Kinetin riboside

Names

[ Name ]:
Kinetin riboside

[Synonym ]:
9H-Purin-6-amine, N-(2-furanylmethyl)-9-pentofuranosyl-
N-(2-Furylmethyl)-9-pentofuranosyl-9H-purin-6-amine
furfuryladenosine
EINECS 224-389-3
6-Furfurylaminopurine riboside (N6-(2-Furanylmethyl)adenosine
Kinetin-9-riboside
MFCD00037987
n-furfuryl-adenosin
Ribosylkinetin
N-Furfuryladenosine

Biological Activity

[Description]:

Kinetin riboside, a cytokinin analog, can induce apoptosis in cancer cells. It inhibits the proliferation of HCT-15 cells with an IC50 of 2.5 μM.

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[Target]

IC50: 2.5 μM (HCT-15 cells)[1]

[In Vitro]

Kinetin riboside displays antiproliferative and apoptogenic activity against various human cancer cell lines. Kinetin riboside is able to inhibit the proliferation in HCT-15 human colon cancer cells in a dose-dependent manner (IC50=2.5 μM)[1]. Kinetin riboside induces apoptosis in HeLa and mouse melanoma B16F-10 cells. Kinetin riboside disrupts the mitochondrial membrane potential and induces the release of cytochrome c and activation of caspase-3. Bad are up-regulated while Bcl-2 is down-regulated under kinetin riboside exposure[2].

[In Vivo]

Kinetin riboside significantly suppresses tumor growth. The most effective anti-melanoma response is elicited at 40 mg/kg[2].

[Cell Assay]

HeLa and mouse melanoma B16F-10 cells are treated with 5, 10, 20 μM kinetin riboside for 48 h. 15 μL of MTT solution (5 mg/mL) is added to each well and cells are maintained for 4 h at 37°C. Hundred microlitres of solubilizing solution is then added. After an overnight incubation at room temperature, absorbance at 490 nm is measured[2].

[Animal admin]

Mice: Male C57BL/6 mice are injected B16 F-10 cells. After 5 days for tumor growth, kinetin riboside (10, 20, 40 mg/kg) is injected to tumor mass directly. Drug injection is performed once a 3 days for three times. After third injection of drug, mice are kept for 3 days with no injection and tumor mass is removed from each mouse and weighed[2].

[References]

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

[2]. Choi BH, et al. 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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
683.7±65.0 °C at 760 mmHg

[ Melting Point ]:
152-154ºC

[ Molecular Formula ]:
C₁₅H₁₇N₅O₅

[ Molecular Weight ]:
347.326

[ Flash Point ]:
367.3±34.3 °C

[ Exact Mass ]:
347.122955

[ PSA ]:
138.69000

[ LogP ]:
0.20

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.798

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AU7400200

CHEMICAL NAME :: Adenosine, N-furfuryl-

CAS REGISTRY NUMBER :: 4338-47-0

BEILSTEIN REFERENCE NO. :: 0059588

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C15-H17-N5-O5

MOLECULAR WEIGHT :: 347.37

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Human Leukocyte

DOSE/DURATION :: 100 umol/L

REFERENCE :: EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 32,29,1976

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AU7400200

[ HS Code ]:
29349990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

High-internal-phase-emulsion polymeric monolith coupled with liquid chromatography-electrospray tandem mass spectrometry for enrichment and sensitive detection of trace cytokinins in plant samples.

Anal. Bioanal. Chem 407 , 6071-9, (2015)

High-internal-phase-emulsion polymers (polyHIPEs) show great promise as solid-phase-extraction (SPE) materials because of the tremendous porosity and highly interconnected framework afforded by the hi...

Constrained NBMPR analogue synthesis, pharmacophore mapping and 3D-QSAR modeling of equilibrative nucleoside transporter 1 (ENT1) inhibitory activity.

Bioorg. Med. Chem. 16 , 3848-65, (2008)

Conformationally constrained analogue synthesis was undertaken to aid in pharmacophore mapping and 3D-QSAR analysis of nitrobenzylmercaptopurine riboside (NBMPR) congeners as equilibriative nucleoside...

Ribose-modified purine nucleosides as ribonucleotide reductase inhibitors. Synthesis, antitumor activity, and molecular modeling of N6-substituted 3'-C-methyladenosine derivatives.

J. Med. Chem. 51 , 4260-9, (2008)

A series of cycloalkyl, bicycloalkyl, aryl, and heteroaryl N (6)-substituted derivatives of the antitumor agent 3'- C-methyladenosine (3'-Me-Ado), an inhibitor of the alpha Rnr1 subunit of mammalian r...