34539-65-6
Chemical Structure
β,β-Dimethylacrylalkannin
Synonym(s): Arnebin 1
- CAS No.: 34539-65-6
- Formula:C21H22O6
- Molecular Weight:370.40
IUPAC Name: (S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbut-2-enoate
InChIKey: BATBOVZTQBLKIL-KRWDZBQOSA-N
SMILES: C/C(C)=C\C(O[C@H](C(C1=O)=CC(C2=C1C(O)=CC=C2O)=O)C/C=C(C)\C)=O
Biological Activity: β,β-Dimethylacrylalkannin (Arnebin 1) is an orally active FGFR1 inhibitor (IC50=2.5 μM) and the main active component of Lithospermum erythrorhizon. β,β-Dimethylacrylalkannin blocks downstream signaling by binding to the ATP pocket of FGFR1, and regulates the CDK1/Cdc25C pathway and ROS-JNK axis, thereby inducing G2/M phase arrest, necrosis and apoptosis in cancer cells, and inhibiting tumor proliferation. β,β-Dimethylacrylalkannin also acts as a colistin adjuvant to disrupt the cell membrane of Gram-negative bacteria. β,β-Dimethylacrylalkannin exhibits significant tumor-inhibitory effects with no obvious toxicity in PDX models, but chronic exposure to high doses may alter the relative lung/liver weights of rats, while acute exposure to high doses causes responses such as reduced motor activity. β,β-Dimethylacrylalkannin finds wide application in studies related to hepatocellular carcinoma, colorectal cancer, colistin-resistant bacterial infections, hepatitis and psoriasis[1][2][3][4].
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β,β-Dimethylacrylalkannin | 99.36% | β,β-Dimethylacrylalkannin (Arnebin 1) is an orally active FGFR1 inhibitor (IC50=2.5 μM) and the main active component of Lithospermum erythrorhizon. β,β-Dimethylacrylalkannin blocks downstream signaling by binding to the ATP pocket of FGFR1, and regulates the CDK1/Cdc25C pathway and ROS-JNK axis, thereby inducing G2/M phase arrest, necrosis and apoptosis in cancer cells, and inhibiting tumor proliferation. β,β-Dimethylacrylalkannin also acts as a colistin adjuvant to disrupt the cell membrane of Gram-negative bacteria. β,β-Dimethylacrylalkannin exhibits significant tumor-inhibitory effects with no obvious toxicity in PDX models, but chronic exposure to high doses may alter the relative lung/liver weights of rats, while acute exposure to high doses causes responses such as reduced motor activity. β,β-Dimethylacrylalkannin finds wide application in studies related to hepatocellular carcinoma, colorectal cancer, colistin-resistant bacterial infections, hepatitis and psoriasis. | ||||||||||||||||||||
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β,β-Dimethylacrylalkannin (Standard) | ≥98% | β,β-Dimethylacrylalkannin (Standard) (Arnebin 1 (Standard)) is the analytical standard of β,β-Dimethylacrylalkannin (HY-N5112A). This product is intended for research and analytical applications. β,β-Dimethylacrylalkannin (Arnebin 1) is a napthoquinone isolated from Alkanna cappadocica , increases collagen and involucrin content in skin cells. | ||||||||||||||||||||
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References
- [1]. Shen LS, et al. β,β-Dimethylacrylalkannin, a key component of Zicao, induces cell cycle arrest and necrosis in hepatocellular carcinoma cells. Phytomedicine. 2024;134:155959. [Content Brief]
- [2]. Zhao R, et al. Targeting FGFR1 by β,β-dimethylacrylalkannin suppresses the proliferation of colorectal cancer in cellular and xenograft models. Phytomedicine. 2024;129:155612. [Content Brief]
- [3]. Liu Y, et al. β,β-Dimethylacrylalkannin Restores Colistin Efficacy Against mcr- and TCS-Mediated Resistant Gram-Negative Bacteria via Membrane Disturbance. Antibiotics (Basel). 2025;15(1):3. Published 2025 Dec 19. [Content Brief]
- [4]. Zhang P P, et al. Oral acute and chronic toxicity studies of β, β-dimethylacrylalkannin in mice and rats[J]. Fundamental Toxicological Sciences, 2017, 4(2): 45-56.
