期刊文献+
任意字段
题名或关键词
题名
关键词
文摘
作者
第一作者
机构
刊名
分类号
参考文献
作者简介
基金资助
栏目信息

Synthesis and Characterization of a Novel Galactosylated Cholesterol 被引量：1

Synthesis and Characterization of a Novel Galactosylated Cholesterol
下载PDF
导出
摘要 A novel galactosylated cholesterol with mono-galactoside moiety, （5-cholesten-3-yl）-4-oxo-4-[2-（lactobionylamido）ethylamido]butanoate 6 was synthesized. Its chemical structure was characterized by IR, ESI-MS, ^13C NMR, ^1H NMR. Doxorubicin entrapped in the liposomes containing 10% mol/mol 6 was rapidly accumulated in liver and mainly uptake by parenchymal cells in mice. A novel galactosylated cholesterol with mono-galactoside moiety, （5-cholesten-3-yl）-4-oxo-4-[2-（lactobionylamido）ethylamido]butanoate 6 was synthesized. Its chemical structure was characterized by IR, ESI-MS, ^13C NMR, ^1H NMR. Doxorubicin entrapped in the liposomes containing 10% mol/mol 6 was rapidly accumulated in liver and mainly uptake by parenchymal cells in mice.
作者 Shao Ning WANG Ying Kun QIU Hui XU Yi Hui DENG Da Wei CHEN
机构地区 School of Pharmacy School of Pharmcy Shandong Engineering Research Center of Natural Drugs
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2006年第2期173-176,共4页 中国化学快报（英文版）
关键词 Galactosylated cholesterol （5-cholesten-3-yl）-4-oxo-4-[2-（lactobionylamido）ethylamido]butanoate hepatocyte-selective targeting doxorubicin. Galactosylated cholesterol, （5-cholesten-3-yl）-4-oxo-4-[2-（lactobionylamido）ethylamido]butanoate, hepatocyte-selective targeting, doxorubicin.
分类号 R735.7 [医药卫生—肿瘤] R979.1 [医药卫生—药品]
  • 相关文献

