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Cat. No.: HY-135771

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Avarone

(Synonyms: (+)-Avarone)

Avarone ((+)-Avarone) is a sesquiterpenoidal quinone that can be isolated from Dysidea avara. Avarone shows cytotoxicity. Avarone shows antileukemic activity.

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

CAS No.: 55303-99-6
Formula: C₂₁H₂₈O₂
Molecular Weight:312.45

Storage:

Please store the product under the recommended conditions in the Certificate of Analysis.

Data Sheet (276 KB)

Avarone Chemical Structure

CAS No.: 55303-99-6

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Use of MCE Products

Fluorescent Dye

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

Biological Activity
- Description
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Purity & Documentation
References
Calculators
Help & FAQs
Classifications
Bioz

Biological Activity

Description

Avarone ((+)-Avarone) is a sesquiterpenoidal quinone that can be isolated from Dysidea avara. Avarone shows cytotoxicity. Avarone shows antileukemic activity^[1]^[2].

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	30.03 μM Compound: 1	Cytotoxicity against human A549 cells assessed as cell survival after 72 hrs by MTT assay Cytotoxicity against human A549 cells assessed as cell survival after 72 hrs by MTT assay	[PMID: 26476666]
A549	IC₅₀	6 μM Compound: 2 (Avarone)	Cytotoxicity was measured against neoplastic cultured A-549 cells of human lung carcinoma. Cytotoxicity was measured against neoplastic cultured A-549 cells of human lung carcinoma.	10.1016/0960-894X(96)00326-5
A549	IC₅₀	6.4 μM Compound: Avarone	Cytotoxic activity against cultured cells of A-549 human lung carcinoma. Cytotoxic activity against cultured cells of A-549 human lung carcinoma.	[PMID: 11312925]
HaCaT	IC₅₀	37 μM Compound: 2	Cytotoxicity against human HaCaT cells after 72 hrs by MTT assay Cytotoxicity against human HaCaT cells after 72 hrs by MTT assay	[PMID: 27128177]
HeLa	IC₅₀	18.12 μM Compound: 1	Cytotoxicity against human HeLa cells assessed as cell survival after 72 hrs by MTT assay Cytotoxicity against human HeLa cells assessed as cell survival after 72 hrs by MTT assay	[PMID: 26476666]
HeLa	IC₅₀	26.8 μM Compound: 2	Cytotoxicity against human HeLa cells assessed as decrease in total cellular protein by kenacid blue R binding method Cytotoxicity against human HeLa cells assessed as decrease in total cellular protein by kenacid blue R binding method	[PMID: 19995673]
HT-29	IC₅₀	6 μM Compound: 2 (Avarone)	Cytotoxicity was measured against neoplastic cultured HT-29 cells of human colon carcinoma. Cytotoxicity was measured against neoplastic cultured HT-29 cells of human colon carcinoma.	10.1016/0960-894X(96)00326-5
HT-29	IC₅₀	6.4 μM Compound: Avarone	Cytotoxic activity against cultured cells of HT-29 human colon carcinoma. Cytotoxic activity against cultured cells of HT-29 human colon carcinoma.	[PMID: 11312925]
K562	IC₅₀	17.08 μM Compound: 1	Cytotoxicity against human K562 cells assessed as cell survival after 72 hrs by MTT assay Cytotoxicity against human K562 cells assessed as cell survival after 72 hrs by MTT assay	[PMID: 26476666]
K562	IC₅₀	4.9 μM Compound: 2	Cytotoxicity against human K562 cells by MTT assay Cytotoxicity against human K562 cells by MTT assay	[PMID: 19995673]
MDA-MB-453	IC₅₀	16.71 μM Compound: 1	Cytotoxicity against human MDA-MB-453 cells assessed as cell survival after 72 hrs by MTT assay Cytotoxicity against human MDA-MB-453 cells assessed as cell survival after 72 hrs by MTT assay	[PMID: 26476666]
MRC5	IC₅₀	>200 μM Compound: 1	Cytotoxicity against human MRC5 cells assessed as cell survival after 72 hrs by MTT assay Cytotoxicity against human MRC5 cells assessed as cell survival after 72 hrs by MTT assay	[PMID: 26476666]
NCI-H460	IC₅₀	24 μM Compound: 2	Cytotoxicity against multidrug resistant human NCI-H460 cells after 72 hrs by MTT assay Cytotoxicity against multidrug resistant human NCI-H460 cells after 72 hrs by MTT assay	[PMID: 27128177]
NCI-H460	IC₅₀	84 μM Compound: 2	Cytotoxicity against human NCI-H460 cells after 72 hrs by MTT assay Cytotoxicity against human NCI-H460 cells after 72 hrs by MTT assay	[PMID: 27128177]
P388	IC₅₀	3.1 μM Compound: 2 (Avarone)	Cytotoxicity was measured against neoplastic cultured P-388 cells of murine leukemia. Cytotoxicity was measured against neoplastic cultured P-388 cells of murine leukemia.	10.1016/0960-894X(96)00326-5
P388	IC₅₀	3.2 μM Compound: Avarone	Cytotoxic Activity against cultured cells of P-388 murine leukemia. Cytotoxic Activity against cultured cells of P-388 murine leukemia.	[PMID: 11312925]
PBMC	IC₅₀	4.5 μM Compound: 2	Cytotoxicity against human phytohemagglutininin-stimulated PBMC cells assessed as growth inhibition by MTT assay Cytotoxicity against human phytohemagglutininin-stimulated PBMC cells assessed as growth inhibition by MTT assay	[PMID: 19995673]
PBMC	IC₅₀	4.8 μM Compound: 2	Cytotoxicity against human PBMC cells by MTT assay Cytotoxicity against human PBMC cells by MTT assay	[PMID: 19995673]
SK-MEL-28	IC₅₀	6 μM Compound: 2 (Avarone)	Cytotoxicity was measured against neoplastic cultured MEL-28 cells of malign human melanoma. Cytotoxicity was measured against neoplastic cultured MEL-28 cells of malign human melanoma.	10.1016/0960-894X(96)00326-5
SK-MEL-28	IC₅₀	6.4 μM Compound: Avarone	Cytotoxic activity against cultured cells of MEL-28 malign human melanoma. Cytotoxic activity against cultured cells of MEL-28 malign human melanoma.	[PMID: 11312925]

