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Synthesis and Design of MS-153 Analogues as Potential Drugs for Treatment of Alcohol and Methamphetamine Co-abuse

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2017, Doctor of Philosophy, University of Toledo, Medicinal Chemistry.
Co-abuse of ethanol and methamphetamine (METH) is considered as a major public health concern (Room, Babor et al. 2005, Marshall and Werb 2010). Several studies from our laboratory and others revealed that glutamatergic, serotoninergic and dopaminergic systems in the brain are altered with co-exposure to drugs of abuse, including METH and ethanol (Tata, Raudensky et al. 2007, Halpin, Northrop et al. 2014, Das, Yamamoto et al. 2015, Alshehri, Althobaiti et al. 2016, Althobaiti, Almalki et al. 2016). In this study, we investigated the effects of sequential exposure to ethanol and METH on these neurotransmitters. Young adult male Wistar rats were orally gavaged with either ethanol (6 g/kg) or water for seven days. On Day 8, rats were administered repeated high dose of METH (10 mg/kg, i.p. every 2 h × 4). Ceftriaxone (200 mg/kg), ß-lactam antibiotic known to upregulate glial glutamate transporter 1 (GLT-1), was injected i.p. for 2 days. Despite evidence of the high prevalence of ethanol and METH co-abuse, less is known about their sequential exposure on the tissue content of neurotransmitters in the striatum and hippocampus. Therefore, we investigated the effect of repeated high-dose METH exposure on the tissue IV content of several neurotransmitters such as glutamate, dopamine and serotonin in the striatum and the hippocampus in rats exposed to ethanol. Both ethanol and METH exposure, compared to ethanol alone, increased glutamate tissue content in the striatum but not in the hippocampus. Interestingly, we showed that sequential exposure of ethanol and METH caused a reduction of dopamine tissue content in the striatum and in the hippocampus when compared to the water-meth-cef group with the water-saline group. Also, METH or sequential ethanol and METH exposure caused depletion of serotonin tissue content in both the striatum and hippocampus. Ceftriaxone normalized the tissue content of glutamate in the WMC group as compared to the WS group, but not in the ethanol group. Also, ceftriaxone did not show any effects on the level of serotonin and dopamine content among all groups in the striatum and the hippocampus. To address the issue of co-abuse of ethanol and other drugs of abuse, new therapeutic drugs for drug dependence are needed. However, designing CNS drugs has been found to be one of the most challenging areas in the drug discovery field. Because the blood-brain barrier, which is made up of endothelial cells, separates blood from interstitial fluid, many neurotherapeutic agents are not delivered to the brain. It has been shown that around 98% of small molecules and almost all large molecules do not cross the blood-brain barrier (Pardridge 1998, Pardridge 2005). It was also found that MS-153 is a GLT-1 activator, hindering the depolarization- and ischemia-induced efflux of glutamate, in the hippocampal region. Since MS-153 was found to have an impact on glutamate neurotransmission, it is believed that it modulates the rewarding effects of morphine, methamphetamine, and cocaine in mice (Nakagawa, Fujio et al. 2005). Sari's lab further studied the effect of MS- 153 on chronic ethanol consumption and the expression of GLT-1 and xCT. Importantly, V MS-153, 50 mg/kg, i.p. injected in P rats showed a reduction in ethanol consumption over 14 days. Also, it was proved to elevate GLT-1 expression in various brain regions (Alhaddad, Das et al. 2014, Aal-Aaboda, Alhaddad et al. 2015). These observations led us to suggest that MS-153 is a lead drug for the syntheses of analogs that might upregulate GLT-1 expression. Heterocycle pyrazolines were synthesized with varying substituents. Each substituent has different properties than the original methyl group. The ester and the amide group can provide hydrogen bonding opportunities while the nitrile and the trifluoromethyl are lipophilic groups. The scheme used for the synthesis of MS-153 analogs was selected because it is simple, efficient, and cost-effective compare to other syntheses. Astrocytes, which are highly variable in their morphology and function, are the main type of brain neuroglia. These cells regulate more than 90% of extracellular glutamate via a major the glutamate transporter, GLT-1. Therefore, we hypothesized that modifications of the MS-153 pharmacophore through substitution of the methyl group with substituents of varying hydrogen bonding character and hydrophobicity will lead to a potent upregulator of GLT-1. Subsequently, these analogs may exhibit different activities in primary cell culture as compared to MS-153. Thus, in vitro assays of MS-153 analogs using primary rat astrocyte culture were used to measure GLT-1 expression. MS-153 did not upregulate GLT-1 activity at different time points. The only drug that upregulated GLT-1 expression at all days was analog 20. Also, even though analog 19 was not effective on day 2, it upregulated GLT-1 expression on day 4 and day 6. GLT-1 expression was upregulated significantly on day 2 and 4 with analog 25. Additionally, the benzoyl and nicotinoyl groups were found to be critical for GLT-1 upregulation by these analogs.
Amanda Bryant-Friedrich (Committee Co-Chair)
Youssef Sari (Committee Co-Chair)
Peter Andreana (Committee Member)
Zahoor Shah (Committee Member)
James Slama (Committee Member)
363 p.

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Citations

  • Almalki , A. H. (2017). Synthesis and Design of MS-153 Analogues as Potential Drugs for Treatment of Alcohol and Methamphetamine Co-abuse [Doctoral dissertation, University of Toledo]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1497905762044506

    APA Style (7th edition)

  • Almalki , Atiah. Synthesis and Design of MS-153 Analogues as Potential Drugs for Treatment of Alcohol and Methamphetamine Co-abuse. 2017. University of Toledo, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=toledo1497905762044506.

    MLA Style (8th edition)

  • Almalki , Atiah. "Synthesis and Design of MS-153 Analogues as Potential Drugs for Treatment of Alcohol and Methamphetamine Co-abuse." Doctoral dissertation, University of Toledo, 2017. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1497905762044506

    Chicago Manual of Style (17th edition)