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Chemical Compound Review

2-Chloroadenosine     (2R,3R,4S,5R)-2-(6-amino-2- chloro-purin-9...

Synonyms: CADO, Cl-Ado, PubChem14159, CHEMBL285819, AG-J-02621, ...
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Disease relevance of 2 Chloroadenosine


Psychiatry related information on 2 Chloroadenosine

  • We found that incubation of the ileum with adenosine, or with the more potent derivative, 2-chloroadenosine, induced a novel form of drug dependence, made manifest by withdrawal of inducing drug, but not by antagonists of opiates or clonidine [6].
  • In conclusion, 2-chloroadenosine not only acts as an anticonvulsant against electrically induced kindled seizures as described here, and against audiogenic seizures, electroshock and a variety of chemical convulsants as described by others, it prevents the development of the epileptic state by kindling-stimulation, i.e., it is antiepileptogenic [7].
  • Moreover, the influence of the adenosine antagonist on 2-chloroadenosine (1 mg/kg, 20 min prior to the test)- and valproate (250 mg/kg, 30 min)-induced inhibitions of locomotor activity was also studied [8].

High impact information on 2 Chloroadenosine


Chemical compound and disease context of 2 Chloroadenosine


Biological context of 2 Chloroadenosine


Anatomical context of 2 Chloroadenosine

  • Depletion of macrophages from the adherent cells by 2-chloroadenosine or silica abrogated the production of this cytotoxic activity, whereas treatment of the adherent cells with anti-Thy-1.2 antibody and complement did not [23].
  • In the present study, we attempted to utilize anti-asialo-GM1 antibody and 2-chloroadenosine, agents that kill natural killer (NK) cells and macrophages, respectively, to determine the relative contribution of each effector cell type to the overall host defense [1].
  • Compounds like 2-chloroadenosine and carbocyclic adenosine are extremely efficient inactivators of the isolated enzyme, but these nucleosides exerted only a limited effect on the enzyme in intact hepatocytes [24].
  • Treatment of Caco-2 cells with 2ClAdo prevented ST-induced increases in [cGMP]i, chloride current and water secretion [25].
  • We investigated the ability of adenosine and its stable analogue 2-chloroadenosine (CADO) to inhibit cytokine production and cytotoxic activity of lymphokine-activated killer (LAK) cells and determined whether both these effects are initiated via a common pathway [26].

