Cat. No.: HY-N5112A

β,β-Dimethylacrylalkannin

(Synonyms: Arnebin 1)

3 Cited Publications

Customer Review

Based on 3 publication(s) in Google Scholar

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.

For research use only. We do not sell to patients.

Purity: 99.36%
CAS No.: 34539-65-6
Formula: C₂₁H₂₂O₆
Molecular Weight:370.40

Storage:

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

β,β-Dimethylacrylalkannin Chemical Structure

CAS No.: 34539-65-6

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Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Publications (3)
Solvent & Solubility
- In Vitro
Purity & Documentation
References
Help & FAQs
Bioz

Biological Activity

Description

IC₅₀ & Target

FGFR1

2.5 μM (IC₅₀)

All CDK Isoforms :

All JNK Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
AU565	IC₅₀	0.62 μM Compound: 2	Cytotoxicity against human AU565 cells after 48 hrs by MTT assay Cytotoxicity against human AU565 cells after 48 hrs by MTT assay	[PMID: 20405844]
DU-145	IC₅₀	4.81 μM Compound: 2	Cytotoxicity against human DU145 cells after 48 hrs by MTT assay Cytotoxicity against human DU145 cells after 48 hrs by MTT assay	[PMID: 20405844]
HeLa	IC₅₀	0.96 μM Compound: 2	Cytotoxicity against human HeLa cells after 48 hrs by MTT assay Cytotoxicity against human HeLa cells after 48 hrs by MTT assay	[PMID: 20405844]
Hep 3B2	IC₅₀	4.09 μM Compound: 2	Cytotoxicity against human Hep3B cells after 48 hrs by MTT assay Cytotoxicity against human Hep3B cells after 48 hrs by MTT assay	[PMID: 20405844]
HepG2	IC₅₀	1 μM Compound: 2	Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay	[PMID: 20405844]
HT-29	IC₅₀	0.8 μM Compound: 2	Cytotoxicity against human HT-29 cells after 48 hrs by MTT assay Cytotoxicity against human HT-29 cells after 48 hrs by MTT assay	[PMID: 20405844]
LNCaP	IC₅₀	11.26 μM Compound: 2	Cytotoxicity against human LNCAP cells after 48 hrs by MTT assay Cytotoxicity against human LNCAP cells after 48 hrs by MTT assay	[PMID: 20405844]
MCF7	IC₅₀	5.15 μM Compound: 2	Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay	[PMID: 20405844]
MDA-MB-231	IC₅₀	0.32 μM Compound: 2	Cytotoxicity against human MDA-MB-231 cells after 48 hrs by MTT assay Cytotoxicity against human MDA-MB-231 cells after 48 hrs by MTT assay	[PMID: 20405844]
NIH3T3	IC₅₀	0.77 μM Compound: 2	Cytotoxicity against mouse 3T3 cells after 48 hrs by MTT assay Cytotoxicity against mouse 3T3 cells after 48 hrs by MTT assay	[PMID: 20405844]
PC-3	IC₅₀	1.1 μM Compound: 2	Cytotoxicity against human PC3 cells after 48 hrs by MTT assay Cytotoxicity against human PC3 cells after 48 hrs by MTT assay	[PMID: 20405844]
SAOS-2	IC₅₀	0.84 μM Compound: 2	Cytotoxicity against human Saos2 cells after 48 hrs by MTT assay Cytotoxicity against human Saos2 cells after 48 hrs by MTT assay	[PMID: 20405844]
SK-BR-3	IC₅₀	0.68 μM Compound: 2	Cytotoxicity against human SKBR3 cells after 48 hrs by MTT assay Cytotoxicity against human SKBR3 cells after 48 hrs by MTT assay	[PMID: 20405844]
Vero	IC₅₀	0.32 μM Compound: 2	Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay	[PMID: 20405844]

