Nebularine

Nebularine is a purine ribonucleoside and an adenosine analog that has been found in L. nebularis and has diverse biological activities.^1,2,3,4,5 It reduces herpes simplex virus 1 (HSV-1) viral plaque formation in Vero cells (IC₅₀ = 0.6 µM) and is active against M. phlei, M. avium, M. tuberculosis, and B. abortus.^1,2 Nebularine (10 and 100 µM) is cytotoxic to COS-7 cells and induces pyknosis in mouse sarcoma 180 cells and mouse embryonic skin explants in a concentration-dependent manner.^3,4 It inhibits root growth of wheat seedlings when used at concentrations ranging from 0.1 to 2 mM.² Nebularine also inhibits adenosine deaminase (K_i = 16 µM).⁵

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1. Julián-Ortiz, J.V., Gálvez, J., Muñoz-Collado, C., et al. Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds. J. Med. Chem. 42(17), 3308-3314 (1999).

2. Brown, E.G., and Konuk, M. Plant cytotoxicity of nebularine (purine riboside). Phytochemistry 37(6), 1589-1592 (1994).

3. Tkacz, K., Cioroch, M., Skladanowski, A.C., et al. The cytotoxic effect of purine riboside on COS-7 cells. Purine and Pyrimidine Metabolism in Man X. Advances in Experimental Medicine and Biology 486, 355-359 (2000).

4. Biesele, J.J., Slautterback, C., and Margolis, M. Unsubstituted purine and its riboside as toxic antimetabolites in mouse tissue cultures. Cancer 8(1), 87-96 (1955).

5. Shewach, D.S., Krawczyk, S.H., Acevedo, O.L., et al. Inhibition of adenosine deaminase by azapurine ribonucleosides. Biochem. Pharmacol. 44(9), 1697-1700 (1992).