Chondroitin sulfate

Details:

Chemical Properties of Chondroitin sulfate

Cas No.	9007-28-7
PubChem ID	24766	Appearance	Off-white powder
Formula	C13H21NO15S	M.Wt	463.37
Type of Compound	Miscellaneous	Storage	Desiccate at -20°C
Synonyms	Chondroitin sulfate A;Chondroitin polysulfate;Chondroitin sulfates;24967-93-9
Solubility	H2O : ≥ 50 mg/mL *"≥" means soluble, but saturation unknown.
Chemical Name	(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES	CC(=O)NC1C(C(C(OC1O)OS(=O)(=O)O)O)OC2C(C(C(C(O2)C(=O)O)O)O)O
Standard InChIKey	KXKPYJOVDUMHGS-OSRGNVMNSA-N
Standard InChI	InChI=1S/C13H21NO15S/c1-2(15)14-3-8(7(19)13(28-11(3)22)29-30(23,24)25)26-12-6(18)4(16)5(17)9(27-12)10(20)21/h3-9,11-13,16-19,22H,1H3,(H,14,15)(H,20,21)(H,23,24,25)/t3-,4+,5+,6-,7-,8-,9+,11-,12-,13-/m1/s1
General tips	For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging	1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment.
Shipping Condition	Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Chondroitin sulfate

From Shark cartilage

Biological Activity of Chondroitin sulfate

Description	Chondroitin sulfate has anti-inflammatory and chondroprotective actions ,it has been widely used in the treatment of osteoarthritis. Chondroitin sulfate reduces inflammation mediators and the apoptotic process and is able to reduce protein production of inflammatory cytokines, iNOS and MMPs.Chondroitin sulfate is a regulator of neuronal patterning in the retina, in the developing mammalian retina, gradual regression of chondroitin sulfate may help control the onset of ganglion cell differentiation and initial direction of their axons.
Targets	TNF-α | COX | NO | NF-kB | JNK | ERK | p38MAPK
In vivo	MicroRNAs in the axon locally mediate the effects of chondroitin sulfate proteoglycans and cGMP on axonal growth.[Pubmed: 25788427] Dev Neurobiol. 2015 Mar 18. Axonal miRNAs locally regulate axonal growth by modulating local protein composition. Whether localized miRNAs in the axon mediate the inhibitory effect of Chondroitin sulfate proteoglycans (CSPGs) on the axon remains unknown. METHODS AND RESULTS: We showed that in cultured cortical neurons, axonal application of CSPGs inhibited axonal growth and altered axonal miRNA profiles, whereas elevation of axonal cyclic guanosine monophosphate (cGMP) levels by axonal application of sildenafil reversed the effect of CSPGs on inhibition of axonal growth and on miRNA profiles. Specifically, CSPGs elevated and reduced axonal levels of miR-29c and integrin β1 (ITGB1) proteins, respectively, while elevation of cGMP levels overcame these CSPG effects. Gain-of- and loss-of-function experiments demonstrated that miR-29c in the distal axon mediates axonal growth downstream of CSPGs and cGMP by regulating axonal protein levels of ITGB1, FAK, and RhoA. CONCLUSIONS: Together, our data demonstrate that axonal miRNAs play an important role in mediating the inhibitory action of CSPGs on axonal growth and that miR-29c at least partially mediates this process. Chondroitin sulfate as a regulator of neuronal patterning in the retina.[Pubmed: 1738848] Science. 1992 Feb 7;255(5045):733-6. Highly sulfated proteoglycans are correlated with axon boundaries in the developing central nervous system which suggests that these molecules affect neural pattern formation. METHODS AND RESULTS: In the developing mammalian retina, gradual regression of Chondroitin sulfate may help control the onset of ganglion cell differentiation and initial direction of their axons. Changes induced by the removal of Chondroitin sulfate from intact retinas in culture confirm the function of Chondroitin sulfate in retinal histogenesis.

