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Kinetin Riboside (N6-Furfuryladenosine) 4338-47-0

Kinetin Riboside (N6-Furfuryladenosine) 4338-47-0

CAS No.: 4338-47-0

Kinetin Riboside, an analotg of cytokinin, is a potent activator of the Parkinson's Disease-associated PTEN-induced Puta
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Kinetin Riboside, an analotg of cytokinin, is a potent activator of the Parkinson's Disease-associated PTEN-induced Putative Kinase 1 (PINK1), and acts independently from mitochondrial depolarization.


Physicochemical Properties


Molecular Formula C15H17N5O5
Molecular Weight 347.32598
Exact Mass 347.122
Elemental Analysis C, 51.87; H, 4.93; N, 20.16; O, 23.03
CAS # 4338-47-0
Related CAS # 4338-47-0
PubChem CID 20345
Appearance White to off-white solid powder
Density 1.8±0.1 g/cm3
Boiling Point 683.7±65.0 °C at 760 mmHg
Melting Point 152-154ºC
Flash Point 367.3±34.3 °C
Vapour Pressure 0.0±2.2 mmHg at 25°C
Index of Refraction 1.798
LogP 0.2
Hydrogen Bond Donor Count 4
Hydrogen Bond Acceptor Count 9
Rotatable Bond Count 5
Heavy Atom Count 25
Complexity 460
Defined Atom Stereocenter Count 4
SMILES

OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C2N=CN=C3NCC4=CC=CO4)O1)O)O

InChi Key CAGLGYNQQSIUGX-SDBHATRESA-N
InChi Code

InChI=1S/C15H17N5O5/c21-5-9-11(22)12(23)15(25-9)20-7-19-10-13(17-6-18-14(10)20)16-4-8-2-1-3-24-8/h1-3,6-7,9,11-12,15,21-23H,4-5H2,(H,16,17,18)/t9-,11-,12-,15-/m1/s1
Chemical Name

(2R,3R,4S,5R)-2-[6-(furan-2-ylmethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
Synonyms

Kinetin Riboside
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)

Biological Activity


Targets HCT-15 cells (IC50 = 2.5 μM)
ln Vitro Kinetin riboside exhibits antiproliferative and apoptogenic activity against different human cancer cell lines. The proliferation of human colon cancer HCT-15 cells can be inhibited by kinetin riboside in a dose-dependent manner (IC50=2.5 μM)[1]. In HeLa and mouse melanoma B16F-10 cells, kinetoin riboside triggers apoptosis. The release of cytochrome c and activation of caspase-3 are caused by kinetoin riboside, which also alters the potential of the mitochondrial membrane. Under kinetin riboside exposure, Bcl-2 is down-regulated and Bad are up-regulated[2].
ln Vivo Kinetin riboside significantly slows the growth of tumors. At 40 mg/kg, the strongest anti-melanoma response is elicited[2].
Cell Assay HeLa and mouse melanoma B16F-10 cells are treated with 5, 10, 20 μM kinetin riboside for 48 h. Cells are kept at 37°C for 4 hours after adding 15 μL of MTT solution (5 mg/mL) to each well. After that, 100 microliters of solubilizing solution are added. A measurement of 490 nm absorbance is made following an overnight incubation at room temperature[2].
References

[1]. Antiproliferative activity of kinetin riboside on HCT-15 colon cancer cell line. Nucleosides Nucleotides Nucleic Acids. 2012;31(6):474-81.

[2]. Kinetin riboside preferentially induces apoptosis by modulating Bcl-2 family proteins and caspase-3 in cancer cells. Cancer Lett. 2008 Mar 8;261(1):37-45.

Additional Infomation (2R,3R,4S,5R)-2-[6-(2-furanylmethylamino)-9-purinyl]-5-(hydroxymethyl)oxolane-3,4-diol is a purine nucleoside.
Kinetin riboside has been reported in Cocos nucifera and Beta vulgaris with data available.

Solubility Data


Solubility (In Vitro) DMSO : ~250 mg/mL (~719.78 mM)
Solubility (In Vivo) Solubility in Formulation 1: ≥ 2.08 mg/mL (5.99 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 (5.99 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.

Solubility in Formulation 3: ≥ 2.08 mg/mL (5.99 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8791 mL 14.3955 mL 28.7911 mL
5 mM 0.5758 mL 2.8791 mL 5.7582 mL
10 mM 0.2879 mL 1.4396 mL 2.8791 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.