摘要
通过X-射线粉末衍射、热分析、扫描电镜、紫外-可见光谱以及分子对接等分析方法,研究了松属素(PIN)分别与2,6-二甲基-β-环糊精(DM-β-CD)和2,3,6-三甲基-β-环糊精(TM-β-CD)的包合行为、包合能力以及包合模式。结果表明,PIN/DM-β-CD和PIN/TM-β-CD包合物的包合比均为1∶1,PIN形成包合物后,其溶解度分别提高817倍和575倍。分子对接显示,PIN从DM-β-CD分子的大口端进入并贯穿在其空腔中,PIN的A环和B环分别位于环糊精分子的大口端和小口端;而对于TM-β-CD,仅有PIN的A环和C环进入到环糊精的空腔内。
The inclusion behavior,inclusion capacity and inclusion mode of pinocembrin (PIN) with dimethyl-β-cyclodextrin (DM-β-CD) and trimethyl-β-cyclodextrin (TM-β-CD) were characterized by X-ray diffraction,differential scanning calorimetry,scanning electron microscopy,UV-visible spectral titration and molecular docking. The results showed that the packing ratio of PIN/DM-β-CD complex and PIN/TM-β-CD complex was 1∶ 1. The water solubility of PIN respectively increased 817 times and 575 times in the inclusion complex with DM-β-CD and TM-β-CD. Molecular docking showed the pinocembrin entered from the large end of the DM-β-CD molecule and penetrated through the cavity. The A and B rings of the PIN were respectively located at the big and small ends of the cyclodextrin molecule. For the TM-β-CD,only A and C rings of the PIN entered cavity of cyclodextrin.
引文
1 Ishida Y,Gao R,Shah N,Bhargava P,Furune T,Kaul S C,Wadhwa R.Integr.Cancer Ther.,2018,17(3):1-7
2 Batista C M,Alves A V F,Queiroz L A,Lima B S,Araújo A A S,Albuquerque R L C,Cardoso J C.J.Photoch.Photobio.B,2018,180:198-207
3 Nair S,Meliani A.World J.Life Sci.,2018,1(1):7-13
4 Gu Y H,Choi H,Yamashita T,Kang K M,Iwasa M,Lee M J,Lee K H,Kim C H.Curr.Pharm.Biotechnol.,2017,18(8):653-661
5 Yan B,Cao G Y,Sun T H,Zhao X,Hu X,Yan J L,Peng Y Y,Shi A X,Li Y,Xue W,Li M,Li K X,Liu Y F.Biomed.Chromatogr.,2014,28(12):1601-1606
6 Estevinho L,Pereira A P,Moreira L,Dias L G,Pereir E.Food Chem.Toxicol.,2008,4(12):3774-3779
7 Zhu X M,Fang L H,Li Y J,Du G H.Vasc.Pharmacol.,2007,46(3):160-165
8 Heyden N V,Rodi C,Ratner L.Res.Hum.Retrov.,1989,5(6):647-653
9 Yang Q,Tong Y,Chen F,Qi Y,Li W,Wu S.Chinese.J.Chem.,2012,30(6):1315-1319
10 Chapekar M S,Glazer R I.Biochem.Biophys.Res.Commun.,1983,115(1):137-143
11 Pant A,Negi J S.Eur.J.Pharm.Sci.,2018,112:180-185
12 Ma S X,Chen W,Yang X D,Zhang N,Wang S J,Liu L,Yang L J.J.Pharmceut.Biomed.,2012,67:193-200
13 SUN Wei,SHE Meng-Yao,MA Si-Yue,CHEN Jiao,SHI Zhen,LI Jian-Li.Chinese J.Anal.Chem.,2018,46(2):246-253孙伟,厍梦尧,马思悦,陈娇,史真,李剑利.分析化学,2018,46(2):246-253
