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Improvement in Aqueous Solubility in Small Molecule Drug Discovery Programs by Disruption of Molecular Planarity and Symmetry

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Ishikawa, Minoru, Hashimoto, Yuichi·2011·Journal of Medicinal Chemistry
DOI 10.1021/jm101356p
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Abstract

ADVERTISEMENT RETURN TO ISSUEPerspectiveNEXTImprovement in Aqueous Solubility in Small Molecule Drug Discovery Programs by Disruption of Molecular Planarity and SymmetryMinoru Ishikawa* and Yuichi HashimotoView Author Information Institute of Molecular and Cellular Biosciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan*Phone: +81.3.5841.7849. Fax: +81.3.5841.8495. E-mail: [email protected]Cite this: J. Med. Chem. 2011, 54, 6, 1539–1554Publication Date (Web):February 23, 2011Publication History Received19 October 2010Published online23 February 2011Published inissue 24 March 2011https://pubs.acs.org/doi/10.1021/jm101356phttps://doi.org/10.1021/jm101356preview-articleACS PublicationsCopyright © 2011 American Chemical SocietyRequest reuse permissionsArticle Views24218Altmetric-Citations449LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Agonists,Hydrophobicity,Partition coefficient,Solubility,Transition temperature Get e-Alerts

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Research works printed but not linked: 73

