yingweiwo

Cordycepin

Alias: 9(3DeoxyDribofuranosyl)adenine; Cordycepin; 3'-Deoxyadenosine; 73-03-0; Cordycepine; 9-Cordyceposidoadenine; ADENOSINE, 3'-DEOXY-; 9-(beta-D-3'-Deoxyribofuranosyl)adenine; (2R,3R,5S)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol; 3Deoxyadenosine
Cat No.:V18635 Purity: ≥98%
Cordycepin (3'-Deoxyadenosine) is a nucleoside analogue that can inhibit IL-1β-induced MMP-1 and MMP-3 expression in rheumatoid arthritis synovial fibroblasts (RASF).
Cordycepin
Cordycepin Chemical Structure CAS No.: 73-03-0
Product category: MMP
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
25mg
50mg
100mg
Other Sizes
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text

 

  • Business Relationship with 5000+ Clients Globally
  • Major Universities, Research Institutions, Biotech & Pharma
  • Citations by Top Journals: Nature, Cell, Science, etc.
Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: ≥98%

Product Description
Cordycepin (3'-Deoxyadenosine) is a nucleoside analogue that can inhibit IL-1β-induced MMP-1 and MMP-3 expression in rheumatoid arthritis synovial fibroblasts (RASF). dose dependent. Cordycepin kills Mycobacterium tuberculosis (TB) by inhibiting the bacterium's adenosine kinase.
Biological Activity I Assay Protocols (From Reference)
Targets
MMP-1/3
ln Vitro
Cordycepin substantially bursts the p38/JNK/AP-1 signaling pathway in RASF and suppresses the generation of chemokines and MMP expression that are triggered by IL-1β. The MTT assay was employed to assess cordycepin's impact on RASF cytotoxicity. Cell viability of RASF treated with cordycepin (50 μM or 100 μM) did not alter significantly during the course of the 24-hour treatment. On the other hand, cell viability was recovered after 48 hours after treatment with 100 μM cordycepin [1].
Enzyme Assay
ELISA of chemokines[1]
RASFs were pre-treated with cordycepin (50 μM and 100 μM) for 1 h and then incubated with IL-1β (5 ng/ml). After 24 h, culture medium was collected and centrifuged at 10 000 g for 5 min at 4°C to remove particulates. Quantities of RANTES, ENA-78, MCP-1 and GRO-α were determined using Quantikine ELISA kits. Optical density was determined with Microplate reader. A standard curve of each cytokine was established using known concentrations of cytokine by plotting optical density vs log of the concentration.[1]
Cordycepin is an efficient component of Cordyceps spp, a traditional Chinese medicine widely used for healthcare in China, and has been recently acted as a strong anticancer agent for clinic. However, whether and how it may play a role in combating tuberculosis, caused by Mycobacterium tuberculosis, remains unknown. Here we report that cordycepin can kill Mycobacterium by hijacking the bacterial adenosine kinase (AdoK), a purine salvage enzyme responsible for the phosphorylation of adenosine (Ado) to adenosine monophosphate (AMP). We show that cordycepin is a poor AdoK substrate but it competitively inhibits the catalytic activity of AdoK for adenosine phosphorylation. Cordycepin does not affect the activity of the human adenosine kinase (hAdoK), whereas hAdoK phosphorylates cordycepin to produce a new monophosphate derivative. Co-use of cordycepin and deoxycoformycin, an inhibitor of adenosine deaminase (ADD), more efficiently kills M. bovis and M. tuberculosis. The add-deleted mycobacterium is more sensitive to cordycepin. This study characterized cordycepin as a new mycobactericidal compound and also uncovered a potential anti-mycobacterial mechanism[2].
Cell Assay
Determination of cell viability[1]
RASFs (2 × l04 cells/well) were treated with various concentrations of cordycepin. After incubation for 1 h, 12 h and 24 h, cells were washed twice with PBS, MTT (0.5 mg/ml PBS) was added to each well and incubated at 37°C for 30 min. Formazan crystals formed were dissolved by adding DMSO (100 μl/well) and the absorbance was read at 570 nm using a microplate reader[1].
Western blot analysis[1]
RASFs (5 × 106 cells) were pre-treated with cordycepin for 1 h and then incubated with IL-1β (5 ng/ml) or TNF-α (5 ng/ml) for 24 h. Cells were lysed with 40 μl of ice-cold lysis buffer (50 mM Tris–HCl pH 7.4, 1% NP-40, 0.5% sodium deoxycholate, 150 mM NaCl, 1 mM EGTA, 0.1% SDS). Samples were separated by SDS–PAGE with 10% polyacrylamide gels and electrotransferred into polyvinylidene fluoride (PVDF). The PVDF membranes were blotted with 1 μg/ml of primary antibodies for p38, p-p38, JNK, p-JNK, ERK, p-ERK, β-actin, MMP-1 and MMP-3. HRP-conjugated IgG was used as a secondary antibody. The protein expression levels were then determined by analysing the signals captured on the PVDF membranes using an image analyser
References

