| Identification | Back Directory | [Name]
KGN | [CAS]
4727-31-5 | [Synonyms]
KGN
100822
CS-612
Kartogenin
KGN USP/EP/BP
Kartogenin(KGN)
4'-Phenylphthalanilic Acid
n-Biphenyl-4-yl-phthalamic acid
4′-Phenyl-phthalanilic acid (8CI)
2-[(Biphenyl-4-yl)carbaMoyl]benzoic Acid
2-[(4-phenylphenyl)carbamoyl]benzoic Acid
2-([1,1'-biphenyl]-4-ylcarbaMoyl)benzoic acid
2-[([1,1'-Biphenyl]-4-ylaMino)carbonyl]benzoic Acid
Benzoic acid, 2-[([1,1'-biphenyl]-4-ylamino)carbonyl]- | [Molecular Formula]
C20H15NO3 | [MDL Number]
MFCD00560510 | [MOL File]
4727-31-5.mol | [Molecular Weight]
317.338 |
| Chemical Properties | Back Directory | [Melting point ]
272 °C | [Boiling point ]
464.4±38.0 °C(Predicted) | [density ]
1.289±0.06 g/cm3(Predicted) | [storage temp. ]
room temp | [solubility ]
DMSO: >15mg/mL | [form ]
powder | [pka]
3.45±0.36(Predicted) | [color ]
White | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. | [InChI]
1S/C20H15NO3/c22-19(17-8-4-5-9-18(17)20(23)24)21-16-12-10-15(11-13-16)14-6-2-1-3-7-14/h1-13H,(H,21,22)(H,23,24) | [InChIKey]
SLUINPGXGFUMLL-UHFFFAOYSA-N | [SMILES]
O=C(NC1=CC=C(C2=CC=CC=C2)C=C1)C(C=CC=C3)=C3C(O)=O |
| Hazard Information | Back Directory | [Description]
Kartogenin potently induces differentiation of human mesenchymal stem cells into chondrocytes with an EC50 value of 100 nM.1 Kartogenin induces chondrogenesis by binding the actin-binding protein, filamin A, which disrupts its interaction with the transcription factor core-binding factor β subunit (CBFβ). When dissociated from filamin A, CBFβ translocates to the nucleus and forms a transcriptional complex with the runt-related transcription factor RUNX1, which enables chondrocyte differentiation. Kartogenin has been shown to promote cartilage repair in a mouse model of osteoarthritis and to protect against cytokine-induced damage in osteoarthritic bovine articular chondrocytes in vitro.1 | [Uses]
Kartogenin is a potent, selective, and non-cytotoxic downstream RUNX1 and RUNX2 modulator. Kartogenin causes mesenchymal stem cells found in joints to differentiate into chondrocyte cells that can build cartilage where it has been destroyed. | [Biochem/physiol Actions]
Kartogenin induces the selective differentiation of multipotent mesenchymal stem cells (MSCs) into chondrocytes. Kartogenin binds to filamin A, and disrupts the specific interaction between filamin A and CBFβ (core-binding factor β subunit). Apparently, kartogenin induces chondrogenesis by regulating the nuclear localization of CBFβ. | [in vivo]
Kartogenin (10 μM in 4 μL of saline; i.a. on days 7 and 21) promotes cartilag erepair in collagenase VII-induced OA models in mice[1]. | [storage]
+4°C | [References]
1) Johnson et al. (2012), A stem cell-based approach to cartilage repair; Science, 336 717 |
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