In Vitro

β,β-Dimethylacrylalkannin (0.1-100 μM; 24, 48 h) significantly reduces the viability of HepG2 and Huh7 hepatocellular carcinoma (HCC) cells in a dose-dependent manner^[1].
β,β-Dimethylacrylalkannin (1-5 μM; 24 h) regulates cell cycle regulatory proteins in HepG2 and Huh7 hepatocellular carcinoma cells, reduces the activity of the Cyclin B1/CDK1 complex, and inhibits Cdc25C function, thereby inducing G2/M phase arrest^[1].
β,β-Dimethylacrylalkannin (30 μM; 8-24 h) induces necrosis in HepG2 and Huh7 hepatocellular carcinoma (HCC) cells, and this effect is not inhibited by ferroptosis or necroptosis inhibitors^[1].
β,β-Dimethylacrylalkannin (2.5 μM; 72 h) inhibits the growth of patient-derived colorectal cancer organoids, such as Huh7 organoids^[1]^[2].
β,β-Dimethylacrylalkannin (5-10 μM; 24 h) induces G1-phase cell cycle arrest in HCT 116, DLD-1, SW 620 and HCT-15 colorectal cancer cells^[2].
β,β-Dimethylacrylalkannin inhibits FGFR1-mediated downstream signaling pathways in HCT 116, DLD-1, SW 620 and HCT-15 colorectal cancer cells, and reduces the phosphorylation levels of FRS2, JAK2, STAT3 and MEK1/2 without altering the total protein levels^[2].
Combination treatment with β,β-Dimethylacrylalkannin (8 μg/mL; 1 h) and polymyxin alters the gene expression profiles of polymyxin-resistant Escherichia coli BW25113-mcr-1 and *Escherichia coli BW25113-pmrBR93P, significantly downregulating lptD and upregulating marR, thereby disrupting LPS transport and efflux pump activity^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Proliferation Assay^[1]

Cell Line:

HepG2, Huh7 (3D spheroids)
Concentration:

1-30 μM
Incubation Time:

8 days
Result:

Suppressed spheroid growth in a dose-dependent manner.
Showed minimal spheroid growth, sparse edges, scattered single cells, and significant PI-positive dead cells in high-dose groups.
Showed inhibited volume growth but fewer PI-positive cells in low-dose groups.

Western Blot Analysis^[1]

Cell Line:

HepG2, Huh7
Concentration:

1-5 μM
Incubation Time:

24 h
Result:

Reduced Cyclin B1 and CDK1 expression, diminished binding between CDK1 and Cyclin B1, decreased CDK1 phosphorylation at Thr-161, increased CDK1 phosphorylation at Tyr-15 and Thr-14, decreased total Cdc25C expression, and increased Cdc25C phosphorylation at Ser-216 in both cell lines.

Western Blot Analysis^[1]

Cell Line:

HepG2, Huh7
Concentration:

1-5 μM (24 h incubation); 10-30 μM (4 h incubation); 5 μM (24 h with SP600125/siRNA); 30 μM (24 h with SP600125/siRNA)
Incubation Time:

4 h (high dose); 24 h (low dose; with SP600125/siRNA)
Result:

Increased phosphorylated JNK levels at both low and high doses, which was reversed by NAC.
Prevented low-dose-induced G2/M phase arrest when co-treated with JNK inhibitor SP600125 (20 μM) or JNK knockdown.
Did not block high-dose-induced necrosis when co-treated with SP600125 or JNK knockdown.

Cell Proliferation Assay^[2]

Cell Line:

CCD-18Co normal colon fibroblasts; HCT 116, HCT-15, SW 620, DLD-1 colorectal cancer cells
Concentration:

1.25-10 μM
Incubation Time:

24-72 h
Result:

Showed no significant toxicity to CCD-18Co normal colon fibroblasts at 10 μM across 24, 48, or 72 h.
Suppressed proliferation of colorectal cancer cells in a dose-dependent and time-dependent manner.
Exhibited greater inhibitory effect on DLD-1 and HCT 116 cell proliferation than oxaliplatin at 2.5 and 10 μM.

In Vivo

β,β-Dimethylacrylalkannin (5-20 mg/kg; p.o.; daily; 14 days) exhibits dose-dependent in vivo anti-hepatocellular carcinoma efficacy, with both 5 mg/kg and 20 mg/kg oral doses significantly reducing tumor growth and proliferation, and the 20 mg/kg dose showing greater potency^[1].
β,β-Dimethylacrylalkannin (60-120 mg/kg; p.o.; daily; 29-57 days) inhibits tumor growth in FGFR1-positive colorectal cancer PDX mice with average tumor weight reductions ranging from 33.6% to 67.8%, and exhibits no notable systemic toxicity^[2].
β,β-Dimethylacrylalkannin (2 mg/kg; i.p.; single dose) combined with colistin (0.2 mg/kg; i.p.; single dose) increases survival to 80% and reduces bacterial organ burdens in mice with systemic Klebsiella pneumoniae infection^[3].
β,β-Dimethylacrylalkannin (10 g/kg; p.o.; single dose) has an oral LD₅₀ greater than 10 g/kg bw in KM mice, with transient mild toxicity signs and no lasting pathological changes in surviving animals^[4].
β,β-Dimethylacrylalkannin (10 g/kg; p.o.; single dose) has an oral MTD greater than 10 g/kg bw in Wistar rats, with only transient mild toxicity signs and no pathological changes observed^[4].
β,β-Dimethylacrylalkannin (10-160 mg/kg/day; p.o.; 6 days per week; 26 weeks) administered orally for 26 weeks at up to 160 mg/kg/day in Wistar rats causes only transient, reversible changes and dose-related renal tubular pigmentation, with a NOAEL of 10 mg/kg/day^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

