MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 564390 | Name: Micheliolide
Featured

Description:

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

Micheliolide is a natural, irreversible activator of pyruvate kinase M2, and a suppressor of leukemia cells.

Chemical Structure

Micheliolide
Micheliolide
CAS#68370-47-8

Theoretical Analysis

MedKoo Cat#: 564390

Name: Micheliolide

CAS#: 68370-47-8

Chemical Formula: C15H20O3

Exact Mass: 248.1412

Molecular Weight: 248.32

Elemental Analysis: C, 72.55; H, 8.12; O, 19.33

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 600.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
MCL, Micheliolide
IUPAC/Chemical Name
(3aS,9R,9aS,9bS)-9-Hydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
InChi Key
RDJAFOWISVMOJY-PWNZVWSESA-N
InChi Code
InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3/t11-,12-,13-,15+/m0/s1
SMILES Code
O=C(O[C@@]1([H])[C@@]2([H])CCC(C)=C3CC[C@@](C)(O)[C@@]31[H])C2=C
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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Micheliolide could effectively attenuate the high glucose-stimulated activation of NF-κB, the degradation of IκBα, and the expression of MCP-1.
In vitro activity:
This study investigated the effect of MCL (micheliolide) on lipopolysaccharide- (LPS-) induced inflammation in renal tubular cells and the related mechanism. MCL significantly suppressed the LPS-induced NF-κB signaling and inflammatory expression of cytokines, such as tumor necrosis factor-α and monocyte chemoattractant protein-1 in a rat renal proximal tubular cell line (NRK-52E). MCL also prevented LPS- and adenosine triphosphate-induced NLRP3 inflammasome activation in vitro, as evidenced by the inhibition of NLRP3 expression, caspase-1 cleavage, and interleukin-1β and interleukin-18 maturation and secretion. Reference: Mediators Inflamm. 2020 Aug 17;2020:3934769. https://pubmed.ncbi.nlm.nih.gov/32879619/
In vivo activity:
Compared with the AS (ankylosing spondylitis) model mice, the protein expression levels of tumor necrosis factor-α (TNF-α), interleukin (IL)-1β, IL-6, and IL-18 were decreased after MCL (micheliolide) treatment. After the addition of celastrol, MCL treatment significantly reduced the levels of p-p65, NLRP3, caspase-1, and ASC. Reference: Ann Transl Med. 2020 Aug;8(16):991. https://pubmed.ncbi.nlm.nih.gov/32953791/
Solvent mg/mL mM comments
Solubility
DMF 5.0 20.14
DMSO 35.0 140.95
DMSO:PBS (pH 7.2) (1:4) 0.2 0.81
Ethanol 25.5 102.69
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 248.32 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.

