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 |