Art. -Nr.: HY-N10361

Drupanin

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Drupanin is an orally active and selective AKR1C3 enzyme inhibitor and an RXRα agonist with an EC₅₀ value of 4.8 μM, which is found in green propolis. Drupanin also activates PPARγ moderately. Drupanin induces adipogenesis and elevates aP2 mRNA levels in 3T3-L1 fibroblasts Drupanin has the potential for the research of breast and prostate cancers.

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Reinheit: 99.35%
CAS. Nr.: 53755-58-1
Formel: C₁₄H₁₆O₃
Molecular Weight:232.28

Speicherung:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

Drupanin Chemical Structure

CAS. Nr.: 53755-58-1

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Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target

PPARα

39.0 μM (EC₅₀)

AKR1C3

PPARγ

14.6 μM (EC₅₀)

PPARδ

N.D.(not d ()

RXR α

2.1 μM (EC₅₀)

RXRγ

4.6 μM (EC₅₀)

Cellular Effect

Cell Line	Type	Value	Description	References
DU-145	IC₅₀	>200 μM Compound: 2	Antiproliferative activity against human DU-145 cells assessed as cell viability for 72 hrs by MTT assay Antiproliferative activity against human DU-145 cells assessed as cell viability for 72 hrs by MTT assay	[PMID: 34454129]
HEK293	IC₅₀	25.6 μM Compound: 9	Modulation of HIF1 expressed in HEK293 cells assessed as luciferase activity under hypoxic condition after 24 hrs by luminometer analysis Modulation of HIF1 expressed in HEK293 cells assessed as luciferase activity under hypoxic condition after 24 hrs by luminometer analysis	[PMID: 21865046]
HeLa	IC₅₀	10.3 μg/mL Compound: 3	Antiallergic activity in Ca(2+)-stimulated differentiated human HeLa cells assessed as inhibition of cys-leukotriene release after 6 days by ELISA Antiallergic activity in Ca(2+)-stimulated differentiated human HeLa cells assessed as inhibition of cys-leukotriene release after 6 days by ELISA	[PMID: 19942440]
MCF-10A	CC₅₀	>200 μM Compound: 2	Cytotoxicity against human MCF-10A cells assessed as cell viability for 72 hrs by MTT assay Cytotoxicity against human MCF-10A cells assessed as cell viability for 72 hrs by MTT assay	[PMID: 34454129]
MCF7	IC₅₀	>200 μM Compound: 2	Antiproliferative activity against human MCF7 cells assessed as cell viability for 72 hrs by MTT assay Antiproliferative activity against human MCF7 cells assessed as cell viability for 72 hrs by MTT assay	[PMID: 34454129]
MDA-MB-231	IC₅₀	>200 μM Compound: 2	Antiproliferative activity against human MDA-MB-231 cells assessed as cell viability for 72 hrs by MTT assay Antiproliferative activity against human MDA-MB-231 cells assessed as cell viability for 72 hrs by MTT assay	[PMID: 34454129]
PC-3	IC₅₀	>200 μM Compound: 2	Antiproliferative activity against human PC-3 cells assessed as cell viability for 72 hrs by MTT assay Antiproliferative activity against human PC-3 cells assessed as cell viability for 72 hrs by MTT assay	[PMID: 34454129]
PNT2	CC₅₀	>200 μM Compound: 2	Cytotoxicity against human PNT2 cells assessed as cell viability for 72 hrs by MTT assay Cytotoxicity against human PNT2 cells assessed as cell viability for 72 hrs by MTT assay	[PMID: 34454129]

In Vitro

Drupanin (2.5-25 μM, 1 h) stimulates the interaction between PPARγ and cAMP responsive element-binding protein-binding protein in HEK 293 cells (EC₅₀ value: 14.6 μM)^[2].
Drupanin (25 μM, 5 days) enhances the adipogenesis of mouse 3T3-L1 fibroblasts^[2].
Drupanin (10^1.7-10^3.5 μM, 48 h) shows cytotoxic effects on PC3 and LnCaP cells^[3].

