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Dehydrocorydalin chloride 10605-03-5

Dehydrocorydalin chloride 10605-03-5

CAS No.: 10605-03-5

Dehydrocorydaline chloride (13-Methylpalmatine chloride) is an alkaloid. Dehydrocorydaline regulates Bax and Bcl-2 prote
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Dehydrocorydaline chloride (13-Methylpalmatine chloride) is an alkaloid. Dehydrocorydaline regulates Bax and Bcl-2 protein expression; activates caspase-7 and caspase-8, and inactivates PARP. Dehydrocorydaline chloride can enhance p38 MAPK activation and has anti~inflammatory, anti-cancer and other effects. Dehydrocorydaline chloride has potent antimalarial effects and low cell toxicity/cytotoxicity (cell viability > 90%) against P. falciparum 3D7 strain (IC50=38 nM).

Physicochemical Properties


Molecular Formula C22H24CLNO4
Molecular Weight 401.8833
Exact Mass 401.139
CAS # 10605-03-5
Related CAS # Dehydrocorydaline;30045-16-0;Dehydrocorydaline (hydroxyl);Dehydrocorydaline nitrate;13005-09-9
PubChem CID 160950
Appearance Light yellow to yellow solid powder
Density 1.23g/cm3
Boiling Point 607.6ºC at 760 mmHg
Flash Point 179.9ºC
Vapour Pressure 1.05E-14mmHg at 25°C
Index of Refraction 1.615
LogP 0.697
Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 5
Rotatable Bond Count 4
Heavy Atom Count 28
Complexity 503
Defined Atom Stereocenter Count 0
InChi Key WXOSEFNJXIPZNV-UHFFFAOYSA-M
InChi Code

InChI=1S/C22H24NO4.ClH/c1-13-15-6-7-18(24-2)22(27-5)17(15)12-23-9-8-14-10-19(25-3)20(26-4)11-16(14)21(13)23;/h6-7,10-12H,8-9H2,1-5H3;1H/q+1;/p-1
Chemical Name

2,3,9,10-tetramethoxy-13-methyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium;chloride
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


ln Vitro Myogenin, MyoD, and myosin heavy chain are among the muscle-specific proteins whose expression levels rise when 500 nM DeHydrocorydaline is administered to C2C12 myoblasts. Treatment with dehydrocorydaline increased the activation of p38 MAPK and the binding of MyoD with E protein. Moreover, dehydrocordinine therapy corrected myoblast differentiation abnormalities and differentiation-induced p38 MAPK activation in C2C12 myoblasts caused by the loss of the early myogenic receptor protein Cdo [2]. DeHydrocorydaline markedly and dose-dependently decreased MCF-7 cell growth, which was reversible with the caspase-8 inhibitor Z-IETD-FMK. DNA fragmentation is increased by dehydrocordinine, but it has no effect on ΔΨm. DeHydrocorydaline exhibited a dose-dependent increase in Bax protein expression and a decrease in Bcl-2 protein expression, according to Western blotting study. Additionally, dehydrocorydaline activated caspase-7,-8 and cleaved PARP without influencing caspase-9. According to these findings, deHydrocorydaline prevents the growth of MCF-7 cells by controlling Bax/Bcl-2, turning on caspase, and cleaving PARP-mediated apoptosis [1].
ln Vivo In the acetate-induced writhing test, dehydrocordine (3.6, 6, or 10 mg/kg, i.p.) demonstrated dose-dependent antinociceptive effects and markedly reduced the formalin-induced pain responses in mice. Dehydrocordine decreased the expression of TNF-α, IL-1β, IL-6, and caspase 6 (CASP6) in the spinal cord during the formalin test. These results support the antinociceptive effects of dehydrocorydaline in mice [4].
References

[1]. Dehydrocorydaline inhibits breast cancer cells proliferation by inducing apoptosis in MCF-7 cells. Am J Chin Med. 2012;40(1):177-85.

[2]. Dehydrocorydaline promotes myogenic differentiation via p38 MAPK activation. Mol Med Rep. 2016 Oct;14(4):3029-36.

[3]. Screening of a library of traditional Chinese medicines to identify anti-malarial compounds and extracts. Malar J. 2018 Jun 25;17(1):244.

[4]. Antinociceptive effects of dehydrocorydaline in mouse models of inflammatory pain involve the opioid receptor and inflammatory cytokines. Sci Rep. 2016 Jun 7;6:27129.


Solubility Data


Solubility (In Vitro) DMSO : ~25 mg/mL (~62.21 mM)
Solubility (In Vivo) Solubility in Formulation 1: ≥ 2.5 mg/mL (6.22 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.

Solubility in Formulation 2: ≥ 2.5 mg/mL (6.22 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.

Solubility in Formulation 3: ≥ 2.5 mg/mL (6.22 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.4883 mL 12.4415 mL 24.8830 mL
5 mM 0.4977 mL 2.4883 mL 4.9766 mL
10 mM 0.2488 mL 1.2442 mL 2.4883 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.