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Chemical Compound Review

Lopac-E-114     (2S,3S)-3-(6-aminopurin-9- yl)nonan-2-ol

Synonyms: CHEMBL1555103, AC1L3ZQR, (+/-)-EHNA, 51350-19-7, 59262-86-1, ...
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Disease relevance of AIDS000491

  • Binding of P815 mastocytoma targets to BCG-activated macrophages, which has been shown to be a necessary event in cytolysis of those targets, was also inhibited by adenosine, EHNA, and L-homocysteine or by DZA at the above concentrations [1].
  • RESULTS: EHNA treatment reduced ischemic contracture and post-ischemic diastolic pressure (14+/-2 vs. 20+/-1 mmHg), increased recovery of developed pressure (66+/-3 vs. 53+/-2%) and reduced LDH efflux (8.9+/-1.6 vs. 18.0+/-1.7 I.U./g) [2].
  • At high calcium, EHNA (1 and 10 micromol/l) and acadesine (500 micromol/l) suppressed the occurrence of ventricular fibrillation from 68% (controls) to 47%, 33% and 38%, respectively [3].
  • Each animal received intravenously 30 ml of either a vehicle solution or 100 M EHNA and 25 M NBMPR 10 min before ischemia [4].
  • Although administration of EHNA/NBMPR did not affect the heart rate, it did cause mild hypotension (about 20-30%) [4].

Psychiatry related information on AIDS000491


High impact information on AIDS000491

  • Erythro-9-[3-(2-hydroxynonyl)]adenine (EHNA) inhibits axonemal dynein ATPase activity and hence the beating of sea urchin and mammalian flagella [6].
  • We have found that EHNA has an unusual effect on the flagella of Leishmania promastigotes in that it alters both the waveform and polarity of the beat [6].
  • EHNA (Erythro-9-[2-hydroxy-3-nonyl]adenine) is a wellknown inhibitor of adenosine deaminase [7].
  • To investigate the role of PDE2 in the regulation of cardiac L-type Ca2+ current (ICa), we have examined the effect of EHNA on ICa in freshly isolated human atrial myocytes [7].
  • erythro-9-[3-(2-Hydroxynonyl)]adenine (EHNA) has been reported previously to be an agent that arrests sperm motility by inhibiting the axonemal dynein ATPase activity and has been used to probe the involvement of putative cytoplasmic dyneins in mitosis and intracellular organelle transport [8].

Chemical compound and disease context of AIDS000491


Biological context of AIDS000491

  • Cotreatment with EHNA and guanosine increased the extracellular accumulation of adenosine and induced apoptosis [11].
  • ITU plus EHNA decreased heart rate (202 +/- 10 to 136 +/- 11 beats/min) and increased coronary flow (8.2 +/- 0.3 to 12.4 +/- 0.9 ml/min/g) without a change in MVO2, developed pressure or dP/dt [12].
  • Myocardial oxygen consumption was similar during metabolic stimulation between the two groups (vehicle vs. ITU plus EHNA) [12].
  • In studies reported here, MdAdo/EHNA, MdGuo and MdCyd inhibited L1210 cell growth with IC50 values of 3.4, 10.6 and 1.4 microM, respectively [13].
  • In whole-blood cultures dAdo alone produced very few if any aberrations, but in the presence of inhibitors of adenosine deaminase (ADA), such as EHNA or coformycin, a high frequency of chromatid gaps, chromatid breaks, and isochromatid breaks were produced [14].

