Kartogenin

Names

[ Name ]:
Kartogenin

[Synonym ]:
2-[([1,1'-biphenyl]-4-ylamino)carbonyl]benzoic acid
Kartogenin
2-([1,1'-Biphenyl]-4-ylcarbamoyl)benzoic acid
Benzoic acid, 2-[([1,1'-biphenyl]-4-ylamino)carbonyl]-
2-(4-Biphenylylcarbamoyl)benzoic acid
2-(Biphenyl-4-ylcarbamoyl)benzoic acid
KGN

Biological Activity

[Description]:

Kartogenin is an inducer of differentiation of human mesenchymal stem cells into chondrocytes.

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> TGF-beta/Smad

Signaling Pathways >> TGF-beta/Smad >> TGF-beta/Smad

Research Areas >> Others

[In Vitro]

Kartogenin enhances cell proliferation in both cell types in a concentration-dependent manner and induces chondrogenic differentiation of stem cells, as demonstrated by high expression levels of chondrogenic markers aggrecan, collagen II and Sox-9. Besides, kartogenin induces the formation of cartilage-like tissues in cell cultures, as observed through the staining of abundant proteoglycans, collagen II and osteocalcin[1]. Kartogenin stimulates type-I collagen synthesis of fibroblasts at the mRNA and protein levels in a time-dependent manner without obvious influence on fibroblasts’ apoptosis and viability. Smad4/smad5 of the TGF-β signaling pathway is activated by kartogenin while MAPK signaling pathway remains unchanged[2]. Kartogenin treatment enhances chondrocyte pericellular matrix assembly and retention in the presence of IL-1β. Kartogenin partially blocks the IL-1β-induced increased expression of ADAMTS-5. Additionally, kartogenin-treated articular chondrocytes exhibits a decrease in CD44 proteolytic fragmentation[3].

[In Vivo]

hen injected into intact rat patellar tendons, kartogenin induces cartilage-like tissue formation in the injected area. When injected into experimentally injured rat Achilles TBJs, wound healing in the TBJs is enhanced, as evidenced by the formation of extensive cartilage-like tissues[1]. Kartogenin stimulates collagen synthesis in the mouse dermis. Dermis in the kartogenin (100 nM)-treated group exhibits increased dermal thickness and intense blue staining, which represents more collagen composition in the dermis[2].

[Cell Assay]

Rabbit BMSCs or PTSCs are treated with various concentrations (1 nM to 5 μM) of kartogenin. The medium is changed every 3 days and after 2 weeks, cell proliferation is measured by population doubling time[1].

[Animal admin]

Rats: Then rats are divided into two groups based on the injections received: six rats are given 10 µL saline injections in each wound (wound-only group) and six rats receive 10 µL of 100 µM kartogenin solution each in the wounded areas (wound+kartogenin group). The injections are given immediately after wounding and repeated on days 2, 4, 7 and 12[1].

[References]

[1]. Zhang J, et al. Kartogenin induces cartilage-like tissue formation in tendon-bone junction. Bone Res. 2014;2. pii: 14008.

[2]. Wang J, et al. A heterocyclic molecule kartogenin induces collagen synthesis of human dermal fibroblasts by activating the smad4/smad5 pathway. Biochem Biophys Res Commun. 2014 Jul 18;450(1):568-74.

[3]. Ono Y, et al. Chondroprotective Effect of Kartogenin on CD44-Mediated Functions in Articular Cartilage and Chondrocytes. Cartilage. 2014 Jul;5(3):172-80.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
464.4±38.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₀H₁₅NO₃

[ Molecular Weight ]:
317.338

[ Flash Point ]:
234.6±26.8 °C

[ Exact Mass ]:
317.105194

[ PSA ]:
66.40000

[ LogP ]:
3.81

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.674

[ Storage condition ]:
room temp

[ Water Solubility ]:
DMSO: >15mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H319-H410

[ Precautionary Statements ]:
P273-P305 + P351 + P338-P501

[ Hazard Codes ]:
Xn,N

[ Risk Phrases ]:
22-36-50/53

[ Safety Phrases ]:
60-61

[ RIDADR ]:
UN 3077 9 / PGIII

[ Hazard Class ]:
9.0

[ HS Code ]:
2924299090

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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