Cat. No.: HY-N5112B

β,β-Dimethylacrylshikonin

(Synonyms: Isoarnebin I)

1 Cited Publications

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Based on 1 publication(s) in Google Scholar

β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone derivative that can be isolated from Lithospermum erythrorhizon Sieb. et Zucc. β,β-Dimethylacrylshikonin promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway. β,β-Dimethylacrylshikonin inhibits Notch-1 activation. β,β-Dimethylacrylshikonin inhibtis tumor cell proliferation, induces tumor cell apoptosis, and inhibits tumor growth.

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

Purity: 99.30%
CAS No.: 24502-79-2
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-Dimethylacrylshikonin Chemical Structure

CAS No.: 24502-79-2

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Biological Activity
- Description
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Publications (1)
Solvent & Solubility
- In Vitro
- In Vivo
Purity & Documentation
References
Help & FAQs
Classifications
Bioz

Biological Activity

Description

All HIF/HIF Prolyl-Hydroxylase Isoforms :

All NO Synthase Isoforms :

All Bcl-2 Family Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
B16-F0	IC₅₀	1.2 μM Compound: DMAS	Cytotoxicity against mouse B16F0 cells assessed as reduction in cell viability after 24 hrs by MTT assay Cytotoxicity against mouse B16F0 cells assessed as reduction in cell viability after 24 hrs by MTT assay	[PMID: 31961147]
B16-F0	IC₅₀	1.2 μM Compound: DMAS	Cytotoxicity against mouse B16F0 cells assessed as reduction in cell viability after 48 hrs by MTT assay Cytotoxicity against mouse B16F0 cells assessed as reduction in cell viability after 48 hrs by MTT assay	[PMID: 31961147]
CCRF-CEM	IC₅₀	1.9 μM Compound: 3	Cytotoxicity against human CCRF-CEM cells after 72 hrs by XTT assay Cytotoxicity against human CCRF-CEM cells after 72 hrs by XTT assay	[PMID: 22530779]
HCT-116	IC₅₀	20 μM Compound: 3	Cytotoxicity against human HCT116 cells after 72 hrs by XTT assay Cytotoxicity against human HCT116 cells after 72 hrs by XTT assay	[PMID: 22530779]
HeLa	IC₅₀	77 μM Compound: 21	Inhibitory activity against DNA topoisomerase-1 obtained from Hela cells Inhibitory activity against DNA topoisomerase-1 obtained from Hela cells	[PMID: 7699697]
MDA-MB-231	IC₅₀	23.2 μM Compound: 3	Cytotoxicity against human MDA-MB-231 cells after 72 hrs by XTT assay Cytotoxicity against human MDA-MB-231 cells after 72 hrs by XTT assay	[PMID: 22530779]
MRC5	IC₅₀	2.4 μM Compound: 3	Cytotoxicity against human MRC5 cells after 72 hrs by XTT assay Cytotoxicity against human MRC5 cells after 72 hrs by XTT assay	[PMID: 22530779]
MRC5	IC₅₀	9.5 μM Compound: DMAS	Cytotoxicity against human MRC5 cells assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human MRC5 cells assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
MUGMel1	IC₅₀	1 μM Compound: DMAS	Cytotoxicity against human MUGMel1 cells assessed as reduction in cell viability after 72 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human MUGMel1 cells assessed as reduction in cell viability after 72 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
MUGMel1	IC₅₀	1.1 μM Compound: DMAS	Cytotoxicity against human MUGMel1 cells assessed as reduction in cell viability after 48 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human MUGMel1 cells assessed as reduction in cell viability after 48 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
MUGMel1	IC₅₀	1.9 μM Compound: DMAS	Cytotoxicity against human MUGMel1 cells assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human MUGMel1 cells assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
MUGMel2	IC₅₀	1.7 μM Compound: DMAS	Cytotoxicity against human MUGMel2 cells harboring NRAS pQ61K mutant assessed as reduction in cell viability after 72 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human MUGMel2 cells harboring NRAS pQ61K mutant assessed as reduction in cell viability after 72 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
MUGMel2	IC₅₀	2.3 μM Compound: DMAS	Cytotoxicity against human MUGMel2 cells harboring NRAS pQ61K mutant assessed as reduction in cell viability after 48 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human MUGMel2 cells harboring NRAS pQ61K mutant assessed as reduction in cell viability after 48 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
