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Study Guide: 5-Aminolevulinic Acid: Biochemistry, Applications, and Properties

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5-Aminolevulinic Acid: Biochemistry, Applications, and Properties Study Guide

Biochemical Properties and Identification

The IUPAC name for Aminolevulinic acid is 5-Amino-4-oxo-pentanoic acid.

Answer: True

Explanation: The provided chemical nomenclature confirms that the IUPAC name for Aminolevulinic acid is indeed 5-Amino-4-oxo-pentanoic acid.

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Aminolevulinic acid has a chemical formula of C5H9NO3 and a molar mass of approximately 131.131 grams per mole.

Answer: True

Explanation: The chemical formula C5H9NO3 and a molar mass of approximately 131.131 g/mol are correctly attributed to Aminolevulinic acid.

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Aminolevulinic acid melts at a temperature significantly below the freezing point of water.

Answer: False

Explanation: Aminolevulinic acid has a melting point of 118 degrees Celsius (244 degrees Fahrenheit), which is substantially above the freezing point of water (0 degrees Celsius).

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The SMILES string O=C(CN)CCC(=O)O represents the chemical structure of delta-Aminolevulinic acid.

Answer: True

Explanation: The provided SMILES string, O=C(CN)CCC(=O)O, accurately represents the chemical structure of 5-aminolevulinic acid.

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What is the correct IUPAC name for Aminolevulinic acid according to the provided text?

Answer: 5-Amino-4-oxo-pentanoic acid

Explanation: The provided text explicitly states that the IUPAC name for Aminolevulinic acid is 5-Amino-4-oxo-pentanoic acid.

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What is the chemical formula for Aminolevulinic acid?

Answer: C5H9NO3

Explanation: The chemical formula for Aminolevulinic acid is C5H9NO3, as stated in the source material.

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According to the source, what is the melting point of Aminolevulinic acid?

Answer: 118 degrees Celsius (244 degrees Fahrenheit)

Explanation: The source specifies that Aminolevulinic acid has a melting point of 118 degrees Celsius, which is equivalent to 244 degrees Fahrenheit.

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What is the significance of the CAS Registry Number 106-60-5?

Answer: It is the CAS Registry Number for Aminolevulinic acid.

Explanation: The CAS Registry Number 106-60-5 is the unique identifier assigned to Aminolevulinic acid within the Chemical Abstracts Service database.

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The SMILES string O=C(CN)CCC(=O)O is a representation of which molecule?

Answer: 5-aminolevulinic acid

Explanation: The Simplified Molecular Input Line Entry System (SMILES) string O=C(CN)CCC(=O)O precisely represents the chemical structure of 5-aminolevulinic acid.

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Biosynthesis Pathways

In animals and certain bacteria, Aminolevulinic acid is synthesized via the Shemin pathway using glycine and succinyl-CoA.

Answer: True

Explanation: The Shemin pathway, utilized by animals and certain bacteria, indeed synthesizes Aminolevulinic acid from glycine and succinyl-CoA.

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The C5 or Beale pathway for Aminolevulinic acid synthesis occurs in mitochondria and uses glycine as a starting material.

Answer: False

Explanation: The C5 or Beale pathway occurs primarily within plastids (like chloroplasts) in plants and algae, and it utilizes glutamic acid as the starting material, not glycine. The Shemin pathway uses glycine and occurs in mitochondria.

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In most plastid-containing species, the C5 pathway for Aminolevulinic acid synthesis takes place within the chloroplasts.

Answer: True

Explanation: In species possessing plastids, the C5 pathway for Aminolevulinic acid synthesis is localized within these organelles, specifically the chloroplasts.

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The Shemin pathway for Aminolevulinic acid synthesis occurs in which type of organism and uses which substrates?

Answer: Animals; uses glycine and succinyl-CoA.

Explanation: The Shemin pathway for Aminolevulinic acid biosynthesis is characteristic of animals and certain bacteria, where it utilizes glycine and succinyl-CoA as substrates.

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In plants, algae, and most bacteria, Aminolevulinic acid is synthesized via the C5 (Beale) pathway, which starts with which amino acid?

Answer: Glutamic acid

Explanation: The C5 (Beale) pathway, employed by plants, algae, and most bacteria for Aminolevulinic acid synthesis, initiates with the amino acid glutamic acid.

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Where does the C5 (Beale) pathway for Aminolevulinic acid synthesis primarily occur in species containing plastids?

Answer: Plastids

Explanation: In species containing plastids, the C5 (Beale) pathway for Aminolevulinic acid synthesis predominantly takes place within these organelles, such as chloroplasts.

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Which enzyme is responsible for the initial step in the Shemin pathway of Aminolevulinic acid biosynthesis?

Answer: ALA synthase

Explanation: ALA synthase is the key enzyme that catalyzes the initial condensation reaction between glycine and succinyl-CoA in the Shemin pathway, producing Aminolevulinic acid.

