d-Evodiamine | CAS#518-17-2 | topoisomerase I and II inhibitor

MedKoo Cat#: 540129 | Name: Evodiamine

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Description:

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

d-Evodiamine is a topoisomerase I and II inhibitor found in the fruit of Evodia rutaecarpa Bentham (Rutaceae). It displays a wide variety of biological activities, including enhancing TRAIL-induced apoptosis in bladder cancer cells, inducing cell cycle arrest in leukemia cells, improving glucose tolerance, and inhibiting viral replication of influenza virus.

Chemical Structure

Evodiamine

CAS#518-17-2

Theoretical Analysis

MedKoo Cat#: 540129

Name: Evodiamine

CAS#: 518-17-2

Chemical Formula: C19H17N3O

Exact Mass: 303.1372

Molecular Weight: 303.36

Elemental Analysis: C, 75.23; H, 5.65; N, 13.85; O, 5.27

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 350.00	2 Weeks
250mg	USD 650.00	2 Weeks

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Related CAS #

518-17-2

Synonym

Evodiamine; D-Evodiamine; (+)-Evodiamine; Evodiamine, (+)-; Q-100579; Q100579; Q 100579; SC-16015; SC16015; SC 16015

IUPAC/Chemical Name

(S)-14-methyl-8,13,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one

InChi Key

TXDUTHBFYKGSAH-SFHVURJKSA-N

InChi Code

InChI=1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3/t18-/m0/s1

SMILES Code

O=C1N2[C@](C(NC3=C4C=CC=C3)=C4CC2)([H])N(C)C5=C1C=CC=C5

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Evodiamine is an alkaloid isolated from the fruit of Evodia rutaecarpa Bentham with diverse biological activities including anti-inflammatory, anti-obesity, and antitumor.

In vitro activity:

Bacterial growth suppression was observed at 5 μM and significant inhibition was observed above 10 μM (Figure 1C). Based on these results, it was demonstrated that evodiamine has an anti-bacterial effect on H. pylori. Reference: Int J Mol Sci. 2021 Apr; 22(7): 3385. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8036659/

In vivo activity:

BALB/c mice were exposed to LPS and subsequent administration of evodiamine (p.o.) for some time, the results of the alveolar lavage fluid and the tissue slices showed that evodiamine treatment alleviated the pulmonary inflammation and fibrosis, stimulated apelin expression and inhibited the inflammatory cytokines. Reference: Phytother Res. 2021 Jun;35(6):3406-3417. https://pubmed.ncbi.nlm.nih.gov/33657655/

	Solvent	mg/mL	mM
Solubility
	DMSO	7.7	25.28
	DMF	2.0	6.59

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 303.36 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. Chou CH, Yang CR. Neuroprotective Studies of Evodiamine in an Okadaic Acid-Induced Neurotoxicity. Int J Mol Sci. 2021 May 19;22(10):5347. doi: 10.3390/ijms22105347. PMID: 34069531; PMCID: PMC8161163. 2. Yang JY, Kim JB, Lee P, Kim SH. Evodiamine Inhibits Helicobacter pylori Growth and Helicobacter pylori-Induced Inflammation. Int J Mol Sci. 2021 Mar 25;22(7):3385. doi: 10.3390/ijms22073385. PMID: 33806161; PMCID: PMC8036659. 3. Ye C, Zhang N, Zhao Q, Xie X, Li X, Zhu HP, Peng C, Huang W, Han B. Evodiamine alleviates lipopolysaccharide-induced pulmonary inflammation and fibrosis by activating apelin pathway. Phytother Res. 2021 Jun;35(6):3406-3417. doi: 10.1002/ptr.7062. Epub 2021 Mar 3. PMID: 33657655. 4. Wang Q, Cui Y, Wu X, Wang J. Evodiamine protects against airway remodelling and inflammation in asthmatic rats by modulating the HMGB1/NF-κB/TLR-4 signalling pathway. Pharm Biol. 2021 Dec;59(1):192-199. doi: 10.1080/13880209.2020.1871374. PMID: 33577738; PMCID: PMC7889089.

