1. Cell Cycle/DNA Damage Apoptosis
  2. Nucleoside Antimetabolite/Analog Apoptosis
  3. 2-Chloroadenosine

2-Chloroadenosine is an adenosine analog, a transporter permeabilizer of nucleoside transporters, and a competitive uridine influx inhibitor (apparent Ki=33 μM). 2-Chloroadenosine binds to nitrobenzylthioinosine with high affinity (apparent Ki=0.18 mM). 2-Chloroadenosine promotes Apoptosis and increases cerebral blood flow. 2-Chloroadenosine has anticonvulsant properties. 2-Chloroadenosine is used to study infection, inflammatory diseases, cancer, blood-related diseases, lung injury, epilepsy, and kidney disease.

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2-Chloroadenosine Chemical Structure

2-Chloroadenosine Chemical Structure

CAS No. : 146-77-0

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Based on 1 publication(s) in Google Scholar

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  • Biological Activity

  • Purity & Documentation

  • References

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Description

2-Chloroadenosine is an adenosine analog, a transporter permeabilizer of nucleoside transporters, and a competitive uridine influx inhibitor (apparent Ki=33 μM). 2-Chloroadenosine binds to nitrobenzylthioinosine with high affinity (apparent Ki=0.18 mM). 2-Chloroadenosine promotes Apoptosis and increases cerebral blood flow. 2-Chloroadenosine has anticonvulsant properties. 2-Chloroadenosine is used to study infection, inflammatory diseases, cancer, blood-related diseases, lung injury, epilepsy, and kidney disease[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17].

In Vitro

2-Chloroadenosine (50 μM; 24-72 h) can lead to increased apoptosis, cell cycle arrest in the S phase, inhibition of DNA synthesis, and DNA strand breaks in PC3 cells[1].
2-Chloroadenosine (10-50 μM, 6-72 h) induces apoptotic cell death in EHEB cells[2].
2-Chloroadenosine (0.01-1.0 mM; 18 h) has a selective lethal effect, leading to a rapid decrease in intracellular ATP content in mouse peritoneal macrophages[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Apoptosis Analysis[2]

Cell Line: EHEB
Concentration: 10, 20, 50 μM
Incubation Time: 6, 24, 48, 72 h
Result: Activated the intrinsic pathway of apoptosis in cells, and ATP consumption played an important role in this process.
Led to a time- and dose-dependent activation of caspase-3.
Showed a significant increase of the percentage of both early apoptosis and late apoptosis.
In Vivo

