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SML0370

Sigma-Aldrich

Kartogenin

≥98% (HPLC)

Synonym(s):

2-[(Biphenyl-4-yl)carbamoyl]benzoic acid, 4′-Phenyl-phthalanilic acid (8CI), KGN

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About This Item

Empirical Formula (Hill Notation):
C20H15NO3
CAS Number:
4727-31-5
Molecular Weight:
317.34
MDL number:
MFCD00560510
UNSPSC Code:
12352200
PubChem Substance ID:
329825371
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: >15 mg/mL

storage temp.

room temp

SMILES string

O=C(NC1=CC=C(C2=CC=CC=C2)C=C1)C(C=CC=C3)=C3C(O)=O

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)

InChI key

SLUINPGXGFUMLL-UHFFFAOYSA-N

Biochem/physiol Actions

Kartogenin induces the selective differentiation of multipotent mesenchymal stem cells (MSCs) into chondrocytes.
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.
Kartogenin is a small heterocyclic compound. It is involved in regulating runt-related transcription factor 1 (RUNX1), which plays an important role in chondrocyte proliferation and survival.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
0000399536
0000399536
0000212134
0000212134
0000212133

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Chun Liu et al.
Tissue engineering. Part A, 24(11-12), 990-1000 (2017-12-29)
Articular cartilage has poor capability of regeneration due to the avascular surrounding and low metabolic activity. Kartogenin (KGN), an emerging nonprotein heterocyclic compound, was screened to stimulate chondrogenic differentiation of bone mesenchymal stem cells (BMSCs). Coculturing BMSCs and chondrocytes was
Dongquan Shi et al.
ACS nano, 10(1), 1292-1299 (2016-01-13)
The regeneration of cartilage, an aneural and avascular tissue, is often compromised by its lack of innate abilities to mount a sufficient healing response. Kartogenin (KGN), a small molecular compound, can induce bone marrow-derived mesenchymal stem cells (BMSCs) into chondrocytes.
Mei Zhang et al.
Cell death & disease, 8(10), e3088-e3088 (2017-10-06)
Oxidative stress impairs follicular development by inducing granulosa cell (GC) apoptosis, which involves enhancement of the transcriptional activity of the pro-apoptotic factor Forkhead box O1 (FoxO1). However, the mechanism by which oxidative stress promotes FoxO1 activity is still unclear. Here
Photo-cross-linked scaffold with kartogenin-encapsulated nanoparticles for cartilage regeneration
Shi D, et al.
ACS Nano, 10(1), 1292-1299 (2016)
Kartogenin induces cartilage-like tissue formation in tendon-bone junction
Zhang J and Wang J H C
Bone research, 2(1), 1-10 (2014)
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