BALB/c nude mice with Hepatocellular carcinoma (male)^[1]
Dosage:

5 mg/kg; 20 mg/kg
Administration:

p.o.; daily; 14 days
Result:

Significantly inhibited tumor volume growth over the 14-day period, with the 20 mg/kg dose showing more pronounced reduction.
Significantly reduced tumor weights compared to controls, with the 20 mg/kg group having the smallest tumor mass.
Induced vacuole formation in tumor tissue.
Reduced Ki67 expression, indicating suppressed tumor cell proliferation.

Animal Model:

BALB/c mice with Systemic bacterial infection (female, 8 weeks old, 20 g)^[3]
Dosage:

2 mg/kg (in combination with colistin 0.2 mg/kg)
Administration:

i.p.; single dose
Result:

Increased mouse survival rate from 20% to 80% at day 5 post-infection.
Reduced bacterial loads in the heart, liver, spleen, lung, and kidneys by 1.5-6 Log₁₀ CFUs/g compared to control groups.
Substantially mitigated tissue damage including cardiac edema, hepatic necrosis, inflammatory infiltration, spleen pulp atrophy, alveolar congestion, and renal interstitial congestion.

Chemical Information

CAS No. 34539-65-6
Appearance Solid
Molecular Weight 370.40
Formula C₂₁H₂₂O₆
Color Brown to reddish brown
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
Synonyms

Arnebin 1
Structure Classification
- Quinones
- Naphthalene Quinones
Initial Source
- Plants
- other families
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Publications (3)

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Phytomedicine

β,β-Dimethylacrylalkannin, a key component of Zicao, induces cell cycle arrest and necrosis in hepatocellular carcinoma cells. [Abstract]

2024 Aug 19:134:155959. PMID: 39178682
Molecules

β,β-Dimethylacrylalkannin, a Natural Naphthoquinone, Inhibits the Growth of Hepatocellular Carcinoma Cells by Modulating Tumor-Associated Macrophages. [Abstract]

2024 Aug 20;29(16):3919. PMID: 39202998
Vet Microbiol

Identification and evaluation of Nordihydroguaiaretic acid (NDGA) as an active traditional Chinese medicine compound inhibiting the 3C-like protease of feline infectious peritonitis virus. [Abstract]

2025 Sep 15:310:110730. PMID: 40976146

Solvent & Solubility

In Vitro:

DMSO : 23.75 mg/mL (64.12 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

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Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.6998 mL

13.4989 mL

26.9978 mL

5 mM

0.5400 mL

2.6998 mL

5.3996 mL

10 mM

0.2700 mL

1.3499 mL

2.6998 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (291 KB)
SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Portuguese - PT (252 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

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.

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.6998 mL	13.4989 mL	26.9978 mL	67.4946 mL
	5 mM	0.5400 mL	2.6998 mL	5.3996 mL	13.4989 mL
	10 mM	0.2700 mL	1.3499 mL	2.6998 mL	6.7495 mL
	15 mM	0.1800 mL	0.8999 mL	1.7999 mL	4.4996 mL
	20 mM	0.1350 mL	0.6749 mL	1.3499 mL	3.3747 mL
	25 mM	0.1080 mL	0.5400 mL	1.0799 mL	2.6998 mL
	30 mM	0.0900 mL	0.4500 mL	0.8999 mL	2.2498 mL
	40 mM	0.0675 mL	0.3375 mL	0.6749 mL	1.6874 mL
	50 mM	0.0540 mL	0.2700 mL	0.5400 mL	1.3499 mL
	60 mM	0.0450 mL	0.2250 mL	0.4500 mL	1.1249 mL

β,β-Dimethylacrylalkannin

3 Cited Publications

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β,β-Dimethylacrylalkannin

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Publications Citing Use of MedChemExpress (MCE) β,β-Dimethylacrylalkannin

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Biological Activity

Chemical Information

Publications (3)

Solvent & Solubility

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

β,β-Dimethylacrylalkannin Related Classifications

Cat. No.: HY-N5112A