In Vitro

Avarone (24, 48, 72 h) inhibits U937 cell growth with IC₅₀s of 95.8, 52.9, 33.5 µM at 24, 48, 72 h, respectively^[1].

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

Cell Cytotoxicity Assay^[2]

Cell Line:

L5178Y, Melanoma, Hela, fibroblasts, human gingival cells
Concentration:
Incubation Time:
Result:

Showed cytotoxicity for L5178Y, Melanoma, Hela, fibroblasts, human gingival cells with ED₅₀s of 0.62, 26.4, 8.7, 11.3, 76.4 µM, respectively.

In Vivo

Avarone (10 mg/kg; i.p.; once daily for 5 days) shows increases life span of leukemic mice^[2].

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

Animal Model:

8-9 months, 32-35 g Male outbred NMIR mice (L5178Y cells)^[2]
Dosage:

10 mg/kg
Administration:

I.p.; once daily for 5 days
Result:

Increased life span over controls by 146% when treatment was begun 1 day after tumor implantation and by 87% when treatment was delayed until day 8.

Chemical Information

CAS No. 55303-99-6
Molecular Weight 312.45
Formula C₂₁H₂₈O₂
SMILES

O=C1C(C[C@]2(C)[C@@H](C)CC[C@]3(C)C(C)=CCC[C@@]23[H])=CC(C=C1)=O
Synonyms

(+)-Avarone
Structure Classification
- Terpenoids
- Sesquiterpenes
- Quinones
- Benzene Quinones
Initial Source
- Marine natural products
Dysidea avara
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (276 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]. Sakurai J, et al. Highly efficient total synthesis of the marine natural products (+)-avarone, (+)-avarol, (-)-neoavarone, (-)-neoavarol and (+)-aureol. Chemistry. 2008;14(3):829-37. [Content Brief]

[2]. Müller WE, et al. Potent antileukemic activity of the novel cytostatic agent avarone and its analogues in vitro and in vivo. Cancer Res. 1985 Oct;45(10):4822-6. [Content Brief]

Calculators

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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.

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100 mg

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