Associations of 2 Chloroadenosine with other chemical compounds


Gene context of 2 Chloroadenosine


Analytical, diagnostic and therapeutic context of 2 Chloroadenosine


  1. Inability of anti-asialo-GM1 and 2-chloroadenosine to abrogate maleic anhydride-divinyl ether-induced resistance against experimental murine lung carcinoma metastases. Schultz, R.M., Tang, J.C., DeLong, D.C., Ades, E.W., Altom, M.G. Cancer Res. (1986) [Pubmed]
  2. Neuroblastoma adenylate cyclase. Role of 2-chloroadenosine, prostaglandin E1, and guanine nucleotides in regulation of activity. Blume, A.J., Foster, C.J. J. Biol. Chem. (1976) [Pubmed]
  3. The effect of 2-chloroadenosine on lipid peroxide level during experimental cerebral ischemia-reperfusion in gerbils. Yavuz, O., Türközkan, N., Bilgihan, A., Doğulu, F., Aykol, S. Free Radic. Biol. Med. (1997) [Pubmed]
  4. Effect of 2-chloroadenosine on cerebrovascular reactivity to hypercapnia in newborn pig. Gidday, J.M., Park, T.S. J. Cereb. Blood Flow Metab. (1992) [Pubmed]
  5. Synergistic regulation of cytosolic Ca2+ concentration in mouse astrocytes by NK1 tachykinin and adenosine agonists. Delumeau, J.C., Petitet, F., Cordier, J., Glowinski, J., Prémont, J. J. Neurochem. (1991) [Pubmed]
  6. Novel form of drug-dependence--on adenosine in guinea pig ileum. Collier, H.O., Tucker, J.F. Nature (1983) [Pubmed]
  7. The protective effect of 2-chloroadenosine against the development of amygdala kindling and on amygdala-kindled seizures. Abdul-Ghani, A.S., Attwell, P.J., Bradford, H.F. Eur. J. Pharmacol. (1997) [Pubmed]
  8. Influence of CGS 15943 A (a nonxanthine adenosine antagonist) on the protection offered by a variety of antiepileptic drugs against maximal electroshock-induced seizures in mice. Czuczwar, S.J., Janusz, W., Szczepanik, B., Kleinrok, Z. J. Neural Transm. Gen. Sect. (1991) [Pubmed]
  9. Adenosine: a physiological modulator of superoxide anion generation by human neutrophils. Cronstein, B.N., Kramer, S.B., Weissmann, G., Hirschhorn, R. J. Exp. Med. (1983) [Pubmed]
  10. Adenosine: an endogenous inhibitor of neutrophil-mediated injury to endothelial cells. Cronstein, B.N., Levin, R.I., Belanoff, J., Weissmann, G., Hirschhorn, R. J. Clin. Invest. (1986) [Pubmed]
  11. A1 adenosine-receptor antagonists activate chloride efflux from cystic fibrosis cells. Eidelman, O., Guay-Broder, C., van Galen, P.J., Jacobson, K.A., Fox, C., Turner, R.J., Cabantchik, Z.I., Pollard, H.B. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  12. Adenosine-activated potassium conductance in cultured striatal neurons. Trussell, L.O., Jackson, M.B. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  13. Antagonism by taxol of effects of microtubule-disrupting agents on lymphocyte cAMP metabolism and cell function. Wolberg, G., Stopford, C.R., Zimmerman, T.P. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  14. An endogenous A2B adenosine receptor coupled to cyclic AMP generation in human embryonic kidney (HEK 293) cells. Cooper, J., Hill, S.J., Alexander, S.P. Br. J. Pharmacol. (1997) [Pubmed]
  15. Prostaglandin E2 and 2-chloroadenosine act in concert to stimulate bone resorption in cultured murine calvarial bones. Lerner, U., Fredholm, B.B. Biochem. Pharmacol. (1985) [Pubmed]
  16. Assessment of purine-dopamine interactions in 6-hydroxydopamine-lesioned rats: evidence for pre- and postsynaptic influences by adenosine. Criswell, H., Mueller, R.A., Breese, G.R. J. Pharmacol. Exp. Ther. (1988) [Pubmed]
  17. Analysis of the bronchoconstrictor responses to adenosine receptor agonists in sensitized guinea-pig lungs and trachea. Thorne, J.R., Danahay, H., Broadley, K.J. Eur. J. Pharmacol. (1996) [Pubmed]
  18. Neurotransmitter- and neuromodulator-dependent alterations in phosphorylation of protein I in slices of rat facial nucleus. Dolphin, A.C., Greengard, P. J. Neurosci. (1981) [Pubmed]
  19. Adenosine A2a receptor activation delays apoptosis in human neutrophils. Walker, B.A., Rocchini, C., Boone, R.H., Ip, S., Jacobson, M.A. J. Immunol. (1997) [Pubmed]
  20. Adenosine receptors are expressed during differentiation of monocytes to macrophages in vitro. Implications for regulation of phagocytosis. Eppell, B.A., Newell, A.M., Brown, E.J. J. Immunol. (1989) [Pubmed]
  21. Juxtamedullary afferent arteriolar responses to P1 and P2 purinergic stimulation. Inscho, E.W., Carmines, P.K., Navar, L.G. Hypertension (1991) [Pubmed]
