8-Chloroadenosine

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

MedKoo CAT#: 527728

CAS#: 34408-14-5

Description: 8-Chloroadenosine, also known as NSC-354258 and 8-Cl-Ado, is an 5' AMP-activated protein kinase (AMPK) agonist potentially for the treatment of chronic lymphocytic leukemia. 8-Chloroadenosine has shown to deplete ATP and inhibit tumor growth in hematological malignancies as well as in lung and breast cancer cell lines. 8-chloroadenosine activity is associated with inhibition of the mTOR pathway, and that phospho RPS6 and PI3K pathway activation status may determine resistance.


Chemical Structure

img
8-Chloroadenosine
CAS# 34408-14-5

Theoretical Analysis

MedKoo Cat#: 527728
Name: 8-Chloroadenosine
CAS#: 34408-14-5
Chemical Formula: C10H12ClN5O4
Exact Mass: 301.06
Molecular Weight: 301.687
Elemental Analysis: C, 39.81; H, 4.01; Cl, 11.75; N, 23.21; O, 21.21

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: 8-Chloroadenosine; 8 Chloroadenosine; 8Chloroadenosine; NSC-354258; NSC 354258; NSC354258; 8-Cl-Ado; 8 Cl Ado; 8ClAdo

IUPAC/Chemical Name: (2R,3R,4S,5R)-2-(6-amino-8-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

InChi Key: MHDPPLULTMGBSI-UUOKFMHZSA-N

InChi Code: InChI=1S/C10H12ClN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)/t3-,5-,6-,9-/m1/s1

SMILES Code: OC[C@@H]1[C@H]([C@H]([C@H](N2C(Cl)=NC3=C(N=CN=C32)N)O1)O)O

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 301.69 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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Dicitore A, Grassi ES, Caraglia M, Borghi MO, Gaudenzi G, Hofland LJ, Persani L, Vitale G. The cAMP analogs have potent anti-proliferative effects on medullary thyroid cancer cell lines. Endocrine. 2016 Jan;51(1):101-12. doi: 10.1007/s12020-015-0597-7. PubMed PMID: 25863490.

2: Kearney AY, Fan YH, Giri U, Saigal B, Gandhi V, Heymach JV, Zurita AJ. 8-Chloroadenosine Sensitivity in Renal Cell Carcinoma Is Associated with AMPK Activation and mTOR Pathway Inhibition. PLoS One. 2015 Aug 27;10(8):e0135962. doi: 10.1371/journal.pone.0135962. PubMed PMID: 26313261; PubMed Central PMCID: PMC4552467.

3: Stellrecht CM, Vangapandu HV, Le XF, Mao W, Shentu S. ATP directed agent, 8-chloro-adenosine, induces AMP activated protein kinase activity, leading to autophagic cell death in breast cancer cells. J Hematol Oncol. 2014 Mar 14;7:23. doi: 10.1186/1756-8722-7-23. PubMed PMID: 24628795; PubMed Central PMCID: PMC4007639.

4: Han YY, Zhou Z, Cao JX, Jin YQ, Li SY, Ni JH, An GS, Zhang YX, Jia HT. E2F1-mediated DNA damage is implicated in 8-Cl-adenosine-induced chromosome missegregation and apoptosis in human lung cancer H1299 cells. Mol Cell Biochem. 2013 Dec;384(1-2):187-96. doi: 10.1007/s11010-013-1797-1. PubMed PMID: 24037421.

5: Jiao YY, Wang XQ, Lu WL, Yang ZJ, Zhang Q. A novel approach to improve the pharmacokinetic properties of 8-chloro-adenosine by the dual combination of lipophilic derivatisation and liposome formulation. Eur J Pharm Sci. 2013 Jan 23;48(1-2):249-58. doi: 10.1016/j.ejps.2012.10.026. PubMed PMID: 23159667.

6: Gao WL, Liu H, Li N, Zong MH. Regioselective enzymatic undecylenoylation of 8-chloroadenosine and its analogs with biomass-based 2-methyltetrahydrofuran as solvent. Bioresour Technol. 2012 Aug;118:82-8. doi: 10.1016/j.biortech.2012.04.104. PubMed PMID: 22705510.

7: Duan HY, Cao JX, Qi JJ, Wu GS, Li SY, An GS, Jia HT, Cai WW, Ni JH. E2F1 enhances 8-chloro-adenosine-induced G2/M arrest and apoptosis in A549 and H1299 lung cancer cells. Biochemistry (Mosc). 2012 Mar;77(3):261-9. doi: 10.1134/S0006297912030042. PubMed PMID: 22803943.

