MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 558498 | Name: Chelidonine
Featured

Description:

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

Chelidonine is a benzophenanthridine derived from scoulerine from Chelidonium majus. It exhibits anticancer properties and promotes apoptosis in HeLa cells through p38-p53 and PI3K/AKT signalling pathways.

Chemical Structure

Chelidonine
Chelidonine
CAS#476-32-4

Theoretical Analysis

MedKoo Cat#: 558498

Name: Chelidonine

CAS#: 476-32-4

Chemical Formula: C20H19NO5

Exact Mass: 353.1300

Molecular Weight: 353.37

Elemental Analysis: C, 67.98; H, 5.42; N, 3.96; O, 22.64

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
Chelidonine; Stylophorin; Khelidonin; Stylophorin;
IUPAC/Chemical Name
(5bR,6S,12bS)-13-methyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol
InChi Key
GHKISGDRQRSCII-ZOCIIQOWSA-N
InChi Code
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
SMILES Code
CN1CC2=C(C=CC3=C2OCO3)[C@]4([C@H](CC5=CC6=C(C=C5[C@]41[H])OCO6)O)[H]
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:
Chelidonine causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, with anticancer and antiviral activity.
In vitro activity:
Treatment with 1 µM chelidonine for 24 hours inhibited cancer cell growth, and this effect was more evident in MIA PaCa-2 populations than in BxPC-3 populations. Incubation with chelidonine (1 µM) for 48 hours blocked proliferation in BxPC-3 cells by 50%, whereas 90% of growth inhibition was observed in MIA PaCa-2. Reference: Integr Cancer Ther. 2021; 20: 15347354211006191. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8077490/
In vivo activity:
In vivo, chelidonine suppressed the growth of NRAS-driven tumor cells in nude mice while exhibiting minimal toxicity. Reference: Clin Cancer Res. 2020 Jul 1;26(13):3408-3419. https://pubmed.ncbi.nlm.nih.gov/32156748/
Solvent mg/mL mM comments
Solubility
DMSO 67.0 189.60
DMF 30.0 84.90
Ethanol 40.0 113.20
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 353.37 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. Jang HJ, Yang JH, Hong E, Jo E, Lee S, Lee S, Choi JS, Yoo HS, Kang H. Chelidonine Induces Apoptosis via GADD45a-p53 Regulation in Human Pancreatic Cancer Cells. Integr Cancer Ther. 2021 Jan-Dec;20:15347354211006191. doi: 10.1177/15347354211006191. PMID: 33884928; PMCID: PMC8077490. 2. Lee YK, Lee KW, Kim M, Lee Y, Yoo J, Hwangbo C, Park KH, Kim KD. Chelidonine Induces Caspase-Dependent and Caspase-Independent Cell Death through G2/M Arrest in the T98G Human Glioblastoma Cell Line. Evid Based Complement Alternat Med. 2019 May 26;2019:6318179. doi: 10.1155/2019/6318179. PMID: 31239863; PMCID: PMC6556348. 3. Xie YJ, Gao WN, Wu QB, Yao XJ, Jiang ZB, Wang YW, Wang WJ, Li W, Hussain S, Liu L, Leung EL, Fan XX. Chelidonine selectively inhibits the growth of gefitinib-resistant non-small cell lung cancer cells through the EGFR-AMPK pathway. Pharmacol Res. 2020 Sep;159:104934. doi: 10.1016/j.phrs.2020.104934. Epub 2020 May 25. PMID: 32464330. 4. Qian L, Chen K, Wang C, Chen Z, Meng Z, Wang P. Targeting NRAS-Mutant Cancers with the Selective STK19 Kinase Inhibitor Chelidonine. Clin Cancer Res. 2020 Jul 1;26(13):3408-3419. doi: 10.1158/1078-0432.CCR-19-2604. Epub 2020 Mar 10. PMID: 32156748.
In vitro protocol:
