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N6-Isopentenyladenosine

Names

[ CAS No. ]:
7724-76-7

[ Name ]:
N6-Isopentenyladenosine

[Synonym ]:
N-(3-Methyl-2-buten-1-yl)adenosine
N-(3-Methylbut-2-en-1-yl)adenosine
N6-(δ2-Isopentenyl)adenosine
6-(g,g-Dimethylallylamino)purine Riboside
N-6-(δ-2-Isopentenyl)adenosine
isopentenyl-Adenosine-[d6]
Adenosine, N-(3-methyl-2-butenyl)-
riboprina
6-N-((3-Methyl-2-butenyl)amino)-9-b-D-ribofuranosyl-9H-purine
N6-isopentenyladenosine
6-(γ,γ-Dimethylallylamino)purine riboside
riboprine
N6-ISOPENTENYLADENOSINE-D6
isopentenyladenosine
riboprinum
Isopentenyl-Adenosine
N(6)-(δ(2)-isopentenyl)adenosine
2-IP RIBOSIDE
EINECS 231-771-3
N6-(D2-Isopentenyl)adenosine
Adenosine, N-(3-methyl-2-buten-1-yl)-
N-6-(δ-2-Isopentenyl)adenosinehemihydrate
2ipa
N(6)-(Delta(2)-isopentenyl)adenosine
n-isopentenyladenosine
MFCD00005741

Biological Activity

[Description]:

N6-Isopentenyladenosine (Riboprine), an RNA modification found in cytokinins, which regulate plant growth/differentiation, and a subset of tRNAs, where it improves the efficiency and accuracy of translation. N6-Isopentenyladenosine, an end product of the mevalonate pathway, is an autophagy inhibitor with an interesting anti-melanoma activity[1][2][3].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Autophagy >> Autophagy

[In Vitro]

N6-isopentenyladenosine dual targeting of AMPK and Rab7 prenylation inhibits melanoma growth through the impairment of autophagic flux[2].

[References]

[1]. Colombo F, et al. Pharmacogenomics and analogues of the antitumour agent N6-isopentenyladenosine. Int J Cancer. 2009;124(9):2179-2185.

[2]. Ranieri R, et al. N6-isopentenyladenosine dual targeting of AMPK and Rab7 prenylation inhibits melanoma growth through the impairment of autophagic flux. Cell Death Differ. 2018;25(2):353-367.

[3]. Cheng HP, et al. Chemical Deprenylation of N6 -Isopentenyladenosine (i6 A) RNA. Angew Chem Int Ed Engl. 2020;59(26):10645-10650.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
647.2±65.0 °C at 760 mmHg

[ Melting Point ]:
143-146°C

[ Molecular Formula ]:
C15H21N5O4

[ Molecular Weight ]:
335.358

[ Flash Point ]:
345.2±34.3 °C

[ Exact Mass ]:
335.159363

[ PSA ]:
125.55000

[ LogP ]:
1.31

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.708

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AU7404910
CHEMICAL NAME :
Adenosine, N-(3-methyl-2-butenyl)-
CAS REGISTRY NUMBER :
7724-76-7
LAST UPDATED :
198602
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C15-H21-N5-O4
MOLECULAR WEIGHT :
335.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Rodent - rat Cells - not otherwise specified
DOSE/DURATION :
3300 ug/L
REFERENCE :
BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 18,847,1969

Safety Information

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
24/25

[ WGK Germany ]:
3

[ RTECS ]:
AU7404910

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds