Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H19NO5 |
Molecular Weight | 353.3686 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12[C@@H](O)CC3=CC4=C(OCO4)C=C3[C@@]1([H])N(C)CC5=C2C=CC6=C5OCO6
InChI
InChIKey=GHKISGDRQRSCII-ZOCIIQOWSA-N
InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1
Molecular Formula | C20H19NO5 |
Molecular Weight | 353.3686 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11211931
https://www.ncbi.nlm.nih.gov/pubmed/26626193
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11211931
https://www.ncbi.nlm.nih.gov/pubmed/26626193
Chelidonine is the major alkaloid component of Chelidonium majus. Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase (a nonspecific cholinesterase) inhibitory activity. It showed strong cytotoxicity in cancer cells. While several modes of death have been identified, most of anti-cancer attempts have focused on stimulation of cells to undergo apoptosis. Chelidonine seems to trigger multiple mechanisms in MCF-7 breast cancer cells. It induces both apoptosis and autophagy modes of cell death in a dose dependent manner. Alteration of expression levels of bax/bcl2, and dapk1a by increasing concentration of chelidonine approves switching the death mode from apoptosis induced by very low to autophagy by high concentrations of this compound. On the other hand, submicromolar concentrations of chelidonine strongly suppressed telomerase at both enzyme activity and hTERT transcriptional level. Long exposure of the cells to 50 nanomolar concentration of chelidonine considerably accelerated senescence. Altogether, chelidonine may provide a promising chemistry from nature to treat cancer. Chelidonine exhibits a broad spectrum of pharmacological properties, such as anti-inflammatory and antiviral activities Its biological activities and clinical applications have been extensively investigated. Especially the usage of chelidonine as an anticancer drug is very important lately. It also has profound inhibitory effects on airway inflammation, which means chelidonine can improve allergic asthma in mice and may also work for human medicine.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
34.51 µM [IC50] | |||
Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27420038 |
3.85 µM [IC50] | ||
Target ID: CHEMBL614909 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26677104 |
23.13 µM [IC50] | ||
Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21213973 |
26.8 µM [IC50] | ||
Target ID: CHEMBL1914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21213973 |
31.9 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
[The inhibition enzymatic hydrolysis of acetylthiocholine by acetylcholinesterase using principal alkaloids isolated from celandine and macleya and their derivatives]. | 2001 |
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The effects of chelidonine on tubulin polymerisation, cell cycle progression and selected signal transmission pathways. | 2001 Jan |
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Inhibitory effects of sanguinarine on monoamine oxidase activity in mouse brain. | 2001 Mar |
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Synthesis of a [18F]labeled chelidonine derivative as a possible antitumor agent. | 2001 Mar |
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Synthesis and biological activity of O-acyl and O-alkyl chelidonine derivatives. | 2001 Nov-Dec |
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[Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood]. | 2002 Jan-Feb |
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Inhibitory activity on binding of specific ligands to the human angiotensin II AT(1) and endothelin 1 ET(A) receptors: bioactive benzo[c]phenanthridine alkaloids from the root of Bocconia frutescens. | 2002 Sep |
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[Inhibition of liver mitochondrial monoamine oxidase activity by alkaloids isolated from Chelidonium and Macleaya and by their derivative drugs]. | 2003 |
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Preliminary evaluation of CNS effects of 6-O-substituted chelidonine derivatives. | 2003 Mar-Apr |
|
[Effect of some isoquinoline alkaloids on enzymatic activity of acetylcholinesterase and monoamine oxidase]. | 2005 Mar-Apr |
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Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS. | 2005 Sep-Oct |
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Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway. | 2006 Jan 17 |
|
[Experimental study of the inhibitory effects of Chelidonium majus L. extractive on Streptococcus mutans in vitro]. | 2006 Jun |
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Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine. | 2006 Jun 8 |
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Concise enantioselective total syntheses of (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine and (+)-norchelidonine by a Pd II-catalyzed ring-opening strategy. | 2008 |
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Transcriptional down regulation of hTERT and senescence induction in HepG2 cells by chelidonine. | 2009 Aug 7 |
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Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection. | 2010 Apr |
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Cytotoxic activity of proteins isolated from extracts of Corydalis cava tubers in human cervical carcinoma HeLa cells. | 2010 Dec 17 |
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Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae). | 2010 Nov |
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[Comparative substrate-inhibitor analysis of liver monoamine oxidases of minks]. | 2010 Sep-Oct |
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Multiple mechanisms of cell death induced by chelidonine in MCF-7 breast cancer cell line. | 2014 Nov 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23850776
Mice: mice were fed once/day for 14 consecutive days of the experimental period, respectively, with 50 mg/kg, 75 mg/kg and 100 mg/kg body weight (bw) of chelidonine dissolved in sterile saline.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27420038
2.5 uM chelidonine arrested the cell cycle in the G2/M
phase with an increase from 25.67% to 88.27% in HeLa cells
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:06:44 GMT 2023
by
admin
on
Fri Dec 15 15:06:44 GMT 2023
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Record UNII |
8K7EK8446J
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Record Status |
Validated (UNII)
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Record Version |
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C062047
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207-504-1
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |