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Chemical Compound Review

CHEMBL341385     (Z)-4-(6-aminopurin-9-yl)but- 3-en-1-ol

Synonyms: AC1O6FGS
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Disease relevance of cis isomer

  • We have identified the cis isomer of N6-(4-hydroxy-isopentenyl)-2-methylthioadenosine (ms2io6A) as a component of the tRNA of Salmonella typhimurium [1].
  • Characterization of torsion angles and transient hydrogen bonds indicates that prolyl isomerization of the pThr-Pro peptide bond results from both destabilization of the N-terminal helix capping box and stabilization of the cis isomer by transient hydrogen bonds [2].
  • Such a difference may be related to the failure of the cis isomer to induce pancreatic cancer in rats [3].
  • Because DACH can exist as the trans-1R,2R, trans-1S,2S or cis isomer, the antitumor activity and toxicity of individual isomers of both DACH(sulfato)Pt(II) and DACH(1,1-cyclobutanedicarboxylato)Pt(II) complexes have been examined [4].
  • Pharmacodynamics of the 1R cis-1'R cis isomer of atracurium (51W89) in health and chronic renal failure [5].

High impact information on cis isomer

  • Knowledge of the number of base pairs between the bends in the cis isomer, which has the lowest electrophoretic mobility, allows calculation of the average helical repeat of the inserted sequence [6].
  • To evaluate the effect of membrane lipid acyl-chain packing on the efficiency of cell lysis by complement, we have studied membrane modulation by 2-(2-methoxy)-ethoxyethyl-8-(cis-2-n-octylcyclopropyl)-octanoate (A2C) and by myristoleyl alcohol, the cis isomer of a C14:1 aliphatic alcohol [7].
  • The basis for idoxifene's antitumor activity was examined by comparing the effectiveness of the clinically used transisomer (referred to here as idoxifene) with its cis-isomer, which has a 50-fold lower relative binding affinity for ER than idoxifene but similar calmodulin-inhibitory activity [8].
  • In vitro, both CYP735As preferentially utilized isopentenyladenine nucleotides rather than the nucleoside and free base forms and produced tZ nucleotides but not the cis-isomer [9].
  • The significant population of the cis isomer (9 %) present after phosphorylation of T20 suggests a potential role of selective recognition of cis versus trans isomers in response to phosphorylation of APP [2].

Chemical compound and disease context of cis isomer


Biological context of cis isomer

  • Fixed ring-trans-4-hydroxytamoxifen is a potent antiestrogen, and its cis isomer is a weak antiestrogen (IC50 congruent to 4 x 10(-8) to 2 x 10(-7) M) [14].
  • The cis isomer also lacked appreciable affinity for [3H]-1a binding sites [15].
  • The present results indicate that beta-C conformation plays a major role in its intestinal absorption and that cis isomer discrimination is at the levels of cellular uptake and incorporation into chylomicrons [16].
  • Although cyclization of the radical derived from either substrate proceeds with modest selectivity for the cis-isomer, as does cycloisomerization of the aryllithium derived from substrate 1 (cis/trans approximately 2), intramolecular cyclization of the alkyllithium derived from substrate 2 is a highly cis-selective process (cis/trans = 12) [17].
  • On the basis of earlier reports of reduced growth rate and fat accumulation in animals fed trans 18:1, a study was conducted to determine whether the effects of trans 18:1 on lipolysis and glucose utilization by adipocytes differed from effects of the cis isomer [18].

Anatomical context of cis isomer


Associations of cis isomer with other chemical compounds


Gene context of cis isomer

  • Moreover, (1S,3S)-ACPD, the cis isomer, shows negligible activity at group I receptors and is a good agonist of mGluR2 [29].
  • A study of the relationship between biological activity and prolyl amide isomer geometry in oxytocin using 5-tert-butylproline to augment the Cys(6)-Pro(7) amide cis-isomer population [30].
  • This is, to the best of our knowledge, the first example where cis isomer selectivity can be demonstrated for a proteinase [31].
  • The rise in NO released was mimicked by either (R)-(+)-methanandamide or the vanilloid receptor agonists resiniferatoxin and (E)-capsaicin but not by its inactive cis-isomer (Z)-capsaicin [32].
  • The absolute configuration at C-4 was determined to be S by locating the 13C label in the lactone ring of the trans isomeric lactone and in the hydroxymethyl group of the cis isomer following HPLC separation of both isomers and analysis by GC/MS/MS techniques [33].