Recalculate based on batch purity %
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. Feng D, Liu M, Liu Y, Zhao X, Sun H, Zheng X, Zhu J, Shang F. Micheliolide suppresses the viability, migration and invasion of U251MG cells via the NF-κB signaling pathway. Oncol Lett. 2020 Oct;20(4):67. doi: 10.3892/ol.2020.11928. Epub 2020 Jul 29. PMID: 32863900; PMCID: PMC7436293. 2. Lei X, Li S, Luo C, Wang Y, Liu Y, Xu Z, Huang Q, Zou F, Chen Y, Peng F, Long H. Micheliolide Attenuates Lipopolysaccharide-Induced Inflammation by Modulating the mROS/NF-κB/NLRP3 Axis in Renal Tubular Epithelial Cells. Mediators Inflamm. 2020 Aug 17;2020:3934769. doi: 10.1155/2020/3934769. PMID: 32879619; PMCID: PMC7448212. 3. Wu DM, Li J, Shen R, Li J, Yu Y, Li L, Deng SH, Liu T, Zhang T, Xu Y, Wang DG. Autophagy Induced by Micheliolide Alleviates Acute Irradiation-Induced Intestinal Injury via Inhibition of the NLRP3 Inflammasome. Front Pharmacol. 2022 Jan 18;12:773150. doi: 10.3389/fphar.2021.773150. PMID: 35115927; PMCID: PMC8804324. 4. Tian ZG, Yao M, Chen J. Micheliolide alleviates ankylosing spondylitis (AS) by suppressing the activation of the NLRP3 inflammasome and maintaining the balance of Th1/Th2 via regulating the NF-κB signaling pathway. Ann Transl Med. 2020 Aug;8(16):991. doi: 10.21037/atm-20-4987. PMID: 32953791; PMCID: PMC7475468.
In vitro protocol:
1. Feng D, Liu M, Liu Y, Zhao X, Sun H, Zheng X, Zhu J, Shang F. Micheliolide suppresses the viability, migration and invasion of U251MG cells via the NF-κB signaling pathway. Oncol Lett. 2020 Oct;20(4):67. doi: 10.3892/ol.2020.11928. Epub 2020 Jul 29. PMID: 32863900; PMCID: PMC7436293. 2. Lei X, Li S, Luo C, Wang Y, Liu Y, Xu Z, Huang Q, Zou F, Chen Y, Peng F, Long H. Micheliolide Attenuates Lipopolysaccharide-Induced Inflammation by Modulating the mROS/NF-κB/NLRP3 Axis in Renal Tubular Epithelial Cells. Mediators Inflamm. 2020 Aug 17;2020:3934769. doi: 10.1155/2020/3934769. PMID: 32879619; PMCID: PMC7448212.
In vivo protocol:
1. Wu DM, Li J, Shen R, Li J, Yu Y, Li L, Deng SH, Liu T, Zhang T, Xu Y, Wang DG. Autophagy Induced by Micheliolide Alleviates Acute Irradiation-Induced Intestinal Injury via Inhibition of the NLRP3 Inflammasome. Front Pharmacol. 2022 Jan 18;12:773150. doi: 10.3389/fphar.2021.773150. PMID: 35115927; PMCID: PMC8804324. 2. Tian ZG, Yao M, Chen J. Micheliolide alleviates ankylosing spondylitis (AS) by suppressing the activation of the NLRP3 inflammasome and maintaining the balance of Th1/Th2 via regulating the NF-κB signaling pathway. Ann Transl Med. 2020 Aug;8(16):991. doi: 10.21037/atm-20-4987. PMID: 32953791; PMCID: PMC7475468.
1: Zhong J, Gong W, Chen J, Qing Y, Wu S, Li H, Huang C, Chen Y, Wang Y, Xu Z, Liu W, Li H, Long H. Micheliolide alleviates hepatic steatosis in db/db mice by inhibiting inflammation and promoting autophagy via PPAR-γ-mediated NF-кB and AMPK/mTOR signaling. Int Immunopharmacol. 2018 Jun;59:197-208. doi: 10.1016/j.intimp.2018.03.036. Epub 2018 Apr 12. PubMed PMID: 29656210. 2: Li J, Li S, Guo J, Li Q, Long J, Ma C, Ding Y, Yan C, Li L, Wu Z, Zhu H, Li KK, Wen L, Zhang Q, Xue Q, Zhao C, Liu N, Ivanov I, Luo M, Xi R, Long H, Wang PG, Chen Y. Natural Product Micheliolide (MCL) Irreversibly Activates Pyruvate Kinase M2 and Suppresses Leukemia. J Med Chem. 2018 May 10;61(9):4155-4164. doi: 10.1021/acs.jmedchem.8b00241. Epub 2018 Apr 29. PubMed PMID: 29641204; PubMed Central PMCID: PMC5949721. 