2-Chloroadenosine (15 nmol; local injection; multiple doses, before ischemia, 4 h and 10 h after reperfusion; 7 days) protects hippocampal CA1 neurons from ischemic cell loss in a rat model of incomplete forebrain ischemia-reperfusion[7].
2-Chloroadenosine (0.3-12 nmoles; intraparenchymal injection; single dose) produces dose-dependent and sustained cerebral vasodilation and increases cerebral blood flow in normal rats as measured by spin-labeled MRI, with significant effects on both local and hemispheric blood flow[8].
2-Chloroadenosine (0.5-4 mg/kg, i.p.) inhibits the shake response in rats induced by ice-water exposure, Icilin (HY-11062) injection, or Naloxone (HY-17417A)-precipitated morphine withdrawal in a dose-dependent manner[9].
2-Chloroadenosine (1-10 mg/kg; intraperitoneal injection; administered after the first successful stimulation) has different degrees of inhibitory effects on cortical postepileptic discharges in rats of different ages, and the inhibitory effects on movement and EEG phenomena are most obvious in 18-day-old rats[10].
2-Chloroadenosine (1 mg/mL; intravenous infusion) can alleviate rabbit lung ischemia-reperfusion injury, reduce pulmonary artery pressure, increase cardiac output, and reduce alveolar leukocyte infiltration and protein exudation[11].
2-Chloroadenosine (9-18 nM/min; intravenous injection) can reduce mean arterial blood pressure, filtration fraction, inulin clearance, urine flow and K excretion rate in anesthetized rats in a dose-dependent manner, while reducing Na excretion rate and fractional Na excretion, and increasing plasma K[12].
2-Chloroadenosine (0.1 mM; local perfusion) increases collateral-dependent and normal cerebral blood flow in canine middle cerebral artery branch occlusion[13].
2-Chloroadenosine (0.25-1 mg/kg; intraperitoneal injection) significantly increases the electroconvulsive threshold and enhances the anticonvulsant activity of carbamazepine and clonazepam in mice[14].
2-Chloroadenosine (10 μg/kg/day; intravenous injection; 5 days) improves the survival rate of BALB/c mice infected with Klebsiella pneumoniae B5055 and reduces the levels of inflammatory markers[15].
2-Chloroadenosine (10 μg/kg; intravenous injection) can alleviate acute lung injury induced by live Escherichia coli or endotoxin plus latex particles in guinea pigs under neutropenia and reduce plasma TNF-α levels[16].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: Male Sprague-Dawley rats (weight 371 g)[8]
Dosage: 0.3, 6.0 or 12 nmoles
Administration: intraparenchymal injection; single dose
Result: Produced dose-dependent and sustained cerebral vasodilation and increased cerebral blood flow.
Increased the cerebral blood flow in the 3.6 mm diameter circular region of interest (ROI) around the injection site by 3.77 and 3.93 times, respectively, and increased the cerebral blood flow in the ipsilateral hemisphere ROI by 2.92 and 2.78 times, respectively, at 90 and 180 minutes after injection.
Molecular Weight

301.69

Formula

C10H12ClN5O4

CAS No.
Appearance

Solid

Color

White to off-white

SMILES

OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC3=C2N=C(Cl)N=C3N)O1

Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

DMSO : 100 mg/mL (331.47 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

H2O : 33.33 mg/mL (110.48 mM; Need ultrasonic)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.3147 mL 16.5733 mL 33.1466 mL
5 mM 0.6629 mL 3.3147 mL 6.6293 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

  • Molarity Calculator

  • Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Concentration
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Volume
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Molecular Weight *

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: ≥ 2.5 mg/mL (8.29 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

    Solubility: ≥ 2.5 mg/mL (8.29 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.

For the following dissolution methods, please prepare the working solution directly. It is recommended to prepare fresh solutions and use them promptly within a short period of time.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  PBS

    Solubility: 18.75 mg/mL (62.15 mM); Clear solution; Need ultrasonic

In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

g

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Calculation results:
Working solution concentration: mg/mL
This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only.If necessary, please contact MedChemExpress (MCE).
Purity & Documentation

Purity: 99.79%

References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
H2O / DMSO 1 mM 3.3147 mL 16.5733 mL 33.1466 mL 82.8665 mL
5 mM 0.6629 mL 3.3147 mL 6.6293 mL 16.5733 mL
10 mM 0.3315 mL 1.6573 mL 3.3147 mL 8.2867 mL
15 mM 0.2210 mL 1.1049 mL 2.2098 mL 5.5244 mL
20 mM 0.1657 mL 0.8287 mL 1.6573 mL 4.1433 mL
25 mM 0.1326 mL 0.6629 mL 1.3259 mL 3.3147 mL
30 mM 0.1105 mL 0.5524 mL 1.1049 mL 2.7622 mL
40 mM 0.0829 mL 0.4143 mL 0.8287 mL 2.0717 mL
50 mM 0.0663 mL 0.3315 mL 0.6629 mL 1.6573 mL
60 mM 0.0552 mL 0.2762 mL 0.5524 mL 1.3811 mL
80 mM 0.0414 mL 0.2072 mL 0.4143 mL 1.0358 mL
100 mM 0.0331 mL 0.1657 mL 0.3315 mL 0.8287 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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2-Chloroadenosine
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