Relationship between oversulfation and conformation of low and high molecular weight fucoidans and evaluation of their in vitro anticancer activity.
Low and high molecular weight fucoidans (F(5-30K) and F(>30K)) were chemically modified through the addition of sulfate groups, and the effect of oversulfation on the in vitro anticancer activity was investigated. After the addition of sulfate groups, a considerable increase of 35.5 to 56.8% was observed in the sulfate content of the F(5-30K) fraction, while the sulfate content of the F(>30K) fraction increased to a lesser extent (from 31.7 to 41.2%). Significant differences in anticancer activity were observed between the oversulfated F(5-30K) and F(>30K) fractions, with activities of 37.3-68.0% and 20.6-35.8%, respectively. This variation in the anticancer activity of oversulfated fucoidan derivatives was likely due to differences in their sulfate content. The results suggest that the molecular conformation of these molecules is closely related to the extent of sulfation in the fucan backbones and that the sulfates are preferably substituted when the fucoidan polymers are in a loose molecular conformation.
Department of Marine Food Science and Technology, Gangneung-Wonju National University, Gangneung, Gangwon 210702, Korea. bylee@cha.ac.kr
Myoung Lae
ML
Cho
Boo-Yong
BY
Lee
Sang Guan
SG
You
D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D008970:Molecular Weight; D011134:Polysaccharides / Q000737:chemistry* / Q000494:pharmacology*; D017550:Spectroscopy, Fourier Transform Infrared; D013431:Sulfates / Q000737:chemistry*; D044648:Undaria / Q000737:chemistry
D000970:Antineoplastic Agents; D011134:Polysaccharides; D013431:Sulfates; C007789:fucoidan
J Biol Chem. 1993 Oct 15;268(29):21770-6
8408031
Biochem J. 1962 Jul;84:106-10
13886865
Thromb Res. 2000 Dec 1;100(5):453-9
11150589
Biochem Pharmacol. 2003 Jan 15;65(2):173-9
12504793
Biochem Pharmacol. 1992 Apr 15;43(8):1853-8
1533520
J Biol Chem. 1988 Dec 5;263(34):18176-83
3142869
Biochim Biophys Acta. 2000 Jun 2;1497(1):127-34
10838166
Carbohydr Res. 1996 Aug 19;289:201-8
8805780
Carbohydr Res. 1999 Jun 30;319(1-4):154-65
10520264
Int J Biol Macromol. 2008 Dec;43(5):433-7
18789961
J Biol Chem. 1951 Nov;193(1):265-75
14907713