The EC₅₀ values of Drupanin for each RXR subtype cofactor^[2]

subtypes	RXRα	RXRγ	RXRδ
EC₅₀ (μM)	2.1	4.6	7.0

The EC₅₀ values of Drupanin for each PPAR subtype cofactor^[2]

subtypes	PPARα	PPARγ	PPARδ
EC₅₀ (μM)	39.0	14.6	N.D. (not detected)

Growth Inhibitory Effect of Drupanin^[3]

	NCI-H460	MCF7	PC3	LnCaP	HL60	U937	S-180
GI₅₀ (μM)	158.5	141.3	501.2	338.8	166.0	323.6	416.9
LC₅₀ (μM)	N.D.	N.D.	885.1	1331.4	N.D.	N.D.	N.D.

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

Real Time qPCR^[2]

Cell Line:

HEK 293 cells
Concentration:

2.5-25 μM
Incubation Time:

1 h
Result:

Slightly increased luciferase activity for each PPAR subtype (α, γ, and δ).

In Vivo

Drupanin (100 mg/kg, p.o., daily for 28 days) inhibits the tumor growth and induces genotoxic damage in DDY mice allografted with sarcoma S-180^[3].

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

Animal Model:

DDY mice allografted with sarcoma S-180^[2]
Dosage:

100 mg/kg
Administration:

p.o., daily for 28 days
Result:

Resulted in a significant decrease of tumor mass at a dosage of 100 mg/kg/d (p<0.05) and caused DNA damage in sarcoma S-180.

Chemical Information

CAS. Nr. 53755-58-1
Appearance Solid
Molecular Weight 232.28
Formel C₁₄H₁₆O₃
Color Off-white to light yellow
SMILES

C/C(C)=C\CC1=C(C=CC(/C=C/C(O)=O)=C1)O
Structure Classification
- Phenols
- Monophenols
Initial Source
- Animals
A. Mellifera
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 100 mg/mL (430.51 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

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

4.3051 mL

21.5257 mL

43.0515 mL

5 mM

0.8610 mL

4.3051 mL

8.6103 mL

10 mM

0.4305 mL

2.1526 mL

4.3051 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. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molaritätsrechner

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

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (275 KB)
SDS (254 KB)
- English - EN (254 KB)
- Français - FR (254 KB)
- Deutsch - DE (254 KB)
- Norwegian - NO (254 KB)
- Español - ES (254 KB)
- Swedish - SV (254 KB)
- Italian - IT (254 KB)
- Korean - KR (254 KB)
- Portuguese - PT (254 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)

Verweise

[1]. Rodrigues DM, et al. Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis. Bioorg Med Chem. 2021;47:116372. [Content Brief]

[2]. Nakashima K, et al. Identification of a naturally occurring retinoid X receptor agonist from Brazilian green propolis. Biochim Biophys Acta. 2014 Oct;1840(10):3034-41. [Content Brief]

[3]. Mishima S, et al. Two related cinnamic Acid derivatives from Brazilian honey bee propolis, baccharin and drupanin, induce growth inhibition in allografted sarcoma S-180 in mice. Biol Pharm Bull. 2005 Jun;28(6):1025-30. [Content Brief]

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

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

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	4.3051 mL	21.5257 mL	43.0515 mL	107.6287 mL
	5 mM	0.8610 mL	4.3051 mL	8.6103 mL	21.5257 mL
	10 mM	0.4305 mL	2.1526 mL	4.3051 mL	10.7629 mL
	15 mM	0.2870 mL	1.4350 mL	2.8701 mL	7.1752 mL
	20 mM	0.2153 mL	1.0763 mL	2.1526 mL	5.3814 mL
	25 mM	0.1722 mL	0.8610 mL	1.7221 mL	4.3051 mL
	30 mM	0.1435 mL	0.7175 mL	1.4350 mL	3.5876 mL
	40 mM	0.1076 mL	0.5381 mL	1.0763 mL	2.6907 mL
	50 mM	0.0861 mL	0.4305 mL	0.8610 mL	2.1526 mL
	60 mM	0.0718 mL	0.3588 mL	0.7175 mL	1.7938 mL
	80 mM	0.0538 mL	0.2691 mL	0.5381 mL	1.3454 mL
	100 mM	0.0431 mL	0.2153 mL	0.4305 mL	1.0763 mL

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Drupanin

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Biologische Aktivität

Chemical Information

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Drupanin Related Classifications

HY-N10361 Related Classifications