Bulletin of the Korean Chemical Society

  • 제24권6호
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  • Pages.731-732
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  • 2003
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Computational Study of Mutagen X

  • Cho, Seung-Joo (Life Science Division, Korea Institute of Science and Technology)
  • 발행 : 2003.06.20
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초록

Mutagen X (MX), 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone is one of the most potent directing acting mutagen ever tested in SAL TA100 assay. Although MX analogues have been synthesized, tested for mutagenicity and modeled by structure-activity relationship (SAR) methods, the mechanism of interaction of these compounds with DNA to produce their remarkable mutagenic potency remains unresolved. MX exists as an equilibrium mixture of both ring and open form in water. This equilibrium is very fast for Ames test. Because the mixture is not separable by experimental methods, it is not clear which one is really responsible for the observed mutagenicity. There have been many debates that which one is really responsible for the observed mutagenicity. We used ab initio methods for the MX analogues. It seems both ring and open form could react with DNA bases as electrophiles. However, every open form has consistently lower LUMO energy than corresponding ring form. It is reasonable to assume that the major reaction will go through via open form for MX analogues. This suggest that the open form is more likely really mutagenic.

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피인용 문헌

  1. Global and local chemical reactivities of mutagen X and simple derivatives vol.19, pp.6, 2013, https://doi.org/10.1007/s00894-013-1799-7
  2. Large variation in electrostatic contours upon addition of steric parameters and the effect of charge calculation schemes in CoMFA on mutagenicity of MX analogues vol.38, pp.11, 2012, https://doi.org/10.1080/08927022.2012.659182
  3. Purine Nucleoside Phosphorylase versus its Ser90Ala Mutant in the Synthesis of Base-Modified Nucleosides vol.21, pp.38, 2015, https://doi.org/10.1002/chem.201501334
  4. Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Index Analysis (CoMSIA) Study of Mutagen X vol.25, pp.10, 2003, https://doi.org/10.5012/bkcs.2004.25.10.1525
  5. Hologram Quantitative Structure Activity Relationship (HQSAR) Study of Mutagen X vol.26, pp.1, 2003, https://doi.org/10.5012/bkcs.2005.26.1.085
  6. 3D-QSAR Studies on Angiotensin-Converting Enzyme (ACE)Inhibitors: a Molecular Design in Hypertensive Agents vol.26, pp.6, 2003, https://doi.org/10.5012/bkcs.2005.26.6.952
  7. Physical Chemistry Research Articles Published in the Bulletin of the Korean Chemical Society: 2003-2007 vol.29, pp.2, 2008, https://doi.org/10.5012/bkcs.2008.29.2.450
  8. Molecular structure and vibrational spectra of 2(5H)-furanone and 2(5H)-thiophenone isolated in low temperature inert matrix vol.887, pp.1, 2008, https://doi.org/10.1016/j.molstruc.2008.02.034