参考文献7

  • 1[1]S.Gao,J.Chen,X.Xu,Z.Ding,et al.,Int.J.Pharm.,2003,255,57.
  • 2[2]P.C.N.Rensen,L.A.J.M.Sliedregt,M.Ferns,E.Kieviet,et al.,J.Biol.Chem.,2001,276,37577.
  • 3[3]S.Kawakami,C.Munakata,S.Fumoto,et al.,J.Pharm.Sci.,2001,90,105.
  • 4[4]C.K.Kim,K.H.Min,Y.K.Oh,et al.,Int.J.Pharm.,1996,128,65.
  • 5[5]H.J.M.Kempen,C.Hose,J.H.van Boom,etal.,J.Med.Chem.,1984,27,1306.
  • 6[6]D.D.Lasic,P.M.Frederick,M.C.A.Stuart,et al.,FEBS Lett.,1992,312,255.
  • 7[7]4:yield 83%,1H NMR (C5D5N,δ ppm):5.33 (m,1H,H-6),4.85 (m,1H,H-3),2.93 (m,2H,H-3′),2.88 (m,2H,H-2′),2.48 (m,2H,H-4),1.97 (m,1H,H-8),0.97 (s,3H,H-19),0.96 (d,3H,J=6.5,H-21),0.90 (d,6H,J=6.5,H-26,27),0.65 (s,3H,H-18); 13C NMR (C5D5N,δ ppm):174.8 (C-4′),172.3 (C-1′),140.0 (C-5),122.8 (C-6),74.2 (C-3),56.8 (C-14),56.4 (C-17),50.2(C-9),42.5 (C-13),39.9 (C-16),39.8 (C-24),38.5 (C-4),37.2 (C-1),36.8 (C-10),36.5 (C-22),36.1 (C-20),32.1 (C-8),32.0 (C-7),30.2 (C-3′),29.9 (C-2′),28.5 (C-2),28.3 (C-12),28.1(C-25),24.5 (C-15),24.2 (C-23),23.0,22.7 (C-26,27),21.3 (C-11),19.3 (C-19),19.0 (C-21),12.0 (C-18); ESI-MS m/z:509.4 (M+Na)+,calcd.for C31H50O4 509.3607.5:yield 93%,1H NMR (C5D5N,δ ppm):5.35 (m,1H,H-6),4.81 (m,1H,H-3),3.12 (t,2H,J=6.4,H-3′),2.84 (t,2H,J=6.4,H-2′),2.82 (s,4H,H-3″,4″),2.47 (m,2H,H-4),1.98 (m,1H,H-8),1.01 (s,3H,H-19),0.97 (d,3H,J=6.5,H-21),0.90 (d,6H,J=6.5,H-26,27),0.65 (s,3H,H-18); 13C NMR (C5D5N,δ ppm):170.68 (C-1'"),169.92 (C-1′),168.95 (C-4"'),139.83 (C-5),122.77 (C-6),74.73 (C-3),56.68 (C-14),56.28 (C-17),50.14 (C-9),42.4 (C-13),39.84 (C-16),39.65 (C-24),38.22 (C-4),37.08 (C-1),36.7 (C-10),36.41 (C-22),35.94 (C-20),32.04 (C-8),31.94 (C-7),29.25 (C-2"'),28.4 (C-2),28.15 (C-12),27.85 (C-25),26.69 (C-3"'),26 (C-5"',6"'),24.39 (C-15),24.06 (C-23),22.84,22.59 (C-26,27),21.17 (C-11),19.25 (C-19),18.86(C-21),11.9 (C-18); ESI-MS m/z:606.4 (M+Na)+,calcd.for C35H53O6 N 606.3771.6:yield 80%,IR (KBr) v/cm-1:3377 (br,OH),2937 (-CH2-),1732 (ester,C=O),1651(amide,C=O),1543 (C=C); 1H NMR (C5D5N,δ ppm):8.68 (brt,2H,J=6.7,-NH×2),5.32 (m,1H,H-6),5.26 (m,1H,J=3.18,H-3′),5.20 (d,1H,J=6.7,H-1″),5.19 (d,1H,J=3.7,H-2′),4.82 (m,1H,H-3),4.78 (m,1H,H-4′),4.70 (m,1H,H-5′),[4.41 (dd,1H,J=2.7,11.2) & 4.26 (dd,1H,J=4.4,11.2),H-6″],4.12 (dd,1H,J=3.0,9.5,H-3″),4.07 (m,1H,H-5″),3.70 (m,2H,H-6"'),3.67 (m,2H,H-5"'),2.87 (m,2H,H-3"'),2.76 (m,2H,H-2"'),[2.45 (dd,1H,J=12.2,3.5) &2.40 (brd,1H,J=12.2),H-4],1.94 (m,1H,H-8),0.96 (d,3H,J=6.5,H-21),0.95 (s,3H,H-19),0.89 (d,6H,J=7.7,H-26,27),0.63 (s,3H,H-18); 13C NMR (C5D5N,δ ppm):174.82 (C-1′),172.70 (C-4"'),172.24 (C-1"'),140.03 (C-5),122.75 (C-6),106.58 (C-1″),84.11 (C-4′),77.54(C-5″),75.26 (C-3″),74.14 (C-3),73.66 (C-2′),73.23 (C-5′),72.99 (C-2″),72.76 (C-3′),70.26(C-4″),64.44 (C-6′),62.57 (C-6″),56.75 (C-14),56.33 (C-17),50.18 (C-9),42.47 (C-13),39.92 (C-16),39.74 (C-5"',6"'),39.60 (C-24),38.46 (C-4),37.19 (C-1),36.78 (C-10),36.49(C-22),36.05 (C-20),32.13 (C-8),31.99 (C-7),31.04 (C-2"'),30.27 (C-3"'),28.52 (C-2),28.27 (C-12),28.08 (C-25),24.50 (C-15),24.16 (C-23),22.97,22.71 (C-26,27),21.25 (C-11),19.36 (C-19),18.95 (C-21),11.99 (C-18); ESI-MS m/z:891.6 (M+Na)+,calcd.forC45H76O14N2 891.5194.

同被引文献24

引证文献1

二级引证文献6

Chinese Chemical Letters
2006年 第2期

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部