  22. Adenosine inhibits growth of rat aortic smooth muscle cells. Possible role of A2b receptor. Dubey, R.K., Gillespie, D.G., Osaka, K., Suzuki, F., Jackson, E.K. Hypertension (1996) [Pubmed]
  23. Induction of a tumor necrosis factor-like activity by Nocardia rubra cell wall skeleton. Izumi, S., Hirai, O., Hayashi, K., Konishi, Y., Okuhara, M., Kohsaka, M., Aoki, H., Yamamura, Y. Cancer Res. (1987) [Pubmed]
  24. Inactivation and reactivation of intracellular S-adenosylhomocysteinase in the presence of nucleoside analogues in rat hepatocytes. Schanche, J.S., Schanche, T., Ueland, P.M., Montgomery, J.A. Cancer Res. (1984) [Pubmed]
  25. Interruption of transmembrane signaling as a novel antisecretory strategy to treat enterotoxigenic diarrhea. Zhang, W., Mannan, I., Schulz, S., Parkinson, S.J., Alekseev, A.E., Gomez, L.A., Terzic, A., Waldman, S.A. FASEB J. (1999) [Pubmed]
  26. Adenosine-mediated inhibition of the cytotoxic activity and cytokine production by activated natural killer cells. Lokshin, A., Raskovalova, T., Huang, X., Zacharia, L.C., Jackson, E.K., Gorelik, E. Cancer Res. (2006) [Pubmed]
  27. Extracellular and intracellular actions of adenosine and related compounds in the reperfused rat intestine. Kaminski, P.M., Proctor, K.G. Circ. Res. (1992) [Pubmed]
  28. Neurotransmitter activation of inwardly rectifying potassium current in dissociated hippocampal CA3 neurons: interactions among multiple receptors. Sodickson, D.L., Bean, B.P. J. Neurosci. (1998) [Pubmed]
  29. Cyclic AMP concentrations modulate both calcium flux and hydrolysis of phosphatidylinositol phosphates in mouse T lymphocytes. Lerner, A., Jacobson, B., Miller, R.A. J. Immunol. (1988) [Pubmed]
  30. Chemotactic peptide induces cAMP elevation in human neutrophils by amplification of the adenylate cyclase response to endogenously produced adenosine. Iannone, M.A., Wolberg, G., Zimmerman, T.P. J. Biol. Chem. (1989) [Pubmed]
  31. 2-Chloroadenosine: a selective lethal effect to mouse macrophages and its mechanism. Saito, T., Yamaguchi, J. J. Immunol. (1985) [Pubmed]
  32. Effects of adenosine deaminase and A1 receptor deficiency in normoxic and ischaemic mouse hearts. Willems, L., Reichelt, M.E., Molina, J.G., Sun, C.X., Chunn, J.L., Ashton, K.J., Schnermann, J., Blackburn, M.R., Headrick, J.P. Cardiovasc. Res. (2006) [Pubmed]
  33. The expression of endothelin-1 and endothelin-converting enzyme-1 (ECE-1) are independently regulated in bovine aortic endothelial cells. Corder, R., Barker, S. J. Cardiovasc. Pharmacol. (1999) [Pubmed]
  34. In vitro formation and expansion of cysts derived from human renal cortex epithelial cells. Neufeld, T.K., Douglass, D., Grant, M., Ye, M., Silva, F., Nadasdy, T., Grantham, J.J. Kidney Int. (1992) [Pubmed]
  35. 2-Chloroadenosine but not adenosine induces apoptosis in rheumatoid fibroblasts independently of cell surface adenosine receptor signalling. Koshiba, M., Kosaka, H., Nakazawa, T., Hayashi, N., Saura, R., Kitamura, N., Kumagai, S. Br. J. Pharmacol. (2002) [Pubmed]
  36. Adenosine receptor-mediated coronary vascular protection in post-ischemic mouse heart. Zatta, A.J., Matherne, G.P., Headrick, J.P. Life Sci. (2006) [Pubmed]
  37. Adenosine modulates N-methyl-D-aspartate-stimulated hippocampal nitric oxide production in vivo. Bhardwaj, A., Northington, F.J., Koehler, R.C., Stiefel, T., Hanley, D.F., Traystman, R.J. Stroke (1995) [Pubmed]
  38. Route dependent effects of 2-chloroadenosine and theophylline in isolated perfused guinea pig hearts. Wei, H.W., Friedrichs, G.S., Merrill, G.F. Cardiovasc. Res. (1991) [Pubmed]
  39. Activation of adenosine-receptor-enhanced iNOS mRNA expression by gingival epithelial cells. Murakami, S., Yoshimura, N., Koide, H., Watanabe, J., Takedachi, M., Terakura, M., Yanagita, M., Hashikawa, T., Saho, T., Shimabukuro, Y., Okada, H. J. Dent. Res. (2002) [Pubmed]
  40. Renal effects of 2-chloroadenosine in the two-kidney Goldblatt rat. Churchill, P.C., Bidani, A.K., Churchill, M.C., Prada, J. J. Pharmacol. Exp. Ther. (1984) [Pubmed]
  41. Spinal adenosine modulates descending antinociceptive pathways stimulated by morphine. DeLander, G.E., Hopkins, C.J. J. Pharmacol. Exp. Ther. (1986) [Pubmed]
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