Luciferin final project

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Firefly Luciferin 1 Firefly Luciferin Kristen Brown Fundamentals of Chemistry, Southern New Hampshire University Chem 101 Final Project Doreena Patrick December, 10, 2023

Firefly Luciferin 2 Firefly Luciferin The term ‘Luciferin’ derives from the Latin word Lucifer, which translates into “Light- Bearer.” This is the perfect way to describe this bioluminescent compound that so often goes unappreciated, mostly due to the creepy crawlies the compound is often found in. Luciferins are organic compounds that vary in chemical structure, usually due to exactly who and what they are found in. Fireflies are what will be specifically referenced in regards to luciferin, since they are a favorite of mine. Firefly luciferin is a fascinating compound that can help illustrate several key concepts in chemistry, particularly in the fields of organic chemistry, biochemistry, and physical chemistry. Bioluminescence is often revered as a wonder of the world, and rightfully so. Molecular Description of Firefly Luciferin Firefly luciferin weighs 280.32 g/mol, with a density of 1.8 g/cm 3 , and a boiling point of approximately 473.8°C at 760 mmHg. Its constituent elements consist of carbon, hydrogen, nitrogen, oxygen, and sulfur. Luciferin-Luciferase produces cold light at 490 nm. In some cases, the color of luminescence is altered by an energy transfer to fluorescent protein that interacts with the luciferase (Lee et al., 2019). Firefly luciferin, like many organic compounds, contains covalent bonds. A firefly luciferin molecule includes single and double bonds, as well as aromatic systems in its benzothiazole and thiazoline rings (Shimomura, O., & Yampolsky, I. L., 2019, page 8). Bioluminescence is produced during an exothermic chemical reaction. In an exothermic reaction,

Firefly Luciferin 3 the excess energy is released to the environment. This is often in the form of heat. However, the excess energy for fireflies is light. Firefly luciferin contains polar functional groups, which includes a carboxylic acid group, contributing to its overall polarity. Solubility of luciferin differs by the specific form of the compound. With that being said, the potassium salt of firefly luciferin is soluble up to 60 mg/ml, while the sodium salt is soluble up to 100 mg/ml. The free acid form of firefly luciferin is not soluble in water, but it is soluble in methanol at 10 mg/ml and in DMSO (Dimethyl Sulfoxide) at 50 mg/ml. Potential Changes in Reaction The reactivity of firefly luciferin is specific to the enzyme luciferase. This specificity is crucial for the bioluminescent reaction to occur. If a similar compound were more or less reactive, it could potentially alter the rate or efficiency of the bioluminescent reaction. For example, some luciferin analogues produce luminescence in different wavelengths and allow for the parallel detection of different target molecules. The usage of luciferin does not change significantly in different physical states or when mixed with other compounds at different concentrations. However, the solubility of luciferin can affect its availability for the bioluminescent reaction. Changes in reaction temperature could potentially affect the rate of the bioluminescent reaction. Lower temperatures result in slower flash rates, and extreme temperatures could potentially denature the luciferase enzyme, making the reaction unsafe, too slow, or unstable. The relatively small molecular size of luciferin allows

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Firefly Luciferin 4 it to easily diffuse through biological membranes, which is crucial for its role in bioluminescence. If a similar compound had a larger molecular weight, it might not be able to diffuse as easily, which could potentially limit its range of uses. Achieving a Bioluminescent Reaction with Firefly Luciferin (C 11 H 8 N 2 O 3 S 2 ) is the light emitting compound found in fireflies. This compound is specific only to fireflies, and also a few other bugs in the same family as fireflies. To get a bioluminescent reaction, an enzyme found in the firefly, called luciferase, bonds together with the substrate (luciferin) and oxygen, creating the bioluminescent reaction humans can physically see. Luciferase acts as the catalyst or accelerator to the reaction (Shimomura, O., & Yampolsky, I. L., 2019, page 5). The chemical reaction takes place in two steps: 1. luciferin + ATP → luciferyl adenylate + PP i 2. luciferyl adenylate + O 2 → oxyluciferin + AMP + light In the above reaction steps, luciferin and ATP are the reactants, luciferase is the catalyst, and oxyluciferin, AMP, and light are the products. Bioluminescence is produced during an exothermic chemical reaction. In an exothermic reaction, the excess energy is released to the environment. This is often in the form of heat. However, the excess energy for fireflies is light. The luciferin-luciferase reaction can be classified as a redox reaction since it involves the transfer of electrons between luciferin and oxygen. Most bioluminescence is created by oxygen