In vitro protocol:

In vivo protocol:

1. Ye C, Zhang N, Zhao Q, Xie X, Li X, Zhu HP, Peng C, Huang W, Han B. Evodiamine alleviates lipopolysaccharide-induced pulmonary inflammation and fibrosis by activating apelin pathway. Phytother Res. 2021 Jun;35(6):3406-3417. doi: 10.1002/ptr.7062. Epub 2021 Mar 3. PMID: 33657655. 2. Wang Q, Cui Y, Wu X, Wang J. Evodiamine protects against airway remodelling and inflammation in asthmatic rats by modulating the HMGB1/NF-κB/TLR-4 signalling pathway. Pharm Biol. 2021 Dec;59(1):192-199. doi: 10.1080/13880209.2020.1871374. PMID: 33577738; PMCID: PMC7889089.

1: Xiong YJ, Chen DP, Peng JY, Wang JY, Lv BC, Liu FF, Lin Y. Characteristics of evodiamine-exerted stimulatory effects on rat jejunal contractility. Nat Prod Res. 2015;29(4):388-91. doi: 10.1080/14786419.2014.947485. Epub 2014 Aug 12. PubMed PMID: 25112370. 2: Gavaraskar K, Dhulap S, Hirwani RR. Therapeutic and cosmetic applications of Evodiamine and its derivatives--A patent review. Fitoterapia. 2015 Oct;106:22-35. doi: 10.1016/j.fitote.2015.07.019. Epub 2015 Aug 6. Review. PubMed PMID: 26255828. 3: Liu X, Yang L, Bi Y, Wang LH, Huang H. [Effect of evodiamine in inducing apoptosis of gastric cancer SGC-7901 cells through mTOR signal pathway]. Zhongguo Zhong Yao Za Zhi. 2015 Aug;40(16):3262-6. Chinese. PubMed PMID: 26790304. 4: Khan M, Bi Y, Qazi JI, Fan L, Gao H. Evodiamine sensitizes U87 glioblastoma cells to TRAIL via the death receptor pathway. Mol Med Rep. 2015 Jan;11(1):257-62. doi: 10.3892/mmr.2014.2705. Epub 2014 Oct 20. PubMed PMID: 25333675. 5: Peng X, Zhang Q, Zeng Y, Li J, Wang L, Ai P. Evodiamine inhibits the migration and invasion of nasopharyngeal carcinoma cells in vitro via repressing MMP-2 expression. Cancer Chemother Pharmacol. 2015 Dec;76(6):1173-84. doi: 10.1007/s00280-015-2902-9. Epub 2015 Nov 6. PubMed PMID: 26546460. 6: Shen H, Zhao S, Xu Z, Zhu L, Han Y, Ye J. Evodiamine inhibits proliferation and induces apoptosis in gastric cancer cells. Oncol Lett. 2015 Jul;10(1):367-371. Epub 2015 Apr 27. PubMed PMID: 26171032; PubMed Central PMCID: PMC4487175. 7: Sachita K, Kim Y, Yu HJ, Cho SD, Lee JS. In Vitro Assessment of the Anticancer Potential of Evodiamine in Human Oral Cancer Cell Lines. Phytother Res. 2015 Aug;29(8):1145-51. doi: 10.1002/ptr.5359. Epub 2015 Apr 22. PubMed PMID: 25903972. 8: Jiang ML, Zhang ZX, Li YZ, Wang XH, Yan W, Gong GQ. Antidepressant-like effect of evodiamine on chronic unpredictable mild stress rats. Neurosci Lett. 2015 Feb 19;588:154-8. doi: 10.1016/j.neulet.2014.12.038. Epub 2014 Dec 26. PubMed PMID: 25545553. 9: Yang L, Liu X, Wu D, Zhang M, Ran G, Bi Y, Huang H. Growth inhibition and induction of apoptosis in SGC 7901 human gastric cancer cells by evodiamine. Mol Med Rep. 2014 Apr;9(4):1147-52. doi: 10.3892/mmr.2014.1924. Epub 2014 Jan 28. PubMed PMID: 24481835. 