Synthesis of a Novel Water-soluble Porphyrin Derivative for Use as a Potential Phototherapeutic Cancer Treatment PDF Download
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Author: Joseph Earl Bradshaw
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Languages : en
Pages :
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Photodynamic therapy (PDT) agents are light-activated materials used for localized disease treatment. Porphyrins are classic representations of photosensitive agents. Identified by their large, planar molecular structure, porphyrins are centrally composed of four pyrrole rings. Through this project, the starting material, H2TPPC, a tetra-carboxylic acid porphyrin, was first synthesized and later modified through the addition of the amine, morpholin-2-ylmethanol. This multi-step synthesis resulted in the highly water-soluble porphyrin product H2TPP-MorphMeOH. Following this synthesis, the compound was purified using liquid chromatography, and then structurally identified and classified using infrared (IR), nuclear magnetic resonance (NMR), and UV-Vis spectroscopies. Lastly, to determine its utility as a potential PDT agent, the cytotoxicity of H2TPP-MorphMeOH was determined using an MTT assay on MDA-MB-231 triple negative breast cancer cells comparing exposure and absence of white light.
Author: Joseph Earl Bradshaw
Publisher:
ISBN:
Category :
Languages : en
Pages :
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Book Description
Photodynamic therapy (PDT) agents are light-activated materials used for localized disease treatment. Porphyrins are classic representations of photosensitive agents. Identified by their large, planar molecular structure, porphyrins are centrally composed of four pyrrole rings. Through this project, the starting material, H2TPPC, a tetra-carboxylic acid porphyrin, was first synthesized and later modified through the addition of the amine, morpholin-2-ylmethanol. This multi-step synthesis resulted in the highly water-soluble porphyrin product H2TPP-MorphMeOH. Following this synthesis, the compound was purified using liquid chromatography, and then structurally identified and classified using infrared (IR), nuclear magnetic resonance (NMR), and UV-Vis spectroscopies. Lastly, to determine its utility as a potential PDT agent, the cytotoxicity of H2TPP-MorphMeOH was determined using an MTT assay on MDA-MB-231 triple negative breast cancer cells comparing exposure and absence of white light.
Author: Catherine Shirley
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Languages : en
Pages :
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Photodynamic cancer therapy (PDT) is a type of treatment involving the use of light in conjunction with a photosensitive agent- a chemical or series of chemicals designed for activation when exposed to light. This research project investigated the synthesis and identification of the novel photosensitive agent, H2TPP-Pro-OH. To create the water-soluble porphyrin, (S)-(+)-prolinol was added to the tetra-carboxyl porphyrin, H2TPPC, to form the final H2TPP-Pro-OH product. This compound was then purified using syringe filtration and column chromatography, and subsequently characterized using infrared (IR), nuclear magnetic resonance (NMR), and UV-vis spectroscopies. Finally, the utility of the material as a PDT agent was determined by examining the cytotoxicity of the H2TPP-Pro-OH product was determined using MTT assay on MDA-MB-231 triple negative breast cancer cells comparing dark and light exposure.
Author: Kayla R. Whittington
Publisher:
ISBN:
Category : Cancer
Languages : en
Pages : 0
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Author: R. Cubeddu
Publisher: Springer Science & Business Media
ISBN: 1468447211
Category : Science
Languages : en
Pages : 442
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This book contains the contributions of the participants to the International Symposium on Porphyrins in Tumor Phototherapy held in Bruzzano (Milano), Italy on May 26-28, 1983. The contributions are written as extended papers to provide a broad and representative coverage of the use of porphyrins in tumor phototherapy and diagnosis. In the last few years, this technique has received increasing interest for its potential applications in clinical oncology. In fact, 1,500 patients have been already treated by this therapy which has been tested in more than 100 clinical centres. Among the reported cases, a significant therapeutic effectiveness was found in some early stage cancers of lung, esophagus and stomach. The development of ·this therapy requires interdisciplinary studies from such diverse fields as physics, chemistry, biology, pharmacology, and experimental and clinical oncology. The contents of the book reflect the character of this research and deal with all the problems, from fundamental to clinical, that still require to be analysed and understood for a better evaluation 'of the potential of this therapy. The first chapter of the book deals with photophysics ?;nd.
