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Palmatine hydrochloride

CAS# 10605-02-4

Palmatine hydrochloride

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Quality Control of Palmatine hydrochloride

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Chemical structure

Palmatine hydrochloride

3D structure

Chemical Properties of Palmatine hydrochloride

Cas No. 10605-02-4 SDF Download SDF
PubChem ID 73442 Appearance Yellow powder
Formula C21H22ClNO4 M.Wt 387.86
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Fibrauretin chloride
Solubility DMSO : ≥ 32 mg/mL (82.50 mM)
H2O : 5 mg/mL (12.89 mM; Need ultrasonic)
*"≥" means soluble, but saturation unknown.
Chemical Name 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium;chloride
SMILES COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC.[Cl-]
Standard InChIKey RLQYRXCUPVKSAW-UHFFFAOYSA-M
Standard InChI InChI=1S/C21H22NO4.ClH/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4;/h5-6,9-12H,7-8H2,1-4H3;1H/q+1;/p-1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Palmatine hydrochloride

1 Berberis sp. 2 Corydalis sp. 3 Jateorhiza sp. 4 Mahonia sp. 5 Zanthoxylum sp.

Biological Activity of Palmatine hydrochloride

DescriptionPalmatine hydrochloride is a hydrochloride salt of palmatine which is a protoberberine alkaloid, it can induce remarkable cell apoptosis, has potential in photodynamic therapy on colon adenocarcinoma. Palmatine hydrochloride has anti-C. albicans effect, it mixes with berberine hydrochloride elicit antifungal activities, it also can reduce blood sugar and oxidative stress in STZ induced diabetic rats.
TargetsAntifection
In vitro

Investigation on the Anti-Candida albicans Effect of Palmatine Hydrochloride Based on Microcalorimetry and Principal Component Analysis[Reference: WebLink]

Acta Chim. Sin. Chinese Edition, 2009, 67(21):2511-6.


METHODS AND RESULTS:
Using an LKB-2277 bioactivity monitor, the metabolic power-time curves of Candida albicans (C albicans) growth affected by Palmatine hydrochloride were measured at 37 degrees C, then nine quantitative thermokinetic parameters were obtained from these curves and investigated by principal component analysis (PCA) to evaluate the anti-C. albicans effect of Palmatine hydrochloride. The results showed that the anti-C. albicans effect of this compound was mainly influenced by the growth rate constant (k(2)) and maximum power output P(m)(2) of phase II, and could be easily, quickly and exactly evaluated by analyzing the change of these two quantitative parameters.
CONCLUSIONS:
This work provides a useful method and idea for further evaluating the anti-bacterial effect of other drugs and compounds.

In vivo

Palmatine hydrochloride improves motor dysfunction in streptozotocin-induced diabetic rats.[Reference: WebLink]

Proceedings of the National Academy of Sciences, 2014, 48(3):461-471.

Diabetes induces motor dysfunctions, Palmatine is an isoquinoline alkaloid, with anti-diabetic and antioxidant activities. This study was conducted to evaluate the effect of Palmatine on motor dysfunction in STZ-induced diabetic rats.
METHODS AND RESULTS:
In this experimental study, 32 male wistar rats were randomly allocated into control, Palmatine-treated non-diabetic, diabetic and Palmatine-treated diabetic groups. Diabetes was induced by STZ administration at the dose of 55 mg/kg/bw, intraperitoneally. Palmatine hydrochloride was administered subcutaneous at doses of 10 mg/kg/bw per day for a period of 6 weeks, one week after induction of diabetes. Blood glucose level was measured 1, 3, 5, 7 weeks after STZ injection. Locomotor activity tests including Y maze, grip-traction and inclined plane tests were performed to determining locomotor activity. Results: In Y maze test, the number of arms entered significantly increased in Palmatine-treated diabetic group compared to diabetic group (P<0.05). Grip traction and inclined plane tests significantly increased in Palmatine-treated diabetic group compared to diabetics animals (P<0.05).
CONCLUSIONS:
Palmatine hydrochloride administration for 6 weeks improves motor dysfunctions in streptozotocin-induced diabetic rats.

Protocol of Palmatine hydrochloride

Cell Research

Photodynamic action of palmatine hydrochloride on colon adenocarcinoma HT-29 cells.[Pubmed: 27181460 ]

Photodiagnosis Photodyn Ther. 2016 Sep;15:53-8.

