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Targeting Tumors: Inclusion of Functional Groups on Ion-Containing Block Copolymers to Combat Cancer

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This research attempts to determine the most effective method of synthesizing a peptide such that it can be utilized as a targeting moiety for polymeric micelles. Two melanoma-associated peptides with high in vitro and in vivo binding affinity for TNF receptors have been identified and synthesized. Matrix Assisted Laser Desorption/Ionization-Time…

This research attempts to determine the most effective method of synthesizing a peptide such that it can be utilized as a targeting moiety for polymeric micelles. Two melanoma-associated peptides with high in vitro and in vivo binding affinity for TNF receptors have been identified and synthesized. Matrix Assisted Laser Desorption/Ionization-Time of Flight Mass Spectrometry (MALDI-ToF) was used to help verify the structure of both peptides, which were purified using Reversed-Phase High Performance Liquid Chromatography (RP-HPLC). The next steps in the research are to attach the peptides to a micelle and determine their impact on micelle stability.
ContributorsMoe, Anna Marguerite (Author) / Green, Matthew (Thesis director) / Jones, Anne (Committee member) / Sullivan, Millicent (Committee member) / Chemical Engineering Program (Contributor) / School of International Letters and Cultures (Contributor) / Sandra Day O'Connor College of Law (Contributor) / Barrett, The Honors College (Contributor)
Created2016-05
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COMBATING CANCER AND ALZHEIMER'S DISEASE: SYNTHESIS OF NOVEL, CHEMOTHERAPEUTIC REXINOIDS

Description

The FDA-approved drug bexarotene has been predominantly utilized for the treatment of cutaneous T-cell lymphoma (CTLC), but has shown promise as an off label treatment for various other cancers as well as Alzheimer's disease (AD). However, harmful side effects such as hypothyroidism have catalyzed a search for alternative rexinoids which…

The FDA-approved drug bexarotene has been predominantly utilized for the treatment of cutaneous T-cell lymphoma (CTLC), but has shown promise as an off label treatment for various other cancers as well as Alzheimer's disease (AD). However, harmful side effects such as hypothyroidism have catalyzed a search for alternative rexinoids which retain similar levels of RXR agonism while reducing the undesirable effects incurred by bexarotene. This honors thesis outlines the steps taken to design and synthesize novel analogues of the selective retinoid-X-receptor (RXR) agonist 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (bexarotene). Corresponding NMR spectra indicates the successful construction of four novel compounds which are structurally similar to known, biologically-evaluated rexinoids that have induced fewer side effects while stimulating greater levels of RXR selectivity as compared to bexarotene. Future In vitro analyses of these four analogues coupled with the recognized efficacy of their parent compounds demonstrate the chemotherapeutic potential of structurally modified bexarotene analogues
ContributorsDavidson, Jesse Raymond (Author) / Wagner, Carl (Thesis director) / Ball, Rebecca (Committee member) / School of Mathematical and Natural Sciences (Contributor) / Barrett, The Honors College (Contributor)
Created2016-05
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Incorporating Sustainability Into Copolymer Design

Description
Polyolefins have dominated global polymer production for the past 60 years, revolutionizing fields of medicine, construction, travel, packaging, and many more. However, with steadily increasing polyolefin production each year and traditionally long polyethylene (PE) and polypropylene degradation times, estimated on the order of 500 years or more, a massive challenge…

Polyolefins have dominated global polymer production for the past 60 years, revolutionizing fields of medicine, construction, travel, packaging, and many more. However, with steadily increasing polyolefin production each year and traditionally long polyethylene (PE) and polypropylene degradation times, estimated on the order of 500 years or more, a massive challenge arises with accumulating plastic waste. While the end-of-life of polyolefins previously manufactured must be addressed, incorporation of sustainability and circularity into future commodity plastic design at the molecular level offers an opportunity to decrease their negative effects on the environment going forward. Herein, several approaches are described which aim to address the need for polymeric materials while introducing a sustainable approach to their design, either through incorporation of biosynthesized polymers or degradable units. In the first project, polymer blends of two biodegradable polymers were studied, and compared to the same blends containing a graft copolymer compatibilizer comprised of the two homopolymer counterparts. The compatibilized blends were expected to have superior mechanical performance to the uncompatibilized blend and potentially offer industrially relevant benefits. While this was not achieved, valuable insight into the polymer blend interactions were gained. The idea of compatibilizing polymer blends was further explored with blends of PE and a cellulose derivative with the aid of a custom ABA triblock compatibilizing agent. It was discovered that the compatibilizer reinforced the polymer blend by providing mechanical strength at the cost of flexibility. To approach sustainability from a different perspective, several segmented copolymer series based on telechelic PE oligomers were then synthesized and analyzed. The segmented systems exhibited similar structure to high density PE (HDPE), retained similar mechanical and thermal properties to commercial HDPE, but contained degradable units throughout the polymer backbone. Several fundamental principles were explored through the segmented and chain-extended polyolefin architecture, including the influence of reactive linkage (amide vs. ester), random vs. alternating segment structure, and PE segment molecular weight. The effects of tailoring polymer structure on thermal, mechanical, and morphological properties are described herein. The relationships established from these experiments may further guide future polymer design and contribute toward more sustainable polyolefin manufacturing.
ContributorsArrington, Anastasia Sergeevna (Author) / Long, Timothy E. (Thesis advisor) / Jin, Kailong (Committee member) / Biegasiewicz, Kyle F. (Committee member) / Matson, John B. (Committee member) / Arizona State University (Publisher)
Created2022
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Molecular Modification of (Iso)quinolines via Earth-Abundant Catalysis

Description

Chemistry has always played a foundational role in the synthesis of pharmaceuticals. With the rapid growth of the global population, the health and medical needs have also rapidly increased. In order to provide drugs capable of mediating symptoms and curing diseases, organic chemistry provides drug derivatives utilizing a limited number…

Chemistry has always played a foundational role in the synthesis of pharmaceuticals. With the rapid growth of the global population, the health and medical needs have also rapidly increased. In order to provide drugs capable of mediating symptoms and curing diseases, organic chemistry provides drug derivatives utilizing a limited number of chemical building blocks and privileged structures. Of these limited building blocks, this project explores Late–stage C–H functionalization of (iso)quinolines using abundant metal catalysis in order to achieve site-selective molecular modification.
ContributorsPearson, Amanda (Author) / Ackerman–Biegasiewicz, Laura (Thesis director) / Biegasiewicz, Kyle (Committee member) / Gould, Ian (Committee member) / Barrett, The Honors College (Contributor) / Chemical Engineering Program (Contributor)
Created2022-05