Analytical, diagnostic and therapeutic context of cis isomer

  • When measured by a high-pressure liquid chromatography method, peak concentrations of 12.09 and 18.04 micrograms of the cis isomer per ml were obtained at 1 h, with mean half-lives of 1.63 and 2.06 h and mean areas under the curve of 30.48 and 49.34 micrograms.h/ml in patients who received the 15- and 30-mg/kg doses, respectively [34].
  • Ultraviolet (UV) irradition converts it to the cis-isomer that is an important mediator in UV-induced immunosuppression [35].
  • The maximum plasma concentration of the cis isomer ranged from 12.3 micrograms/mL in subjects with normal renal function to 36.7 micrograms/mL in hemodialysis patients [36].
  • Suberythemal sun exposures caused near-maximal UCA isomerization, and during heliotherapy the cis isomer constituted 63.7-74.3% of the total UCA concentration [37].
  • The cis-isomer of ebelin lactone was also obtained as one of the artefacts of the aglycone and its structure revised [38].


  1. cis 2-Methylthio-ribosylzeatin (ms2io6A) is present in the transfer RNA of Salmonella typhimurium, but not Escherichia coli. Buck, M., McCloskey, J.A., Basile, B., Ames, B.N. Nucleic Acids Res. (1982) [Pubmed]
  2. Phosphorylation-induced structural changes in the amyloid precursor protein cytoplasmic tail detected by NMR. Ramelot, T.A., Nicholson, L.K. J. Mol. Biol. (2001) [Pubmed]
  3. Metabolism of the cis and trans isomers of N-nitroso-2,6-dimethylmorpholine and their deuterated analogs by liver microsomes of rat and hamster. Kokkinakis, D., Hollenberg, P.F., Scarpelli, D.G. Carcinogenesis (1984) [Pubmed]
  4. Differential antitumor activity and toxicity of isomeric 1,2-diaminocyclohexane platinum (II) complexes. Siddik, Z.H., al-Baker, S., Burditt, T.L., Khokhar, A.R. J. Cancer Res. Clin. Oncol. (1993) [Pubmed]
  5. Pharmacodynamics of the 1R cis-1'R cis isomer of atracurium (51W89) in health and chronic renal failure. Boyd, A.H., Eastwood, N.B., Parker, C.J., Hunter, J.M. British journal of anaesthesia. (1995) [Pubmed]
  6. Helical repeat and chirality effects on DNA gel electrophoretic mobility. Drak, J., Crothers, D.M. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  7. Effect of agents that produce membrane disorder on lysis of erythrocytes by complement. Shin, M.L., Hänsch, G., Mayer, M.M. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  8. Idoxifene antagonizes estradiol-dependent MCF-7 breast cancer xenograft growth through sustained induction of apoptosis. Johnston, S.R., Boeddinghaus, I.M., Riddler, S., Haynes, B.P., Hardcastle, I.R., Rowlands, M., Grimshaw, R., Jarman, M., Dowsett, M. Cancer Res. (1999) [Pubmed]
  9. Arabidopsis CYP735A1 and CYP735A2 encode cytokinin hydroxylases that catalyze the biosynthesis of trans-Zeatin. Takei, K., Yamaya, T., Sakakibara, H. J. Biol. Chem. (2004) [Pubmed]
  10. Radiosensitizing and toxic properties of quinoline and nitroquinoline complexes of platinum [PtCl2(NH3)quinoline]. Skov, K.A., Adomat, H., Doedee, M., Farrell, N. Anticancer Drug Des. (1994) [Pubmed]
