Construction and Characterization of a Novel pH-insensitive Self-crosslinked Ufasome of Conjugated Linoleic Acid†

doi:10.7503/cjcu20140158

Abstract

Abstract:

Conjugated linoleic acid(CLA) was employed as a molecular building block to construct a novel pH-insensitive fatty acid vesicle(FAV). First, CLA was semi-synthesized from linoleic acid through alkali isomerization. Subsequently, the ufasome(unsaturated fatty acid liposome) of CLA was self-assembled from the CLA molecules together with the CLA ions in response to pH, and a novel pH-insensitive FAV, the self-crosslinked-CLA FAV, was prepared by chemical tethering the CLA-ufasome through UV irradiation. The sui-table pH ranges and the CLA concentrations were determined by acid-base titration and surface tension mea-surement. The morphology of the self-crosslinked-CLA FAV was imaged by transmission electro microscopy(TEM) and the pH-insensitive characteristic of the self-crosslinked-CLA FAV was tested by dynamic light scattering(DLS). The experimental results indicated that the self-crosslinked-CLA FAV with diameter of 10—20 nm and wall thickness of 2.0 nm was obtained through a two-step procedure. At first, the CLA-ufasome formed using the CLA species as a molecular building block at pH=8.6 and CLA concentration of 3 mmol/L, and then followed by UV irradiation self-crosslinking for 2.5 h. It was verified by DLS data that the self-crosslinked-CLA FAV is pH-insensitive in almost all pH ranges. Finally, the in vitro release results of 5-fluorouracil from the self-crosslinked-CLA FAV showed that the process was slow and sustainable.

Key words: Conjugated linoleic acid, Ufasome, Fatty acid vesicle, pH-Insensitive, Self-assembling, Self-crosslinking

CLC Number:

O648

TrendMD:

FAN Ye, FANG Yun, GAO Di. Construction and Characterization of a Novel pH-insensitive Self-crosslinked Ufasome of Conjugated Linoleic Acid^†[J]. Chem. J. Chinese Universities, 2014, 35(8): 1746.

Figures/Tables 6

Fig.1 Titration curve of 10 mmol/L CLA at 25 ℃ Area a. micelle; b. ufasome; c. emulsion; d. oil drop.

Fig.2 γ-lgc curve of CLA with pH=8.6 at 25 ℃

Fig.3 UV spectra(A) and IR spectra(B) of the aqueous CLA solution at pH=8.6 before and after UV irradiation for 2.5 h and the size distribution(C) and TEM image(D) of the 3 mmol/L self-crosslinked-CLA FAV using QTX as initiator

Fig.4 Schematic illustration of the formation of the self-crosslinked-CLA FAV

Fig.5 pH insensitive test of the self-crosslinked-CLA FAV (A) Before UV irradiation; (B)—(D) after UV irradiation; (C), (D) DLS and corresponding diameter distribution with different pH values, respectively.

Fig.6 In vitro released rate of 5-FU from the self-crosslinked-CLA FAV in PBS buffer

