Liensinine

Cat No.:V9242 Purity: ≥98%

COA Product Data Instructions for use SDS

Liensinine is an autophagy/mitophagy inhibitor.

Liensinine Chemical Structure CAS No.: 2586-96-1
Product category: Autophagy

This product is for research use only, not for human use. We do not sell to patients.

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Top Publications Citing lnvivochem Products

Nature 2024 Dec 18.

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nat Neurosci 2024, 27:1468-1474.

Nat Metab 2024, 6: 1108-1127.

Cell Stem Cell 2024, 31:106-126.e13.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2024,57:2651-2668.e12.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Biological Data

Product Description

Liensinine is an autophagy/mitophagy inhibitor. Liensinine is a major isoquinoline alkaloid found in the seed embryos of Nelumbo nucifera Gaertn and has a wide range of bioactivities like antiarrhythmia, anti-hypertensive (blood pressure lowering), antipulmonary fibrosis, vascular smooth muscle relaxation, etc.

Biological Activity I Assay Protocols (From Reference)

ln Vivo	Similar to metronidazole medications, lenisinine (oral gavage, 100 or 200 mg/kg, once day, 10 weeks) can successfully treat periodontitis in a quantitative dose-dependent manner [2].
Animal Protocol	Animal/Disease Models: KM mice [2] Doses: 100 mg/kg, 200 mg/kg Route of Administration: po (oral gavage), daily, 10 weeks Experimental Results: Reduce gingival index, increase SOD levels, CAT, GSH-Px levels, diminished levels of NO, MDA and ET compared with controls. Animal/Disease Models: Institute of Cancer Research (ICR) mice (male, 20-22 grams) [3] Doses: Route of Administration: Oral 5 mg/kg; 1 mg/kg intravenous (iv) (iv)administration Experimental Results: The effect of lianxining in mice pharmacokinetic/PK/PK parameters po (5 mg/kg) iv (1 mg/kg) AUC(0-t) (ng/mLh) 18.8 ± 2.7 211.2 ± 54.9 AUC(0-∞) (ng/mL h) 19.1 ± 2.8 227.9 ± 60.1 MRT(0-t)(h) 3.2 ± 0.4 2.6 ± 0.5 MRT(0-∞) (h) 3.4 ± 0.5 3.5 ± 0.9 t1 /2z (h) 1.9 ± 0.2 3.8 ± 0.8 CLz/F (L/h/kg) 266.0 ± 41.3 4.7 ± 1.2 Vz/F (L/kg) 708.5 ± 79.9 25.9 ± 11.0 Cmax (ng/mL) 5.3 ± 0.2 169.5±53.5
References	[1]. A novel autophagy/mitophagy inhibitor liensinine sensitizes breast cancer cells to chemotherapy through DNM1L-mediated mitochondrial fission. Autophagy. 2015;11(8):1259-79. [2]. Protective effect of liensinine on periodontitis through its antioxidant effect in mice. Journal of the Korean Society for Applied Biological Chemistry volume 58, pages927-936. [3]. Pharmacokinetics and bioavailability of liensinine in mouse blood by UPLC-MS/MS. Acta Chromatographica,Volume 33: Issue 4,14 Oct 2020.
Additional Infomation	Liensinine is a member of isoquinolines. Liensinine has been reported in Nelumbo nucifera with data available.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C37H42N2O6
Molecular Weight	610.7392
Exact Mass	610.304
CAS #	2586-96-1
Related CAS #	Liensinine Diperchlorate;5088-90-4;Liensinine perchlorate;2385-63-9
PubChem CID	160644
Appearance	White to off-white solid powder
Density	1.2±0.1 g/cm3
Boiling Point	722.0±60.0 °C at 760 mmHg
Melting Point	95-99ºC
Flash Point	390.4±32.9 °C
Vapour Pressure	0.0±2.4 mmHg at 25°C
Index of Refraction	1.618
LogP	4.84
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Heavy Atom Count	45
Complexity	917
Defined Atom Stereocenter Count	2
SMILES	CN1CCC2=CC(=C(C=C2[C@H]1CC3=CC=C(C=C3)O)OC4=C(C=CC(=C4)C[C@@H]5C6=CC(=C(C=C6CCN5C)OC)OC)O)OC
InChi Key	XCUCMLUTCAKSOZ-FIRIVFDPSA-N
InChi Code	InChI=1S/C37H42N2O6/c1-38-14-13-26-20-35(43-4)37(22-29(26)30(38)16-23-6-9-27(40)10-7-23)45-33-18-24(8-11-32(33)41)17-31-28-21-36(44-5)34(42-3)19-25(28)12-15-39(31)2/h6-11,18-22,30-31,40-41H,12-17H2,1-5H3/t30-,31-/m1/s1
Chemical Name	4-[[(1R)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2-[[(1R)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl]oxy]phenol
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: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)	DMSO : ~50 mg/mL (~81.87 mM)
Solubility (In Vivo)	Solubility in Formulation 1: ≥ 2.08 mg/mL (3.41 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 20.8 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: ≥ 2.08 mg/mL (3.41 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 20.8 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. View More Solubility in Formulation 3: ≥ 2.08 mg/mL (3.41 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 20 mg/mL (32.75 mM) in 50% PEG300 50% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.)

Solubility (In Vitro)

DMSO : ~50 mg/mL (~81.87 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (3.41 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 20.8 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: ≥ 2.08 mg/mL (3.41 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 20.8 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.