MUGMel2	IC₅₀	5.1 μM Compound: DMAS	Cytotoxicity against human MUGMel2 cells harboring NRAS pQ61K mutant assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human MUGMel2 cells harboring NRAS pQ61K mutant assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
MUGMel2	IC₅₀	7.2 μM Compound: 1-76	Antitumor activity against human MUG-Mel2 cells assessed as reduction in cell viability incubated for 72 hrs by XTT assay Antitumor activity against human MUG-Mel2 cells assessed as reduction in cell viability incubated for 72 hrs by XTT assay	[PMID: 35367708]
SBcl2	IC₅₀	1.1 μM Compound: 1-76	Antitumor activity against human SBcl2 cells assessed as reduction in cell viability incubated for 72 hrs by XTT assay Antitumor activity against human SBcl2 cells assessed as reduction in cell viability incubated for 72 hrs by XTT assay	[PMID: 35367708]
SBcl2	IC₅₀	1.1 μM Compound: 3	Cytotoxicity against human SBcl2 cells after 72 hrs by XTT assay Cytotoxicity against human SBcl2 cells after 72 hrs by XTT assay	[PMID: 22530779]
SBcl2	IC₅₀	1.1 μM Compound: DMAS	Cytotoxicity against human SBcl2 cells harboring NRAS Q61I mutant assessed as reduction in cell viability after 48 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human SBcl2 cells harboring NRAS Q61I mutant assessed as reduction in cell viability after 48 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
SBcl2	IC₅₀	1.2 μM Compound: DMAS	Cytotoxicity against human SBcl2 cells harboring NRAS Q61I mutant assessed as reduction in cell viability after 72 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human SBcl2 cells harboring NRAS Q61I mutant assessed as reduction in cell viability after 72 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
SBcl2	IC₅₀	1.9 μM Compound: DMAS	Cytotoxicity against human SBcl2 cells harboring NRAS Q61I mutant assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human SBcl2 cells harboring NRAS Q61I mutant assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
U-251	IC₅₀	30.8 μM Compound: 3	Cytotoxicity against human U251 cells after 72 hrs by XTT assay Cytotoxicity against human U251 cells after 72 hrs by XTT assay	[PMID: 22530779]
WM164	IC₅₀	2.4 μM Compound: DMAS	Cytotoxicity against human WM164 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 72 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human WM164 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 72 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
WM164	IC₅₀	3 μM Compound: DMAS	Cytotoxicity against human WM164 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 48 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human WM164 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 48 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
WM164	IC₅₀	3.8 μM Compound: DMAS	Cytotoxicity against human WM164 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human WM164 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
WM164	IC₅₀	8.3 μM Compound: 1-76	Antitumor activity against human WM164 cells assessed as reduction in cell viability incubated for 72 hrs by XTT assay Antitumor activity against human WM164 cells assessed as reduction in cell viability incubated for 72 hrs by XTT assay	[PMID: 35367708]
WM164	IC₅₀	8.3 μM Compound: 3	Cytotoxicity against human WM164 cells after 72 hrs by XTT assay Cytotoxicity against human WM164 cells after 72 hrs by XTT assay	[PMID: 22530779]
WM793	IC₅₀	0.7 μM Compound: DMAS	Cytotoxicity against human WM793 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 72 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human WM793 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 72 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
WM793	IC₅₀	0.8 μM Compound: DMAS	Cytotoxicity against human WM793 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 48 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human WM793 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 48 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]
WM793	IC₅₀	1.2 μM Compound: DMAS	Cytotoxicity against human WM793 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method Cytotoxicity against human WM793 cells harboring BRAF V600E mutant assessed as reduction in cell viability after 24 hrs by EZ4U reagent based spectrophotometric method	[PMID: 31961147]

