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Chondroitin sulfate

Names

[ CAS No. ]:
9007-28-7

[ Name ]:
Chondroitin sulfate

[Synonym ]:
Cholyltaurine
[14C]-Taurocholic acid
α-L-arabino-Hexopyranose, 2-(carboxyamino)-2-deoxy-3-O-β-D-glucopyranuronosyl-, 4-(hydrogen sulfate), (5ξ)-
chondroitin-4-sulfate
MFCD00146419
EINECS 232-696-9
chonodroitinsufuric acid
(5ξ)-2-(Carboxyamino)-2-deoxy-3-O-β-D-glucopyranuronosyl-4-O-sulfo-α-L-arabino-hexopyranose
2-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydrocyclopenta[a]phenanthren-17-yl)pentanoylamino]ethanesulfonic acid
Chondroitin (sulfate)

Biological Activity

[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.

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Signaling Pathways >> Immunology/Inflammation >> NO Synthase
Research Areas >> Inflammation/Immunology
Natural Products >> Others

[Target]

iNOS[1]MMPs[1]


[In Vitro]

Chondroitin sulfate is a class of sulfated glycosaminoglycans that are linear polysaccharides consisting of repeating disaccharide units composed of uronic acid and N-acetylhexosamine. Several pathogens including parasites, bacteria, and viruses have been shown to utilize cell surface chondroitin sulfate chains to attach to and infect host cells[1]. Chondroitin sulfate occurs naturally in the extracellular matrix of connective tissues, e.g., bone, cartilage, skin, ligaments and tendons. Chondroitin sulfate has been shown to elicit a range of beneficial effects: anti-inflammatory effects, an increase in type II collagen and proteoglycans, a reduction in bone resorption and a better anabolic/catabolic balance in chondrocytes[2]. A large range of chondroitin sulfate concentrations has been used (e.g. 12.5 to 2000 mg/mL, but generally less than200 mg/mL) in in vitro studies. Chondroitin sulfate (200 mg/mL) decreases the chondrocyte susceptibility to single nucleotide polymorphism-induced apoptosis[3]. Chondroitin sulfate reduces inflammation mediators and the apoptotic process and is able to reduce protein production of inflammatory cytokines, iNOS, MMPs[4].

[In Vivo]

The high content of chondroitin sulfate in the aggrecan plays a major part in allowing cartilage to resist tensile stresses during various loading conditions by providing this tissue with resistance and elasticity. It has been shown that chondroitin sulphate interferes with the progression of structural changes in joint tissues and is used in the management of patients with osteoarthritis[3]. Chondroitin sulfate is mostly administered orally at doses ranging from 800 to 1200mg/day. Chondroitin sulfate is rapidly absorbed by the gastrointestinal tract. The absorbed chondroitin sulfate reaches the blood compartment as 10% chondroitin sulfate and 90% depolymerized low-molecular-weight derivatives[5].

[Cell Assay]

Chondrocytes are cultured into six-well culture plates. 12 hours after plating, the culture medium is replaced with 2.0 mL of fresh medium containing LPS at a concentration of 50 mg/mL. 4 hours later, HA, Chondroitin sulfate, HS, keratan sulphate and DS are added separately to each of the wells at concentrations of 0.5 and 1.0 mg/mL. The number of viable chondrocytes is then quantified by trypan blue dye exclusion test from several randomly chosen areas of each well[4].

[Related Small Molecules]

3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Retinoic acid | Melatonine | GM 6001 | T-5224 | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | L-NAME HCl | Dehydroepiandrosterone | Corticosterone

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Molecular Formula ]:
(C14H21NO14S)n

[ Molecular Weight ]:
479.368

[ Exact Mass ]:
479.058105

[ PSA ]:
287.45000

[ LogP ]:
-4.28

[ Index of Refraction ]:
1.686

[ Storage condition ]:
Store at RT.

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GA8430000
CHEMICAL NAME :
Chondroitin sulfuric acids
CAS REGISTRY NUMBER :
9007-28-7
LAST UPDATED :
199701

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2340 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,506,1972 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
455 gm/kg/26W-I
TOXIC EFFECTS :
Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 6,478,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1680 mg/kg/14D-I
TOXIC EFFECTS :
Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 14,3371,1980 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3876 No. of Facilities: 3 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 19 (estimated) No. of Female Employees: 19 (estimated)

Safety Information

[ Hazard Codes ]:
T+


Related Compounds