Curdione | CAS# 13657-68-6 | CYP3A4 inhibitory activity

MedKoo Cat#: 413411 | Name: Curdione

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Curdione plays an important role in the CYP3A4 inhibitory activity and curdione might inhibit the activity by accelerating the degradation of CYP3A4.

Chemical Structure

Curdione

CAS#13657-68-6

Theoretical Analysis

MedKoo Cat#: 413411

Name: Curdione

CAS#: 13657-68-6

Chemical Formula: C15H24O2

Exact Mass: 236.1776

Molecular Weight: 236.36

Elemental Analysis: C, 76.23; H, 10.24; O, 13.54

Price and Availability

Size	Price	Availability
5mg	USD 265.00	2 Weeks
10mg	USD 450.00	2 Weeks
50mg	USD 950.00	2 Weeks

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Synonym

Curdione; (+)-Curdione

IUPAC/Chemical Name

Cyclodecene-1,4-dione, 6,10-dimethyl-3-(1-methylethyl)-, (3S-(3R*,6E,10R*))-

InChi Key

KDPFMRXIVDLQKX-NHFJXKHHSA-N

InChi Code

InChI=1S/C15H24O2/c1-10(2)13-9-14(16)12(4)7-5-6-11(3)8-15(13)17/h6,10,12-13H,5,7-9H2,1-4H3/b11-6+/t12-,13-/m0/s1

SMILES Code

O=C1C[C@@H](C(C)C)C(C/C(C)=C/CC[C@@H]1C)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Curdione, one of the major sesquiterpene compounds from Rhizoma Curcumae, has been shown to exhibit multiple bioactive properties.

In vitro activity:

Curdione attenuated DOX-induced growth inhibition and release of lactic dehydrogenase in a concentration-dependent manner. And curdione ameliorated the histopathological damage, reduced the elevation of serum creatine kinase-MB isoenzyme (CK-MB) and lactic dehydrogenase by DOX. Furthermore, curdione inhibited DOX-induced cell apoptosis and modulated the expression of Bcl-2 and Bax proteins, as well as abrogated DOX-induced reactive oxygen species accumulation and prevented mitochondria dysfunction. Reference: J Cardiovasc Pharmacol. 2019 Aug;74(2):118-127. https://pubmed.ncbi.nlm.nih.gov/31356549/

In vivo activity:

Indeed, compared with control group, significantly higher levels of hydroxyproline were detected in BLM-induced mice, while curdione administration attenuated BLM-induced hydroxyproline content by 1.6-fold (Fig. 3 f). Reference: Respir Res. 2020; 21: 58. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7031930/

	Solvent	mg/mL	mM
Solubility
	DMSO	59.0	249.62
	DMF	30.0	126.93
	Ethanol	30.0	126.93

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 236.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Wu Z, Zai W, Chen W, Han Y, Jin X, Liu H. Curdione Ameliorated Doxorubicin-Induced Cardiotoxicity Through Suppressing Oxidative Stress and Activating Nrf2/HO-1 Pathway. J Cardiovasc Pharmacol. 2019 Aug;74(2):118-127. doi: 10.1097/FJC.0000000000000692. PMID: 31356549. 2. Fang H, Gao B, Zhao Y, Fang X, Bian M, Xia Q. Curdione inhibits thrombin-induced platelet aggregation via regulating the AMP-activated protein kinase-vinculin/talin-integrin αIIbβ3 sign pathway. Phytomedicine. 2019 Aug;61:152859. doi: 10.1016/j.phymed.2019.152859. Epub 2019 Feb 4. PMID: 31039534. 3. Wei C, Li D, Liu Y, Wang W, Qiu T. Curdione Induces Antiproliferation Effect on Human Uterine Leiomyosarcoma via Targeting IDO1. Front Oncol. 2021 Feb 26;11:637024. doi: 10.3389/fonc.2021.637024. PMID: 33718227; PMCID: PMC7953905. 4. Liu P, Miao K, Zhang L, Mou Y, Xu Y, Xiong W, Yu J, Wang Y. Curdione ameliorates bleomycin-induced pulmonary fibrosis by repressing TGF-β-induced fibroblast to myofibroblast differentiation. Respir Res. 2020 Feb 19;21(1):58. doi: 10.1186/s12931-020-1300-y. PMID: 32075634; PMCID: PMC7031930.

