Kinetin Riboside | CAS#4338-47-0 | PINK1 activator

MedKoo Cat#: 562070 | Name: Kinetin Riboside

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Kinetin Riboside is an activator of the Parkinson's Disease-associated PTEN-induced Putative Kinase 1 (PINK1), and acts independently from mitochondrial depolarization.

Chemical Structure

Kinetin Riboside

CAS#4338-47-0

Theoretical Analysis

MedKoo Cat#: 562070

Name: Kinetin Riboside

CAS#: 4338-47-0

Chemical Formula: C15H17N5O5

Exact Mass: 347.1230

Molecular Weight: 347.33

Elemental Analysis: C, 51.87; H, 4.93; N, 20.16; O, 23.03

Price and Availability

Size	Price	Availability	Quantity
1g	USD 285.00	2 Weeks
5g	USD 650.00	2 Weeks

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Related CAS #

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Synonym

Kinetin Riboside;

IUPAC/Chemical Name

(2R,3R,4S,5R)-2-(6-((furan-2-ylmethyl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

InChi Key

CAGLGYNQQSIUGX-SDBHATRESA-N

InChi Code

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

SMILES Code

O[C@H]1[C@H](N2C=NC3=C(NCC4=CC=CO4)N=CN=C23)O[C@H](CO)[C@H]1O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Kinetin riboside inhibits the proliferation of HCT-15 cells with an IC50 of 2.5 μM.

In vitro activity:

KR decreases the mitochondrial membrane potential, reduces glutathione level, depletes cellular ATP, and induces reactive oxygen species (ROS) production in the OXPHOS state, leading to the loss of cell viability. Taken together, these results demonstrate that KR directly acts on the mitochondria to limit their function and that the sensitivity of cells is dependent on their ability to cope with energetic stress. Reference: Apoptosis. 2020 Dec;25(11-12):835-852. https://pubmed.ncbi.nlm.nih.gov/32955614/

In vivo activity:

Kinetin riboside induced marked suppression of CCND2 transcription and rapidly suppressed cyclin D1 and D2 protein expression in primary myeloma cells and tumor lines, causing cell-cycle arrest, tumor cell-selective apoptosis, and inhibition of myeloma growth in xenografted mice. Reference: J Clin Invest. 2008 May;118(5):1750-64. https://pubmed.ncbi.nlm.nih.gov/18431519/

	Solvent	mg/mL	mM
Solubility
	DMF	3.0	8.64
	DMSO	250.0	719.77

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 347.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Orlicka-Płocka M, Gurda-Wozna D, Fedoruk-Wyszomirska A, Wyszko E. Circumventing the Crabtree effect: forcing oxidative phosphorylation (OXPHOS) via galactose medium increases sensitivity of HepG2 cells to the purine derivative kinetin riboside. Apoptosis. 2020 Dec;25(11-12):835-852. doi: 10.1007/s10495-020-01637-x. Epub 2020 Sep 21. PMID: 32955614; PMCID: PMC7679298. 2. Rajabi M, Gorincioi E, Santaniello E. Antiproliferative activity of kinetin riboside on HCT-15 colon cancer cell line. Nucleosides Nucleotides Nucleic Acids. 2012;31(6):474-81. doi: 10.1080/15257770.2012.681825. PMID: 22646087. 3. Tiedemann RE, Mao X, Shi CX, Zhu YX, Palmer SE, Sebag M, Marler R, Chesi M, Fonseca R, Bergsagel PL, Schimmer AD, Stewart AK. Identification of kinetin riboside as a repressor of CCND1 and CCND2 with preclinical antimyeloma activity. J Clin Invest. 2008 May;118(5):1750-64. doi: 10.1172/JCI34149. PMID: 18431519; PMCID: PMC2323188. 4. Choi BH, Kim W, Wang QC, Kim DC, Tan SN, Yong JW, Kim KT, Yoon HS. 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. doi: 10.1016/j.canlet.2007.11.014. Epub 2007 Dec 26. PMID: 18162289.