Protocol of Chondroitin sulfate

Kinase Assay

Anti-inflammatory activity of chondroitin sulfate.[Pubmed: 18667340 ] Osteoarthritis Cartilage. 2008;16 Suppl 3:S14-8. Osteoarthritis is primarily characterized by areas of destruction of articular cartilage and by synovitis. METHODS AND RESULTS: Articular damage and synovitis are secondary to local increase of pro-inflammatory cytokines (interleukin-1beta and tumor necrosis factor-alpha), enzymes with proteolytic activity (matrix metalloproteinases), and enzymes with pro-inflammatory activity (cyclooxygenase-2 and nitric oxide synthase-2). Enhanced expression of these proteins in chondrocytes and in synovial membrane appears associated to the activation and nuclear translocation of nuclear factor-kappaB (NF-kappaB). Chondroitin sulfate (CS) prevents joint space narrowing and reduces joint swelling and effusion. To produce these effects, CS elicits an anti-inflammatory effect at the chondral and synovial levels. CS and its disaccharides reduce NF-kappaB nuclear translocation, probably by diminishing extracellular signal-regulated kinase1/2, p38mitogen-activated protein kinase and c-Jun N-terminal kinase activation. CONCLUSIONS: This review discusses the evidence supporting that CS pleiotropic effects in chondrocytes and synoviocytes are primarily due to a common mechanism, e.g., the inhibition of NF-kappaB nuclear translocation.

Structure Identification

Carbohydr Polym. 2015 May 5;121:362-71. Inhibitory effect of chondroitin sulfate oligosaccharides on bovine testicular hyaluronidase.[Pubmed: 25659711] Hyaluronan and Chondroitin sulfates are prominent components of the extracellular matrices of animal tissues; however, their functions in relation to their oligosaccharide structures have not yet been fully elucidated. METHODS AND RESULTS: The oligosaccharides of hyaluronan and Chondroitin sulfate were prepared and used to investigate their effects on the hydrolysis and transglycosylation reactions of bovine testicular hyaluronidase when hyaluronan was used as a substrate. Hydrolysis and transglycosylation activities were assessed in independent reaction systems by analyzing the products by HPLC. The hydrolysis and transglycosylation reactions of bovine testicular hyaluronidase were dose-dependently inhibited by Chondroitin sulfate oligosaccharides, but not by hyaluronan or chondroitin oligosaccharides. CONCLUSIONS: A kinetic analysis of the hydrolysis reaction using hyaluronan octasaccharide revealed that the inhibition mode by Chondroitin sulfate oligosaccharides was competitive.

Preparing Stock Solutions of Chondroitin sulfate

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.1581 mL	10.7905 mL	21.581 mL	43.1621 mL	53.9526 mL
5 mM	0.4316 mL	2.1581 mL	4.3162 mL	8.6324 mL	10.7905 mL
10 mM	0.2158 mL	1.0791 mL	2.1581 mL	4.3162 mL	5.3953 mL
50 mM	0.0432 mL	0.2158 mL	0.4316 mL	0.8632 mL	1.0791 mL
100 mM	0.0216 mL	0.1079 mL	0.2158 mL	0.4316 mL	0.5395 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

 

References on Chondroitin sulfate

Anti-inflammatory activity of chondroitin sulfate.[Pubmed:18667340]

Osteoarthritis Cartilage. 2008;16 Suppl 3:S14-8.

Osteoarthritis is primarily characterized by areas of destruction of articular cartilage and by synovitis. Articular damage and synovitis are secondary to local increase of pro-inflammatory cytokines (interleukin-1beta and tumor necrosis factor-alpha), enzymes with proteolytic activity (matrix metalloproteinases), and enzymes with pro-inflammatory activity (cyclooxygenase-2 and nitric oxide synthase-2). Enhanced expression of these proteins in chondrocytes and in synovial membrane appears associated to the activation and nuclear translocation of nuclear factor-kappaB (NF-kappaB). Chondroitin sulfate (CS) prevents joint space narrowing and reduces joint swelling and effusion. To produce these effects, CS elicits an anti-inflammatory effect at the chondral and synovial levels. CS and its disaccharides reduce NF-kappaB nuclear translocation, probably by diminishing extracellular signal-regulated kinase1/2, p38mitogen-activated protein kinase and c-Jun N-terminal kinase activation. This review discusses the evidence supporting that CS pleiotropic effects in chondrocytes and synoviocytes are primarily due to a common mechanism, e.g., the inhibition of NF-kappaB nuclear translocation.

