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...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.