Organic Chemicals Commons^™

Synthesis Of Novel Long Chain Unsaturated Fatty Acid Analogs Of Capsaicin, Eli Bettiga

Honors Theses

A number of key studies have shown that the natural product capsaicin displays in vitro and in vivo antitumor effects against a variety of cancers, however, both the analgesic and cancer-related therapeutic potential of capsaicin have been limited by its unpleasant pungent side effects and modest potency. N-acyl vanillylamides (N-AVAMs) are a unique class of compounds that are simple side chain modified capsaicin derivatives. Limited structure-activity relationship (SAR) studies of N-AVAMs demonstrated that substitution of the capsaicin side-chain with longer unsaturated fatty acid groups results in non-pungent analogs with improved anti-invasive activity relative to capsaicin. In an effort to ultimately ...

Biological Activity And Solubility Of 5-Methoxy-1,4-Benzoquinone Having Bromoheptyl And Bromodecyl Substituents In The N-Octanol/Water System, Siti Mariyah Ulfa, Fath Dwisari, Laras Pangesti, Mohammad Farid Rahman

Makara Journal of Science

The biological activity and solubility of compounds are influenced by its chemical structure. These properties can be improved by substituting alkyl, alkoxy, and/or haloalkane in the parent skeleton. In this research, the synthesis of 3-(7-bromoheptyl)-2-methyl-5-methoxy-1,4-benzoquinone (3a) and 3-(10-bromodecyl)-2-methyl-5-methoxy-1,4-benzoquinone (3b) was achieved through the decarboxylation reaction. The solubility and biological activity of 3a and 3b were compared with that of thymoquinone (TQ), which acts as an anti-inflammatory agent. Compounds 3a and 3b were successfully synthesized and analyzed using Fourier Transform Infra-Red (FTIR) and Nuclear Magnetic Resonance (NMR). The FTIR spectrum showed the increasing intensity ...

Synthesis Of 1-(4-Ethoxy-3-Methoxybenzyl)-1,10-Phenanthrolin-1-Ium Bromide And Its Evaluation As Antiplasmodium Through Heme Polymerization Inhibitory Activity (Hpia) Assay, Dhina Fitriastuti, Viny Alfiyah, Mustofa Mustofa, Jumina Jumina, Muhammad Idham Darussalam Mardjan

Makara Journal of Science

This study describes the development of N-benzyl-1,10-phenantrolinium salt as an antiplasmodium agent. The salt, that is, 1-(4-ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide, was prepared using vanillin as the starting material in four simple synthetic steps. First, the alkylation of vanillin using diethyl sulfate produced 4-ethoxy-3-methoxybenzaldehyde in 79% yield. Second, the reduction of the protected vanillin by NaBH₄ through the grinding method allowed us to obtain 4-ethoxy-3-methoxybenzyl alcohol in 96% yield. Next, the bromination of the benzyl alcohol under solvent-free condition led to the formation of the corresponding benzyl bromide, which in turn underwent bimolecular nucleophilic substitution with 1 ...

Lowering The Cost And Raising The Efficiency Of A Cure To Chagas Disease, Madeleine Peters

Arkansas Women in STEM Conference

Chagas disease, classified as a neglected tropical disease (NTD), is caused by the parasite Trypanosoma cruzi and is an underfunded and under researched disease. The only FDA-approved drug in the United States is benznidazole which is expensive, harmful, and only effective in the illness’ acute phase. The goal is to create a more effective, lower costing and less harmful drug by using a condensation reaction to substitute different amines to diethyl squarate (DES) to make cycloalkylsquaramides. Both DES and the amines used are relatively low in price with a simple, efficient, and high yielding synthesis. Low synthetic cost and ability ...