  1. Stegemann S., 2007, Eur. J. Pharm. Sci., 31, 249, 10.1016/j.ejps.2007.05.110 · DOI · Paper page
  2. Alelyunas Y. W., 2010, Bioorg. Med. Chem. Lett., 20, 7312, 10.1016/j.bmcl.2010.10.068 · DOI
  3. Bhattachar S. N., 2006, Drug Discovery Today, 11, 1012, 10.1016/j.drudis.2006.09.002 · DOI
  4. Yalkowsky S. H., 1999, Solubility and Solubilization in Aqueous Media
  5. Palucki M., 2010, J. Med. Chem., 53, 5897, 10.1021/jm1002638 · DOI
  6. Lipinski C. A., 2000, J. Pharmacol. Toxicol. Methods, 44, 235, 10.1016/S1056-8719(00)00107-6 · DOI · Paper page
  7. Hansch C., 1968, J. Org. Chem., 33, 347, 10.1021/jo01265a071 · doi:10.1021/jo01265a071
  8. Valvani S. C., 1981, J. Pharm. Sci., 70, 502, 10.1002/jps.2600700510 · DOI · Paper page
  9. Banerjee S, 1980, Environ. Sci. Technol., 10, 1227, 10.1021/es60170a013 · DOI · Paper page
  10. Jain N., 2001, J. Pharm. Sci., 90, 234, 10.1002/1520-6017(200102)90:2<234::AID-JPS14>3.0.CO;2-V · DOI
  11. Yalkowsky S. H., 1980, J. Pharm. Sci., 69, 912, 10.1002/jps.2600690814 · DOI · Paper page
  12. Ran Y., 2001, J. Chem. Inf. Comput. Sci., 41, 354, 10.1021/ci000338c · DOI · Paper page
  13. Gavezzotti A., 1994, Acc. Chem. Res., 27, 309, 10.1021/ar00046a004 · DOI · Paper page
  14. 1991, Handbook of Chemistry and Physics
  15. Lovering F., 2009, J. Med. Chem., 52, 6752, 10.1021/jm901241e · DOI · Paper page
  16. Hoover T. B., 1971, PCB Newsl., 3, 4
  17. Lee M. C., 1979, Water Res., 13, 1249, 10.1016/0043-1354(79)90169-6 · doi:10.1016/0043-1354(79)90169-6
  18. Gavezzotti A., 1995, J. Chem. Soc., Perkin Trans. 2, 1399, 10.1039/p29950001399 · doi:10.1039/p29950001399
  19. Dannenfelser R.-M., 1996, Ind. Eng. Chem. Res., 35, 1483, 10.1021/ie940581z · doi:10.1021/ie940581z
  20. Lipinski, C. A.InMolecular Drug Properties: Measurement and Prediction;Mannhold, R., Ed.; Methods and Principles in Medicinal Chemistry, Vol.37;Wiley-VCH Verlag GmbH & Co. KGaA:Weinheim, Germany, 2008; pp257−282.
  21. Chu K. A., 2009, Curr. Drug Metab., 10, 1184, 10.2174/138920009790820110 · doi:10.2174/138920009790820110
  22. Yalkowsky S. H., 2010, J. Pharm. Sci., 99, 1100, 10.1002/jps.21897 · doi:10.1002/jps.21897
  23. Wang H. L., 2007, J. Med. Chem., 50, 3528, 10.1021/jm070191h · DOI
  24. Doherty E. M., 2007, J. Med. Chem., 50, 3415, 10.1021/jm070190p · DOI
  25. Brown A., 2008, Bioorg. Med. Chem. Lett., 18, 5242, 10.1016/j.bmcl.2008.08.066 · doi:10.1016/j.bmcl.2008.08.066
  26. Kim I. H., 2005, J. Med. Chem., 48, 3621, 10.1021/jm0500929 · doi:10.1021/jm0500929
  27. Kubota D., 2006, Bioorg. Med. Chem., 14, 2089, 10.1016/j.bmc.2005.10.060 · doi:10.1016/j.bmc.2005.10.060
  28. Ishikawa M., 2006, Bioorg. Med. Chem., 14, 2109, 10.1016/j.bmc.2005.10.061 · doi:10.1016/j.bmc.2005.10.061
  29. Ishikawa M., 2006, Bioorg. Med. Chem., 14, 2131, 10.1016/j.bmc.2005.10.055 · doi:10.1016/j.bmc.2005.10.055
  30. Mehta J. L., 1988, J. Am. Coll. Cardiol., 11, 1309, 10.1016/0735-1097(88)90297-5 · DOI · Paper page
  31. Reynolds J. M., 1989, Am. J. Physiol.: Heart Circ. Physiol., 256, H982
  32. Engler R. L., 1986, Am. J. Physiol.: Heart Circ. Physiol., 251, H314
  33. Tam S. H., 1998, Circulation, 98, 1085, 10.1161/01.CIR.98.11.1085 · DOI · Paper page
  34. Cherny R. C., 1993, J. Biol. Chem., 268, 9725, 10.1016/S0021-9258(18)98408-5 · DOI
  35. Pfaff M., 1994, J. Biol. Chem., 269, 20233, 10.1016/S0021-9258(17)31981-6 · DOI · Paper page
  36. Haubner R., 1996, J. Am. Chem. Soc., 118, 7461, 10.1021/ja9603721 · DOI · Paper page
  37. Haubner R., 1997, Angew. Chem., Int. Ed. Engl., 36, 1374, 10.1002/anie.199713741 · DOI · Paper page
  38. Bach A. C., 1996, J. Am. Chem. Soc., 118, 293, 10.1021/ja953163+ · DOI
  39. Valkó K., 2004, J. Chromatogr., A, 1037, 299, 10.1016/j.chroma.2003.10.084 · DOI · Paper page
  40. Ishikawa M., 2008, Soyaku Shien Kenkyu no Tenbo, 3
  41. Ishikawa M., 2008, Org. Process Res. Dev., 12, 596, 10.1021/op800073z · doi:10.1021/op800073z
