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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Autor principal: Ciancia, M.
Otros Autores: Quintana, I., Cerezo, A.S
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2010
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 scopus  |a 2-s2.0-77955602234 
024 7 |2 cas  |a antithrombin, 9000-94-6; arabinose, 147-81-9; fucose, 3615-37-0, 3713-31-3; galactose, 26566-61-0, 50855-33-9, 59-23-4; heparin cofactor II, 81604-65-1; rhamnose, 10485-94-6, 3615-41-6; sulfate, 14808-79-8; thrombin, 869858-13-9, 9002-04-4; Anticoagulants; Polysaccharides; Sulfates 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a CMCHE 
100 1 |a Ciancia, M. 
245 1 0 |a Overview of anticoagulant activity of sulfated polysaccharides from seaweeds in relation to their structures, focusing on those of green seaweeds 
260 |c 2010 
270 1 0 |m Cerezo, A. S.; CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina; email: cerezo@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
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520 3 |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. © 2010 Bentham Science Publishers Ltd.  |l eng 
593 |a Cátedra 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 
593 |a CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina 
593 |a Laboratorio 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 
690 1 0 |a ANTICOAGULANT ACTIVITY 
690 1 0 |a CHEMICAL STRUCTURE 
690 1 0 |a DISULFATED STRUCTURAL UNITS 
690 1 0 |a GREEN SEAWEED 
690 1 0 |a STRUCTURE-ACTIVITY RELATIONSHIP 
690 1 0 |a SULFATED POLYSACCHARIDES 
690 1 0 |a ANTITHROMBIN 
690 1 0 |a ARABINOSE 
690 1 0 |a CARBOHYDRATE 
690 1 0 |a FUCOSE 
690 1 0 |a GALACTOSE 
690 1 0 |a GLYCOSAMINOGLYCAN 
690 1 0 |a HEPARIN COFACTOR II 
690 1 0 |a MONOSACCHARIDE 
690 1 0 |a POLYSACCHARIDE 
690 1 0 |a RHAMNOSE 
690 1 0 |a SULFATE 
690 1 0 |a THROMBIN 
690 1 0 |a ANTICOAGULANT THERAPY 
690 1 0 |a ARTICLE 
690 1 0 |a DRUG ACTIVITY 
690 1 0 |a DRUG BINDING 
690 1 0 |a DRUG CONFORMATION 
690 1 0 |a DRUG INHIBITION 
690 1 0 |a DRUG MECHANISM 
690 1 0 |a DRUG STRUCTURE 
690 1 0 |a HUMAN 
690 1 0 |a HYDROPHOBICITY 
690 1 0 |a NONHUMAN 
690 1 0 |a SEAWEED 
690 1 0 |a STRUCTURE ACTIVITY RELATION 
690 1 0 |a ANIMALS 
690 1 0 |a ANTICOAGULANTS 
690 1 0 |a BLOOD COAGULATION 
690 1 0 |a HUMANS 
690 1 0 |a MOLECULAR STRUCTURE 
690 1 0 |a POLYSACCHARIDES 
690 1 0 |a SEAWEED 
690 1 0 |a SULFATES 
700 1 |a Quintana, I. 
700 1 |a Cerezo, A.S. 
773 0 |d 2010  |g v. 17  |h pp. 2503-2529  |k n. 23  |p Curr. Med. Chem.  |x 09298673  |t Current Medicinal Chemistry 
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856 4 0 |u https://doi.org/10.2174/092986710791556069  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_09298673_v17_n23_p2503_Ciancia  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09298673_v17_n23_p2503_Ciancia  |y Registro en la Biblioteca Digital 
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962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
999 |c 68651 

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