8: McBrayer SK, Yarrington M, Qian J, Feng G, Shanmugam M, Gandhi V, Krett NL, Rosen ST. Integrative gene expression profiling reveals G6PD-mediated resistance to RNA-directed nucleoside analogues in B-cell neoplasms. PLoS One. 2012;7(7):e41455. doi: 10.1371/journal.pone.0041455. PubMed PMID: 22848499; PubMed Central PMCID: PMC3407247.

9: Stellrecht CM, Ayres M, Arya R, Gandhi V. A unique RNA-directed nucleoside analog is cytotoxic to breast cancer cells and depletes cyclin E levels. Breast Cancer Res Treat. 2010 Jun;121(2):355-64. doi: 10.1007/s10549-009-0481-3. PubMed PMID: 19641990.

10: Dennison JB, Ayres ML, Kaluarachchi K, Plunkett W, Gandhi V. Intracellular succinylation of 8-chloroadenosine and its effect on fumarate levels. J Biol Chem. 2010 Mar 12;285(11):8022-30. doi: 10.1074/jbc.M109.085803. PubMed PMID: 20064937; PubMed Central PMCID: PMC2832953.

11: Dennison JB, Balakrishnan K, Gandhi V. Preclinical activity of 8-chloroadenosine with mantle cell lymphoma: roles of energy depletion and inhibition of DNA and RNA synthesis. Br J Haematol. 2009 Nov;147(3):297-307. doi: 10.1111/j.1365-2141.2009.07850.x. PubMed PMID: 19709085; PubMed Central PMCID: PMC2778754.

12: Chen LS, Nowak BJ, Ayres ML, Krett NL, Rosen ST, Zhang S, Gandhi V. Inhibition of ATP synthase by chlorinated adenosine analogue. Biochem Pharmacol. 2009 Sep 15;78(6):583-91. doi: 10.1016/j.bcp.2009.05.019. PubMed PMID: 19477165; PubMed Central PMCID: PMC2763632.

13: Jia XZ, Yang SY, Zhou J, Li SY, Ni JH, An GS, Jia HT. Inhibition of CHK1 kinase by Gö6976 converts 8-chloro-adenosine-induced G2/M arrest into S arrest in human myelocytic leukemia K562 cells. Biochem Pharmacol. 2009 Mar 1;77(5):770-80. doi: 10.1016/j.bcp.2008.11.008. PubMed PMID: 19059218.

14: Zhang HJ, Li WJ, Yang SY, Li SY, Ni JH, Jia HT. 8-Chloro-adenosine-induced E2F1 promotes p14ARF gene activation in H1299 cells through displacing Sp1 from multiple overlapping E2F1/Sp1 sites. J Cell Biochem. 2009 Feb 15;106(3):464-72. doi: 10.1002/jcb.22033. PubMed PMID: 19115249.

15: Yang SY, Jia XZ, Feng LY, Li SY, An GS, Ni JH, Jia HT. Inhibition of topoisomerase II by 8-chloro-adenosine triphosphate induces DNA double-stranded breaks in 8-chloro-adenosine-exposed human myelocytic leukemia K562 cells. Biochem Pharmacol. 2009 Feb 1;77(3):433-43. doi: 10.1016/j.bcp.2008.10.022. PubMed PMID: 19014910.

16: Li WJ, Gu YY, Zhang HJ, Zhou J, Jia HT. Induction of p14ARF by E2F1 contributes to 8-chloro-adenosine-induced apoptosis in human lung cancer H1299 cells. Chemotherapy. 2009;55(5):335-43. doi: 10.1159/000230697. PubMed PMID: 19641316.

17: Robinson-White AJ, Hsiao HP, Leitner WW, Greene E, Bauer A, Krett NL, Nesterova M, Stratakis CA. Protein kinase A-independent inhibition of proliferation and induction of apoptosis in human thyroid cancer cells by 8-Cl-adenosine. J Clin Endocrinol Metab. 2008 Mar;93(3):1020-9. PubMed PMID: 18073299; PubMed Central PMCID: PMC2266951.

18: Stellrecht CM, Phillip CJ, Cervantes-Gomez F, Gandhi V. Multiple myeloma cell killing by depletion of the MET receptor tyrosine kinase. Cancer Res. 2007 Oct 15;67(20):9913-20. PubMed PMID: 17942923.

19: Gu YY, Zhang HY, Zhang HJ, Li SY, Ni JH, Jia HT. 8-Chloro-adenosine inhibits growth at least partly by interfering with actin polymerization in cultured human lung cancer cells. Biochem Pharmacol. 2006 Aug 28;72(5):541-50. PubMed PMID: 16844099.

20: Janković D, Pesić M, Marković J, Kanazir S, Marković I, Rakić L, Ruzdijić S. The combination of sulfinosine and 8-Cl-cAMP induces synergistic cell growth inhibition of the human neuroblastoma cell line in vitro. Invest New Drugs. 2006 Jan;24(1):15-25. PubMed PMID: 16379041.