136098-10-7 , Heparin disaccharide I-S, tetrasodium salt
C12H15NO19S3·4Na / 665.40
Heparin disaccharide I-S sodium salt is a synthetic glycosaminoglycan that has numerous potential applications in various fields of research and industry. In this paper, we provide a detailed overview of this compound, including its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.
Definition and Background
Heparin disaccharide I-S sodium salt is a synthetic disaccharide unit of heparin, which is a heavily sulfated glycosaminoglycan that is widely used as an anticoagulant drug. Heparin disaccharide I-S sodium salt contains two uronic acid residues, glucuronic acid and iduronic acid, which are connected by a 1-4 glycosidic bond. Heparin disaccharide I-S sodium salt is an intermediate compound in the synthesis of larger heparin oligosaccharides and provides a useful tool for studying the biological activities of heparin.
Physical and Chemical Properties
Heparin disaccharide I-S sodium salt is a white to off-white powder that is freely soluble in water. It has a molecular weight of 636.5 g/mol and a chemical formula of C_24H_30NaO_21S_2. The compound has a carboxyl group and two sulfate groups that confer a negative charge to the molecule.
Synthesis and Characterization
Heparin disaccharide I-S sodium salt can be synthesized by chemically cleaving larger heparin oligosaccharides using chemical or enzymatic methods. The resulting disaccharide can be purified and characterized using a variety of analytical techniques, including high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry.
Analytical Methods
Analytical methods used to study heparin disaccharide I-S sodium salt include HPLC, NMR spectroscopy, and mass spectrometry. HPLC is commonly used to separate and quantify heparin disaccharide I-S sodium salt and other heparin oligosaccharides. NMR spectroscopy provides detailed structural information about the molecule, including its conformation and sulfation pattern. Mass spectrometry is used to determine the molecular weight of the compound and to identify the presence of sulfate groups.
Biological Properties
Heparin disaccharide I-S sodium salt has been shown to exhibit anticoagulant and anti-inflammatory activities in vitro and in vivo. The compound binds to antithrombin III to accelerate the inhibition of clotting factors, preventing the formation of blood clots. Heparin disaccharide I-S sodium salt also inhibits the activity of heparanase, an enzyme that degrades the extracellular matrix, which can lead to inflammation and tissue damage.
Toxicity and Safety in Scientific Experiments
Studies have shown that heparin disaccharide I-S sodium salt is relatively safe and non-toxic in animal models, with no significant adverse effects observed at doses of up to 100 mg/kg. However, further studies are needed to determine the long-term safety and toxicity of this compound.
Applications in Scientific Experiments
Heparin disaccharide I-S sodium salt is used as a tool compound for studying the biological activities of heparin. The compound can be used to investigate the mechanisms of heparin's anticoagulant and anti-inflammatory activities and to develop new therapies for thrombotic and inflammatory diseases. Heparin disaccharide I-S sodium salt can also be used to develop new heparin-based biomaterials for tissue engineering and drug delivery.
Current State of Research
There is growing interest in the potential applications of heparin disaccharide I-S sodium salt in various fields of research and industry. Recent studies have focused on elucidating the structure-activity relationships of this compound and developing new synthetic methods for producing larger heparin oligosaccharides.
Potential Implications in Various Fields of Research and Industry
Heparin disaccharide I-S sodium salt has potential implications in various fields of research and industry, including drug discovery, biomaterials, and tissue engineering. The anticoagulant and anti-inflammatory properties of this compound make it a promising candidate for the development of new therapies for thrombotic and inflammatory diseases. Heparin disaccharide I-S sodium salt can also be used to create new heparin-based biomaterials for tissue engineering and drug delivery.
Limitations and Future Directions
One limitation of heparin disaccharide I-S sodium salt is its relatively low bioavailability, which may limit its therapeutic potential in vivo. Future research will focus on developing new synthetic methods and formulations to improve the pharmacokinetic and pharmacodynamic properties of this compound. Other future directions include elucidating the structure-activity relationships of heparin disaccharide I-S sodium salt and developing new applications for this compound in various fields of research and industry.
In conclusion, heparin disaccharide I-S sodium salt is a valuable tool compound for studying the biological activities of heparin and has potential applications in various fields of research and industry. Further research is needed to fully understand the properties and potential of this compound, but current studies suggest that it may hold promise for the development of new therapies for thrombotic and inflammatory diseases, as well as the creation of new biomaterials for tissue engineering and drug delivery.
CAS Number | 136098-10-7 |
Product Name | Heparin disaccharide I-S sodium salt |
IUPAC Name | tetrasodium;(2R,3R,4S)-2-[(2R,3S,4R,5R)-4,6-dihydroxy-5-(sulfonatoamino)-2-(sulfonatooxymethyl)oxan-3-yl]oxy-4-hydroxy-3-sulfonatooxy-3,4-dihydro-2H-pyran-6-carboxylate |
Molecular Formula | C12H15NNa4O19S3 |
Molecular Weight | 665.38 |
InChI | InChI=1S/C12H19NO19S3.4Na/c14-3-1-4(10(16)17)30-12(8(3)32-35(25,26)27)31-9-5(2-28-34(22,23)24)29-11(18)6(7(9)15)13-33(19,20)21;;;;/h1,3,5-9,11-15,18H,2H2,(H,16,17)(H,19,20,21)(H,22,23,24)(H,25,26,27);;;;/q;4*+1/p-4/t3-,5+,6+,7+,8+,9+,11?,12-;;;;/m0..../s1 |
InChI Key | RTDJNTXPZMQNEV-LXFQAIKPSA-J |
SMILES | C1=C(OC(C(C1O)OS(=O)(=O)[O-])OC2C(OC(C(C2O)NS(=O)(=O)[O-])O)COS(=O)(=O)[O-])C(=O)[O-].[Na+].[Na+].[Na+].[Na+] |
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