  42. Sakuma T., 2005, Cardiovasc. Res., 66, 552, 10.1016/j.cardiores.2005.01.016 · DOI
  43. Kaul S., 2006, Basic Res. Cardiol., 101, 391, 10.1007/s00395-006-0618-z · doi:10.1007/s00395-006-0618-z
  44. Fujita Y., 2010, Bioorg. Med. Chem., 18, 1194, 10.1016/j.bmc.2009.12.036 · DOI
  45. Mimura J., 2003, Biochim. Biophys. Acta, 1619, 263, 10.1016/S0304-4165(02)00485-3 · DOI · Paper page
  46. Esser C., 2009, Trends Immunol., 30, 447, 10.1016/j.it.2009.06.005 · DOI · Paper page
  47. Marple L., 1986, Environ. Sci. Technol., 20, 180, 10.1021/es00144a012 · DOI
  48. Sugihara K., 2008, Arch. Toxicol., 82, 5, 10.1007/s00204-007-0232-3 · DOI
  49. Holth T. F., 2009, Environ. Sci. Technol., 43, 3329, 10.1021/es803479p · doi:10.1021/es803479p
  50. Frisch M. J., 2004, Gaussian 03
  51. Kasuga J., 2010, Bioorg. Med. Chem., 18, 7164, 10.1016/j.bmc.2010.08.041 · DOI
  52. Kliewer S. A., 1994, Proc. Natl. Acad. Sci. U.S.A., 91, 7355, 10.1073/pnas.91.15.7355 · DOI · Paper page
  53. Gross B., 2007, Best Pract. Res., Clin. Endocrinol. Metab., 21, 687, 10.1016/j.beem.2007.09.004 · DOI · Paper page
  54. Lee C. H., 2006, Proc. Natl. Acad. Sci. U.S.A., 103, 3444, 10.1073/pnas.0511253103 · DOI · Paper page
  55. Epple R., 2010, J. Med. Chem., 53, 77, 10.1021/jm9007399 · DOI
  56. Sauerberg P., 2007, J. Med. Chem., 50, 1495, 10.1021/jm061202u · DOI
  57. Kasuga J., 2009, Bioorg. Med. Chem. Lett., 19, 6595, 10.1016/j.bmcl.2009.10.021 · DOI
  58. Bergström C. A., 2007, J. Med. Chem., 50, 5858, 10.1021/jm0706416 · DOI · Paper page
  59. Anderson D. R., 2007, J. Med. Chem., 50, 2647, 10.1021/jm0611004 · DOI · Paper page
  60. Dublanchet A. C., 2005, Bioorg. Med. Chem. Lett., 15, 3787, 10.1016/j.bmcl.2005.05.079 · DOI
  61. Leach A. G., 2006, J. Med. Chem., 49, 6672, 10.1021/jm0605233 · DOI · Paper page
  62. Jones C. D., 2008, Bioorg. Med. Chem. Lett., 18, 6486, 10.1016/j.bmcl.2008.10.075 · doi:10.1016/j.bmcl.2008.10.075
  63. Schroeder G. M., 2009, J. Med. Chem., 52, 1251, 10.1021/jm801586s · DOI · Paper page
  64. Brown D. G., 2003, Bioorg. Med. Chem. Lett., 13, 3553, 10.1016/S0960-894X(03)00750-9 · doi:10.1016/s0960-894x(03)00750-9
  65. Fray J. M., 2001, J. Med. Chem., 44, 1951, 10.1021/jm001124p · doi:10.1021/jm001124p
  66. Ballard P., 2006, Bioorg. Med. Chem. Lett., 16, 4908, 10.1016/j.bmcl.2006.06.054 · doi:10.1016/j.bmcl.2006.06.054
  67. Li X., 2008, Bioorg. Med. Chem. Lett., 18, 2256, 10.1016/j.bmcl.2008.03.011 · DOI
  68. Wang X., 2007, Bioorg. Med. Chem. Lett., 17, 6539, 10.1016/j.bmcl.2007.09.080 · DOI
  69. Li Q., 1996, J. Med. Chem., 39, 3070, 10.1021/jm960207w · doi:10.1021/jm960207w
  70. Lange J. H. M., 2004, J. Med. Chem., 47, 627, 10.1021/jm031019q · DOI · Paper page
  71. Kim I.-H., 2005, J. Med. Chem., 48, 3621, 10.1021/jm0500929 · doi:10.1021/jm0500929
  72. Hodous B. L., 2007, J. Med. Chem., 50, 611, 10.1021/jm061107l · DOI
  73. Li J. J., 2007, J. Med. Chem., 50, 3015, 10.1021/jm070312d · DOI

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Metadata

Authors
Ishikawa, M., & Hashimoto, Y.
Venue
Journal of Medicinal Chemistry
Publisher
American Chemical Society (ACS)
Published
2011-02-23
Volume
54
Issue
6
Pages
1539-1554
ISSN
  • 0022-2623 (ISSN-L)
  • 1520-4804
DOI
10.1021/jm101356p
OpenAlex
W1999197232
Cited by
619
References
4
FWCI
20.65
Type
journal article
Language
en
Open access
green

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CoChat. (2026). Citation check: Improvement in Aqueous Solubility in Small Molecule Drug Discovery Programs by Disruption of Molecular Planarity and Symmetry. https://app.cochat.ai/papers/10.1021/jm101356p
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Ishikawa, M., & Hashimoto, Y. (2011). Improvement in Aqueous Solubility in Small Molecule Drug Discovery Programs by Disruption of Molecular Planarity and Symmetry. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm101356p

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