Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds

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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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Detalles Bibliográficos
Autor principal: Ciancia, Marina
Otros Autores: Quintana, Irene, Cerezo, A. S.
Formato: Artículo
Lenguaje:Inglés
Materias:
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
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
SULFATES
Acceso en línea:http://ri.agro.uba.ar/files/intranet/articulo/2010Ciancia.pdf
LINK AL EDITOR
Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central (FAUBA) de Universidad de Buenos Aires
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245 0 0 |a Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds 
520 |a 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. 
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653 0 |a HUMAN 
653 0 |a HYDROPHOBICITY 
653 0 |a NONHUMAN 
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653 0 |a ANIMALS 
653 0 |a ANTICOAGULANTS 
653 0 |a BLOOD COAGULATION 
653 0 |a HUMANS 
653 0 |a MOLECULAR STRUCTURE 
653 0 |a POLYSACCHARIDES 
653 0 |a SEAWEED 
653 0 |a SULFATES 
700 1 |9 67122  |a Quintana, Irene 
700 1 |a Cerezo, A. S.  |9 69393 
773 |t Current Medicinal Chemistry  |g Vol. 17, no. 23 (2010) 2503-2529 
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900 |a ^aCiancia, M.^tCátedra de Química de Biomoléculas, Departamento de Biología Aplicada y Alimentos, Facultad de Agronomía, Universidad de Buenos Aires, Av. San Martín 4453, 1417 Buenos Aires, Argentina 
900 |a ^aQuintana, I.^tCIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina 
900 |a ^aCerezo, A.S.^tLaboratorio de Hemostasia y Trombosis, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina 
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900 |a DISULFATED STRUCTURAL UNITS 
900 |a GREEN SEAWEED 
900 |a STRUCTURE-ACTIVITY RELATIONSHIP 
900 |a SULFATED POLYSACCHARIDES 
900 |a ANTITHROMBIN 
900 |a ARABINOSE 
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900 |a HEPARIN COFACTOR II 
900 |a MONOSACCHARIDE 
900 |a POLYSACCHARIDE 
900 |a RHAMNOSE 
900 |a SULFATE 
900 |a THROMBIN 
900 |a ANTICOAGULANT THERAPY 
900 |a DRUG ACTIVITY 
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900 |a DRUG CONFORMATION 
900 |a DRUG INHIBITION 
900 |a DRUG MECHANISM 
900 |a DRUG STRUCTURE 
900 |a HUMAN 
900 |a HYDROPHOBICITY 
900 |a NONHUMAN 
900 |a SEAWEED 
900 |a STRUCTURE ACTIVITY RELATION 
900 |a ANIMALS 
900 |a ANTICOAGULANTS 
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900 |a SEAWEED 
900 |a SULFATES 
900 |a 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. 
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