Author: Catherine Shirley
Publisher:
ISBN:
Category : Cancer
Languages : en
Pages : 58
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Author: Katriann Arja
Publisher: Linköping University Electronic Press
ISBN: 9176852555
Category :
Languages : en
Pages : 105
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Organic compounds that interact both with certain biological targets and display specific photophysical properties can be utilized as molecular tools to visualize and possibly effect disease related processes taking place in living organisms. In this regard, porphyrins are a class of naturally occurring molecules that possess intriguingly interesting photophysical properties where they can act as luminescent probes by emitting detectable light, as well as photosensitizers in the light mediated therapy called photodynamic therapy. In this thesis, the porphyrin structure has been synthetically combined with other molecule classes to achieve compounds with desirable multimodal characteristics. Firstly, luminescent conjugated oligothiophenes (LCOs) that have extensively, and with great success, been utilized as fluorescent ligands for amyloid formations, have been conjugated to porphyrins to render oligothiophene porphyrin hybrids (OTPHs) comprising two optically active modalities. When applied as fluorescent amyloidophilic dyes for visualization of amyloid-? (A?), one of the pathological hallmarks in Alzheimer’s disease, an enhanced optical assignment of distinct aggregated forms of A? was afforded. Thus, properly functionalized OTPHs could give us more information about pathological processes underlying devastating disorders, such as Alzheimer’s disease. In addition, the OTPHs can be associated with synthetic peptides inducing peptide folding into certain three-dimensional helical structures giving rise to novel optically active materials. Secondly, this thesis also embraces porphyrins’ potential as photosensitizers in photodynamic therapy to kill cancer cells. Grounded on the prerequisites for an optimal photosensitizer, we designed porphyrin-based conjugates equipped with common carbohydrates for improved cancer cell selectivity and with a fluorinated glucose derivative, 2-fluoro 2-deoxy glucose, for advantageous metabolism in cancer cells. Furthermore, incorporation of a radioisotopic fluorine-18 atom into the glycoporphyrins could give the means for diagnostic use of the conjugates in positron emission tomography (PET). In order to tether together the above-mentioned molecular moieties in a controlled fashion, we developed a robust synthetic strategy for asymmetrical functionalization of porphyrin core. The method involves chlorosulfonation of this otherwise inert tetrapyrrolic structure, followed by alkynylation. Parallelly to amide coupling reactions, copper(I)-catalyzed alkyne azide cycloaddition is used for fast and high-yielding late-stage conjugations. Overall, this thesis demonstrates how combining different molecular moieties in synthetic organic chemistry yields novel molecules with combined and improved multimodal properties for biological and medicinal applications, guided by the design-by-function methodology.
Author:
Publisher:
ISBN:
Category :
Languages : en
Pages : 40
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Author: Francesca Bryden
Publisher:
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Category :
Languages : en
Pages :
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Author:
Publisher:
ISBN:
Category :
Languages : en
Pages : 41
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Water-soluble core-modified porphyrins have been designed as photosensitizers for the use in Photodynamic Therapy, a cancer treatment regime introduced over 100 years ago. These photosensitizers are recognized by the substitution in the porphyrin chromophore with different chalcogens, providing longer wavelengths. Substitutions at the meso - positions of the chromophore, however, have shown to correlate to the solubility of the molecule. Dicarboxylic and monocarboxylic acid derivatives have been reported as potent photosensitizers, where the dicarboxylic acid has been furthered investigated with varying substituents located at the other meso - positions. These studies showed that the symmetrical dicarboxylic acid molecules were prone to aggregate in polar solvents, believed to lead to low cellular uptake or a false positive activity result in the tumor cells. The following chapters will discuss background work leading to the design and synthesis of unsymmetrical core-modified porphyrins as photosensitizers. The major impetus in the design of these compounds is to examine (1) whether the unsymmetrical structures would have a positive effect on the aggregation issues observed with the dicarboxylic acid derivatives, and (2) whether increasing the log P values would affect the cellular uptake significantly. The major isomer of 20(4- tert -butylphenyl)-5,10-diphenyl-15-(4-methoxy)phenyl-21,23-dithiaporphyrin was successfully isolated and identified as the cis -isomer by X-ray crystallography.
Author: Suzanne M. Moeller Quintavalla
Publisher:
ISBN:
Category :
Languages : en
Pages : 548
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