View More

Solubility in Formulation 3: ≥ 2.08 mg/mL (3.41 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

Solubility in Formulation 4: 20 mg/mL (32.75 mM) in 50% PEG300 50% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.6374 mL	8.1868 mL	16.3736 mL
	5 mM	0.3275 mL	1.6374 mL	3.2747 mL
	10 mM	0.1637 mL	0.8187 mL	1.6374 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.

Calculator

Mass

Concentration

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

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Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Biological Data

Figure 1 (See previous page). Liensinine induces autophagic/mitophagic alterations in MDA-MB-231 and MCF-7 cells. (A) The chemical structure of liensinine. (B) EGFP-LC3 expressing MDA-MB-231 and MCF-7 cells were treated without or with liensinine (Lien, 20 μM) for 24 h, the EGFP-LC3 puncta were observed under confocal microscopy; scale bars: 10 μm. (C) Quantification of average EGFP puncta per cell in (B) from 3 independent experiments. Data was presented as mean ± SD (**P < 0.01); 50 cells were analyzed per treatment condition. (D and E) Cells were exposed to various concentrations of Lien for 24 h, or treated with 20 μM Lien for different time intervals as indicated. The expression of autophagy-related proteins (LC3B-I/LC3B-II, SQSTM1, BECN1 and LAMP1) was detected by western blot analysis. GAPDH was used as a loading control. (F) Representative TEM images depicting ultrastructure of MDA-MB-231 and MCF-7 cells treated without or with Lien (20 μM) for 24 h. N, nucleus; M, mitochondria; red arrows indicates autophagic vacuoles. Scale bars: 2 μm. (G) Confocal microscopy images of MDA-MB-231 and MCF-7 cells treated without or with Lien (20 μM) for 24 h after co-expressing RFP-mito and EGFP-LC3; scale bars: 10 μm. Quantitation of EGFP puncta with RFP-mito per cell. Data was presented as mean ± SD (**P < 0.01); 50 cells were analyzed per treatment condition.[1].Zhou J, et al. A novel autophagy/mitophagy inhibitor liensinine sensitizes breast cancer cells to chemotherapy through DNM1L-mediated mitochondrial fission. Autophagy. 2015;11(8):1259-79.

Liensinine inhibits autophagic degradation in MDA-MB-231 cells. (A) MDA-MB-231 cells stably expressing EGFP-LC3 were treated without or with Lien (20 μM) in the presence or absence of 25 nM Baf for 24 h, and total EGFP intensity was measured by flow cytometry. Data are presented as mean ± SD from 3 independent experiments (n.s, not significant, **P < 0.01). (B) Cells were treated without or with Lien (20 μM), or Rapa (0.25 μM) in the presence or absence of 25 nM Baf for 4 h or 24 h; the expression of SQSTM1 and LC3B-II was analyzed by western blot. (C) Cells were transfected with a tandem reporter construct (tfLC3), and were exposed to Lien (20 µM), Baf (20 nM) and Rapa (0.25 μM) as indicated. The colocalization of EGFP and mRFP-LC3 puncta was examined by confocal microscopy. Scale bars: 10 μm. (D) Cells were treated without or with Rapa (0.25 μM) in the presence or absence of 20 μM Lien for 24 h, the expression of SQSTM1 and LC3B-II was analyzed by western blot. Comparisons of the intensities were statistically estimated and represented as mean ± SD for 3 independent experiments (n.s, not significant; **P < 0.01).[1].Zhou J, et al. A novel autophagy/mitophagy inhibitor liensinine sensitizes breast cancer cells to chemotherapy through DNM1L-mediated mitochondrial fission. Autophagy. 2015;11(8):1259-79.

Liensinine blocks autophagosome-lysosome fusion by preventing RAB7A recruitment to lysosomes. (A) MDA-MB-231 cells were transiently transfected with EGFP-LC3 and treated with vehicle, Lien (20 µM), Baf (20 nM) or Rapa (0.25 μM) for 24 h. The fluorescent signals were detected by confocal microscopy after staining with LysoTracker Red. Scale bars: 10 µm. (B) Cells cotransfected with LAMP1-mGFP and mRFP-LC3, were treated and detected for fluorescent signals as in (A). Scale bars: 10 µm. (C) Cells were treated without or with 20 μM Lien for different time intervals as indicated; the expression of LAMP2 and RAB7A in whole cell lysates were determined by western blot. The intensities of band normalization to GAPDH is represented as mean ± SD for 3 independent experiments. (D and E) Cells were treated without or with Lien (20 µM) or Rapa (0.25 µM) for 24 h, whole cell lysate was prepared and subjected to immunoprecipitation using anti-LAMP1 (left panel) or anti-RAB7A (right panel), and the associated LC3B-I/LC3B-II, RAB7A, and LAMP1 were determined using immunoblotting. (F and G) The representative images of MDA-MB-231 cells stained for RAB7A (green), LAMP1 (red) or transfected with mRFP-LC3 after treating with Lien (20 µM) or Rapa (0.25 µM) for 24 h. The Pearson's correlation coefficient (Rr) of RAB7A and LAMP1 or mRFP-LC3 colocalization were represented as mean ± SD (n.s, not significant; *P < 0.05; **P < 0.01), 50 cells. Scale bars: 10 μm.[1].Zhou J, et al. A novel autophagy/mitophagy inhibitor liensinine sensitizes breast cancer cells to chemotherapy through DNM1L-mediated mitochondrial fission. Autophagy. 2015;11(8):1259-79.