Palmatine hydrochloride (PaH) is a natural active compound from a traditional Chinese medicine (TCM). The present study aims to evaluate the effect of PaH as a new photosensitizer on colon adenocarcinoma HT-29 cells upon light irradiation.
METHODS AND RESULTS:
Firstly, the absorption and fluorescence spectra of PaH were measured using a UV-vis spectrophotometer and RF-1500PC spectrophotometer, respectively. Singlet oxygen ((1)O2) production of PaH was determined using 1, 3-diphenylisobenzofuran (DPBF). Dark toxicity of PaH was estimated using the 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay. Cellular uptake of PaH in HT-29 cells was detected at different time intervals. Subellular localization of PaH in HT-29 cells was observed using confocal laser fluorescence microscopy. For photodynamic treatment, HT-29 cells were incubated with PaH and then irradiated by visible light (470nm) from a LED light source. Photocytotoxicity was investigated 24h after photodynamic treatment using MTT assay. Cell apoptosis was observed 18h after photodynamic treatment using a flow cytometry with Annexin V/PI staining. Results showed that PaH has an absorption peak in the visible region from 400nm to 500nm and a fluorescence emission peak at 406nm with an excitation wavelength of 365nm. PaH was activated by the 470nm visible light from a LED light source to produce (1)O2. Dark toxicity showed that PaH alone treatment had no cytotoxicity to HT-29 cancer cells and NIH-3T3 normal cells after incubation for 24h. After incubation for 40min, the cellular uptake of PaH reached to the maximum and PaH was located in mitochondria. Photodynamic treatment of PaH demonstrated a significant photocytotoxicity on HT-29 cells. The rate of cell death increased significantly in a PaH concentration-dependent and light dose-dependent manner. Further evaluation revealed that the early and late apoptotic rate of HT-29 cells increased remarkably up to 21.54% and 5.39% after photodynamic treatment of PaH at the concentration of 5μM and energy density of 10.8J/cm(2).
CONCLUSIONS:
Our findings demonstrated that PaH as a naturally occurring photosensitizer has potential in photodynamic therapy on colon adenocarcinoma.

Structure Identification
Luminescence. 2014 May;29(3):211-8.

Studies on the interaction of palmatine hydrochloride with bovine hemoglobin.[Pubmed: 23696111 ]

The interaction between bovine hemoglobin (BHb) and Palmatine hydrochloride (PMT) was investigated at different temperatures using multispectroscopy, as well as the effect of common metal ions (Ca(2+) , Mg(2+) , Zn(2+) , Cu(2+) , Fe(2+) , Fe(3+) , Co(2+) , Ni(2+) ) on the BHb-PMT system. Results showed that the quenching mechanism of PMT on BHb was a static process. The electrostatic force played an important role in the conjugation reaction between BHb and PMT. The order of magnitude of the binding constants (Ka ) was 10(4) , and the number of binding sites (n) in the binary system was ~ 1. The binding distance (r) was ~ 2.44 nm and the primary binding for PMT was located at β-37 tryptophan in the hydrophobic cavity of BHb. In addition, the Hill's coefficients were ~ 1. Synchronous and circular dichroism spectra revealed that the microenvironment and the conformation of BHb were changed during the binding reaction.

Palmatine hydrochloride Dilution Calculator

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Preparing Stock Solutions of Palmatine hydrochloride

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.5782 mL 12.8912 mL 25.7825 mL 51.565 mL 64.4562 mL
5 mM 0.5156 mL 2.5782 mL 5.1565 mL 10.313 mL 12.8912 mL
10 mM 0.2578 mL 1.2891 mL 2.5782 mL 5.1565 mL 6.4456 mL
50 mM 0.0516 mL 0.2578 mL 0.5156 mL 1.0313 mL 1.2891 mL
100 mM 0.0258 mL 0.1289 mL 0.2578 mL 0.5156 mL 0.6446 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Palmatine hydrochloride

Palmatine chloride an isoquinoline alkaloid, is an important medicinal herbal extract with diverse pharmacological and biological properties. IC50 value: Target: In vitro: Experimental set examined the influence of palmatine on osteoblast-like cells in vitro. In the culture supernatant of MC3T3-E1 cells, RANKL and OPG levels were significantly reduced by palmatine addition [1]. In vivo: The first experimentaI set was designed to histologically and biochemically examine mice randomly divided into four groups: sham-operated, OVX, and OVX-palmatine intake groups (1 mg/kg and 10 mg/kg). In palmatine-treated mice, RANKL and OPG expression decreased [1].