Inhibitory effect of chondroitin sulfate oligosaccharides on bovine testicular hyaluronidase.[Pubmed:25659711]

Carbohydr Polym. 2015 May 5;121:362-71.

Hyaluronan and Chondroitin sulfates are prominent components of the extracellular matrices of animal tissues; however, their functions in relation to their oligosaccharide structures have not yet been fully elucidated. The oligosaccharides of hyaluronan and Chondroitin sulfate were prepared and used to investigate their effects on the hydrolysis and transglycosylation reactions of bovine testicular hyaluronidase when hyaluronan was used as a substrate. Hydrolysis and transglycosylation activities were assessed in independent reaction systems by analyzing the products by HPLC. The hydrolysis and transglycosylation reactions of bovine testicular hyaluronidase were dose-dependently inhibited by Chondroitin sulfate oligosaccharides, but not by hyaluronan or chondroitin oligosaccharides. A kinetic analysis of the hydrolysis reaction using hyaluronan octasaccharide revealed that the inhibition mode by Chondroitin sulfate oligosaccharides was competitive.

Chondroitin sulfate as a regulator of neuronal patterning in the retina.[Pubmed:1738848]

Science. 1992 Feb 7;255(5045):733-6.

Highly sulfated proteoglycans are correlated with axon boundaries in the developing central nervous system which suggests that these molecules affect neural pattern formation. In the developing mammalian retina, gradual regression of Chondroitin sulfate may help control the onset of ganglion cell differentiation and initial direction of their axons. Changes induced by the removal of Chondroitin sulfate from intact retinas in culture confirm the function of Chondroitin sulfate in retinal histogenesis.

TGF-ss Regulates Cathepsin Activation during Normal and Pathogenic Development.[Pubmed:29539424]

Cell Rep. 2018 Mar 13;22(11):2964-2977.

Cysteine cathepsins play roles during development and disease beyond their function in lysosomal protein turnover. Here, we leverage a fluorescent activity-based probe (ABP), BMV109, to track cysteine cathepsins in normal and diseased zebrafish embryos. Using this probe in a model of mucolipidosis II, we show that loss of carbohydrate-dependent lysosomal sorting alters the activity of several cathepsin proteases. The data support a pathogenic mechanism where TGF-ss signals enhance the proteolytic processing of pro-Ctsk by modulating the expression of chondroitin 4-sulfate (C4-S). In MLII, elevated C4-S corresponds with TGF-ss-mediated increases in chst11 expression. Inhibiting chst11 impairs the proteolytic activation of Ctsk and alleviates the MLII phenotypes. These findings uncover a regulatory loop between TGF-ss signaling and Ctsk activation that is altered in the context of lysosomal disease. This work highlights the power of ABPs to identify mechanisms underlying pathogenic development in living animals.

MicroRNAs in the axon locally mediate the effects of chondroitin sulfate proteoglycans and cGMP on axonal growth.[Pubmed:25788427]

Dev Neurobiol. 2015 Dec;75(12):1402-19.

Axonal miRNAs locally regulate axonal growth by modulating local protein composition. Whether localized miRNAs in the axon mediate the inhibitory effect of Chondroitin sulfate proteoglycans (CSPGs) on the axon remains unknown. We showed that in cultured cortical neurons, axonal application of CSPGs inhibited axonal growth and altered axonal miRNA profiles, whereas elevation of axonal cyclic guanosine monophosphate (cGMP) levels by axonal application of sildenafil reversed the effect of CSPGs on inhibition of axonal growth and on miRNA profiles. Specifically, CSPGs elevated and reduced axonal levels of miR-29c and integrin beta1 (ITGB1) proteins, respectively, while elevation of cGMP levels overcame these CSPG effects. Gain-of- and loss-of-function experiments demonstrated that miR-29c in the distal axon mediates axonal growth downstream of CSPGs and cGMP by regulating axonal protein levels of ITGB1, FAK, and RhoA. Together, our data demonstrate that axonal miRNAs play an important role in mediating the inhibitory action of CSPGs on axonal growth and that miR-29c at least partially mediates this process.

Description

Chondroitin sulfate, one of five classes of glycosaminoglycans, has been widely used in the treatment of osteoarthritis. Chondroitin sulfate reduces inflammation mediators and the apoptotic process and is able to reduce protein production of inflammatory cytokines, iNOS and MMPs.

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