Prepara tion and character iza tion of or idon in2loaded block copolym er m icelles
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1 1, 1, 2, 2, 2, 2, 1, 2 (1, ; 2, ) [ ] : 2 ( PEDLA ) (OR I), : PEDLA, OR I, OR I Zeta : OR I ( ) nm, Zeta ( ) mv, ( ) %, ( ) %,OR I H iguchi : Q = t 1 / ( r = ) : OR I,, [ ] ; 2 ; ; [ ] R ; R [ ] A [ ] (2009) Prepara tion and character iza tion of or idon in2loaded block copolym er m icelles ZHANG W en2tao 1,WANG Dong2kai 1, HE Xiao2xia 2, PAN Yin 2, HUANG Q ing2bai 2, HAN L ing 2, L IN L i2feng 1, L IU Xiao2tang 2 (1 Shenyang Pharm aceutical U niversity, Shenyang , China; 2 N ational Engineering R esea rch Center for the Pha rm aceu tics of Traditional Ch inese M edicines, B enxi , China) [ Abstract] O bjectives: To p repare oridonin2loaded methoxy poly ( ethylene glycol) 2poly (D, L2lactide ) ( PEDLA ) block copolymer m icelles, and to study the characteristics and in vitro release behaviors of the m icelles. M ethods: The PEDLA were p repared by melting polymerization. were made by the solvent exchange method w ith PEDLA as carrier materials. m icelles were determ ined by dynam ic light scattering. exam ined by ultraviolet spectrophotometry. uated using a dialysis method. The oridonin2loaded block copolymer m icelles The mean size and Zeta potential of The drug loading and encap sulation efficiency of m icells were The in vitro release of oridonin2loaded block copolymer m icelles was eval2 Results: The mean size of oridonin2loaded block copolymer m icelles was ( ) nm, and Zeta potential, drug loading and encap sulation efficiency were estimated to be ( ) mv, ( ) % and ( ) %, respectively. In vitro release behavior was described by H iguchi equation: Q = t 1 / ( r = ). Conclusion:O ridonin can be encap sulated in PEDLA by solvent exchange method. The m ethod is simp le and rep roducible. The in vitro release study showed significant sustained release of oridonin2loaded block copolymer m icelles. [ Key words] oridonin; PEDLA; block copolymer m icells; in vitro release, [ ],, : , E2mail: hzwt7@163. com [ ],,,,, : ( 024 ) , E2mail: wangdksy@ 126. com, 10 [ 1-2 ],,, ( reticuloen2 dothelial system, RES) 1560
2 ,, [ 3-4 ] (O ridonin, OR I) (Labt2 ea) (Rabdosia) ( ent2kau2rene2diterpenoid),,, [ 5-6 ],,, 280,,, 2 (Methoxy poly ( ethylene glycol) 2poly( lactide), mpeg2pla; PEDLA ),, (OR I ), OR I ARX 300 ( BRUKER ) ; DSC 60 ( ) ; IFS55 ( BRUKER ) ; (LC 10A, SPD 10A, ), N2010 ( ), D iamonsil C 18 ( 250 mm 4. 6 mm, 5 m, ) ; PF 101T ( ) ; LS230 ( BECKMAN ) ; COULTER DELSA440 SX Zeta ( BECK2 MAN ) ; ( PALL ) ; ( 7000, ) (, : ) 5000 ( Sigma2 A ldrich ) ; D, L2 ( ) ; ( ) ; (, ) ; ( ) 1 PEDLA [ 7-11] 5000 (mpeg 5000),, , D, L2 (D, L2LA ), 140, 0. 5% 12 h,,, CDCl 3, 1 H2NMR, ;, ( IR ) ; (DSC) PEDLA 1 H2NMR ( 1) : ( 1a) ( PDLLA) 2 CH 3 ; ( 1c) PDLLA 2CH2 ; ( 1b) (mpeg) 2 CH 2 2 ; ( 1d) mpeg CH 3 O2 mpeg 5 000, PLA, PEDLA, 1 1 PEDLA 1 1 H2NMR 1 PEDLA mpeg/d, L2LA ( 1 H2NMR) / PEDLA 0. 5 PEDLA 1 PEDLA
3 PEDLA : cm - 1 C =O, C = O, C = O cm - 1, mpeg2oh cm - 1 C2O, 2COO2 ; cm - 1 mpeg C2O2C, cm - 1 mpeg C2O2C ; cm - 1 C2H ; cm - 1 C2H ; cm ( PEDLA) PEDLA DSC, PDLLA, 1 [ 12-13] 2 O R I, OR I : OR I PEDLA,, 500 r m in - 1,,, OR I 3 O R I [ 14 ] : D iamonsil C 18 ( 250 mm 4. 6 mm, 5 m, ) ; 2 (60 40) ; 238 nm; 1. 0 ml m in - 1 ; 25 ; 20 L mg L - 1, OR I ( C, mg L - 1 ) (A ), : A = C ( r = ) ml OR I, 25 ml, 20 L, OR I OR I,,, OR I, : /% = (W - W ) /W 100, /% = (W - W ) /W 100 :W OR I OR I ; W OR I ; W OR I O R I 4. 1, PEDLA 1 ( PEDLA 200 mg, OR I 10 mg), / ,,, 2,, ;,, ;,,, ; (1 1) 2 OR I /nm /%, 232 ( ) 61. 5, , 461 ( ) (1 1), OR I 10 mg, PEDLA mg,,,, 3,,,, V /V 1 1,, V / V V /V OR I V /V /nm /% PEDLA 2 (1 1), PEDLA OR I ( PEDLA 200 mg, OR I 10 mg), 4,,, PEDLA 2 OR I
4 4 PEDLA OR I / nm /% PEDLA ( ) PEDLA PEDLA PEDLA 2 ( 1 1 ), OR I 10 mg, PEDLA 2 OR I,, 5,,,, 5 PEDLA OR I /mg ml - 1 /nm /% OR I, OR I,, 6,,,,,,, 6 OR I OR I OR I/mg / nm /% ( ) OR I, 25, 40 60, OR I, OR I, 7,,,, 60, 20 40, 20, 40 OR I 7 OR I / /nm /% , (A) PEDLA 2 (B ) (C),,, L 9 (3 4 ) 8 OR I,, S 1 S 2, S = S A /mg + S 2, B /mg ml - 1 C (V /V ) OR I A B C S 1 /% S 2 /% S/ % j j j R j R j, A > C > B, 1563
5 PEDLA A 2 B 2 C 3, 15 mg, PEDLA 200 mg, O R I 3 OR I, ( ) %, ( ) %, LS230 COULTER DELSA440 SX Zeta Zeta ( ) nm, Zeta - ( ) mv [ 12, 15] 6 1 ml OR I, 100 ml (ph 7. 4), 37, 0. 5, 1, 2, 4, 6, 8, 12, 24, 48, 72 h 0. 5 ml, HPLC,,, 2 2 OR I PBS (ph = 7. 4) ( n = 3) H ig2 chi OR I, H igchi OR I, Q = t 1 / ( r = ) Q, t 1 PEDLA PEDLA mpeg D, L2LA, mpeg, 1564 D, L2LA PEDLA D, L2 LA,, PDLLA, PDLLA, mpeg, mpeg,, Tm [ 16 ] 2 PEDLA O R I, OR I,,,,, ;,,,, 3 O R I OR I,,,,,, PEDLA, 4 O R I 2, OR I 2 h, 26%, ; (mpeg),,, 72 h 80%, 20%, OR I
6 PEDLA OR I, OR I, OR I, OR I, OR I, OR I 80%,,, OR I [ 17 ] PEDLA,, OR I PEDLA, [ ] [ 1 ] KATAOKA K, HARADA A, NAGASAKI Y. B lock copolymer m i2 celles for drug delivery: design, characterization and biological sig2 nificance[ J ]. Adv D rug D eliv R ev, 2001, 47 (1) : [ 2 ] ALLEN C,MAYSINGER D, E ISENBENBERG A. Nano2engineer2 ing block copolymer aggregates for drug delivery[ J ]. Colloids Surf B B iointerfaces, 1999, 16 (1) : [ 3 ] ROSLER A, VANDERMEULEN GWM, KLOK H. Advanced drug delivery devices via self2assembly of amphiphilic block copoly2 mers[ J ]. Adv D rug D eliv R ev, 2001, 53 (1) : [ 4 ] SHUA I X, A I H, NASONGKLA N, et al. M icellar carriers based on block copolymers of poly ( 2cap rolactone) and poly ( ethylene glycol) for dox2orubicin delivery[ J ]. J Control Release, 2004, 98 (3) : [ 5 ] CHEN S, GOA J, HAL IEKA HD, et al. The cytostatic and cyto2 toxic effets of oridonin (Rubescenin), a ditep renoid from Rabdo2 sia rubeseens, on tumor cells of dieffrent linegae[ J ]. Int J Oncol, 2005, 26 (3) : [ 6 ] IKEZOE T, CHEN SS, TONG XJ, et al. O ridonin induces growth inhibition and Apop tosis of a variety of human cancer cells[ J ]. Int J O ncol, 2003, 23 (4) : [ 7 ] M IURA H, ON ISH I H, SASATSU M, et al. Antitumo characteris2 tics of methoxy polyethylene glycol2poly (D, L2lactic acid) nano2 particles containing camptothecin [ J ]. J Control Release, 2004, 97 (1) : [ 8 ],. 2 ( 2co2 ) NMR [ J ]., 2007, 24 ( 3 ) : [ 9 ],,,. PLA2mPEG [ J ]., 2005, 22 (4) : [ 10 ],,,. 2 [ J ]., 2007, 24 (2) : [ 11 ] AVGOUSTAKIS K, BELETSI A, PANAGI Z, et al. Effect of co2 polymer composition on the physicochem ical charaetelistics, in vitro stability, and biodistribution of PLGA2mPEG nanoparticles [ J ]. Int J Pharm, 2003, 259 (1) : [ 12 ],,,. [ J ]., 2007, 42 (13) : [ 13 ],,,. [ J ]., 2005, 3 (5) : [ 14 ],,,. [ J ]., 2005, 40 (6) : [ 15 ],,,. B 2 [ J ]., 2007, 42 (7) : [ 16 ],,,. 2 (D, L2 ) [ J ]., 2005, 24 (6) : [ 17 ],. 2 [ J ]., 2007, 19 (6) : : / : ( 1584 ),, [ 1-3 ],,,, : PT INR,,,,, [ ] [ 1 ],,. [ J ]., 2000, 7 (3) : 148. [ 2 ]. 4 [ J ]., 1999, 11 (5) : 226. [ 3 ],,. 6 [ J ]., 2007, 29 (8) : : / :
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