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Solid State Characterization of 3-(5-methoxy, 2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one (MOMIPP) and its solvates

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2019, Master of Science in Pharmaceutical Science (MSP), University of Toledo, Pharmaceutical Sciences (Industrial Pharmacy).
MoMIPP is a new anti-cancer compound with potent anti-cancer activity. Its action is mediated by the process of methuosis that causes cancer cell death. Even though in vitro cell culture studies and in vivo animal studies were thoroughly performed on MoMIPP, there was no clear understanding regarding its different solid-state forms (polymorphs or solvates). Various solid-state forms differ in physiochemical properties which made it essential to explore the possible forms in early development of drug and drug product. In this study polymorphs and solvates of MOMIPP from polar solvents (ethanol, methanol, ethyl acetate, acetone and tetrahydro fluoride (THF) were formed and characterized. Pseudo polymorph (solvates) of MOMIPP were prepared using different polar solvents. Solvates were obtained by crystallization using a supersaturated solution of MOMIPP in selected solvents followed by slow evaporation in vacuum drying at -10pa pressure in room temperature. Solid-state characterization was carried out using PXRD, thermal analysis (DSC, TGA) and further confirmed the attachment of the solvent molecule in the crystal lattice by spectroscopic analysis (FTIR, Raman, NMR). The morphological study was done using optical microscopy as well as SEM. DSC thermogram of MoMIPP showed two endothermic peaks at around 230°C and 260⁰C which was considered form I and heating MoMIPP to 230°C followed by cooling the endothermic peak at 230⁰C, the first endothermic peak disappeared, and it was considered form II. DSC thermogram showed the desolvation peak for crystal from methanol, ethanol and ethyl acetate and corresponding mass loss was shown in TGA confirming the solvate formation of MoMIPP with these solvents. This was further confirmed by the presence of respective solvent signal in NMR. The PXRD gave unique pattern for all the crystals and crystalline property were intact. Solvate formation of MoMIPP with ethanol, methanol and ethyl acetate were also supported by FTIR spectra. So, this study clearly indicates two forms of MoMIPP and solvates of MoMIPP with ethanol, methanol and ethyl acetate were formed.
Jerry Nesamony (Committee Chair)
Jeffrey. G Sarver (Committee Member)
Gabriella Baki (Committee Member)
67 p.

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Citations

  • Gwachha, K. (2019). Solid State Characterization of 3-(5-methoxy, 2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one (MOMIPP) and its solvates [Master's thesis, University of Toledo]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=mco1556641812034105

    APA Style (7th edition)

  • Gwachha, Kabita. Solid State Characterization of 3-(5-methoxy, 2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one (MOMIPP) and its solvates. 2019. University of Toledo, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=mco1556641812034105.

    MLA Style (8th edition)

  • Gwachha, Kabita. "Solid State Characterization of 3-(5-methoxy, 2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one (MOMIPP) and its solvates." Master's thesis, University of Toledo, 2019. http://rave.ohiolink.edu/etdc/view?acc_num=mco1556641812034105

    Chicago Manual of Style (17th edition)