1. Jang HJ, Yang JH, Hong E, Jo E, Lee S, Lee S, Choi JS, Yoo HS, Kang H. Chelidonine Induces Apoptosis via GADD45a-p53 Regulation in Human Pancreatic Cancer Cells. Integr Cancer Ther. 2021 Jan-Dec;20:15347354211006191. doi: 10.1177/15347354211006191. PMID: 33884928; PMCID: PMC8077490. 2. Lee YK, Lee KW, Kim M, Lee Y, Yoo J, Hwangbo C, Park KH, Kim KD. Chelidonine Induces Caspase-Dependent and Caspase-Independent Cell Death through G2/M Arrest in the T98G Human Glioblastoma Cell Line. Evid Based Complement Alternat Med. 2019 May 26;2019:6318179. doi: 10.1155/2019/6318179. PMID: 31239863; PMCID: PMC6556348.
In vivo protocol:
1. Xie YJ, Gao WN, Wu QB, Yao XJ, Jiang ZB, Wang YW, Wang WJ, Li W, Hussain S, Liu L, Leung EL, Fan XX. Chelidonine selectively inhibits the growth of gefitinib-resistant non-small cell lung cancer cells through the EGFR-AMPK pathway. Pharmacol Res. 2020 Sep;159:104934. doi: 10.1016/j.phrs.2020.104934. Epub 2020 May 25. PMID: 32464330. 2. Qian L, Chen K, Wang C, Chen Z, Meng Z, Wang P. Targeting NRAS-Mutant Cancers with the Selective STK19 Kinase Inhibitor Chelidonine. Clin Cancer Res. 2020 Jul 1;26(13):3408-3419. doi: 10.1158/1078-0432.CCR-19-2604. Epub 2020 Mar 10. PMID: 32156748.
1: Kim O, Hwangbo C, Kim J, Li DH, Min BS, Lee JH. Chelidonine suppresses migration and invasion of MDA-MB-231 cells by inhibiting formation of the integrin-linked kinase/PINCH/α-parvin complex. Mol Med Rep. 2015 Aug;12(2):2161-8. doi: 10.3892/mmr.2015.3621. Epub 2015 Apr 15. PubMed PMID: 25890994. 2: Qu Z, Zou X, Zhang X, Sheng J, Wang Y, Wang J, Wang C, Ji Y. Chelidonine induces mitotic slippage and apoptotic-like death in SGC-7901 human gastric carcinoma cells. Mol Med Rep. 2016 Feb;13(2):1336-44. doi: 10.3892/mmr.2015.4683. Epub 2015 Dec 14. PubMed PMID: 26677104. 3: Noureini SK, Esmaili H. Multiple mechanisms of cell death induced by chelidonine in MCF-7 breast cancer cell line. Chem Biol Interact. 2014 Nov 5;223:141-9. doi: 10.1016/j.cbi.2014.09.013. Epub 2014 Sep 30. PubMed PMID: 25265580. 4: Kim SH, Hong JH, Lee YC. Chelidonine, a principal isoquinoline alkaloid of Chelidonium majus, attenuates eosinophilic airway inflammation by suppressing IL-4 and eotaxin-2 expression in asthmatic mice. Pharmacol Rep. 2015 Dec;67(6):1168-77. doi: 10.1016/j.pharep.2015.04.013. Epub 2015 May 11. PubMed PMID: 26481537. 5: El-Readi MZ, Eid S, Ashour ML, Tahrani A, Wink M. Modulation of multidrug resistance in cancer cells by chelidonine and Chelidonium majus alkaloids. Phytomedicine. 2013 Feb 15;20(3-4):282-94. doi: 10.1016/j.phymed.2012.11.005. Epub 2012 Dec 11. PubMed PMID: 23238299. 6: Havelek R, Seifrtova M, Kralovec K, Krocova E, Tejkalova V, Novotny I, Cahlikova L, Safratova M, Opletal L, Bilkova Z, Vavrova J, Rezacova M. Comparative cytotoxicity of chelidonine and homochelidonine, the dimethoxy analogues isolated from Chelidonium majus L. (Papaveraceae), against human leukemic and lung carcinoma cells. Phytomedicine. 2016 Mar 15;23(3):253-66. doi: 10.1016/j.phymed.2016.01.001. Epub 2016 Jan 22. PubMed PMID: 26969379. 7: Paul A, Das S, Das J, Samadder A, Khuda-Bukhsh AR. Cytotoxicity and apoptotic signalling cascade induced by chelidonine-loaded PLGA nanoparticles in HepG2 cells in vitro and bioavailability of nano-chelidonine in mice in vivo. Toxicol Lett. 2013 Sep 12;222(1):10-22. doi: 10.1016/j.toxlet.2013.07.006. Epub 2013 Jul 11. PubMed PMID: 23850776. 