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Chemical Compound Review

ADENAZOLE     (1S,6R,8R,9R)-8-(6-amino-8- chloro-purin-9...

Synonyms: Tocladesine, c-amp, CCRIS 846, SureCN125595, ICN-1256, ...
 
 
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Disease relevance of Tocladesine

  • 8-Cl-cAMP, a site-selective analogue of cAMP, decreased mdr-1 expression in multidrug-resistant human breast cancer cells [1].
  • A reduction in mdr-1 expression after 8-Cl-cAMP treatment was also observed in multidrug-resistant human ovarian cancer cell lines [1].
  • Our results showing that 8-Cl-cAMP is a powerful inhibitor of clonogenic growth of leukemic blast progenitors by primarily suppressing their self-renewal capacity indicate that this site-selective cAMP analog represents a promising biological agent for acute myeloblastic leukemia therapy in humans [2].
  • A cooperative antitumor effect was also observed in vivo, because treatment with paclitaxel followed by 8-Cl-cAMP markedly inhibited the growth of GEO human colon cancer xenografts as compared to paclitaxel alone without signs of toxicity [3].
  • 8-Chloro-cAMP (8-Cl-cAMP) is a novel agent that is able to inhibit the growth of a wide variety of cancer cell types in vitro and in vivo and, at doses devoid of toxicity, to achieve plasma concentrations in cancer patients in a range effective for cancer cell growth inhibition [3].
 

High impact information on Tocladesine

  • Downregulation of mdr-1 expression by 8-Cl-cAMP in multidrug resistant MCF-7 human breast cancer cells [1].
  • We observed that RI alpha decreased within 24 h of 8-Cl-cAMP treatment, that RII beta increased after as few as 3 h of treatment, and that PKA catalytic activity remained unchanged during 48 h of 8-Cl-cAMP treatment [1].
  • A sixfold reduction of mdr-1 mRNA expression by 8-Cl-cAMP began within 8 h of treatment and was associated with a decrease in the synthesis of P-glycoprotein and with an increase in vinblastine accumulation [1].
  • Thus, 8-Cl-cAMP is able to downregulate mdr-1 expression and suggests a new approach to reversal of drug resistance in human breast cancer [1].
  • Although 8-Cl-cAMP has been used to differentiate cells in other model systems, the only differentiating effect that could be detected after 8-Cl-cAMP treatment in the MCF-7TH cells was an increase in cytokeratin expression [1].
 

Chemical compound and disease context of Tocladesine

 

Biological context of Tocladesine

 

Anatomical context of Tocladesine

 

Associations of Tocladesine with other chemical compounds

 

Gene context of Tocladesine

 

