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Sigma-Aldrich

Kinetin riboside

proapoptotic anitproliferative plant growth regulator

Synonym(s):

6-Furfurylaminopurine riboside, N6-(2-Furanyl­methyl)adenosine, N6-Furfuryladenosine

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About This Item

Empirical Formula (Hill Notation):
C15H17N5O5
CAS Number:
4338-47-0
Molecular Weight:
347.33
EC Number:
224-389-3
MDL number:
MFCD00037987
UNSPSC Code:
12352207
PubChem Substance ID:
24896224
NACRES:
NA.72

assay

≥98% (HPLC)
≥98% (TLC)

form

powder

solubility

acetic acid: 49.00-51.00 mg/mL, clear, colorless to yellow

storage temp.

2-8°C

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NCc4ccco4)ncnc23

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

InChI key

CAGLGYNQQSIUGX-SDBHATRESA-N

Gene Information

rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

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General description

Kinetin riboside is a ribosylated form of kinetin. It is a natural cytokinin plant hormone.[1]

Application

Kinetin riboside may be used:
  • to study its cytotoxic effects on plant and animal tumor cells[2]
  • to investigate its apoptotic effects in both cancer and immortalized cells[3]
  • to elucidate its influence on human prostate cell epithelial-mesenchymal transition in vitro[1]

Biochem/physiol Actions

Kinetin riboside exhibits cytotoxic[2] and antiproliferative activities.[1] In addition, it also shows anticancer activity by inducing apoptosis in various types of cancers including myeloid leukemia cells, mouse melanoma B16F-10 cells, and plant tumor cells.[3]

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
13190701
117M4114V
076M4034V
099K4068
099K4067

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Yuki Ishii et al.
Cell growth & differentiation : the molecular biology journal of the American Association for Cancer Research, 13(1), 19-26 (2002-01-22)
We examined the effects of various adenine analogues on the growth and differentiation of human myeloid leukemia HL-60 cells. Some of these analogues inhibit growth and induce nitroblue tetrazolium reducing activity in HL-60 cells. Cytokinins such as kinetin, isopentenyladenine, and
Dennison Trinh et al.
Journal of neurochemistry, 156(6), 715-752 (2021-02-23)
Mitochondria are essential for neuronal function. They produce ATP to meet energy demands, regulate homeostasis of ion levels such as calcium and regulate reactive oxygen species that cause oxidative cellular stress. Mitochondria have also been shown to regulate protein synthesis
Effects of kinetin riboside on proliferation and proapoptotic activities in human normal and cancer cell lines.
Dudzik P, Dulinska-Litewka J, Wyszko E, et al.
The Journal of Cell Biology, 112, 2115-2124 (2011)
Bernard Griffaut et al.
International journal of biological macromolecules, 34(4), 271-275 (2004-09-18)
The cytotoxicity of two plant hormone compounds, kinetin and kinetin riboside, was studied on tumour cells, by colony forming assay with increased amount of cytotoxic molecules. The concentration of inhibitor required to reduce cell growth to 50% was determined for
Michael Webb et al.
Bioorganic & medicinal chemistry letters, 29(11), 1270-1277 (2019-04-08)
Mitochondrial dysfunction is a causative and/or exacerbating feature of many pathologies. We discuss below approaches to modulate mitochondrial dysfunction that involve (1) increasing their energetic efficiency by targeting gene expression regulators such as PPAR or AMPK, (2) using antioxidant compounds
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