References:
[1]. SHINTARO ISHIKAWA, et al. Influence of Palmatine on Bone Metabolism in Ovariectomized Mice and Cytokine Secretion of Osteoblasts. [2]. Chen-Wen Xiao, er al. Antifungal activity of berberine hydrochloride and palmatine hydrochloride against Microsporum canis -induced dermatitis in rabbits and underlying mechanism. BMC Complement Altern Med. 2015; 15: 177.

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References on Palmatine hydrochloride

Photodynamic action of palmatine hydrochloride on colon adenocarcinoma HT-29 cells.[Pubmed:27181460]

Photodiagnosis Photodyn Ther. 2016 Sep;15:53-8.

Palmatine hydrochloride (PaH) is a natural active compound from a traditional Chinese medicine (TCM). The present study aims to evaluate the effect of PaH as a new photosensitizer on colon adenocarcinoma HT-29 cells upon light irradiation. Firstly, the absorption and fluorescence spectra of PaH were measured using a UV-vis spectrophotometer and RF-1500PC spectrophotometer, respectively. Singlet oxygen ((1)O2) production of PaH was determined using 1, 3-diphenylisobenzofuran (DPBF). Dark toxicity of PaH was estimated using the 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay. Cellular uptake of PaH in HT-29 cells was detected at different time intervals. Subellular localization of PaH in HT-29 cells was observed using confocal laser fluorescence microscopy. For photodynamic treatment, HT-29 cells were incubated with PaH and then irradiated by visible light (470nm) from a LED light source. Photocytotoxicity was investigated 24h after photodynamic treatment using MTT assay. Cell apoptosis was observed 18h after photodynamic treatment using a flow cytometry with Annexin V/PI staining. Results showed that PaH has an absorption peak in the visible region from 400nm to 500nm and a fluorescence emission peak at 406nm with an excitation wavelength of 365nm. PaH was activated by the 470nm visible light from a LED light source to produce (1)O2. Dark toxicity showed that PaH alone treatment had no cytotoxicity to HT-29 cancer cells and NIH-3T3 normal cells after incubation for 24h. After incubation for 40min, the cellular uptake of PaH reached to the maximum and PaH was located in mitochondria. Photodynamic treatment of PaH demonstrated a significant photocytotoxicity on HT-29 cells. The rate of cell death increased significantly in a PaH concentration-dependent and light dose-dependent manner. Further evaluation revealed that the early and late apoptotic rate of HT-29 cells increased remarkably up to 21.54% and 5.39% after photodynamic treatment of PaH at the concentration of 5muM and energy density of 10.8J/cm(2). Our findings demonstrated that PaH as a naturally occurring photosensitizer has potential in photodynamic therapy on colon adenocarcinoma.

Studies on the interaction of palmatine hydrochloride with bovine hemoglobin.[Pubmed:23696111]

Luminescence. 2014 May;29(3):211-8.

The interaction between bovine hemoglobin (BHb) and Palmatine hydrochloride (PMT) was investigated at different temperatures using multispectroscopy, as well as the effect of common metal ions (Ca(2+) , Mg(2+) , Zn(2+) , Cu(2+) , Fe(2+) , Fe(3+) , Co(2+) , Ni(2+) ) on the BHb-PMT system. Results showed that the quenching mechanism of PMT on BHb was a static process. The electrostatic force played an important role in the conjugation reaction between BHb and PMT. The order of magnitude of the binding constants (Ka ) was 10(4) , and the number of binding sites (n) in the binary system was ~ 1. The binding distance (r) was ~ 2.44 nm and the primary binding for PMT was located at beta-37 tryptophan in the hydrophobic cavity of BHb. In addition, the Hill's coefficients were ~ 1. Synchronous and circular dichroism spectra revealed that the microenvironment and the conformation of BHb were changed during the binding reaction.

Description

Palmatine chloride is an orally active and irreversible indoleamine 2,3-dioxygenase 1 (IDO-1) inhibitor. Palmatine chloride can ameliorate DSS-induced colitis by mitigating colonic injury, preventing gut microbiota dysbiosis, and regulating tryptophan catabolism. Palmatine has the potential for colitis treatment.

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