Display options
Share it on

Beilstein J Org Chem. 2016 Jan 25;12:125-38. doi: 10.3762/bjoc.12.14. eCollection 2016.

A journey in bioinspired supramolecular chemistry: from molecular tweezers to small molecules that target myotonic dystrophy.

Beilstein journal of organic chemistry

Steven C Zimmerman

Affiliations

  1. Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, United States.

PMID: 26877815 PMCID: PMC4734311 DOI: 10.3762/bjoc.12.14

Abstract

This review summarizes part of the author's research in the area of supramolecular chemistry, beginning with his early life influences and early career efforts in molecular recognition, especially molecular tweezers. Although designed to complex DNA, these hosts proved more applicable to the field of host-guest chemistry. This early experience and interest in intercalation ultimately led to the current efforts to develop small molecule therapeutic agents for myotonic dystrophy using a rational design approach that heavily relies on principles of supramolecular chemistry. How this work was influenced by that of others in the field and the evolution of each area of research is highlighted with selected examples.

Keywords: RNA recognition; RNase mimic; catenanes; intercalation; macrocycles; multi-target drug discovery

References

  1. J Am Chem Soc. 2005 May 11;127(18):6520-1 - PubMed
  2. Biochemistry. 1990 Dec 11;29(49):10918-27 - PubMed
  3. ACS Chem Biol. 2013 May 17;8(5):1037-43 - PubMed
  4. Biopolymers. 1999;52(2):65-83 - PubMed
  5. Science. 1996 Feb 23;271(5252):1095-8 - PubMed
  6. Chem Soc Rev. 2008 Jan;37(1):101-8 - PubMed
  7. J Am Chem Soc. 2007 Jan 31;129(4):934-41 - PubMed
  8. ACS Appl Mater Interfaces. 2015 Apr 29;7(16):8906-14 - PubMed
  9. Nucleic Acids Res. 2011 Nov 1;39(20):8881-90 - PubMed
  10. Elife. 2015 Aug 18;4: - PubMed
  11. Science. 1992 Mar 6;255(5049):1256-8 - PubMed
  12. Nucleic Acids Res. 2013 Jul;41(13):6687-97 - PubMed
  13. Proc Natl Acad Sci U S A. 1971 Aug;68(8):1678-83 - PubMed
  14. Biochemistry. 1988 May 31;27(11):3997-4003 - PubMed
  15. J Am Chem Soc. 2011 Nov 2;133(43):17118-21 - PubMed
  16. Proc Natl Acad Sci U S A. 2005 Nov 15;102(46):16626-31 - PubMed
  17. Angew Chem Int Ed Engl. 2015 May 18;54(21):6110-50 - PubMed
  18. Proc Natl Acad Sci U S A. 2009 Sep 22;106(38):16068-73 - PubMed
  19. Acc Chem Res. 2004 Nov;37(11):862-73 - PubMed
  20. Proc Natl Acad Sci U S A. 1981 Jul;78(7):4046-50 - PubMed
  21. J Am Chem Soc. 2013 May 15;135(19):7288-95 - PubMed
  22. N Engl J Med. 2006 Oct 26;355(17):1825-7 - PubMed
  23. J Am Chem Soc. 2012 Jan 18;134(2):832-5 - PubMed
  24. Nucleic Acids Res. 2008 Sep;36(15):5000-12 - PubMed
  25. J Am Chem Soc. 2011 Oct 26;133(42):16958-69 - PubMed
  26. J Am Chem Soc. 2005 Dec 28;127(51):18133-42 - PubMed
  27. PLoS Genet. 2011 Mar;7(3):e1002018 - PubMed
  28. J Am Chem Soc. 2009 Mar 18;131(10):3499-508 - PubMed
  29. Proc Natl Acad Sci U S A. 1975 Aug;72(8):2915-9 - PubMed
  30. Proc Natl Acad Sci U S A. 1993 Feb 15;90(4):1190-3 - PubMed
  31. Cell. 1992 Feb 21;68(4):799-808 - PubMed
  32. Proc Natl Acad Sci U S A. 2011 Jan 4;108(1):260-5 - PubMed
  33. Biopolymers. 2010 Sep;93(9):777-90 - PubMed
  34. J Am Chem Soc. 2006 Nov 1;128(43):13986-7 - PubMed
  35. Biol Rev Camb Philos Soc. 2011 Nov;86(4):947-58 - PubMed
  36. Chembiochem. 2003 Dec 5;4(12):1326-31 - PubMed
  37. Beilstein J Org Chem. 2015 Nov 02;11:2057-71 - PubMed
  38. Biopolymers. 1968 Apr;6(4):575-84 - PubMed
  39. Chem Soc Rev. 2014 May 21;43(10):3630-65 - PubMed
  40. Bioorg Med Chem. 1996 Jul;4(7):1107-12 - PubMed
  41. J Am Chem Soc. 2015 Nov 11;137(44):14180-9 - PubMed
  42. Nat Chem. 2010 Aug;2(8):653-60 - PubMed
  43. J Am Chem Soc. 2008 Oct 8;130(40):13190-1 - PubMed
  44. Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5040-5 - PubMed
  45. J Med Chem. 2002 Nov 7;45(23):5098-111 - PubMed
  46. Biochemistry. 1999 Oct 26;38(43):14205-13 - PubMed
  47. J Am Chem Soc. 2014 Apr 30;136(17):6355-61 - PubMed
  48. Acc Chem Res. 2003 Dec;36(12):919-32 - PubMed
  49. J Med Chem. 2013 Dec 12;56(23):9471-9481 - PubMed
  50. J Am Chem Soc. 2002 Nov 20;124(46):13757-69 - PubMed

Publication Types

Grant support