In vitro protocol:

In vivo protocol:

1. Tiedemann RE, Mao X, Shi CX, Zhu YX, Palmer SE, Sebag M, Marler R, Chesi M, Fonseca R, Bergsagel PL, Schimmer AD, Stewart AK. Identification of kinetin riboside as a repressor of CCND1 and CCND2 with preclinical antimyeloma activity. J Clin Invest. 2008 May;118(5):1750-64. doi: 10.1172/JCI34149. PMID: 18431519; PMCID: PMC2323188. 2. Choi BH, Kim W, Wang QC, Kim DC, Tan SN, Yong JW, Kim KT, Yoon HS. 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. doi: 10.1016/j.canlet.2007.11.014. Epub 2007 Dec 26. PMID: 18162289.

1: Kadlecová A, Jirsa T, Novák O, Kammenga J, Strnad M, Voller J. Natural plant hormones cytokinins increase stress resistance and longevity of Caenorhabditis elegans. Biogerontology. 2017 Dec 18. doi: 10.1007/s10522-017-9742-4. [Epub ahead of print] PubMed PMID: 29255944. 2: Rogalińska M, Góralski P, Błoński JZ, Robak P, Barciszewski J, Koceva-Chyła A, Piekarski H, Robak T, Kilianska ZM. Personalized therapy tests for the monitoring of chronic lymphocytic leukemia development. Oncol Lett. 2017 Apr;13(4):2079-2084. doi: 10.3892/ol.2017.5725. Epub 2017 Feb 13. PubMed PMID: 28454364; PubMed Central PMCID: PMC5403444. 3: Osgerby L, Lai YC, Thornton PJ, Amalfitano J, Le Duff CS, Jabeen I, Kadri H, Miccoli A, Tucker JHR, Muqit MMK, Mehellou Y. Kinetin Riboside and Its ProTides Activate the Parkinson's Disease Associated PTEN-Induced Putative Kinase 1 (PINK1) Independent of Mitochondrial Depolarization. J Med Chem. 2017 Apr 27;60(8):3518-3524. doi: 10.1021/acs.jmedchem.6b01897. Epub 2017 Mar 28. PubMed PMID: 28323427; PubMed Central PMCID: PMC5410652. 4: Voller J, Béres T, Zatloukal M, Kaminski PA, Niemann P, Doležal K, Džubák P, Hajdúch M, Strnad M. The natural cytokinin 2OH3MeOBAR induces cell death by a mechanism that is different from that of the "classical" cytokinin ribosides. Phytochemistry. 2017 Apr;136:156-164. doi: 10.1016/j.phytochem.2017.01.004. Epub 2017 Jan 30. PubMed PMID: 28153445. 5: Nashalian O, Yaylayan VA. Reactivity of nitrogen atoms in adenine and (Ade)2Cu complexes towards ribose and 2-furanmethanol: Formation of adenosine and kinetin. Food Chem. 2017 Jan 15;215:463-9. doi: 10.1016/j.foodchem.2016.08.012. Epub 2016 Aug 5. PubMed PMID: 27542499. 6: Zhang Q, Li G, Xiao X, Zhan S, Cao Y. Efficient and Selective Enrichment of Ultratrace Cytokinins in Plant Samples by Magnetic Perhydroxy-Cucurbit[8]uril Microspheres. Anal Chem. 2016 Apr 5;88(7):4055-62. doi: 10.1021/acs.analchem.6b00408. Epub 2016 Mar 24. PubMed PMID: 26977773. 7: Du F, Sun L, Zhen X, Nie H, Zheng Y, Ruan G, Li J. 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. 2015 Aug;407(20):6071-9. doi: 10.1007/s00216-015-8782-3. Epub 2015 May 30. PubMed PMID: 26025552. 8: Aremu AO, Plačková L, Bairu MW, Novák O, Szüčová L, Doležal K, Finnie JF, Van Staden J. Endogenous cytokinin profiles of tissue-cultured and acclimatized 'Williams' bananas subjected to different aromatic cytokinin treatments. Plant Sci. 2014 Jan;214:88-98. doi: 10.1016/j.plantsci.2013.09.012. Epub 2013 Oct 2. PubMed PMID: 24268166. 9: Kumari P, Kumar M, Reddy CR, Jha B. Nitrate and phosphate regimes induced lipidomic and biochemical changes in the intertidal macroalga Ulva lactuca (Ulvophyceae, Chlorophyta). Plant Cell Physiol. 