  11. Platinum complexes with one radiosensitizing ligand [PtCl2(NH3) (sensitizer)]: radiosensitization and toxicity studies in vitro. Skov, K.A., Farrell, N.P., Adomat, H. Radiat. Res. (1987) [Pubmed]
  12. Long-term effectiveness of photodynamic therapy by using a hydrophilic photosensitizer ATX-S10(Na) against experimental choroidal neovascularization in rats. Kanai, M., Obana, A., Gohto, Y., Nagata, S., Miki, T., Kaneda, K., Nakajima, S. Lasers in surgery and medicine. (2000) [Pubmed]
  13. Intranasal medications for the treatment of migraine and cluster headache. Rapoport, A.M., Bigal, M.E., Tepper, S.J., Sheftell, F.D. CNS drugs. (2004) [Pubmed]
  14. Structure-function relationships of hydroxylated metabolites of tamoxifen that control the proliferation of estrogen-responsive T47D breast cancer cells in vitro. Murphy, C.S., Langan-Fahey, S.M., McCague, R., Jordan, V.C. Mol. Pharmacol. (1990) [Pubmed]
  15. trans-10,11-dihydroxy-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthridine: a highly potent selective dopamine D1 full agonist. Brewster, W.K., Nichols, D.E., Riggs, R.M., Mottola, D.M., Lovenberg, T.W., Lewis, M.H., Mailman, R.B. J. Med. Chem. (1990) [Pubmed]
  16. Carotenoid uptake and secretion by CaCo-2 cells: beta-carotene isomer selectivity and carotenoid interactions. During, A., Hussain, M.M., Morel, D.W., Harrison, E.H. J. Lipid Res. (2002) [Pubmed]
  17. Comparative study of anionic and radical cyclization for the preparation of 1,3-dimethylindans: highly stereoselective preparation of cis-1,3-disubstituted indans via intramolecular carbolithiation. Bailey, W.F., Mealy, M.J., Wiberg, K.B. Org. Lett. (2002) [Pubmed]
  18. Replacing cis octadecenoic acid with trans isomers in media containing rat adipocytes stimulates lipolysis and inhibits glucose utilization. Cromer, K.D., Jenkins, T.C., Thies, E.J. J. Nutr. (1995) [Pubmed]
  19. Penetration of cefprozil into tonsillar and adenoidal tissues. Shyu, W.C., Reilly, J., Campbell, D.A., Wilber, R.B., Barbhaiya, R.H. Antimicrob. Agents Chemother. (1993) [Pubmed]
  20. Carcinogenesis in Syrian hamsters by N-nitroso-2,6-dimethylmorpholine, its cis and trans isomers, and the effect of deuterium labeling. Rao, M.S., Scarpelli, D.G., Lijinsky, W. Carcinogenesis (1981) [Pubmed]
  21. 13-cis-retinoic acid is an endogenous compound in human serum. Tang, G.W., Russell, R.M. J. Lipid Res. (1990) [Pubmed]
  22. Stereoselective modulatory actions of oleamide on GABA(A) receptors and voltage-gated Na(+) channels in vitro: a putative endogenous ligand for depressant drug sites in CNS. Verdon, B., Zheng, J., Nicholson, R.A., Ganelli, C.R., Lees, G. Br. J. Pharmacol. (2000) [Pubmed]
  23. Metabolism and biological activity of cis- and trans-phylloquinone in the rat. Knauer, T.E., Siegfried, C., Willingham, A.K., Matschiner, J.T. J. Nutr. (1975) [Pubmed]
  24. Phencyclidine metabolism: resolution, structure, and biological activity of the isomers of the hydroxy metabolite, 4-phenyl-4-(1-piperidinyl)cyclohexanol. Carroll, F.I., Brine, G.A., Boldt, K.G., Cone, E.J., Yousefnejad, D., Vaupel, D.B., Buchwald, W.F. J. Med. Chem. (1981) [Pubmed]