Firefly Luciferin 5 reactions (Haddock, S. H., Moline, M. A., & Case, J. F., 2010, page 5). When air (oxygen) goes into the firefly’s body, it reacts with the organic compound luciferin. This causes luciferin to oxidize and form oxyluciferin, and releases energy in the process. At this point, the reaction is sped up by the enzyme known as luciferase. As a result, this transformation produces an excited state that releases a photon of light right before decaying into its ground state. Luciferase can function in two different pathways which include a bioluminescence pathway and a CoA-ligase pathway. In both pathways, luciferase initially catalyzes an adenylation reaction with MgATP. However, in the CoA-ligase pathway, CoA can displace AMP to form luciferyl CoA. This alternate reaction illustrates the versatility of the luciferase enzyme. Safety Measures Firefly luciferin is safe to handle with bare hands. There were not any known skin irritants listed in regards to this compound. Safety considerations for handling luciferase and luciferin include the avoidance of raising up dust and breathing the dust. Adequate ventilation is needed to handle the compound. Firefly luciferin are generally marked as not harmful to humans or animals otherwise. Bioluminescence in Bioengineering Bioluminescent reactions involving luciferin-luciferase are a chemiluminescent process, where chemical energy is converted into light energy. This conversion can be understood in

Firefly Luciferin 6 terms of the principles of quantum mechanics and the behavior of electrons in molecules. This reaction is an example of an enzyme-catalyzed reaction, which is a fundamental concept in biochemistry. Firefly luciferin has emerged as a pivotal tool in the field of bioengineering due to its unique properties. Luciferins require ATP (adenosine triphosphate) for light emission, which ties into the central role of ATP in energy transfer within cells. The compound is harvested specifically for this purpose, contributing to its economic value. It is used in vivo imaging, allowing for non-invasive detection of images and in molecular imaging, illustrating the principle of energy flow from chemical potential energy (in the form of ATP) to light energy. Its bioluminescent system has been extensively utilized for analyzing physiological processes, monitoring environmental conditions, diagnosing diseases, and screening potential drugs. The firefly luciferase gene, which catalyzes the oxidation of luciferin, has been widely used as a reporter in gene expression studies and for cell tracking in normal biological and pathological processes. This includes cell proliferation studies, cytotoxicity assays, and metastasis in model animals. The application of firefly luciferin is replacing animal testing with cell assays, thereby aiding the pharmaceutical industry in the discovery of new therapeutic drugs. Furthermore, the pH and metal sensitivities of firefly luciferases have been harnessed to estimate intracellular pH variations and toxic metal concentrations. Thus, firefly luciferin is not only enhancing our understanding of bioluminescent systems but also driving advancements in bioengineering and biotechnology, and are of significant economic importance due to this factor. Firefly Luciferin Significance

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Firefly Luciferin 7 In conclusion, firefly luciferin, also known as beetle luciferin, is a crucial component in the bioluminescent systems of several species, including fireflies. Firefly luciferin is a small molecule that emits light when oxidized by the enzyme luciferase. Its molecular structure consists of a benzothiazole ring fused to a thiazoline ring, with a carboxylic acid group attached to the chiral carbon atom. Firefly luciferin is widely used in bioengineering as a bioluminescent reporter for various applications, such as gene expression analysis, disease diagnosis, drug screening, and environmental monitoring. Firefly luciferin can also be modified to create new probes with different spectral properties, sensitivity, and selectivity. Therefore, firefly luciferin is not only a fascinating natural compound that is beautiful to witness in the summer, but also a versatile tool for biomedical research and innovation. References

Firefly Luciferin 8 Haddock, S. H., Moline, M. A., & Case, J. F. (2010). Bioluminescence in the sea. Annual Review of Marine Science, 2, 443-493. https://www.researchgate.net/publication/49667852_Bioluminescence_in_the_Sea Shimomura, O., & Yampolsky, I. L. (2019). Bioluminescence: Chemical Principles and Methods. World Scientific. https://worldscientific.com/doi/pdf/10.1142/9789813277113_0001 Lee, J., Müller, F., & Visser, A. J. W. G. (2019). The Sensitized Bioluminescence Mechanism of Bacterial Luciferase. Photochemistry and photobiology, 95(3), 679–704. https://pubmed.ncbi.nlm.nih.gov/30485901/ Viviani, V. R., Pelentir, G. F., & Bevilaqua, V. R. (2022). Bioluminescence color-tuning firefly luciferases: Engineering and prospects for real-time intracellular pH imaging and heavy metal biosensing. Biosensors, 12(6), 400. https://www.mdpi.com/2079-6374/12/6/400 Syed, A. J., and Anderson, J. C. (2021). Applications of bioluminescence in biotechnology and beyond. Chem. Soc. Rev. 50, 5668–5705. https://pubmed.ncbi.nlm.nih.gov/33735357/

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