References 41

[1]	Gebicki J., Hicks M., Nature, 1973, 243(5404), 232—234
[2]	Hargreaves W. R., Deamer D. W., Biochem., 1978, 17(18), 3759—3768
[3]	Cistola D. P., Hamilton J. A., Jackson D., Small D. M., Biochem., 1988, 27(6), 1881—1888
[4]	Morigaki K., Walde P., Misran M., Robinson B. H., Colloids Surf. A, 2003, 213(1), 37—44
[5]	Gebicki J. M., Hicks M., Chem. Phys. Lipids, 1976, 16(2), 142—160
[6]	Namani T., Ishikawa T., Morigaki K., Walde P., Colloids Surf. B, 2007, 54(1), 118—123
[7]	Namani T., Walde P., Langmuir, 2005, 21(14), 6210—6219
[8]	Rogerson M. L., Robinson B. H., Bucak S., Walde P., Colloids Surf. B, 2006, 48(1), 24—34
[9]	Chen I. A., Salehi-Ashtiani K., Szostak J. W., J. Am. Chem. Soc., 2005, 127(38), 13213—13219
[10]	Dowling M. B., Lee J. H., Raghavan S. R., Langmuir, 2009, 25(15), 8519—8525
[11]	Markvoort A. J., Pfleger N., Staffhorst R., Hilbers P. A. J., van Santen R. A., Killian J. A., de Kruijff B., Biophys. J., 2010, 99(5), 1520—1528
[12]	Xu W., Wang X., Zhong Z., Song A., Hao J., J. Phys. Chem. B, 2013, 117(1), 242—251
[13]	Morigaki K., Walde P., Curr. Opin. Colloid Interface Sci., 2007, 12(2), 75—80
[14]	Deamer D., Singaram S., Rajamani S., Kompanichenko V., Guggenheim S., Philos. T. Roy. Soc. B, 2006, 361(1474), 1809—1818
[15]	Fukuda H., Goto A., Yoshioka H., Goto R., Morigaki K., Walde P., Langmuir, 2001, 17(14), 4223—4231
[16]	Li X., Ni X. F., Liang Z. H., Shen Z. Q., Chem. J. Chinese Universities, 2012, 33(6), 1333—1338
	(李雪, 倪旭峰, 梁振华, 沈之荃. 高等学校化学学报, 2012, 33(6), 1333—1338)
[17]	Liu Y. H., Li G. J., Luo X. W., Peng X. Y., Wang L. Y., Chem. J. Chinese Universities, 2013, 34(6), 1527—1535
	(刘云鸿, 李光吉, 罗熙雯, 彭新艳, 王立莹. 高等学校化学学报, 2012, 33(6), 1527—1535)
[18]	Nayak R. R., Roy S., Dey J., Colloid Polym. Sci., 2006, 285(2), 219—224
[19]	van Nostrum C. F., Soft Matter, 2011, 7(7), 3246—3259
[20]	Zhu Z., Xu H., Liu H., González Y. I., Kaler E. W., Liu S., J. Phys. Chem. B, 2006, 110(33), 16309—16317
[21]	Abe M., Koike T., Nishiyama H., Sharma S. C., Tsubone K., Tsuchiya K., Sakai K., Sakai H., Shchipunov Y. A., Schmidt J., J. Colloid Interface Sci., 2009, 330(1), 250—253
[22]	Roy S., Dey J., Langmuir, 2003, 19(23), 9625—9629
[23]	Lee J. H., Danino D., Raghavan S. R., Langmuir, 2009, 25(3), 1566—1571
[24]	Gomes J. F. P. d. S., Sonnen A. F. P., Kronenberger A., Fritz J., Coelho M. Á. N., Fournier D., Fournier-Nöel C., Mauzac M., Winterhalter M., Langmuir, 2006, 22(18), 7755—7759
[25]	Yan X., An X., Nanoscale, 2013, 5(14), 6280—6283
[26]	Storrs R. W., Tropper F. D., Li H. Y., Song C. K., Kuniyoshi J. K., Sipkins D. A., Li K. C., Bednarski M. D., J. Am. Chem. Soc., 1995, 117(28), 7301—7306
[27]	Mueller A., O'Brien D. F., Chem. Rev., 2002, 102(3), 727—727
[28]	Puri A., Blumenthal R., Acc. Chem. Res., 2011, 44(10), 1071—1079
[29]	Chiaramoni N. S., Biophys. J., 2013, 104(2), 243a
[30]	Yavlovich A., Singh A., Tarasov S., Capala J., Blumenthal R., Puri A., J. Therm. Anal. Calorim., 2009, 98(1), 97—104
[31]	Jung Y. K., Kim T. W., Jung C., Cho D. Y., Park H. G., Small, 2008, 4(10), 1778—1784
[32]	Fan Y., Ma L., Fang Y., Li Y. J., Li Y. D., Fine Chem., 2013, 30(7), 729—733
	(樊晔, 马琳, 方云, 李宇婕, 李延頔. 精细化工, 2013, 30(7), 729—733)
[33]	Megias-Alguacil D., Tervoort E., Cattin C., Gauckler L. J., J. Colloid Interface Sci., 2011, 353(2), 512—518
[34]	Hanczyc M. M., Fujikawa S. M., Szostak J. W., Science, 2003, 302(5645), 618—622
[35]	Guo C., Liu S., Jiang C., Li W., Dai Z., Fritz H., Wu X., Langmuir, 2009, 25(22), 13114—13119
[36]	Qin G., Li Z., Xia R., Li F., O'Neill B. E., Goodwin J. T., Khant H. A., Chiu W., Li K. C., Nanotechnology, 2011, 22(15), 155605—155619
[37]	Becucci L., Papini M., Verardi R., Veglia G., Guidelli R., Soft Matter, 2012, 8(14), 3881—3888
[38]	Zhou Y. F., Yan D. Y., Angew. Chem. Int. Ed., 2004, 43(37), 4896—4899
[39]	Zhou Y.F., Yan D. Y.,Chem. Commun., 2009, (10), 1172—1188
[40]	Li X. J., Pivkin I. V., Liang H. J., Karniadakis G. E., Macromolecules, 2009, 42(8), 3195—3200
[41]	Li X. J., Soft Matter, 2009, 9(48), 11663—11670