Analytical, diagnostic and therapeutic context of Tocladesine

References

  1. Downregulation of mdr-1 expression by 8-Cl-cAMP in multidrug resistant MCF-7 human breast cancer cells. Scala, S., Budillon, A., Zhan, Z., Cho-Chung, Y.S., Jefferson, J., Tsokos, M., Bates, S.E. J. Clin. Invest. (1995) [Pubmed]
  2. Inhibition of the self-renewal capacity of blast progenitors from acute myeloblastic leukemia patients by site-selective 8-chloroadenosine 3',5'-cyclic monophosphate. Pinto, A., Aldinucci, D., Gattei, V., Zagonel, V., Tortora, G., Budillon, A., Cho-Chung, Y.S. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  3. Synergistic inhibition of growth and induction of apoptosis by 8-chloro-cAMP and paclitaxel or cisplatin in human cancer cells. Tortora, G., di Isernia, G., Sandomenico, C., Bianco, R., Pomatico, G., Pepe, S., Bianco, A.R., Ciardiello, F. Cancer Res. (1997) [Pubmed]
  4. Synergistic effects of retinoic acid and 8-Cl-cAMP on apoptosis require caspase-3 activation in human ovarian cancer cells. Srivastava, R.K., Srivastava, A.R., Cho-Chung, Y.S., Longo, D.L. Oncogene (1999) [Pubmed]
  5. The combination of sulfinosine and 8-Cl-cAMP induces synergistic cell growth inhibition of the human neuroblastoma cell line in vitro. Janković, D., Pesić, M., Marković, J., Kanazir, S., Marković, I., Rakić, L., Ruzdijić, S. Investigational new drugs. (2006) [Pubmed]
  6. 8-chloroadenosine induced HL-60 cell growth inhibition, differentiation, and G(0)/G(1) arrest involves attenuated cyclin D1 and telomerase and up-regulated p21(WAF1/CIP1). Zhu, B., Zhang, L.H., Zhao, Y.M., Cui, J.R., Strada, S.J. J. Cell. Biochem. (2006) [Pubmed]
  7. Selective modulation of protein kinase isozymes by the site-selective analog 8-chloroadenosine 3',5'-cyclic monophosphate provides a biological means for control of human colon cancer cell growth. Ally, S., Tortora, G., Clair, T., Grieco, D., Merlo, G., Katsaros, D., Ogreid, D., Døskeland, S.O., Jahnsen, T., Cho-Chung, Y.S. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  8. Induction of megakaryocytic differentiation and modulation of protein kinase gene expression by site-selective cAMP analogs in K-562 human leukemic cells. Tortora, G., Clair, T., Katsaros, D., Ally, S., Colamonici, O., Neckers, L.M., Tagliaferri, P., Jahnsen, T., Robins, R.K., Cho-Chung, Y.S. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  9. Isolation and characterization of an apoptosis-resistant variant of human leukemia HL-60 cells that has switched expression from Bcl-2 to Bcl-xL. Han, Z., Chatterjee, D., Early, J., Pantazis, P., Hendrickson, E.A., Wyche, J.H. Cancer Res. (1996) [Pubmed]
  10. 8-Chloro-cAMP inhibits transforming growth factor alpha transformation of mammary epithelial cells by restoration of the normal mRNA patterns for cAMP-dependent protein kinase regulatory subunit isoforms which show disruption upon transformation. Ciardiello, F., Tortora, G., Kim, N., Clair, T., Ally, S., Salomon, D.S., Cho-Chung, Y.S. J. Biol. Chem. (1990) [Pubmed]
  11. 8-chloro-cAMP inhibits smooth muscle cell proliferation in vitro and neointima formation induced by balloon injury in vivo. Indolfi, C., Di Lorenzo, E., Rapacciuolo, A., Stingone, A.M., Stabile, E., Leccia, A., Torella, D., Caputo, R., Ciardiello, F., Tortora, G., Chiariello, M. J. Am. Coll. Cardiol. (2000) [Pubmed]
  12. 8-Chloroadenosine mediates 8-chloro-cyclic AMP-induced down-regulation of cyclic AMP-dependent protein kinase in normal and neoplastic mouse lung epithelial cells by a cyclic AMP-independent mechanism. Lange-Carter, C.A., Vuillequez, J.J., Malkinson, A.M. Cancer Res. (1993) [Pubmed]
  13. A novel cyclic adenosine monophosphate analog induces hypercalcemia via production of 1,25-dihydroxyvitamin D in patients with solid tumors. Saunders, M.P., Salisbury, A.J., O'Byrne, K.J., Long, L., Whitehouse, R.M., Talbot, D.C., Mawer, E.B., Harris, A.L. J. Clin. Endocrinol. Metab. (1997) [Pubmed]
  14. 8-Chloro-cAMP induces apoptotic cell death in a human mammary carcinoma cell (MCF-7) line. Bøe, R., Gjertsen, B.T., Døskeland, S.O., Vintermyr, O.K. Br. J. Cancer (1995) [Pubmed]
  15. Rap1 and p38 MAPK mediate 8-chloro-cAMP-induced growth inhibition in mouse fibroblast DT cells. Ahn, Y.H., Han, J.H., Hong, S.H. J. Cell. Physiol. (2006) [Pubmed]
  16. 8-Cl-cAMP antagonizes mitogen-activated protein kinase activation and cell growth stimulation induced by epidermal growth factor. Budillon, A., Di Gennaro, E., Caraglia, M., Barbarulo, D., Abbruzzese, A., Tagliaferri, P. Br. J. Cancer (1999) [Pubmed]
  17. Synergistic growth inhibition and induction of apoptosis by a novel mixed backbone antisense oligonucleotide targeting CRIPTO in combination with C225 anti-EGFR monoclonal antibody and 8-Cl-cAMP in human GEO colon cancer cells. Normanno, N., Tortora, G., De Luca, A., Pomatico, G., Casamassimi, A., Agrawal, S., Mendelsohn, J., Bianco, A.R., Ciardiello, F. Oncol. Rep. (1999) [Pubmed]
  18. 8-Cl-cAMP and tiazofurin affect vascular endothelial growth factor production and glial fibrillary acidic protein expression in human glioblastoma cells. Drabek, K., Pesić, M., Piperski, V., Ruzdijić, S., Medić-Mijacević, L., Pietrzkowski, Z., Rakić, L. Anticancer Drugs (2000) [Pubmed]
  19. Interactions between the epidermal growth factor receptor and type I protein kinase A: biological significance and therapeutic implications. Ciardiello, F., Tortora, G. Clin. Cancer Res. (1998) [Pubmed]
  20. Reversal of resistance to adriamycin by 8-chloro-cyclic AMP in adriamycin-resistant HL-60 leukemia cells is associated with reduction of type I cyclic AMP-dependent protein kinase and cyclic AMP response element-binding protein DNA-binding activities. Rohlff, C., Safa, B., Rahman, A., Cho-Chung, Y.S., Klecker, R.W., Glazer, R.I. Mol. Pharmacol. (1993) [Pubmed]
  21. Synergistic interaction between paclitaxel and 8-chloro-adenosine 3',5'-monophosphate in human ovarian carcinoma cell lines. McDaid, H.M., Johnston, P.G. Clin. Cancer Res. (1999) [Pubmed]
  22. Activation of protein kinase A (PKA) by 8-Cl-cAMP as a novel approach for antileukaemic therapy. Weissinger, E.M., Oettrich, K., Evans, C., Genieser, H.G., Schwede, F., Dangers, M., Dammann, E., Kolb, H.J., Mischak, H., Ganser, A., Kolch, W. Br. J. Cancer (2004) [Pubmed]
 
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