The Inhibition Of Growth Of S. Cerevisiae, U. Maydis, And M. Lychinidis-Dioicae By Apiaecea Plant Extracts, Jackson M Hoffman, Jared Scott, David Schultz Phd

Undergraduate Arts and Research Showcase

The Apiaceae family of plants contains over 3,500 species, many of which are used as food crops: vegetables (carrot, parsnip, celery, etc.), herbs (cilantro, fennel, dill, etc.), and spices (cumin, anise, caraway, etc.). Many spices have been shown to exhibit antimicrobial properties against both bacteria and fungi. We set out to determine if the Apiaceae spice extracts currently used in our lab for anticancer studies exhibit any antimicrobial properties. Ethanolic extracts were made from several Apiaceae seeds: Apium graveolens (celery), Cuminum cyminum (cumin), Anethum graveolens(dill), Foeniculum vulgare (fennel), Coriandrum satvium (coriander), Pimpinella ansium (anise), Trachyspermum ammi (ajwain), Carum ...

Imaging The Tumor Microenvironment Using 1,2-Dioxetane Chemiluminescence Agents, Lucas Ryan

Chemistry Theses and Dissertations

As complex organisms, animals and humans rely on a delicate interplay between many connected systems to maintain proper cellular and whole-body function. Oxygen regulation and homeostasis are vital for proper function in healthy cells, as are core components of aerobic metabolism and efficient ATP generation to supply our energy needs. Maintaining pH homeostasis is also of primary importance; cells maintain pH homeostasis through a host of active and passive transporters to maintain pH balance both inside and outside of the cell.

Events of uncontrolled cellular proliferation, also known as cancer, survive and thrive under conditions that perturb the delicate balance ...

Antibacterial Efficacy Of Novel Eastern Medicine-Inspired Toothpastes Compared To Commercial Formulations, Joshua S. Goldfaden

Pacific Journal of Health

Toothpaste is an oral health care agent that dates back to the 5^th Century B.C. in East Asia. Following the conception of dentistry in the 7^th Century B.C. and the field’s subsequent growth, the embodiment of toothpaste has evolved from containing natural substances such as tea leaves to abrasive chemicals, particularly: fluoride, triclosan, and sodium lauryl sulfate (SLS). Regarding how each respective reagent functions, fluoride forms a complex with calcium ions in the teeth to prevent erosion of the protective enamel coating. This ion also disrupts metabolic activities of Streptococcus mutans (S. mutans), which are ...

Synthesis And Characterization Of Pamam-Fatty Acid “Janus-Type” Dendritic Hybrids For Biomedical Applications, Abigail Grace Barker

Honors Theses

Janus dendrimers are amphiphilic macromolecules that have shown promising potential in the biomedical field. Due to their unique structure and properties, these branched block copolymers have the ability to self-assemble into bioinspired spherical nanoaggregates. Because they possess a hydrophobic and hydrophilic moiety, these aggregates show potential as drug delivery systems that can transport both hydrophobic and hydrophilic drugs. However, many of the proposed dendrimer systems suffer from certain weaknesses that hinder their practical usage as clinical treatment options. Some of these shortcomings include specificity, solubility, size, surface charge, and mechanical properties. To combat these problems, we synthesized and characterized a ...

The Effects Of Alpha-Tocopherol And Ascorbic Acid On Metastatic Breast Cancer Cells, Scout Treadwell

Honors Theses

Breast cancer is a multifaceted, complex disease that affects hundreds of thousands of patients every year. Although there has a been a decline in the mortality rate of this disease, it is still vital to investigate and discover new possible treatments. One area of research involves the generation of reactive oxygen species (ROS) in cancer cells and the possibility of ROS-induced apoptosis. Antioxidants such as Vitamin C and Vitamin E have been shown to serve as pro-oxidants. Instead of detoxifying the cell from damaging ROS, these compounds can stimulate ROS production, triggering an apoptotic cascade in the cell. In this ...

