4727-31-5

Basic information

• Product Name: KGN
• Synonyms: 2-[([1,1'-Biphenyl]-4-ylaMino)carbonyl]benzoic Acid;2-[(Biphenyl-4-yl)carbaMoyl]benzoic Acid;4'-Phenylphthalanilic Acid;Kartogenin;KGN;2-([1,1'-biphenyl]-4-ylcarbaMoyl)benzoic acid;4′-Phenyl-phthalanilic acid (8CI);Kartogenin(KGN)
• CAS NO: 4727-31-5
• Molecular Formula: C₂₀H₁₅NO₃
• Molecular Weight: 317.338
• Product Categories: Inhibitors
• Mol File: 4727-31-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 272 °C
• Boiling Point: 464.4±38.0 °C(Predicted)
• Appearance: /
• Density: 1.289±0.06 g/cm3(Predicted)
• Storage Temp.: room temp
• Solubility: DMSO: >15mg/mL
• PKA: 3.45±0.36(Predicted)
• 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.
• CAS DataBase Reference: KGN(CAS DataBase Reference)
• NIST Chemistry Reference: KGN(4727-31-5)
• EPA Substance Registry System: KGN(4727-31-5)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36-50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 4727-31-5(Hazardous Substances Data)

Usage

Description

Kartogenin is a potent, selective, and non-cytotoxic downstream RUNX1 and RUNX2 modulator that plays a crucial role in the differentiation of human mesenchymal stem cells into chondrocytes, which are essential for cartilage formation and repair. With an EC50 value of 100 nM, Kartogenin induces chondrogenesis by binding to the actin-binding protein, filamin A, and disrupting its interaction with the transcription factor core-binding factor β subunit (CBFβ). This interaction leads to the translocation of CBFβ to the nucleus, where it forms a transcriptional complex with the runt-related transcription factor RUNX1, enabling chondrocyte differentiation. Kartogenin has demonstrated its effectiveness in promoting cartilage repair in a mouse model of osteoarthritis and protecting against cytokine-induced damage in osteoarthritic bovine articular chondrocytes in vitro.

Uses

Used in Cartilage Repair and Regeneration:
Kartogenin is used as a therapeutic agent for cartilage repair and regeneration, particularly in the treatment of osteoarthritis. The application reason is its ability to induce differentiation of human mesenchymal stem cells into chondrocytes, which are essential for building and repairing cartilage. This property makes Kartogenin a promising candidate for the development of novel treatments for cartilage-related diseases and injuries.
Used in Osteoarthritis Treatment:
Kartogenin is used as a potential treatment for osteoarthritis, a degenerative joint disease that affects millions of people worldwide. The application reason is its demonstrated ability to promote cartilage repair in a mouse model of osteoarthritis and protect against cytokine-induced damage in osteoarthritic bovine articular chondrocytes in vitro. By targeting the underlying cause of cartilage degradation, Kartogenin may offer a novel approach to managing and treating osteoarthritis, potentially improving the quality of life for patients suffering from this condition.
Used in Tissue Engineering and Regenerative Medicine:
Kartogenin is used as a key component in tissue engineering and regenerative medicine applications, specifically for the development of cartilage and joint tissue replacements. The application reason is its potent induction of chondrogenesis and its potential to enhance the differentiation of mesenchymal stem cells into chondrocytes, which are vital for the formation and maintenance of healthy cartilage. By incorporating Kartogenin into tissue engineering strategies, researchers and clinicians may be able to develop more effective treatments for cartilage damage and joint disorders, ultimately improving patient outcomes and reducing the need for invasive surgical interventions.

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.

References

1) Johnson et al. (2012), A stem cell-based approach to cartilage repair; Science, 336 717

Relevant articles and documents

Compounds and methods for inducing chondrogenesis

The present invention provides compounds and compositions for the amelioration of arthritis and joint injuries by inducing mesenchymal stem cells into chondrocytes.

NOVEL IMMUNOMODULATOR AND ANTI INFLAMMATORY COMPOUNDS

The present invention provides dihydroorotate dehydrogenase inhibitors of formula (I), methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of diseases or disorders wherein the inhibition of Dihydroorotate dehydrogenase is known to show beneficial effect.