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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
Chemical Compound Review

Oxetane     oxetane

Synonyms: Oxetan, Cyclooxabutane, Oxacyclobutane, SureCN27771, CCRIS 4707, ...
 
 
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Disease relevance of oxetane

  • 1,7-Deoxy-4-deacetylbaccatin III (12) and its five analogues 6-9, 13, and their oxetane ring opened derivatives 14, 16, and 17, which were synthesized from taxinine, showed significant activity as MDR reversal agent by the assay of the calcein accumulation toward MDR human ovarian cancer 2780AD cells [1].
  • Taking advantage of the electrochemical signature of these mimics, enzymatic assay with Escherichia coli CPD photolyase coupled to electrochemical monitoring of the reaction brings evidence that enzymatic repair of (6-4) DNA photoproducts does involve a catalytic dissociative electron-transfer mechanism at the level of an oxetane intermediate [2].
 

High impact information on oxetane

  • Furthermore, we provide evidence that the (6-4) photoproduct photolyase converts the photoproduct to unmodified bases probably through an oxetane intermediate [3].
  • CONCLUSIONS: The structure of the first oxygenated intermediate on the taxol pathway establishes that the hydroxylation reaction proceeds with an unusual double bond migration that limits the mechanistic possibilities for subsequent elaboration of the oxetane moiety of taxol [4].
  • Irradiation of bicyclic enone 16, constructed through cyclopentenone alkylation followed by a domino oxy-/carbopalladation reaction, produces the tetracyclic oxetane 17 in excellent yield, having the core carbon skeleton of the target compound merrilactone A [5].
  • The addition of methyl substituents to the oxetane precursor of the commonly used [2.2.2]-bicyclic OBO orthoester significantly increased the ease of orthoester formation and its resistance to hydrolysis [6].
  • In this way, we evaluate the two characteristics considered responsible for oxetane function: (1) rigidification of the tetracyclic Taxol core to provide an appropriate framework for presenting the C-2, C-4, C-13 side chains to the microtubule protein and (2) service as a hydrogen-bond acceptor [7].
 

Biological context of oxetane

  • Rationally targeted, conformationally constrained, oxetane-modified oligonucleotides demonstrate efficient gene-silencing activity in a cellular system [8].
  • Temperature dependent hydration studies by NMR demonstrate that the central T(7).A(6)/A(6).T(7) base pairs of the T(7) oxetane modified Dickerson-Drew dodecamer have at least one order of magnitude higher water exchange rates (correlated to the opening rate of the base pair) than the corresponding base pairs in the native duplex [9].
  • The C modified AONs (with 3'-DPPZ), as in the T counterpart, showed an enhanced tolerance towards the endonuclease and exonuclease degradation compared to the native (the oxetane-sugar and the DPPZ based AONs are non-toxic to K562 cell growth, ref. 18) [10].
 

Anatomical context of oxetane

 

Associations of oxetane with other chemical compounds

  • The potency of VDR affinities of the C-23-substituted analogues (keto group (4); OH group (5a,5b); fluorine atom (6a,6b); and oxetane ring (7a,7b)) was found to vary depending upon both the nature and stereochemistry of the substituents [12].
  • Human platelets as well as guinea pig lung and spleen converted the endoperoxides into thromboxane A2, an unstable (t1/2 at 37 degrees C about 30 s) oxetane/oxane derivative [13].
  • Electron transfer from the excited tryptophan residue to the oxetane unit is the origin of fluorescence quenching of the tryptophan residue, and is more efficient in strong polar solvents [14].
 

Gene context of oxetane

  • Topics discussed include side chain attachment to baccatin III (3a), the effect of oxygenation of the taxane ring system on bioactivity, the importance of the oxetane ring for bioactivity, the synthesis of a C-6/C-4 bridged analogue, and the conformation of the side chain when taxol is bound in a complex with polymerized tubulin [15].
  • Analysis of the 1H NMR data of paclitaxel in comparison with its oxetane ring-opened analogue D-secopaclitaxel suggests that the oxetane moiety (D-ring) of paclitaxel serves as a conformational lock for the diterpene moiety and the C13 side chain [16].