Fluorometric Characterization Of A Methylene Blue Derivative Sensitive To Reactive Oxygen Species (Ros), Matthew Weeks

Honors Theses

Methylene blue (MB) has many uses within both microbiology and pharmacology. MB can treat disorders such as methemoglobinemia, malaria, Alzheimer’s disease, and certain forms of cancer. MB is also useful for molecular imaging due to its off-on fluorescent capabilities. MB derivatives with a urea bond at the 10-N position have been cleavable by triggers such as light. However, I was interested in sensitivity to reactive oxygen species (ROS). In this study, I wanted to determine if the MB derivative MB-EA exhibited sensitivity to ROS. MB-EA was exposed to varying concentrations of hydrogen peroxide and MB release was measured. I ...

Effects Of Nicotinamide Riboside And Beta-Hydroxybutyrate On C. Elegans Lifespan, Jeffery Peters

Undergraduate Honors Theses

The nicotinamide riboside (NR) form of vitamin B₃and the ketone body ß-hydroxybutyrate (BHB) are two of the most promising natural compounds yet identified for the treatment of aging and aging-related diseases. Forms of vitamin B₃are precursors for the synthesis of the coenzymes nicotinamide adenine dinucleotide (NAD(H)) and nicotinamide adenine dinucleotide phosphate (NADP(H)). In aged cells levels of NAD⁺decline, decreasing metabolism and decreasing activity of protective sirtuin protein deacetylases. In aged cells NR, but not more common forms of vitamin B3, boost NAD⁺levels. BHB is naturally produced by the body when individuals fast ...

Engineered Nanoparticles For Site-Specific Bioorthogonal Catalysis: Imaging And Therapy, Riddha Das

Doctoral Dissertations

Bioorthogonal catalysis offers a strategy for chemical transformations complementary to bioprocesses and has proven to be a powerful tool in biochemistry and medical sciences. Transition metal catalysts (TMCs) have emerged as a powerful tool to execute selective chemical transformations, however, lack of biocompatibility and stability limits their use in biological applications. Incorporation of TMCs into nanoparticle monolayers provides a versatile strategy for the generation of bioorthogonal nanocatalysts known as “nanozymes”. We have fabricated a family of nanozymes using gold nanoparticles (AuNPs) as scaffolds featuring diverse chemical functional groups for controlled localization of nanozymes in biological environments, providing unique strategies for ...

Case Report: An Isolated Dematologic Reaction To Isosulfan Blue Dye After Lumpectomy, Micaela Moen Md, Aaron Pinnola, M Pahlkotter

General Surgery

P 154. CASE REPORT: AN ISOLATED DERMATOLOGIC REACTION TO ISOSULFAN BLUE DYE AFTER LUMPECTOMY Presenter: Micaela Moen MD | Grand Strand Medical Center Moen MR, Pahlkotter M, Nicholson G, Pinnola A Introduction: The use of isosulfan blue dye for sentinel lymph node mapping in breast cancer is considered routine (1). An array of adverse side effects from this dye have been described in the literature (2-3). Here we describe an atypical isolated dermatologic reaction. A 79 year old female with history of hypothyroidism, GERD, hypercholesterolemia, iron deficiency anemia who was found to have infiltrating ductal carinoma after a core biopsy of ...

The Nuclear Legacy In Appalachia, Michele Morrone, Harold Perkins

Journal of Appalachian Health

Nestled in the rolling hills of Appalachia Ohio is a reminder of the role that the region played in winning the Cold War. For more than 40 years in rural Pike County, the 3,700-acre Portsmouth Gaseous Diffusion Plant (PORTS), or the “A-Plant” as the locals refer to it, enriched uranium for use in nuclear weapons. While the facility produced nuclear fuel for national security, it simultaneously exposed plant workers to chemicals and radiation and discharged pollution into the surrounding community. The A-Plant is now being demolished and the site repurposed. However, the site continues to affect the community as ...