In vitro protocol:

In vivo protocol:

1. Wei C, Li D, Liu Y, Wang W, Qiu T. Curdione Induces Antiproliferation Effect on Human Uterine Leiomyosarcoma via Targeting IDO1. Front Oncol. 2021 Feb 26;11:637024. doi: 10.3389/fonc.2021.637024. PMID: 33718227; PMCID: PMC7953905. 2. Liu P, Miao K, Zhang L, Mou Y, Xu Y, Xiong W, Yu J, Wang Y. Curdione ameliorates bleomycin-induced pulmonary fibrosis by repressing TGF-β-induced fibroblast to myofibroblast differentiation. Respir Res. 2020 Feb 19;21(1):58. doi: 10.1186/s12931-020-1300-y. PMID: 32075634; PMCID: PMC7031930.

1: Wei C, Li D, Liu Y, Wang W, Qiu T. Curdione Induces Antiproliferation Effect on Human Uterine Leiomyosarcoma via Targeting IDO1. Front Oncol. 2021 Feb 26;11:637024. doi: 10.3389/fonc.2021.637024. PMID: 33718227; PMCID: PMC7953905. 2: Liu P, Miao K, Zhang L, Mou Y, Xu Y, Xiong W, Yu J, Wang Y. Curdione ameliorates bleomycin-induced pulmonary fibrosis by repressing TGF-β-induced fibroblast to myofibroblast differentiation. Respir Res. 2020 Feb 19;21(1):58. doi: 10.1186/s12931-020-1300-y. Erratum in: Respir Res. 2023 Apr 17;24(1):114. PMID: 32075634; PMCID: PMC7031930. 3: Wang H, Xie B, Shi S, Zhang R, Liang Q, Liu Z, Cheng Y. Curdione inhibits ferroptosis in isoprenaline-induced myocardial infarction via regulating Keap1/Trx1/GPX4 signaling pathway. Phytother Res. 2023 Jul 27. doi: 10.1002/ptr.7964. Epub ahead of print. PMID: 37500597. 4: Ma Y, Wang P, Wu Z, Li M, Gu Y, Wu H, Liu H. Curdione Relieved Isoproterenol- Induced Myocardial Damage through Inhibiting Oxidative Stress and Apoptosis. Am J Chin Med. 2023;51(1):73-89. doi: 10.1142/S0192415X23500052. Epub 2022 Dec 3. PMID: 36472847. 5: Yang K, Wu B, Wei W, Li C, Li L, Cong Z, Xiang Q. Curdione ameliorates sepsis-induced lung injury by inhibiting platelet-mediated neutrophil extracellular trap formation. Int Immunopharmacol. 2023 May;118:110082. doi: 10.1016/j.intimp.2023.110082. Epub 2023 Mar 28. PMID: 36989889. 6: Wu Z, Zai W, Chen W, Han Y, Jin X, Liu H. Curdione Ameliorated Doxorubicin- Induced Cardiotoxicity Through Suppressing Oxidative Stress and Activating Nrf2/HO-1 Pathway. J Cardiovasc Pharmacol. 2019 Aug;74(2):118-127. doi: 10.1097/FJC.0000000000000692. PMID: 31356549. 7: Li J, Bian WH, Wan J, Zhou J, Lin Y, Wang JR, Wang ZX, Shen Q, Wang KM. Curdione inhibits proliferation of MCF-7 cells by inducing apoptosis. Asian Pac J Cancer Prev. 2014;15(22):9997-10001. doi: 10.7314/apjcp.2014.15.22.9997. PMID: 25520141. 8: Zhang D, Qiao W, Zhao Y, Fang H, Xu D, Xia Q. Curdione attenuates thrombin- induced human platelet activation: β1-tubulin as a potential therapeutic target. Fitoterapia. 2017 Jan;116:106-115. doi: 10.1016/j.fitote.2016.11.016. Epub 2016 Nov 30. PMID: 27915054. 9: Fang H, Gao B, Zhao Y, Fang X, Bian M, Xia Q. Curdione inhibits thrombin- induced platelet aggregation via regulating the AMP-activated protein kinase- vinculin/talin-integrin αIIbβ3 sign pathway. Phytomedicine. 