3: Sun Z, Li G, Tong T, Chen J. Micheliolide suppresses LPS-induced neuroinflammatory responses. PLoS One. 2017 Oct 17;12(10):e0186592. doi: 10.1371/journal.pone.0186592. eCollection 2017. PubMed PMID: 29040306; PubMed Central PMCID: PMC5645131. 4: Jiang X, Wang Y, Qin Y, He W, Benlahrech A, Zhang Q, Jiang X, Lu Z, Ji G, Zheng Y. Micheliolide provides protection of mice against Staphylococcus aureus and MRSA infection by down-regulating inflammatory response. Sci Rep. 2017 Feb 6;7:41964. doi: 10.1038/srep41964. PubMed PMID: 28165033; PubMed Central PMCID: PMC5292736. 5: Qi Z, Li YH, Ding YH, Ji Q, Yang M, Gao YD. [Study of effects of micheliolide on ovarian cancer cell lines and its mechanism]. Zhonghua Fu Chan Ke Za Zhi. 2016 Sep 25;51(9):688-692. doi: 10.3760/cma.j.issn.0529-567X.2016.09.010. Chinese. PubMed PMID: 27671051. 6: Ji Q, Ding YH, Sun Y, Zhang Y, Gao HE, Song HN, Yang M, Liu XL, Zhang ZX, Li YH, Gao YD. Antineoplastic effects and mechanisms of micheliolide in acute myelogenous leukemia stem cells. Oncotarget. 2016 Oct 4;7(40):65012-65023. doi: 10.18632/oncotarget.11342. PubMed PMID: 27542251; PubMed Central PMCID: PMC5323134. 7: Qin X, Jiang X, Jiang X, Wang Y, Miao Z, He W, Yang G, Lv Z, Yu Y, Zheng Y. Micheliolide inhibits LPS-induced inflammatory response and protects mice from LPS challenge. Sci Rep. 2016 Mar 17;6:23240. doi: 10.1038/srep23240. PubMed PMID: 26984741; PubMed Central PMCID: PMC4794649. 8: Jia Y, Zhou L, Tian C, Shi Y, Wang C, Tong Z. Dynamin-related protein 1 is involved in micheliolide-induced breast cancer cell death. Onco Targets Ther. 2015 Nov 16;8:3371-81. doi: 10.2147/OTT.S91805. eCollection 2015. PubMed PMID: 26622184; PubMed Central PMCID: PMC4654538. 9: Jia Y, Zhang C, Zhou L, Xu H, Shi Y, Tong Z. Micheliolide overcomes KLF4-mediated cisplatin resistance in breast cancer cells by downregulating glutathione. Onco Targets Ther. 2015 Aug 28;8:2319-27. doi: 10.2147/OTT.S88661. eCollection 2015. PubMed PMID: 26356142; PubMed Central PMCID: PMC4559251. 10: An Y, Guo W, Li L, Xu C, Yang D, Wang S, Lu Y, Zhang Q, Zhai J, Fan H, Qiu C, Qi J, Chen Y, Yuan S. Micheliolide derivative DMAMCL inhibits glioma cell growth in vitro and in vivo. PLoS One. 2015 Feb 6;10(2):e0116202. doi: 10.1371/journal.pone.0116202. eCollection 2015. PubMed PMID: 25658946; PubMed Central PMCID: PMC4320118. 11: Xu H, Wang J, Wang C, Chang G, Lin Y, Zhang H, Zhang H, Li Q, Pang T. Therapeutic effects of micheliolide on a murine model of rheumatoid arthritis. Mol Med Rep. 2015 Jan;11(1):489-93. doi: 10.3892/mmr.2014.2767. Epub 2014 Oct 24. PubMed PMID: 25351212. 12: Viennois E, Xiao B, Ayyadurai S, Wang L, Wang PG, Zhang Q, Chen Y, Merlin D. Micheliolide, a new sesquiterpene lactone that inhibits intestinal inflammation and colitis-associated cancer. Lab Invest. 2014 Sep;94(9):950-65. doi: 10.1038/labinvest.2014.89. Epub 2014 Jul 28. PubMed PMID: 25068660. 13: Ma WW, Shi QQ, Ding YH, Long J, Zhang Q, Chen Y. Synthesis of micheliolide derivatives and their activities against AML progenitor cells. Molecules. 2013 May 21;18(5):5980-92. doi: 10.3390/molecules18055980. PubMed PMID: 23698050.

View History

MI-888 free base

MI-888 free base