  25. Isolation and characterization of 3-[(carboxymethyl)thio]-3-(1H-imidazol-4-yl)propanoic acid from human urine and preparation of its proposed precursor, S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]cysteine. Kinuta, M., Yao, K., Masuoka, N., Ohta, J., Teraoka, T., Ubuka, T. Biochem. J. (1991) [Pubmed]
  26. Comparative study of the active site caging of serine proteases: thrombin and factor Xa. Thuring, J.W., Li, H., Porter, N.A. Biochemistry (2002) [Pubmed]
  27. Influences of solvent water on protein folding: free energies of solvation of cis and trans peptides are nearly identical. Radzicka, A., Pedersen, L., Wolfenden, R. Biochemistry (1988) [Pubmed]
  28. Synthesis, pharmacological action, and receptor binding affinity of the enantiomeric 1-(1-phenyl-3-methylcyclohexyl)piperidines. Thurkauf, A., Hillery, P., Mattson, M.V., Jacobson, A.E., Rice, K.C. J. Med. Chem. (1988) [Pubmed]
  29. Synthesis and biology of the conformationally restricted ACPD analogue, 2-aminobicyclo[2.1.1]hexane-2,5-dicarboxylic acid-I, a potent mGluR agonist. Kozikowski, A.P., Steensma, D., Araldi, G.L., Tückmantel, W., Wang, S., Pshenichkin, S., Surina, E., Wroblewski, J.T. J. Med. Chem. (1998) [Pubmed]
  30. A study of the relationship between biological activity and prolyl amide isomer geometry in oxytocin using 5-tert-butylproline to augment the Cys(6)-Pro(7) amide cis-isomer population. Bélec, L., Slaninova, J., Lubell, W.D. J. Med. Chem. (2000) [Pubmed]
  31. A conserved cis peptide bond is necessary for the activity of Bowman-Birk inhibitor protein. Brauer, A.B., Domingo, G.J., Cooke, R.M., Matthews, S.J., Leatherbarrow, R.J. Biochemistry (2002) [Pubmed]
  32. Anandamide elicits an acute release of nitric oxide through endothelial TRPV1 receptor activation in the rat arterial mesenteric bed. Poblete, I.M., Orliac, M.L., Briones, R., Adler-Graschinsky, E., Huidobro-Toro, J.P. J. Physiol. (Lond.) (2005) [Pubmed]
  33. Vitamin K dependent carboxylation: determination of the stereochemical course using 4-fluoroglutamyl-containing substrate. Dubois, J., Dugave, C., Fourès, C., Kaminsky, M., Tabet, J.C., Bory, S., Gaudry, M., Marquet, A. Biochemistry (1991) [Pubmed]
  34. Pharmacokinetics of cefprozil in infants and children. Sáez-Llorens, X., Shyu, W.C., Shelton, S., Kumiesz, H., Nelson, J. Antimicrob. Agents Chemother. (1990) [Pubmed]
  35. Stereospecific modulation of GABA(A) receptor function by urocanic acid isomers. Uusi-Oukari, M., Soini, S.L., Heikkilä, J., Koivisto, A., Neuvonen, K., Pasanen, P., Sinkkonen, S.T., Laihia, J.K., Jansén, C.T., Korpi, E.R. Eur. J. Pharmacol. (2000) [Pubmed]
  36. Pharmacokinetics of cefprozil in healthy subjects and patients with renal impairment. Shyu, W.C., Pittman, K.A., Wilber, R.B., Matzke, G.R., Barbhaiya, R.H. Journal of clinical pharmacology. (1991) [Pubmed]
  37. Effect of psoriasis heliotherapy on epidermal urocanic acid isomer concentrations. Snellman, E., Koulu, L., Pasanen, P., Lammintausta, K., Neuvonen, K., Ayräs, P., Jansén, C.T. Acta Derm. Venereol. (1992) [Pubmed]
  38. Bacoside A3--a triterpenoid saponin from Bacopa monniera. Rastogi, S., Pal, R., KulshreshthaDK, n.u.l.l. Phytochemistry (1994) [Pubmed]
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