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Synthetic and Conformational Studies in Molecular Encapsulation with a Twisted Molecular Basket Complexing Organophosphorus Molecules and Fentanyl Analogues

Warrell, Rachel Marie
http://rave.ohiolink.edu/etdc/view?acc_num=osu1502899516087168

Abstract Details

2017, Master of Science, Ohio State University, Chemistry.
Supramolecular chemistry has from the beginning sought to mimic the elaborate host-guest interactions found in nature. Starting with the complexation of ions explored by Pederson and moving towards stabilization of guests and catalysis, chemists have diversified the topography and capabilities of their synthetic host molecules over the last five decades. The Badjic group has recently developed a family of basket-shaped hosts featuring hydrophobic cavities and variable gates. These characteristics govern the specificity of the hosts for certain guests by virtue of their size, shape, and electronic landscape. One of these “baskets” is unique in that it possesses 1) a larger cavity than the other two families of baskets, and 2) a twist in either the left- or right-handed direction, introducing asymmetry to the cavity. Previous studies have found this basket to have a high affinity (Ka, ITC titration experiments) for small guests containing an ethylbenzene moiety. These experiments have led us to explore the possibility of entrapping analogues to the opioid drug fentanyl. Here we describe the optimized synthesis of the twisted basket modified with a glutamic acid gate, the synthesis of novel guests analogous to fentanyl, and experiments (ITC, NMR titrations) performed to determine the affinity constant (Ka) of the host for two of these guests. Preliminary results suggest the binding affinity to be very sensitive to the size of the upper portion of the guest molecule, encouraging further studies with the newly developed fentanyl analogues.
Jovica Badjic, Ph.D. (Advisor)
Psaras McGrier, Ph.D. (Committee Member)
53 p.
Chemistry; Materials Science

Recommended Citations

Citations

  • Warrell, R. M. (2017). Synthetic and Conformational Studies in Molecular Encapsulation with a Twisted Molecular Basket Complexing Organophosphorus Molecules and Fentanyl Analogues [Master's thesis, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1502899516087168

    APA Style (7th edition)

  • Warrell, Rachel. Synthetic and Conformational Studies in Molecular Encapsulation with a Twisted Molecular Basket Complexing Organophosphorus Molecules and Fentanyl Analogues. 2017. Ohio State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1502899516087168.

    MLA Style (8th edition)

  • Warrell, Rachel. "Synthetic and Conformational Studies in Molecular Encapsulation with a Twisted Molecular Basket Complexing Organophosphorus Molecules and Fentanyl Analogues." Master's thesis, Ohio State University, 2017. http://rave.ohiolink.edu/etdc/view?acc_num=osu1502899516087168

    Chicago Manual of Style (17th edition)

osu1502899516087168
287
© 2017, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.