Anatomical context of AIDS000491

  • Unexpectedly, EHNA alone inhibited the motility., This observation was confirmed in intact spermatozoa from rats, rabbits, and humans [15].
  • Kinetic analysis demonstrated that EHNA produced mixed inhibition of both the axonemal ATPase and the partially purified dynein 1 from sea urchin sperm tails, as well as the axonemal ATPase of rat sperm tails [15].
  • As Leu 2a+ T cells were more sensitive to the cytotoxic action of dAdo than Leu 3a+ T cells, it was thought that a dose of dAdo plus EHNA could be chosen which would abrogate suppression but leave T helper cell function intact [16].
  • The concentration of endogenous adenosine in the cerebrospinal fluid increased 2-3-fold of the original level in the area of rat superior colliculus after the intraperitoneal administration of an adenosine deaminase inhibitor, EHNA (erythro-9-(2-hydroxy-3-nonyl)adenosine, 10 mg/kg) [17].
  • Cytochalasin D (2 nmol/eye), a disruptor of actin filaments and the dynein ATPase inhibitor erythro-9-[3-(2-hydroxynonyl)]adenine (EHNA) both inhibited 125I-betaNGF retrograde transport [18].

Associations of AIDS000491 with other chemical compounds


Gene context of AIDS000491


Analytical, diagnostic and therapeutic context of AIDS000491

  • Mathematical models were utilized to show that in full-length intestinal perfusions an optimal log mean lumenal EHNA perfusate concentration of 0.5 microg/ml could achieve an intestinal bioavailability of 80% with <20% systemic inhibition [24].


