Chelidonine (5, 10 and 20 μM; 3–4 days) resulted in lesions and ventral curling in Dugesia japonica; at 20 μM, Djmcm2 expression was greatly reduced, but at 5 and 10 μM, no reduction was seen; also, it blocked stem cells' ability to advance through the cell cycle [2]. Melanoma cell lines are susceptible to the cytotoxic effects of chelidonine (0–3 μg/mL; 48 hours) [3]. In A-375 cells, the mitochondrial membrane potential (MMP) was 50% lower at 1 and 1.5 μg/mL and at 3 μg/mL of chelidonine (1, 2, and 3 μg/mL; 24 hours). 62% decrease [3].

Cytotoxicity assay [3]
Cell Types: A-375, A-375-p53DD and A-375-p53sh
Tested Concentrations: 0-3 μg/mL
Incubation Duration: 48 hrs (hours)
Experimental Results: demonstrated cytotoxic activity against melanoma cell lines, The values were 0.910±0.017 μg/ml, 0.634±0.009 μg/ml and 0.772±0.045 μg/ml in A-375, A-375-p53DD and A-375-p53sh, respectively.

Metabolism / Metabolites
Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.

Toxicity Summary
Chelidonine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
Chelidonine has an acetylcholinesterase and butyrylcholinesterase inhibitory activity. (Wikipedia)
Generally, some of the alkaloid extract from Chelidonium majus, which contains protoberberine and benzo[c]phenanthridine alkaloids such as chelidonine, intercalate DNA, and in consequence inhibit DNA and RNA polymerase, topoisomerase, telomerase, and even ribosomal protein biosynthesis or bind to tubulin/microtubules, thus acting as spindle poisons. Chelidonine has the ability to overcome multidrug resistance (MDR) of different cancer cell lines through interaction with ABC-transporters, CYP3A4 and GST, by induction of apoptosis, and cytotoxic effects. It induced apoptosis in MDR cells which was accompanied by an activation of caspase-3, -8,-6/9, and phosphatidyl serine (PS) exposure. (A15442) Chelidonine is known to cause mitotic arrest and to interact weakly with tubulin. Chelidonine has proven to be a weak inhibitor of cell growth in two normal (monkey kidney and Hs27), two transformed (Vero and Graham 293) and two malignant (WHCO5 and HeLa) cell lines. (A15443)

[1]. 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.

[2]. The in vivo effect of chelidonine on the stem cell system of planarians. Eur J Pharmacol. 2012 Jul 5;686(1-3):1-7.

[3]. Benzo[c]phenanthridine alkaloids exhibit strong anti-proliferative activity in malignant melanoma cells regardless of their p53 status. J Dermatol Sci. 2011 Apr;62(1):22-35.

Chelidonine is an alkaloid fundamental parent, a benzophenanthridine alkaloid and an alkaloid antibiotic.
Chelidonine has been reported in Stylophorum lasiocarpum, Chelidonium majus, and other organisms with data available.
Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.
See also: Chelidonium majus flowering top (part of); Chelidonine (+) (annotation moved to).

C20H19NO5

353.37

353.126

476-32-4

4312-31-6 (hydrochloride);63937-19-9 (sulfate)

197810

White to off-white solid powder

1.4±0.1 g/cm3

507.4±50.0 °C at 760 mmHg

135-140ºC

260.7±30.1 °C

0.0±1.4 mmHg at 25°C

1.667

2.75

1

6

0

26

560

3

CN1CC2=C(C=CC3=C2OCO3)[C@@H]4[C@H]1C5=CC6=C(C=C5C[C@@H]4O)OCO6

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

(1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol

Chelidonine Khelidonin Stylophorin Stylophorin

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~282.99 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.07 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (7.07 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.07 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)