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Triphenylmethanol Conjugates of Triptorelin as Cell-Penetrating Anti-Cancer Prodrugs

Journal of Biosciences and Medicines 2023年第11期11卷 208-218页

作者： jawzah al.akhl. Samiyah alhamed William Boadi Ryan Beni Department of Chemistry Tennessee State University Nashville USA

Some Triptorelin® (TRP) conjugates of triphenylmethanol derivatives (TPMs) with optimized hydrophobicity were synthesized by reacting 2-substituted methoxy benzenes with 1,3,5-trioxane, followed by the conjugation with TRP and sebacic acid to produce TRP-TPMs derivatives. Comparative antiproliferative assays between TRP-TPMs conjugates and the corresponding non-covalent physical mixtures of the TPMs derivatives and TRP were used to treat human acute lymphoblastic leukemia (CCRF-CEM), human ovarian adenocarcinoma (SK-OV-3) and mouse preadipocytes (3T3-L1) cells. TRP-TPMs conjugates at the 50 μM inhibited cell proliferation in CCRF-CEM, SK-OV-3 and 3T3-L1 cells by 21% - 37%, 24% - 73%, 37% - 56%, respectively following incubation for 72 h. These findings indicate that TRP-TPMs derivatives have the potential to enhance the biological activity of TRP.

关键词： Prodrugs Triptorelin Polyphenols Prostate Cancer Triphenylmethanol

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Triphenylmethanol Conjugates of Triptorelin as Anti-Lipid Peroxidation Prodrugs

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Open Journal of Medicinal Chemistry 2019年第3期9卷 49-62页

作者： Samiyah alhamed jawzah al.akhl. William Boadi Ryan Beni Department of Chemistry Tennessee State University Nashville TN USA

Antioxidants are substances that can prevent or slow damage to cells caused by free radicals, unstable molecules that the body produces as a reaction to environmental and other pressures. Free radicals may play a role in heart disease, cancer and other diseases. If the body cannot process and remove free radicals efficiently, oxidative stress can result. This can harm cells and body function. Free radicals are also known as reactive oxygen species (ROS). In this research, Triptorelin®(TRP) conjugates of triphenylmethanol derivatives (TPMs) were synthesized to evaluate their in vitro lipid peroxidation potency. Comparative lipid peroxidation assays between TRP-TPMs conjugates and the corresponding TPMs derivatives were measured using thiobarbituric reactive substance (TBARS) in a dose- and time-dependent manner following the Fenton’s pathway. Overall, TBARS decreased between 20% - 30% for the treated samples of synthesized conjugates compared to their respective control physical mixtures. These data suggest that TRP-TPMs derivatives can be used to improve the biological activity of TRP.

关键词： Antioxidants Prodrugs Triptorelin Polyphenols Lipid Peroxidation Triphenylmethanol

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Synthesis and Antiproliferative Activities of Triphenylmethanol Conjugates of Leuprorelin

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Open Journal of Medicinal Chemistry 2019年第2期9卷 37-47页

作者： Ryan Beni William Boadi Kaleh Karim jawzah al.akhl. Samiyah alhamed Department of Chemistry Tennessee State University Nashville TN USA

Leuprorelin®(LEP) is an FDA drug for breast cancer and prostate cancer treatment. There are several reported adverse effects such as transient hypertension, excessive salivation, and increased dysuria during treatment with LEP. In this study, the efficacy and toxicity of LEP were modified by using a drug delivery system to adjust the physicochemical properties. In this regard, Leuprorelin®conjugates of triphenylmethanol derivatives (TPMs) were synthesized as prodrugs. Comparative antiproliferative assays showed that LEP-TPMs conjugates had significantly higher antiproliferative activities than the corresponding non-covalent physical mixtures of the TPMs and LEP against human invasive ductal carcinoma (BT-549), human prostate carcinoma (PC3), human lung cancer (A549) and mouse pre-adipocytes (3T3-L1) cells.

关键词： Prodrugs Leuprorelin Polyphenols Prostate Cancer Triphenylmethanol

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Triphenylmethanol and Tris(2-(hydroxymethyl)phenol) Derivatives: Synthesis and Application as Indicators for Acid-Base Volumetric Titration

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Journal of Analytical Sciences, Methods and Instrumentation 2019年第2期9卷 13-21页

作者： Ryan Beni William Boadi jawzah al.akhl. Samiyah alhamed Tiffany Robinson Melanie Mootry Nahom Iyob Jamill Jackson Natalie Spicer Anterrial Harris Ibrahim Bamidad Renner Antwi Shania Richardson Tralynn Williams Department of Chemistry Tennessee State University Nashville TN USA Department of Chemistry Columbus State University Columbus GA USA

Polyphenols are naturally occurring compounds found largely in fruits, vegetables, cereals and beverages. Currently, there is much interest in the potential health benefits of dietary plant polyphenols as antioxidants. The effect of polyphenols on human cancer cells is most often protective and induces a reduction in the number of tumors or rate of growth. During our course of study on anticancer prodrugs, twelve triphenylmethanol and one tris(2-(hydroxymethyl) phenol derivatives were synthesized as a carrier of several drugs with optimized lipophilicity. Besides application of these compounds as a foundation for anticancer drug delivery systems, these compounds were evaluated as indicators for the acid-base volumetric titration of a standard solution of hydrochloric acid with a standard solution of sodium hydroxide. The experiments indicated a moderate-to-sharp color transition of the solutions near the neutralization point for most indicators. These indicators may have potential applications for acid-base titrations in a narrow range.

关键词： Polyphenols Triphenylmethanol Acid-Base Indicators Volumetric Titration Neutralization

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