2019 Aug;61:152859. doi: 10.1016/j.phymed.2019.152859. Epub 2019 Feb 4. PMID: 31039534. 10: Dai W, Qin Q, Li Z, Lin L, Li R, Fang Z, Han Y, Mu W, Ren L, Liu T, Zhan X, Xiao X, Bai Z. Curdione and Schisandrin C Synergistically Reverse Hepatic Fibrosis via Modulating the TGF-β Pathway and Inhibiting Oxidative Stress. Front Cell Dev Biol. 2021 Nov 10;9:763864. doi: 10.3389/fcell.2021.763864. PMID: 34858986; PMCID: PMC8631446. 11: Hikino H, Sakurai Y, Takahashi H, Takemoto T. Structure of curdione. Chem Pharm Bull (Tokyo). 1966 Nov;14(11):1310-1. doi: 10.1248/cpb.14.1310. PMID: 5979177. 12: Hikino H, Sakurai Y, Takahashi H, Takemoto T. Structure of curdione. Chem Pharm Bull (Tokyo). 1967 Sep;15(9):1390-4. doi: 10.1248/cpb.15.1390. PMID: 5583715. 13: Chen Y, Zhang L, Qin B, Zhang X, Jia X, Wang X, Jin D, You S. An insight into the curdione biotransformation pathway by Aspergillus niger. Nat Prod Res. 2014;28(7):454-60. doi: 10.1080/14786419.2013.873434. Epub 2014 Jan 23. PMID: 24456521. 14: Ma J, Dong J, Lin G, Yue L, Xiang Z, Xu R, Hu L, Wang X. Determination of curdione in rabbit plasma by liquid chromatography mass spectrometry. Biomed Chromatogr. 2012 May;26(5):655-9. doi: 10.1002/bmc.1711. Epub 2011 Sep 19. PMID: 21932392. 15: Hou XL, Hayashi-Nakamura E, Takatani-Nakase T, Tanaka K, Takahashi K, Komatsu K, Takahashi K. Curdione Plays an Important Role in the Inhibitory Effect of Curcuma aromatica on CYP3A4 in Caco-2 Cells. Evid Based Complement Alternat Med. 2011;2011:913898. doi: 10.1093/ecam/nep229. Epub 2011 Mar 13. PMID: 21785639; PMCID: PMC3137788. 16: Li XJ, Liang L, Shi HX, Sun XP, Wang J, Zhang LS. Neuroprotective effects of curdione against focal cerebral ischemia reperfusion injury in rats. Neuropsychiatr Dis Treat. 2017 Jun 30;13:1733-1740. doi: 10.2147/NDT.S139362. PMID: 28721054; PMCID: PMC5501624. 17: Hashem S, Nisar S, Sageena G, Macha MA, Yadav SK, Krishnankutty R, Uddin S, Haris M, Bhat AA. Therapeutic Effects of Curcumol in Several Diseases; An Overview. Nutr Cancer. 2021;73(2):181-195. doi: 10.1080/01635581.2020.1749676. Epub 2020 Apr 14. PMID: 32285707. 18: Xia Q, Wang X, Xu DJ, Chen XH, Chen FH. Inhibition of platelet aggregation by curdione from Curcuma wenyujin essential Oil. Thromb Res. 2012 Sep;130(3):409-14. doi: 10.1016/j.thromres.2012.04.005. Epub 2012 May 3. PMID: 22560337. 19: Yarmohammadi F, Rezaee R, Karimi G. Natural compounds against doxorubicin- induced cardiotoxicity: A review on the involvement of Nrf2/ARE signaling pathway. Phytother Res. 2021 Mar;35(3):1163-1175. doi: 10.1002/ptr.6882. Epub 2020 Sep 28. PMID: 32985744. 20: Liu P, Miao K, Zhang L, Mou Y, Xu Y, Xiong W, Yu J, Wang Y. Correction to: Curdione ameliorates bleomycin-induced pulmonary fibrosis by repressing TGF-β- induced fibroblast to myofibroblast differentiation. Respir Res. 2023 Apr 17;24(1):114. doi: 10.1186/s12931-023-02416-3. Erratum for: Respir Res. 2020 Feb 19;21(1):58. PMID: 37069594; PMCID: PMC10108457.