2014 Jan;55(1):52-63. doi: 10.1093/pcp/pct156. Epub 2013 Nov 4. PubMed PMID: 24192295. 10: Tomek M, Akiyama T, Dass CR. Role of Bcl-2 in tumour cell survival and implications for pharmacotherapy. J Pharm Pharmacol. 2012 Dec;64(12):1695-702. doi: 10.1111/j.2042-7158.2012.01526.x. Epub 2012 Apr 25. Review. PubMed PMID: 23146031. 11: Rajabi M, Gorincioi E, Santaniello E. Antiproliferative activity of kinetin riboside on HCT-15 colon cancer cell line. Nucleosides Nucleotides Nucleic Acids. 2012;31(6):474-81. doi: 10.1080/15257770.2012.681825. PubMed PMID: 22646087. 12: McDermott SP, Eppert K, Notta F, Isaac M, Datti A, Al-Awar R, Wrana J, Minden MD, Dick JE. A small molecule screening strategy with validation on human leukemia stem cells uncovers the therapeutic efficacy of kinetin riboside. Blood. 2012 Feb 2;119(5):1200-7. doi: 10.1182/blood-2011-01-330019. Epub 2011 Dec 9. PubMed PMID: 22160482. 13: Gupta V, Kumar M, Brahmbhatt H, Reddy CR, Seth A, Jha B. Simultaneous determination of different endogenetic plant growth regulators in common green seaweeds using dispersive liquid-liquid microextraction method. Plant Physiol Biochem. 2011 Nov;49(11):1259-63. doi: 10.1016/j.plaphy.2011.08.004. Epub 2011 Aug 22. PubMed PMID: 22000048. 14: Dudzik P, Dulińska-Litewka J, Wyszko E, Jędrychowska P, Opałka M, Barciszewski J, Laidler P. Effects of kinetin riboside on proliferation and proapoptotic activities in human normal and cancer cell lines. J Cell Biochem. 2011 Aug;112(8):2115-24. doi: 10.1002/jcb.23132. Erratum in: J Cell Biochem. 2015 Jan;116(1): 202. PubMed PMID: 21465535. 15: Voller J, Zatloukal M, Lenobel R, Dolezal K, Béres T, Krystof V, Spíchal L, Niemann P, Dzubák P, Hajdúch M, Strnad M. Anticancer activity of natural cytokinins: a structure-activity relationship study. Phytochemistry. 2010 Aug;71(11-12):1350-9. doi: 10.1016/j.phytochem.2010.04.018. Epub 2010 Jun 1. PubMed PMID: 20553699. 16: Choi BH, Feng L, Yoon HS. FKBP38 protects Bcl-2 from caspase-dependent degradation. J Biol Chem. 2010 Mar 26;285(13):9770-9. doi: 10.1074/jbc.M109.032466. Epub 2010 Feb 5. PubMed PMID: 20139069; PubMed Central PMCID: PMC2843226. 17: Cabello CM, Bair WB 3rd, Ley S, Lamore SD, Azimian S, Wondrak GT. The experimental chemotherapeutic N6-furfuryladenosine (kinetin-riboside) induces rapid ATP depletion, genotoxic stress, and CDKN1A(p21) upregulation in human cancer cell lines. Biochem Pharmacol. 2009 Apr 1;77(7):1125-38. doi: 10.1016/j.bcp.2008.12.002. Epub 2008 Dec 24. PubMed PMID: 19186174; PubMed Central PMCID: PMC2656390. 18: Cheong J, Goh D, Yong JW, Tan SN, Ong ES. Inhibitory effect of kinetin riboside in human heptamoa, HepG2. Mol Biosyst. 2009 Jan;5(1):91-8. doi: 10.1039/b712807j. Epub 2008 Nov 25. PubMed PMID: 19081935. 19: Tiedemann RE, Mao X, Shi CX, Zhu YX, Palmer SE, Sebag M, Marler R, Chesi M, Fonseca R, Bergsagel PL, Schimmer AD, Stewart AK. Identification of kinetin riboside as a repressor of CCND1 and CCND2 with preclinical antimyeloma activity. J Clin Invest. 2008 May;118(5):1750-64. doi: 10.1172/JCI34149. PubMed PMID: 18431519; PubMed Central PMCID: PMC2323188. 20: Choi BH, Kim W, Wang QC, Kim DC, Tan SN, Yong JW, Kim KT, Yoon HS. 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. Epub 2007 Dec 26. PubMed PMID: 18162289.