[1]. Cordycepin inhibits IL-1beta-induced MMP-1 and MMP-3 expression in rheumatoid arthritis synovial fibroblasts. Rheumatology (Oxford). 2009 Jan;48(1):45-8.

[2]. Cordycepin kills Mycobacterium tuberculosis through hijacking the bacterial adenosine kinase. PLoS One. 2019 Jun 14;14(6):e0218449.

Additional Infomation
Cordycepin is a 3'-deoxyribonucleoside and a member of adenosines. It has a role as an antimetabolite and a nucleoside antibiotic.
Cordycepin has been used in trials studying the treatment of Leukemia.
Cordycepin has been reported in Cordyceps militaris, Streptomyces sparsogenes, and other organisms with data available.
Cordycepin is a purine nucleoside antimetabolite and antibiotic isolated from the fungus Cordyceps militaris with potential antineoplastic, antioxidant, and anti-inflammatory activities. Cordycepin is an inhibitor of polyadenylation, activates AMP-activated protein kinase (AMPK) and reduces mammalian target of rapamycin (mTOR) signaling, which may result in both the induction of tumor cell apoptosis and a decrease in tumor cell proliferation. mTOR, a serine/threonine kinase belonging to the phosphatidylinositol 3-kinase (PI3K)-related kinase (PIKK) family, plays an important role in the PI3K/AKT/mTOR signaling pathway that regulates cell growth and proliferation, and its expression or activity is frequently dysregulated in human cancers.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H13N5O3
Molecular Weight
251.24
Exact Mass
251.101
Elemental Analysis
C, 47.81; H, 5.22; N, 27.87; O, 19.10
CAS #
73-03-0
Related CAS #
73-03-0;
PubChem CID
6303
Appearance
White to off-white solid powder
Density
1.9±0.1 g/cm3
Boiling Point
627.2±65.0 °C at 760 mmHg
Melting Point
225-229ºC
Flash Point
333.1±34.3 °C
Vapour Pressure
0.0±1.9 mmHg at 25°C
Index of Refraction
1.863
LogP
-0.41
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
2
Heavy Atom Count
18
Complexity
307
Defined Atom Stereocenter Count
3
SMILES
O1[C@]([H])(C([H])([H])O[H])C([H])([H])[C@]([H])([C@]1([H])N1C([H])=NC2=C(N([H])[H])N=C([H])N=C12)O[H]
InChi Key
OFEZSBMBBKLLBJ-BAJZRUMYSA-N
InChi Code
InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1
Chemical Name
(2R,3R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
Synonyms
9(3DeoxyDribofuranosyl)adenine; Cordycepin; 3'-Deoxyadenosine; 73-03-0; Cordycepine; 9-Cordyceposidoadenine; ADENOSINE, 3'-DEOXY-; 9-(beta-D-3'-Deoxyribofuranosyl)adenine; (2R,3R,5S)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol; 3Deoxyadenosine
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

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 : ~33.33 mg/mL (~132.66 mM)
H2O : ~2 mg/mL (~7.96 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.95 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 (9.95 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.

View More

Solubility in Formulation 3: ≥ 2.5 mg/mL (9.95 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.


Solubility in Formulation 4: 5.56 mg/mL (22.13 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.9803 mL 19.9013 mL 39.8026 mL
5 mM 0.7961 mL 3.9803 mL 7.9605 mL
10 mM 0.3980 mL 1.9901 mL 3.9803 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

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
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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.

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
g/mol

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.
/

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)
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.)
+
+
+

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.

(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.

Clinical Trial Information
Chemotherapy With Cordycepin Plus Pentostatin in Treating Patients With Refractory Acute Lymphocytic or Chronic Myelogenous Leukemia
CTID: NCT00003005
Phase: Phase 1
Status: Completed Date: 2012-06-13
Contact Us