In Vitro

β,β-Dimethylacrylshikonin (0-80 μM, 24 or 48 h) inhibits the G2/M phase transition and suppresses TNBC cell proliferation^[3].
β,β-Dimethylacrylshikonin (0-10 μM, 24 h) induces mitochondrial-dependent apoptosis and reduces TNBC cell migration by antagonizing epithelial-mesenchymal transition^[3].
β,β-Dimethylacrylshikonin (0-30 μg/mL, 48 h) reduces Notch-1 activation, expression of Jagged-1 and its downstream target Hes-1 in SGC-7901 cells^[4].

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

Apoptosis Analysis^[3]

Cell Line:

TNBC cells: MDA-MB-231, BT-549, HS578T cells
Concentration:

2.5, 5, 10 μM
Incubation Time:

24 h
Result:

Increased the proportion of late apoptotic and necrotic cells.
Downregulated Bcl2, and increased Bax expression.
Increased the level of cleaved-caspase3.

In Vivo

β,β-Dimethylacrylshikonin (0.1% suspension in PBS, applied topically on wounds, daily for 12d) accelerates Hydrocortisone (HY-N0583)-induced impaired wound healing in rats^[2].
β,β-Dimethylacrylshikonin (1 or 2 mg/kg, i.p., on alternate days) suppresses tumor growth in BT-549 xenograft mice model by inhibiting STAT3 phosphorylation^[3].
β,β-Dimethylacrylshikonin (0.5-1.5 mg/kg, i.p.) suppresses tumor growth in MFC gastric xenograft mice model^[4].

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

Animal Model:

Hydrocortisone induced impaired wound healing in cutaneous punch wound rat model^[1]
Dosage:

0.1% suspension in PBS; Hydrocortisone (30 mg/kg, i.m., daily, 11d)
Administration:

applied topically on wounds, daily for 11 days
Result:

HE staining: Showed more number of cells and vessels in the granulation tissue, and enhanced epidermal regeneration and collagen synthesis.
Enhanced the formation and migration of the epidermis over the wound.
Increased gap closure during normal and impaired healing

Animal Model:

Athymic BALB/c nu/nu female mice (6- 8 week-old, 18-22 g), BT-549 cells were injected subcutaneously into the right thigh root of mice^[3].
Dosage:

1 or 2 mg/kg
Administration:

i.p., on alternate days
Result:

Decreased the expression of Ki67, CyclinB1 and CDK1 in tumor.
Up-regulated Bax expression and down-regulated Bcl-2 expression.
Increased the expression of E-cadherin and decreased N-cadherin and vimentin.
Decreased the level of p-STAT3 without changing total STAT3 levels.

Chemical Information

CAS No. 24502-79-2
Appearance Solid
Molecular Weight 370.40
Formula C₂₁H₂₂O₆
Color Brown to reddish brown
SMILES

O=C1C2=C(O)C=CC(O)=C2C(C=C1[C@@H](C/C=C(C)/C)OC(/C=C(C)/C)=O)=O
Synonyms

Isoarnebin I
Structure Classification
- Quinones
- Naphthalene Quinones
- Phenols
- Polyphenols
Initial Source
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 (1)

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Phytomedicine

β, β-Dimethylacrylshikonin potentiates paclitaxel activity, suppresses immune evasion and triple negative breast cancer progression via STAT3Y705 phosphorylation inhibition based on network pharmacology and transcriptomics analysis. [Abstract]

2023 Jun:114:154769. PMID: 36940580

Solvent & Solubility

In Vitro:

DMSO : 12.5 mg/mL (33.75 mM; ultrasonic and warming and heat to 60°C; 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

View the Complete Stock Solution Preparation Table

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.

Molarity Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

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Molecular Weight Molecular Weight

Dilution Calculator

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: 1.25 mg/mL (3.37 mM); Suspended solution; Need ultrasonic

This protocol yields a suspended solution of 1.25 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (12.5 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: 1.25 mg/mL (3.37 mM); Suspended solution; Need ultrasonic

This protocol yields a suspended solution of 1.25 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (12.5 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (284 KB)
SDS (702 KB)
- English - EN (702 KB)
- Français - FR (702 KB)
- Deutsch - DE (702 KB)
- Norwegian - NO (702 KB)
- Español - ES (702 KB)
- Swedish - SV (702 KB)
- Italian - IT (702 KB)
- Korean - KR (702 KB)
- Portuguese - PT (702 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]. Zeng Z, et al. Arnebin-1 promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway. Int J Mol Med. 2015 Sep;36(3):685-97. [Content Brief]

[2]. Sidhu GS, et al. Arnebin-1 accelerates normal and hydrocortisone-induced impaired wound healing. J Invest Dermatol. 1999 Nov;113(5):773-81. [Content Brief]

[3]. Wu Z, et al. β, β-Dimethylacrylshikonin potentiates paclitaxel activity, suppresses immune evasion and triple negative breast cancer progression via STAT3Y705 phosphorylation inhibition based on network pharmacology and transcriptomics analysis. Phytomedicine. 2023 Jun;114:154769. [Content Brief]

[4]. Zhen-Jun S, et al. β,β-Dimethylacrylshikonin exerts antitumor activity via Notch-1 signaling pathway in vitro and in vivo. Biochem Pharmacol. 2012 Aug 15;84(4):507-12.

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

Keywords

β,β-Dimethylacrylshikonin

1 Cited Publications

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β,β-Dimethylacrylshikonin

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

All HIF/HIF Prolyl-Hydroxylase Isoforms

All NO Synthase Isoforms

All Bcl-2 Family Isoforms

Biological Activity

Chemical Information

Publications (1)

Solvent & Solubility

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

β,β-Dimethylacrylshikonin Related Classifications

HY-N5112B Related Classifications