N6-Isopentenyladenosine (Riboprine), an RNA modification found in cytokinins, which regulates plant growth/differentiation, and tRNA, which increases the efficiency and accuracy of translation. N6-Isopentenyladenosine, the end product of the mevalonate pathway, is an autophagy inhibitor (antagonist) with anti-melanoma activity.

Physicochemical Properties

Molecular Formula	C15H21N5O4
Molecular Weight	335.36
Exact Mass	335.159
CAS #	7724-76-7
PubChem CID	24405
Appearance	White to off-white solid powder
Density	1.6±0.1 g/cm3
Boiling Point	647.2±65.0 °C at 760 mmHg
Melting Point	143-146°C
Flash Point	345.2±34.3 °C
Vapour Pressure	0.0±2.0 mmHg at 25°C
Index of Refraction	1.708
LogP	1.31
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Heavy Atom Count	24
Complexity	461
Defined Atom Stereocenter Count	4
SMILES	CC(=CCNC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)C
InChi Key	USVMJSALORZVDV-SDBHATRESA-N
InChi Code	InChI=1S/C15H21N5O4/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(5-21)24-15/h3,6-7,9,11-12,15,21-23H,4-5H2,1-2H3,(H,16,17,18)/t9-,11-,12-,15-/m1/s1
Chemical Name	(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolane-3,4-diol
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 Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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

ln Vitro	Through the disruption of autophagic flow, N6-isopentenyladenosine dual targeting of AMPK and Rab7 prenylation suppresses the growth of melanoma[2].
References	[1]. Pharmacogenomics and analogues of the antitumour agent N6-isopentenyladenosine. Int J Cancer. 2009;124(9):2179-2185. [2]. 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]. Chemical Deprenylation of N6 -Isopentenyladenosine (i6 A) RNA. Angew Chem Int Ed Engl. 2020;59(26):10645-10650.
Additional Infomation	N(6)-(Delta(2)-isopentenyl)adenosine is a nucleoside analogue in which adenosine has been modified by substitution at the 6-amino nitrogen by a Delta(2)-isopentenyl group. It has a role as an antineoplastic agent, a plant growth regulator and a plant metabolite. It is a nucleoside analogue and a N-ribosyl-N(6)-isopentenyladenine. It is functionally related to an adenosine. Ipa has been used in trials studying the treatment of Nausea and Surgical Site Infection. Riboprine has been reported in Arabidopsis thaliana and Rhodococcus fascians with data available. Riboprine is an isopentenyl derivative of adenosine naturally derived from certain plants and purine nucleoside with potential antineoplastic activity. Riboprine may cause cell cycle arrest and apoptosis. N(6)-[delta(3)-isopentenyl]adenosine. Isopentenyl derivative of adenosine which is a member of the cytokinin family of plant growth regulators.

Solubility Data

Solubility (In Vitro)

DMSO : 100 mg/mL (298.19 mM) 1M HCl : 100 mg/mL (298.19 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.45 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 25.0 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: ≥ 2.5 mg/mL (7.45 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 25.0 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: ≥ 2.5 mg/mL (7.45 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 25.0 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	2.9819 mL	14.9094 mL	29.8187 mL
	5 mM	0.5964 mL	2.9819 mL	5.9637 mL
	10 mM	0.2982 mL	1.4909 mL	2.9819 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.