14 Terauchi M,Tamura A,Yamaguchi S,Yui N.Int.J.Pharmaceut.,2018,547(1-2):53-60
15 DENG Ying-Hui,SU Li-Na,PANG Yan-Hua,GUO Ya-Fei,WANG Fen,LIAO Xia-Li,YANG Bo.Chinese J.Anal.Chem.,2017,45(5):648-653邓颖慧,苏丽娜,庞艳华,郭亚飞,王芬,廖霞俐,杨波.分析化学,2017,45(5):648-653
16 ZHAO Fang,ZHAO Xue-Qiu,CHANG Qing,WANG Shu-Hui,DU Yao,YANG Li-Juan.Chinese J.Anal.Chem.,2017,45(10):1547-1555赵芳,赵雪秋,常清,王淑慧,杜瑶,杨丽娟.分析化学,2017,45(10):1547-1555
17 Misiuk W.J.Mol.Liq.,2016,224(A):387-392
18 Zhou S Y,Ma S X,Cheng H L.J.Mol.Struct.,2014,1058(1):181-188
19 Yang L J,Wang S H,Zhou S Y,Zhao F,Chang Q,Li M Y,Chen W,Yang X D.Mat.Sci.Eng.C,2017,76:1136-1145
20 Yang L J,Chang Q,Zhou S Y,Yang Y H,Xia F T,Chen W,Li M Y,Yang X D.Dyes Pigments,2018,150:193-201
21 Renny J S,Tomasevich L L,Tallmadge E H,Collum D B.Angew.Chem.Int.Edit.,2013,52(46):11998-12013
22 Montassier P,Duchêne D,Poelman M C.Int.J.Pharmaceut.,1997,153(2):199-209
23 Vargas-Snchez R D,Mendoza-Wilson A M,Balandrn-Quintana R R,Torrescano-Urrutia G R,Snchez-Escalante A.Comput.Theor.Chem.,2015,1058:21-27
24 Morris G M,Huey R,Lindstrom W,Sanner M F,Belew R K,Goodsell D S,Olson A J.J.Comput.Chem.,2009,30(16):2785-2791
25 Gaussian 03,Revision E.01,Frisch M J,Trucks G W,Schlegel H B,Scuseria G E,Robb M A,Cheeseman J R,Montgomery J A,Jr,Vreven T,Kudin K N,Burant J C,Millam J M,Iyengar S S,Tomasi J,Barone V,Mennucci B,Cossi M,Scalmani G,Rega N,Petersson G A,Nakatsuji H,Hada M,Ehara M,Toyota K,Fukuda R,Hasegawa J,Ishida M,Nakajima T,Honda Y,Kitao O,Nakai H,Klene M,Li X,Knox J E,Hratchian H P,Cross J B,Bakken V,Adamo C,Jaramillo J,Gomperts R,Stratmann R E,Yazyev O,Austin A J,Cammi R,Pomelli C,Ochterski J W,Ayala PY,Morokuma K,Voth G A,Salvador P,Dannenberg J J,Zakrzewski V G,Dapprich S,Daniels A D,Strain M C,Farkas O,Malick D K,Rabuck A D,Raghavachari K,Foresman J B,Ortiz J V,Cui Q,Baboul A G,Clifford S,Cioslowski J,Stefanov B B,Liu G,Liashenko A,Piskorz P,Komaromi I,Martin R L,Fox D J,Keith T,Al-Laham M A,Peng C Y,Nanayakkara A,Challacombe M,Gill P M W,Johnson B,Chen W,Wong M W,Gonzalez C and Pople J A,Gaussian,Inc.,Wallingford,CT,2004
26 Malkondu S,Turhan D,Kocak A.Tetrahedron Lett.,2015,56(1):162-167
27 Caso J V,Russo L,Palmieri M,Malgieri G,Galdiero S,Falanga A,Isernia C,Iacovino R.Amino Acids,2015,47(10):2215-2227
28 Liu Y,Li B,Wada T,Inoue Y.Supramol.Chem.,1999,10(4):279-285