The Effect of Unsaturation on the Formation of Self-Assembled Gels from Fatty Acid L-Serine Amides and their Cytotoxicity Towards Caco-2 Cancer Cells

被引：8

作者：

Lim, Li Yun Grace ^{[1
]}

Su, Yingying ^{[2
]}

Braet, Filip ^{[2
]}

Thordarson, Pall ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

[2] Univ Sydney, Australian Key Ctr Microscopy & Microanal, Sydney, NSW 2006, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2009年 / 62卷 / 07期

基金：

澳大利亚研究理事会;

关键词：

DELIVERY; GROWTH;

D O I：

10.1071/CH09211

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of saturated and unsaturated fatty acid L-serines 3 were synthesized and their ability to form self-assembled gels was investigated. The saturated (lauroyl 3a and steraoyl 3b) and monounsaturated (oleoyl 3c) fatty acid L-serines form gels in both water and organic solvent, whereas the diunsaturated linoleyl-L-serine 3d does not form gels in these solvents, indicating that unsaturation adversely affects the gelation process. Cytotoxicity studies on these compounds with Caco-2 cancer cells in vitro show that these gels are only moderately cytotoxic at concentrations up to 0.5 mM, making them a promising candidate for applications such as drug delivery.

引用

页码：653 / 656

页数：4

共 17 条

[1] Hydrophobized dextran-spermine conjugate as potential vector for in vitro gene transfection [J].

Azzam, T ;

Eliyahu, H ;

Makovitzki, A ;

Linial, M ;

Domb, AJ .

JOURNAL OF CONTROLLED RELEASE, 2004, 96 (02) :309-323

[2]

Baumann E., 1886, CHEMBER, V19, P3218

[3] Comparative cryo-electron microscopy of noncovalent N-dodecanoyl- (D- and L-) serine assemblies in vitreous toluene and water [J].

Boettcher, C ;

Schade, B ;

Fuhrhop, JH .

LANGMUIR, 2001, 17 (03) :873-877

[4] COLORIMETRIC GROWTH ASSAY FOR EPIDERMAL-CELL CULTURES BY THEIR CRYSTAL VIOLET BINDING-CAPACITY [J].

BONNEKOH, B ;

WEVERS, A ;

JUGERT, F ;

MERK, H ;

MAHRLE, G .

ARCHIVES OF DERMATOLOGICAL RESEARCH, 1989, 281 (07) :487-490

[5] Culture conditions influence uptake and intracellular localization of the membrane permeable cGMP-dependent protein kinase inhibitor DT-2 [J].

Foley, KF ;

De Frutos, S ;

Laskovski, KE ;

Tegge, W ;

Dostmann, WR .

FRONTIERS IN BIOSCIENCE-LANDMARK, 2005, 10 :1302-1312

[6] Entrapment and release of quinoline derivatives using a hydrogel of a low molecular weight gelator [J].

Friggeri, A ;

Feringa, BL ;

van Esch, J .

JOURNAL OF CONTROLLED RELEASE, 2004, 97 (02) :241-248

[7]

LAPIDOT Y, 1967, J LIPID RES, V8, P142

[8] Enantioselective crystallization in miniemulsions based on chiral surfactants [J].

Menahem, Tali ;

Mastai, Yitzhak .

NEW JOURNAL OF CHEMISTRY, 2008, 32 (06) :925-928

[9] Isolation and total synthesis of gymnastatin N, a POLO-like kinase 1 active constituent from the fungus Arachniotus punctatus [J].

Phoon, CW ;

Somanadhan, B ;

Heng, SCH ;

Ngo, A ;

Ng, SB ;

Butler, MS ;

Buss, AD ;

Sim, MM .

TETRAHEDRON, 2004, 60 (50) :11619-11628

[10] Heparin binding nanostructures to promote growth of blood vessels [J].

Rajangam, Kanya ;

Behanna, Heather A. ;

Hui, Michael J. ;

Han, Xiaoqiang ;

Hulvat, James F. ;

Lomasney, Jon W. ;

Stupp, Samuel I. .

NANO LETTERS, 2006, 6 (09) :2086-2090

← 1 2 →