. k w ƒ g l w e Journal of the Korean Chemical Society
6 k ù : w y ù p 469 w g l w û k ƒ w ƒ. g l w ù 48 ü ù l k e x w g l 13 1 w 80 ¾ w y w. w g l 3, 5 š 7 w ù ù w y w. k z ù š w g l 20.0 % w w. t w p ù ƒ t w j» w eš k»» w z w e w. HSPC g l w š wš DDAB DOTAP w ù wš j» t w d w Table 3 ùkü. w ù x, sw ƒ w» w ù ƒ x y w. ü d x wš x d d x w d w zw w» Fig. 3. Loading efficiency of dexamethasone into lipid nanosphere according to the mole ratio of cationic lipid in total lipid composition. ƒ. wr, w y k z y Fig. 3 ùkü. DDAB w ƒw k z ƒw 81% z ùkü. DDAB ƒ w ƒw w k ƒw k» ƒw» ƒ. DDAB w ƒ w DOTAP 3 ¾ k z ƒw 71% z ùkü š z DOTAP w ƒ z w. p 7 DOTAP w w ù 453 nm j» ù ƒ x ù ü Table 3. Zeta potential and mean particle diameter of lipid nanosphere containing dexamethasone according to the mole ratio of cationic lipid HSPC : CHOL : cationic lipid Zeta potential (mv) Mean particle diameter (nm) DDAB DOTAP DDAB DOTAP 7 : 3 : 0 1) : 3 : ± ± : 3 : ± ± : 3 : ± ± : 3 : ) - 134± ) Physical properties could not be characterized because of formation of lipid aggregates. 2) Rapid precipitation due to release of dexamethasone from lipid nanoparticles. 2006, Vol. 50, No. 6
7 470 xá Á w Á k ù l e x w. w w DOTAP w ƒw ù x w ƒ ƒw ƒ w k z ƒw ƒ DOTAP 2 e» œ ƒw ù w jš k» ƒ. ù x w ù w w w w w x ù w w. ù w ù w w w w w ù x z w. y- y ù wš ù k ù w, g l w w ù p z e w š w. k ƒ k z g. g l k z ùk ü k g l w ù x w» w w. ù g l w û ù w w yƒ v w. w w ù x ƒ ƒ w ù j» wš k z ƒw. DDAB DOTAP w j»ƒ š z ƒw. g l 7 : 3 š w z DDAB w ƒƒ 1, 3, 5 7 ƒ k k z 50.5, 61.0, % ƒw j» ƒƒ 100, 103, nm ùkü ù š ƒ ywš z ww. l ù ù wù k ƒ». w»» yw m IMT-2000» (01-PJ11-PG9-01NT ). x 1. Wissing, S. A.; Kayser, O.; Muller, R. H. Adv. Drug. Deliver. Rev., 2004, 56, Yokoyama, K.; Watanabe, M. Adv. Drug. Deliver. Rev., 1996, 20, McCormack, B.; Gregoriadis, G. Biochim. Biophys. Acta., 1996, 1291, Tauchi, Y.; Takase, M.; Zushida, I.; Chono, S.; Sato, J.; Ito, K.; Morimoto, K. J. Pharm. Sci., 1999, 88, Turkoglu, O. F.; Eroglu, H.; Okutan, O.; Burul, E.; Sargon, M. F.; Ozer, N.; Oner, L.; Beskonakli, E. Surg. Neurol., 2005, 64, S2:11-S2: Seki, J.; Sonoke, S.; Saheki, A.; Fukui, H.; Sasaki, H.; Mayumi, T. Int. J. Pharm., 2004, 273, Murakami, H.; Kobayashi, M.; Takeuchi, H.; Kawashima, Y. Int. J. Pharm., 1999, 187, Murakami, H.; Kobayashi, M.; Takeuchi, H.; Kawashima, Y. Powder. Technol., 2000, 107, Song, C. X.; Labhasetwar, V.; Murphy, H.; Qu, X.; Humphrey, W. R.; Shebuski, R. J.; Levy, R. J. J. Control. Release., 1997, 43, w 7, w œ xz, 1, 2, Hickey, T.; Kreutzer, D.; Burgess, D. J.; Moussy, F. Biomaterials., 2002, 23, Fukui, H.; Koike, T.; Saheki, A.; Sonoke, S.; Seki, J. Int. J. Pharm., 2003, 265, Niwa, T.; Takeuchi, H.; Hino, T.; Kunou, N.; Kawashima, Y. J. Control. Rel. 1993, 25, Mohammed, A. R.; Weston, N.; Coombes, A. G. A.; Fitzgerald, M.; Perrie, Y. Int. J. Pharm., 2004, 285, Sanchez, A.; Vila-Jato, J. L.; Alonso, M. J. Int. J. Pharm., 1993, 99, Journal of the Korean Chemical Society
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