Discovery And Analysis Of New Cocrystal Solid Forms Of The Anti-Hiv Drug: Emtricitabine, Elizabeth Keene

Honors Theses at the University of Iowa

Emtricitabine (trade name: Emtriva) is an anti-HIV prevention and treatment drug. Emtricitabine (EMT) is used along with Tenofovir to form the combination-drug, Truvada, which is extremely effective in the prevention and treatment of HIV. Emtricitabine works by inhibiting reverse transcriptase and is conventionally administered orally in a tablet. Only one solid form corresponding to the pure drug is currently known. Cocrystallization is a method of creating novel solid forms by combining two or more components. In this context, cocrystallization is a good strategy to generate new and enhanced solid forms of Emtricitabine. Through our work with Emtricitabine, we generated new ...

Silver Salt-Mediate Benzylation Of Carbohydrates Under Mildly Acidic Conditions, Nicholas Forsythe, Samira Escopy, Yashapal Singh 2436808, Alexei Demchenko

Undergraduate Research Symposium

When looking at biomolecules, carbohydrate represent a large group of macromolecules that play an important role in the body. Most importantly, carbohydrates provide an energy supply for organisms, but it is proven that they are also involved in a myriad of other processes. Furthermore, synthesizing these molecules leads to advancements in chemistry, such as drug design, and other structures such as glycolipids play important roles in the immune system. Understanding this, an efficient and reliable way to create these carbohydrates is needed.

The protection and deprotection manipulations of carbohydrates play an essential role in synthetic carbohydrate chemistry.¹ Using benzyl ...

Determining The Antibacterial Activity And Mode Of Action Of Tirandamycin, Hailey Bouchard

CMC Senior Theses

Tirandamycin is a small molecule natural product that has been isolated from various species of marine and terrestrial Streptomyces. The natural product has shown antibacterial activity against an array of Gram-positive and Gram-negative bacteria, showing promise as a pharmaceutical drug. Tirandamycin has 14 known derivatives, many of which have been created synthetically. Some of its derivatives are particularly potent against the high-risk bacteria vancomycin-resistant Enterococcus faecium, Staphylococcus aureus, Streptococcus agalactiae, Streptococcus pneumoniae and Escherichia coli. However, the antibacterial potency of these derivatives has not been tested systematically leading to the possibility of discovering more potent derivatives of the drug which ...

Correlating The Physicochemical Properties Of Magnesium Stearate With Tablet Dissolution And Lubrication, Julie L. Calahan

Theses and Dissertations--Pharmacy

Magnesium stearate (MgSt) is the most commonly used pharmaceutical excipient and is present in over half the tablet formulations on the market. In spite of its popularity as an effective lubricant, it has been repeatedly recognized that there is significant variability between MgSt samples, which can cause inconsistent lubrication between batches of MgSt. The hypothesis of this research is that the batch-to-batch variability in tablet lubrication and dissolution observed in tablet formulations containing different MgSt samples can be correlated with differences in MgSt physicochemical properties (fatty acid salt composition, crystal hydrate form, particle size and surface area). Developing correlations between ...

Organic Compound Farnesol Reduces Disease Severity And Onset In Mouse Model Of Multiple Sclerosis, Lacey B. Sell

EWU Masters Thesis Collection

No abstract provided.

Evaluating Volatile Organic Compounds For Contact-Independent Antagonism Of Pseudogymnoascus Destructans

Symposium of Student Scholars

White-nose syndrome (WNS), a disease caused by the fungus Pseudogymnoascus destructans, is responsible for the extensive mortality of bats in the United States. In an effort to develop tools to reduce bat mortality attributed to WNS, an in vitro experiment was conducted to quantify the inhibitory effects of select volatile organic compounds (VOCs) as well as explore potential synergistic activities. The experiment involved exposing mycelial plugs of P. destructans to various concentrations of B23 as well as B23 and decanal together at equimolar ratios. Measurements of the plugs were taken over the course of the 13 day experiment allowing the ...