title: A heparin-like compound isolated from a marine crab rich in glucuronic acid 2-O-sulfate presents low anticoagulant activity.
abstract: A natural heparin-like compound isolated from the crab Goniopsis cruentata was structurally characterized and its anticoagulant and hemorrhagic activities were determined. Enzymatic and nuclear magnetic resonance analysis revealed that its structure is rich in disulfated disaccharides, possessing significant amounts of 2-O-sulfated-β-D-glucuronic acid units. Furthermore, low amounts of trisulfated disaccharide units containing 2-O-sulfated-α-L-iduronic acid were detected, when compared to mammalian heparin. In addition, this heparin-like structure showed negligible in vitro anticoagulant activity and low bleeding potency, facts that make it a suitable candidate for the development of structure-driven, heparin based therapeutic agents with fewer undesirable effects.
authors.affiliation: Departamento de Bioquímica, Universidade Federal do Rio Grande do Norte, Natal, RN, Brazil.
authors.forename: Giulianna P V
authors.initials: GP
authors.lastname: Andrade
authors.forename: Marcelo A
authors.initials: MA
authors.lastname: Lima
authors.forename: Airton A
authors.initials: AA
authors.lastname: de Souza Junior
authors.forename: Jawed
authors.initials: J
authors.lastname: Fareed
authors.forename: Debra A
authors.initials: DA
authors.lastname: Hoppensteadt
authors.forename: Elizeu A
authors.initials: EA
authors.lastname: Santos
authors.forename: Suely F
authors.initials: SF
authors.lastname: Chavante
authors.forename: Fernanda W
authors.initials: FW
authors.lastname: Oliveira
authors.forename: Hugo A O
authors.initials: HA
authors.lastname: Rocha
authors.forename: Helena B
authors.initials: HB
authors.lastname: Nader
mesh_terms: D000818:Animals; D000925:Anticoagulants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D003386:Brachyura / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002417:Cattle; D004187:Disaccharides / Q000737:chemistry; D005944:Glucosamine / Q000737:chemistry; D005965:Glucuronates / Q000737:chemistry* / Q000302:isolation & purification; D006493:Heparin / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006497:Heparan Sulfate / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008970:Molecular Weight; D010314:Partial Thromboplastin Time; D051381:Rats; D014574:Uronic Acids / Q000737:chemistry
chemical_list: D000925:Anticoagulants; D004187:Disaccharides; D005944:Glucosamine; D005965:Glucuronates; D006493:Heparin; D006497:Heparan Sulfate; D014574:Uronic Acids; C046100:glucuronic acid 2-sulfate