References

  1. Structure-activity relationships of some taxoids as multidrug resistance modulator. Hasegawa, T., Bai, J., Zhang, S., Wang, J., Matsubara, J., Kawakami, J., Tomida, A., Tsuruo, T., Hirose, K., Sakai, J., Kikuchi, M., Abe, M., Ando, M. Bioorg. Med. Chem. Lett. (2007) [Pubmed]
  2. Electrochemical approach to the repair of oxetanes mimicking DNA (6-4) photoproducts. Boussicault, F., Robert, M. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2006) [Pubmed]
  3. Characterization of (6-4) photoproduct DNA photolyase. Kim, S.T., Malhotra, K., Smith, C.A., Taylor, J.S., Sancar, A. J. Biol. Chem. (1994) [Pubmed]
  4. Cytochrome P450-catalyzed hydroxylation of taxa-4(5),11(12)-diene to taxa-4(20),11(12)-dien-5alpha-ol: the first oxygenation step in taxol biosynthesis. Hefner, J., Rubenstein, S.M., Ketchum, R.E., Gibson, D.M., Williams, R.M., Croteau, R. Chem. Biol. (1996) [Pubmed]
  5. A Paterno-Büchi approach to the synthesis of merrilactone A. Iriondo-Alberdi, J., Perea-Buceta, J.E., Greaney, M.F. Org. Lett. (2005) [Pubmed]
  6. DMOBO: an improvement on the OBO orthoester protecting group. Giner, J.L. Org. Lett. (2005) [Pubmed]
  7. The oxetane ring in taxol. Wang, M., Cornett, B., Nettles, J., Liotta, D.C., Snyder, J.P. J. Org. Chem. (2000) [Pubmed]
  8. Rationally targeted, conformationally constrained, oxetane-modified oligonucleotides demonstrate efficient gene-silencing activity in a cellular system. Opalinska, J.B., Gewirtz, A.M. Ann. N. Y. Acad. Sci. (2005) [Pubmed]
  9. Oxetane locked thymidine in the Dickerson-Drew dodecamer causes local base pairing distortions -- an NMR structure and hydration study. Isaksson, J., Plashkevych, O., Pradeepkumar, P.I., Chatterjee, S., Barman, J., Pathmasiri, W., Shrivastava, P., Petit, C., Chattopadhyaya, J. J. Biomol. Struct. Dyn. (2005) [Pubmed]
  10. Antisense oligonuclotides with oxetane-constrained cytidine enhance heteroduplex stability, and elicit satisfactory RNase H response as well as showing improved resistance to both exo and endonucleases. Pradeepkumar, P.I., Amirkhanov, N.V., Chattopadhyaya, J. Org. Biomol. Chem. (2003) [Pubmed]
  11. A novel cytotoxic oxetane ent-kauranoid from Isodon japonicus. Han, Q., Zhang, J., Lu, Y., Wu, Y., Zheng, Q., Sun, H. Planta Med. (2004) [Pubmed]
  12. Synthesis and biological evaluations of C-23-modified 26,26,26,27,27,27-F6-vitamin D3 analogues. Ikeda, M., Matsumura, H., Sawada, N., Hashimoto, K., Tanaka, T., Noguchi, T., Hayashi, M. Bioorg. Med. Chem. (2000) [Pubmed]
  13. Biosynthesis and biological properties of prostaglandin endoperoxides and thromboxane A2. Svensson, J. Acta Biol. Med. Ger. (1978) [Pubmed]
  14. Model studies of the (6-4) photoproduct photoreactivation: efficient photosensitized splitting of thymine oxetane units by covalently linked tryptophan in high polarity solvents. Song, Q.H., Wang, H.B., Tang, W.J., Guo, Q.X., Yu, S.Q. Org. Biomol. Chem. (2006) [Pubmed]
  15. Recent advances in the chemistry of taxol. Kingston, D.G. J. Nat. Prod. (2000) [Pubmed]
  16. The oxetane conformational lock of paclitaxel: structural analysis of D-secopaclitaxel. Boge, T.C., Hepperle, M., Vander Velde, D.G., Gunn, C.W., Grunewald, G.L., Georg, G.I. Bioorg. Med. Chem. Lett. (1999) [Pubmed]
 
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