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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

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 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

11 - Combustible Solids

wgk_germany

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hanyong Jin et al.
PloS one, 11(7), e0159112-e0159112 (2016-07-16)
Anti-Müllerian hormone (AMH) is required for proper sexual differentiation by regulating the regression of the Müllerian ducts in males. Recent studies indicate that AMH could be an important factor for maintaining the ovarian reserve. However, the mechanisms of AMH regulation
He Huang et al.
The American journal of sports medicine, 45(14), 3289-3297 (2017-09-02)
The meniscus is one of the most commonly injured parts of the body, and meniscal healing is difficult. Kartogenin (KGN) induces tendon stem cells (TSCs) to differentiate into cartilage cells in vitro and form meniscus-like tissue in vivo. A damaged
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
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
Yoshitaka Imamichi et al.
Scientific reports, 7(1), 8374-8374 (2017-08-23)
Diethylstilbestrol (DES), a strong estrogenic compound, is well-known to affect the reproductive system. In this study, we investigated the effects of DES administration on gonadotropin levels and ovarian steroidogenesis in prepubertal rats. DES treatment acutely reduced serum LH levels, followed
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