8: Isolani ME, Pietra D, Balestrini L, Borghini A, Deri P, Imbriani M, Bianucci AM, Batistoni R. The in vivo effect of chelidonine on the stem cell system of planarians. Eur J Pharmacol. 2012 Jul 5;686(1-3):1-7. doi: 10.1016/j.ejphar.2012.03.036. Epub 2012 Apr 3. PubMed PMID: 22503932. 9: Paul A, Das J, Das S, Samadder A, Khuda-Bukhsh AR. Poly (lactide-co-glycolide) nano-encapsulation of chelidonine, an active bioingredient of greater celandine (Chelidonium majus), enhances its ameliorative potential against cadmium induced oxidative stress and hepatic injury in mice. Environ Toxicol Pharmacol. 2013 Nov;36(3):937-47. doi: 10.1016/j.etap.2013.08.008. Epub 2013 Aug 28. PubMed PMID: 24035924. 10: Paul A, Bishayee K, Ghosh S, Mukherjee A, Sikdar S, Chakraborty D, Boujedaini N, Khuda-Bukhsh AR. Chelidonine isolated from ethanolic extract of Chelidonium majus promotes apoptosis in HeLa cells through p38-p53 and PI3K/AKT signalling pathways. Zhong Xi Yi Jie He Xue Bao. 2012 Sep;10(9):1025-38. PubMed PMID: 22979935. 11: Koriem KM, Arbid MS, Asaad GF. Chelidonium majus leaves methanol extract and its chelidonine alkaloid ingredient reduce cadmium-induced nephrotoxicity in rats. J Nat Med. 2013 Jan;67(1):159-67. doi: 10.1007/s11418-012-0667-6. Epub 2012 Apr 8. PubMed PMID: 22484604. 12: Yao JY, Zhou ZM, Pan XY, Hao GJ, Li XL, Xu Y, Shen JY, Ru HS, Yin WL. In vivo anthelmintic activity of chelidonine from Chelidonium majus L. against Dactylogyrus intermedius in Carassius auratus. Parasitol Res. 2011 Nov;109(5):1465-9. doi: 10.1007/s00436-011-2416-2. Epub 2011 May 3. PubMed PMID: 21537985. 13: Kleinrok Z, Szponar J, Matuszek B, Jagiełło-Wójtowicz E. Studies on the participation of the dopaminergic system in the central effects of chelidonine. Pol J Pharmacol Pharm. 1990 Sep-Oct;42(5):417-24. PubMed PMID: 2098751. 14: Panzer A, Joubert AM, Bianchi PC, Hamel E, Seegers JC. The effects of chelidonine on tubulin polymerisation, cell cycle progression and selected signal transmission pathways. Eur J Cell Biol. 2001 Jan;80(1):111-8. PubMed PMID: 11211931. 15: Jagiełło-Wójtowicz E, Jusiak L, Szponar J, Kleinrok Z. Preliminary pharmacological evaluation of chelidonine in rodents. Pol J Pharmacol Pharm. 1989 Mar-Apr;41(2):125-31. PubMed PMID: 2594578. 16: Ma ZX, Feltenberger JB, Hsung RP. Total syntheses of chelidonine and norchelidonine via an enamide-benzyne-[2 + 2] cycloaddition cascade. Org Lett. 2012 Jun 1;14(11):2742-5. doi: 10.1021/ol300967a. Epub 2012 May 10. PubMed PMID: 22575071; PubMed Central PMCID: PMC3366029. 17: Noureini SK, Wink M. Transcriptional down regulation of hTERT and senescence induction in HepG2 cells by chelidonine. World J Gastroenterol. 2009 Aug 7;15(29):3603-10. PubMed PMID: 19653337; PubMed Central PMCID: PMC2721233. 18: Kaminskyy V, Lin KW, Filyak Y, Stoika R. Differential effect of sanguinarine, chelerythrine and chelidonine on DNA damage and cell viability in primary mouse spleen cells and mouse leukemic cells. Cell Biol Int. 2008 Feb;32(2):271-7. Epub 2007 Sep 19. PubMed PMID: 18029203. 19: Hiller KO, Ghorbani M, Schilcher H. Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, and Chelidonium majus extracts on isolated guinea-pig ileum. Planta Med. 1998 Dec;64(8):758-60. PubMed PMID: 9933996. 20: Kemény-Beke A, Aradi J, Damjanovich J, Beck Z, Facskó A, Berta A, Bodnár A. Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine. Cancer Lett. 2006 Jun 8;237(1):67-75. Epub 2005 Jul 12. PubMed PMID: 16019128.