Anticoagulant and antithrombotic properties of synthetic sulfated bis-lactobionic acid amides

Raake, W; Klauser, R.; Elling, H; Meinetsberger, E.

doi:10.1016/0049-3848(89)90289-2

Cited by 15 publications

(9 citation statements)

References 17 publications

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“…Raake et al. synthesized low MW polysulfated bis‐lactobionic acid amides which possessed moderate to low anticoagulant activity . One of the compounds, LW10082 (Aprosulate, 16 ) showed similar antithrombotic activity to LMWH and was initially found to stimulate HCII; but inactivation of both FV, FX, and FVIII has also been reported.…”

Section: Heparin Mimeticsmentioning

confidence: 99%

“…75 Raake et al synthesized low MW polysulfated bis-lactobionic acid amides which possessed moderate to low anticoagulant activity. 76 One of the compounds, LW10082 (Aprosulate, 16) showed similar antithrombotic activity to LMWH and was initially found to stimulate HCII 77 ; but inactivation of both FV, FX, 78 and FVIII has also been reported. Abendschein and co-workers synthesized the highly sulfated tetrasaccharide derivative maltodapoh (17) as an anticoagulant consisting of two maltose sugars linked through 1,3-diamino-2-propanol.…”

Section: Polysulfated Non-heparin Oligosaccharides and Derivativesmentioning

confidence: 99%

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Heparin mimetics with anticoagulant activity

Al-Nahain

Ignjatović

Monagle

et al. 2018

Medicinal Research Reviews

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Heparin, a sulfated polysaccharide belonging to the glycosaminoglycan family, has been widely used as an anticoagulant drug for decades and remains the most commonly used parenteral anticoagulant in adults and children. However, heparin has important clinical limitations and is derived from animal sources which pose significant safety and supply problems. The ever growing shortage of the raw material for heparin manufacturing may become a very significant issue in the future. These global limitations have prompted much research, especially following the recent well-publicized contamination scandal, into the development of alternative anticoagulants derived from non-animal and/or totally synthetic sources that mimic the structural features and properties of heparin. Such compounds, termed heparin mimetics, are also needed as anticoagulant materials for use in biomedical applications (e.g., stents, grafts, implants etc.). This review encompasses the development of heparin mimetics of various structural classes, including synthetic polymers and non-carbohydrate small molecules as well as sulfated oligo- and polysaccharides, and fondaparinux derivatives and conjugates, with a focus on developments in the past 10 years.

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Section: Heparin Mimeticsmentioning

confidence: 99%

Section: Polysulfated Non-heparin Oligosaccharides and Derivativesmentioning

confidence: 99%

Heparin mimetics with anticoagulant activity

Al-Nahain

Ignjatović

Monagle

et al. 2018

Medicinal Research Reviews

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“…The most important physiological effect of LBA is the anticoagulant and antithrombotic activity of its sulfated derivative bislactobionic acid amides, which have been studied as potential anticoagulant and antithrombotic agents, without a risk of bleeding (Colwell, Grupe, & Tollefsen, 1999;Raake, Klauser, Elling, & Meinetsberger, 1989). This compound, also known as Aprosulate sodium, stimulated HCII activity in vitro (Klauser, 1991) and has been found to delay the activation of factor X and prothrombin in plasma and to inhibit factor IXa/VIIIa complex (Xase) (Ofosu et al, 1992;Sugidachi, Asai, & Koike, 1994).…”

Section: Physiological Effects Of Lactobionic Acidmentioning

confidence: 97%

Lactobionic acid: A high value-added lactose derivative for food and pharmaceutical applications

Gutiérrez

Hamoudi

Belkacemi

2012

International Dairy Journal

112

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“…synthesis of bis-aldonic acid amides involved lactonization of aldonic acids, 2 reaction of the aldonic acid lac tones with α,ω)-diamines, and sulfation of the intermedi ates by use of pyridine-SO 3 complex. The identity and purity of the substances were established by routine quality control procedures, including elemental analysis, 13 C nuclear magnetic resonance (NMR) spectroscopy, 1 H NMR spectroscopy (360 MHz), cellulose acetate electrophoresis, and high-performance gel-permeation chromatography. All analyses gave satisfactory results, indicating identity and purity of the synthesized com pounds.…”

mentioning

confidence: 99%

Derivatives of Bis-Aldonic Acid Amides and Their Anticoagulant and Antithrombotic Properties

Raake

Klauser²,

Elling³

et al. 1994

Semin Thromb Hemost

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Aprosulate sodium was the first representative of a new class of synthetic polyanions showing antithrombotic efficacy in different animal models. In several clinical trails (Phase I) in human volunteers aprosulate demonstrated anticoagulant properties, too. Searching for other active substances of similar structure, a series of bis-aldonic acid amides were synthesized. These compounds exhibited interesting antithrombotic and anticoagulant activities. The pharmacodynamic activities of the compounds LW 10121, LW 10125, LW 10114, 10244, and LW 10168 are summarized in this article. These substances prolonged the APTT to 150% of the blank values at concentrations of 1.5 to 13.5 micrograms/mL. The thrombin time and anti-Xa test were only slightly influenced by concentrations up to 100 micrograms/mL. All compounds were investigated in a jugular vein hemostasis model in rats to examine their antithrombotic potential. They all had an antithrombotic activity lower than aprosulate, except compound LW 10121, which seemed to be a little more active. The subcutaneous injection of 10 mg/kg LW 10121 resulted in a longer duration of action than aprosulate and heparin. On the basis of the chemical structure and the profile of action, it is assumed that the new compounds may possess the same mode of action as aprosulate, but the mechanism of action may be different from heparin and low molecular weight heparins.

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Anticoagulant and antithrombotic properties of synthetic sulfated bis-lactobionic acid amides

Cited by 15 publications

References 17 publications

Heparin mimetics with anticoagulant activity

Heparin mimetics with anticoagulant activity

Lactobionic acid: A high value-added lactose derivative for food and pharmaceutical applications

Derivatives of Bis-Aldonic Acid Amides and Their Anticoagulant and Antithrombotic Properties

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