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  2. Cardioprotection with adenosine metabolism inhibitors in ischemic-reperfused mouse heart. Peart, J., Matherne, G.P., Cerniway, R.J., Headrick, J.P. Cardiovasc. Res. (2001) [Pubmed]
  3. Endogenous adenosine reduces the occurrence of ischemia-induced ventricular fibrillation in rat heart. Schreieck, J., Richardt, G. J. Mol. Cell. Cardiol. (1999) [Pubmed]
  4. Role of nucleoside transport and purine release in a rabbit model of myocardial stunning. Abd-Elfattah, A.S., Maddox, R.P., Jessen, M.E., Rebeyka, I.M., Wechsler, A.S. Mol. Cell. Biochem. (1998) [Pubmed]
  5. Effect of a dynein inhibitor on vasopressin action in toad urinary bladder. Marples, D., Barber, B., Taylor, A. J. Physiol. (Lond.) (1996) [Pubmed]
  6. Differential inhibition by erythro-9-[3-(2-hydroxynonyl)]adenine of flagella-like and cilia-like movement of Leishmania promastigotes. Alexander, J., Burns, R.G. Nature (1983) [Pubmed]
  7. cGMP-stimulated cyclic nucleotide phosphodiesterase regulates the basal calcium current in human atrial myocytes. Rivet-Bastide, M., Vandecasteele, G., Hatem, S., Verde, I., Bénardeau, A., Mercadier, J.J., Fischmeister, R. J. Clin. Invest. (1997) [Pubmed]
  8. erythro-9-[3-(2-Hydroxynonyl)]adenine is an effective inhibitor of cell motility and actin assembly. Schliwa, M., Ezzell, R.M., Euteneuer, U. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  9. Adenine nucleotides and ventricular fibrillation. Lubbe, W.F., Gilchrist, A.I., Holland, R.K., Pybus, J. J. Mol. Cell. Cardiol. (1987) [Pubmed]
  10. Positive inotropic effect of the inhibition of cyclic GMP-stimulated 3',5'-cyclic nucleotide phosphodiesterase (PDE2) on guinea pig left atria in eu- and hyperthyroidism. Gesztelyi, R., Zsuga, J., Hajdú, P., Szabó, J.Z., Cseppento, A., Szentmiklósi, A.J. Gen. Physiol. Biophys. (2003) [Pubmed]
  11. Mechanisms of apoptosis induced by purine nucleosides in astrocytes. Di Iorio, P., Kleywegt, S., Ciccarelli, R., Traversa, U., Andrew, C.M., Crocker, C.E., Werstiuk, E.S., Rathbone, M.P. Glia (2002) [Pubmed]
  12. Inhibition of adenosine metabolism increases myocardial interstitial adenosine concentrations and coronary flow. Ely, S.W., Matherne, G.P., Coleman, S.D., Berne, R.M. J. Mol. Cell. Cardiol. (1992) [Pubmed]
  13. 2'-Deoxy-2'-methylene derivatives of adenosine, guanosine, tubercidin, cytidine and uridine as inhibitors of L1210 cell growth in culture. Cory, A.H., Samano, V., Robins, M.J., Cory, J.G. Biochem. Pharmacol. (1994) [Pubmed]
  14. The effect of G2-treatments with 2'-deoxyadenosine on the frequency of chromatid aberrations in human lymphocytes depends on the type of culture. Kihlman, B.A., Andersson, H.C. Chromosoma (1984) [Pubmed]
  15. erythro-9-[3-(2-Hydroxynonyl)]adenine is an inhibitor of sperm motility that blocks dynein ATPase and protein carboxylmethylase activities. Bouchard, P., Penningroth, S.M., Cheung, A., Gagnon, C., Bardin, C.W. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  16. Relative sensitivity of human T cell subsets to deoxyadenosine toxicity. Callard, R.E., Ewing, T.M., Fox, R.M. Clin. Exp. Immunol. (1984) [Pubmed]
  17. Endogenous adenosine facilitates neurotransmission via A2A adenosine receptors in the rat superior colliculus in vivo. Ishikawa, S., Saijoh, K., Okada, Y. Brain Res. (1997) [Pubmed]
  18. Signalling events regulating the retrograde axonal transport of 125I-beta nerve growth factor in vivo. Reynolds, A.J., Bartlett, S.E., Hendry, I.A. Brain Res. (1998) [Pubmed]
  19. Isolation and characterization of human cDNAs encoding a cGMP-stimulated 3',5'-cyclic nucleotide phosphodiesterase. Rosman, G.J., Martins, T.J., Sonnenburg, W.K., Beavo, J.A., Ferguson, K., Loughney, K. Gene (1997) [Pubmed]
  20. An improved purification method for cytoplasmic dynein. Pratt, M.M., Hisanaga, S., Begg, D.A. J. Cell. Biochem. (1984) [Pubmed]
  21. Modulation by presynaptic adenosine A1 receptors of nicotinic receptor antagonist-induced neuromuscular block in the mouse. Prior, C., Breadon, E.L., Lindsay, K.E. Eur. J. Pharmacol. (1997) [Pubmed]
  22. Adenosine and deoxyadenosine induces apoptosis in oestrogen receptor-positive and -negative human breast cancer cells via the intrinsic pathway. Hashemi, M., Karami-Tehrani, F., Ghavami, S., Maddika, S., Los, M. Cell Prolif. (2005) [Pubmed]
  23. Decreased 5'-nucleotidase activity in suppressor (OKT8) T lymphocytes from homosexuals with AIDS-related complex: nonassociation with enhanced deoxynucleoside toxicity. Murray, J.L., Bywaters, D.W., Reuben, J.M., Mansell, P.W., Hersh, E.M. Clin. Immunol. Immunopathol. (1987) [Pubmed]
  24. Enhanced oral bioavailability of 2'- beta-fluoro-2',3'-dideoxyadenosine (F-ddA) through local inhibition of intestinal adenosine deaminase. DeGraw, R.T., Anderson, B.D. Pharm. Res. (2001) [Pubmed]
  25. Adenosine deaminase activity in the serum and malignant tumors of breast cancer: the assessment of isoenzyme ADA1 and ADA2 activities. Aghaei, M., Karami-Tehrani, F., Salami, S., Atri, M. Clin. Biochem. (2005) [Pubmed]
  26. Inhibition of adenosine deaminase from several sources by deaza derivatives of adenosine and EHNA. Lupidi, G., Cristalli, G., Marmocchi, F., Riva, F., Grifantini, M. J. Enzym. Inhib. (1985) [Pubmed]
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