10: Bai X, Meng H, Ma L, Guo A. Inhibitory effects of evodiamine on human osteosarcoma cell proliferation and apoptosis. Oncol Lett. 2015 Feb;9(2):801-805. Epub 2014 Dec 11. PubMed PMID: 25621054; PubMed Central PMCID: PMC4301500. 11: Jiang DF, Li WT, Yang HL, Zhang ZZ, Chen D, Sun C. Long-term effects of evodiamine on expressions of lipogenesis and lipolysis genes in mouse adipose and liver tissues. Genet Mol Res. 2014 Feb 20;13(1):1038-46. doi: 10.4238/2014.February.20.5. PubMed PMID: 24634125. 12: Wei L, Jin X, Cao Z, Li W. [Evodiamine induces extrinsic and intrinsic apoptosis of ovarian cancer cells via the mitogen-activated protein kinase/phosphatidylinositol-3-kinase/protein kinase B signaling pathways]. J Tradit Chin Med. 2016 Jun;36(3):353-9. Chinese. PubMed PMID: 27468551. 13: Zhang T, Qu S, Shi Q, He D, Jin X. Evodiamine induces apoptosis and enhances TRAIL-induced apoptosis in human bladder cancer cells through mTOR/S6K1-mediated downregulation of Mcl-1. Int J Mol Sci. 2014 Feb 21;15(2):3154-71. doi: 10.3390/ijms15023154. PubMed PMID: 24566141; PubMed Central PMCID: PMC3958903. 14: Hong JY, Park SH, Min HY, Park HJ, Lee SK. Anti-proliferative effects of evodiamine in human lung cancer cells. J Cancer Prev. 2014 Mar;19(1):7-13. PubMed PMID: 25337567; PubMed Central PMCID: PMC4189475. 15: Shi L, Yang F, Luo F, Liu Y, Zhang F, Zou M, Liu Q. Evodiamine exerts anti-tumor effects against hepatocellular carcinoma through inhibiting β-catenin-mediated angiogenesis. Tumour Biol. 2016 Sep;37(9):12791-12803. Epub 2016 Jul 23. PubMed PMID: 27449032. 16: Ge X, Chen S, Liu M, Liang T, Liu C. Evodiamine Attenuates PDGF-BB-Induced Migration of Rat Vascular Smooth Muscle Cells through Activating PPARγ. Int J Mol Sci. 2015 Nov 26;16(12):28180-93. doi: 10.3390/ijms161226093. PubMed PMID: 26703570; PubMed Central PMCID: PMC4691040. 17: Wen B, Roongta V, Liu L, Moore DJ. Metabolic activation of the indoloquinazoline alkaloids evodiamine and rutaecarpine by human liver microsomes: dehydrogenation and inactivation of cytochrome P450 3A4. Drug Metab Dispos. 2014 Jun;42(6):1044-54. doi: 10.1124/dmd.114.057414. Epub 2014 Apr 2. PubMed PMID: 24696463. 18: Feng H, Guo B, Kong X, Wu B. [Evodiamine enhances the radiosensitivity of esophageal squamous cell cancer Eca-109 cells]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2016 Jul;32(7):940-4. Chinese. PubMed PMID: 27363277. 19: Zou Y, Qin X, Xiong H, Zhu F, Chen T, Wu H. Apoptosis of human non-small-cell lung cancer A549 cells triggered by evodiamine through MTDH-dependent signaling pathway. Tumour Biol. 2015 Jul;36(7):5187-93. doi: 10.1007/s13277-015-3174-z. Epub 2015 Feb 5. PubMed PMID: 25652471. 20: Yu H, Jin H, Gong W, Wang Z, Liang H. Pharmacological actions of multi-target-directed evodiamine. Molecules. 2013 Jan 31;18(2):1826-43. doi: 10.3390/molecules18021826. Review. PubMed PMID: 23434865.