Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds
The anticoagulant behavior of sulfated polysaccharides from seaweeds is reviewed based on their chemical structures. Analysis of the literature suggested that the driving force for the formation of the sulfated polysaccharide/ protein complex is the non-specific polar interaction between the negativ...
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todo:paper_09298673_v17_n23_p2503_Ciancia2023-10-03T15:47:38Z Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds Ciancia, M. Quintana, I. Cerezo, A.S. anticoagulant activity chemical structure disulfated structural units green seaweed structure-activity relationship Sulfated polysaccharides antithrombin arabinose carbohydrate fucose galactose glycosaminoglycan heparin cofactor II monosaccharide polysaccharide rhamnose sulfate thrombin anticoagulant therapy article drug activity drug binding drug conformation drug inhibition drug mechanism drug structure human hydrophobicity nonhuman seaweed structure activity relation Animals Anticoagulants Blood Coagulation Humans Molecular Structure Polysaccharides Seaweed Sulfates The anticoagulant behavior of sulfated polysaccharides from seaweeds is reviewed based on their chemical structures. Analysis of the literature suggested that the driving force for the formation of the sulfated polysaccharide/ protein complex is the non-specific polar interaction between the negatively and positively charged groups in the polysaccharide and protein, respectively and that the complex is further stabilized by short-range interactions. The polysaccharide binding site should be able to go through the following conformational steps in the formation of the complex: random coil→ordered conformation→low distortion of this conformation to form a complementary fitting structure with the protein backbone. The sulfated monosaccharide units with the highest potential for anticoagulant activity should have two sulfate groups and a glycosidic linkage on the pyranose ring with C-2, C-3 and C-4 in 2S, 3R, 4R or 2R, 3S, 4S configurations for galactose, fucose and arabinose and 2S, 3S, 4R, for rhamnose. Three distributions of these substituents appear: 3-linked 2,4-disulfated units, 4-linked 2,3-disulfated units and 2-linked 3,4-disulfated residues. These types of units have the possibility, through the equilibrium of the chair conformations, to place their sulfate groups in adequate spacial positions to interact with basic groups of the protein. The anticoagulant activity is mainly attributed to thrombin inhibition mediated by antithrombin and/or heparin cofactor II, with different effectivenesses depending of the compound. Other mechanisms are also proposed and these differences could be attributed to the diversity of structures of the polysaccharides evaluated and to the fact that one compound may have more than one target protease. © 2010 Bentham Science Publishers Ltd. Fil:Ciancia, M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Quintana, I. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cerezo, A.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09298673_v17_n23_p2503_Ciancia |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
anticoagulant activity chemical structure disulfated structural units green seaweed structure-activity relationship Sulfated polysaccharides antithrombin arabinose carbohydrate fucose galactose glycosaminoglycan heparin cofactor II monosaccharide polysaccharide rhamnose sulfate thrombin anticoagulant therapy article drug activity drug binding drug conformation drug inhibition drug mechanism drug structure human hydrophobicity nonhuman seaweed structure activity relation Animals Anticoagulants Blood Coagulation Humans Molecular Structure Polysaccharides Seaweed Sulfates |
| spellingShingle |
anticoagulant activity chemical structure disulfated structural units green seaweed structure-activity relationship Sulfated polysaccharides antithrombin arabinose carbohydrate fucose galactose glycosaminoglycan heparin cofactor II monosaccharide polysaccharide rhamnose sulfate thrombin anticoagulant therapy article drug activity drug binding drug conformation drug inhibition drug mechanism drug structure human hydrophobicity nonhuman seaweed structure activity relation Animals Anticoagulants Blood Coagulation Humans Molecular Structure Polysaccharides Seaweed Sulfates Ciancia, M. Quintana, I. Cerezo, A.S. Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds |
| topic_facet |
anticoagulant activity chemical structure disulfated structural units green seaweed structure-activity relationship Sulfated polysaccharides antithrombin arabinose carbohydrate fucose galactose glycosaminoglycan heparin cofactor II monosaccharide polysaccharide rhamnose sulfate thrombin anticoagulant therapy article drug activity drug binding drug conformation drug inhibition drug mechanism drug structure human hydrophobicity nonhuman seaweed structure activity relation Animals Anticoagulants Blood Coagulation Humans Molecular Structure Polysaccharides Seaweed Sulfates |
| description |
The anticoagulant behavior of sulfated polysaccharides from seaweeds is reviewed based on their chemical structures. Analysis of the literature suggested that the driving force for the formation of the sulfated polysaccharide/ protein complex is the non-specific polar interaction between the negatively and positively charged groups in the polysaccharide and protein, respectively and that the complex is further stabilized by short-range interactions. The polysaccharide binding site should be able to go through the following conformational steps in the formation of the complex: random coil→ordered conformation→low distortion of this conformation to form a complementary fitting structure with the protein backbone. The sulfated monosaccharide units with the highest potential for anticoagulant activity should have two sulfate groups and a glycosidic linkage on the pyranose ring with C-2, C-3 and C-4 in 2S, 3R, 4R or 2R, 3S, 4S configurations for galactose, fucose and arabinose and 2S, 3S, 4R, for rhamnose. Three distributions of these substituents appear: 3-linked 2,4-disulfated units, 4-linked 2,3-disulfated units and 2-linked 3,4-disulfated residues. These types of units have the possibility, through the equilibrium of the chair conformations, to place their sulfate groups in adequate spacial positions to interact with basic groups of the protein. The anticoagulant activity is mainly attributed to thrombin inhibition mediated by antithrombin and/or heparin cofactor II, with different effectivenesses depending of the compound. Other mechanisms are also proposed and these differences could be attributed to the diversity of structures of the polysaccharides evaluated and to the fact that one compound may have more than one target protease. © 2010 Bentham Science Publishers Ltd. |
| format |
JOUR |
| author |
Ciancia, M. Quintana, I. Cerezo, A.S. |
| author_facet |
Ciancia, M. Quintana, I. Cerezo, A.S. |
| author_sort |
Ciancia, M. |
| title |
Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds |
| title_short |
Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds |
| title_full |
Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds |
| title_fullStr |
Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds |
| title_full_unstemmed |
Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds |
| title_sort |
overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds |
| url |
http://hdl.handle.net/20.500.12110/paper_09298673_v17_n23_p2503_Ciancia |
| work_keys_str_mv |
AT cianciam overviewofanticoagulantactivityofsulfatedpolysaccharidesfromseaweedsinrelationtotheirstructuresfocusingonthoseofgreenseaweeds AT quintanai overviewofanticoagulantactivityofsulfatedpolysaccharidesfromseaweedsinrelationtotheirstructuresfocusingonthoseofgreenseaweeds AT cerezoas overviewofanticoagulantactivityofsulfatedpolysaccharidesfromseaweedsinrelationtotheirstructuresfocusingonthoseofgreenseaweeds |
| _version_ |
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