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Biological Roles and Metabolism

Delta-Aminolevulinic acid is a proteinogenic amino acid essential for building proteins in humans.

Answer: False

Explanation: The source identifies delta-Aminolevulinic acid as a non-proteinogenic amino acid, meaning it is not one of the standard amino acids incorporated into proteins during translation.

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The primary role of delta-Aminolevulinic acid in mammals is as the initial compound in the pathway for synthesizing chlorophyll.

Answer: False

Explanation: While delta-Aminolevulinic acid is the initial compound in the pathway for synthesizing chlorophyll in plants, its primary role in mammals is as the precursor for heme synthesis.

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Heme, derived from Aminolevulinic acid, plays a role in enhancing mitochondrial activity and ATP production.

Answer: True

Explanation: Heme, synthesized via the pathway initiated by Aminolevulinic acid, is integral to mitochondrial function, enhancing processes like the Krebs cycle and electron transport chain to facilitate ATP production.

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Heme Oxygenase-1 (HO-1) is involved in breaking down excess heme into biliverdin, which acts as an antioxidant.

Answer: True

Explanation: The enzyme Heme Oxygenase-1 (HO-1) catalyzes the degradation of excess heme into biliverdin, a compound recognized for its antioxidant properties.

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In plants, the rate of chlorophyll synthesis is primarily regulated by the production rate of Aminolevulinic acid.

Answer: True

Explanation: The production rate of 5-aminolevulinic acid (5-ALA) is indeed the primary regulatory factor controlling the rate of chlorophyll synthesis in plants.

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Aminolevulinic acid is considered a standard amino acid found in proteins synthesized during translation.

Answer: False

Explanation: Aminolevulinic acid is classified as a non-proteinogenic amino acid, meaning it is not one of the standard amino acids incorporated into proteins during ribosomal translation.

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In the porphyrin synthesis pathway, Aminolevulinic acid is formed as an intermediate product after heme is synthesized.

Answer: False

Explanation: Aminolevulinic acid is the *initial* compound formed in the porphyrin synthesis pathway; it precedes the synthesis of heme.

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What is delta-Aminolevulinic acid (dALA) primarily known as in biological pathways?

Answer: The initial compound in the porphyrin synthesis pathway.

Explanation: Delta-Aminolevulinic acid (dALA) is recognized as the critical initial compound in the porphyrin synthesis pathway, which is fundamental for the production of heme and chlorophyll.

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What is the role of heme, which is synthesized using Aminolevulinic acid as a precursor, in cellular energy production?

Answer: It enhances mitochondrial activity, including the Krebs cycle and electron transport chain, to produce ATP.

Explanation: Heme plays a vital role in cellular energy production by augmenting mitochondrial activity, specifically enhancing the efficiency of the Krebs cycle and the electron transport chain for ATP generation.

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What is the function of Heme Oxygenase-1 (HO-1) in the context of heme metabolism?

Answer: Catalyzes the conversion of excess heme into biliverdin and ferrous ions.

Explanation: Heme Oxygenase-1 (HO-1) functions to catabolize excess heme, breaking it down into biliverdin and ferrous ions, playing a role in heme homeostasis and antioxidant defense.

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How does the rate of Aminolevulinic acid production influence chlorophyll synthesis in plants?

Answer: The rate of chlorophyll synthesis is primarily controlled by the production rate of 5-ALA.

Explanation: In plants, the rate of chlorophyll synthesis is principally regulated by the endogenous production rate of 5-aminolevulinic acid (5-ALA).

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What does the term 'non-proteinogenic amino acid' signify regarding Aminolevulinic acid?

Answer: It is not one of the standard amino acids used in protein synthesis.

Explanation: The designation 'non-proteinogenic amino acid' indicates that Aminolevulinic acid is not among the 20 standard amino acids that are directly incorporated into proteins during the process of translation.

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Biliverdin, a breakdown product of excess heme involving HO-1, is noted in the source for its role as:

Answer: An important antioxidant.

Explanation: Biliverdin, produced from heme degradation via HO-1, is recognized for its significant role as an antioxidant within biological systems.

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Medical Applications: Photodynamic Therapy and Surgery

The primary medical use of Aminolevulinic acid mentioned is for treating bacterial infections.

Answer: False

Explanation: The primary medical application described for Aminolevulinic acid is related to the photodynamic detection and surgery of cancer, not the treatment of bacterial infections.

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Aminolevulinic acid functions as a direct photosensitizer molecule in photodynamic therapy.

Answer: False

Explanation: Aminolevulinic acid functions as a *precursor* to a photosensitizer molecule. It is converted intracellularly into protoporphyrin IX (PpIX), which then acts as the photosensitizer.

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Photodynamic detection utilizes Aminolevulinic acid's fluorescence under specific light to help visualize cancerous tissues.

Answer: True

Explanation: The text confirms that photodynamic detection leverages the fluorescence of Aminolevulinic acid (or its metabolites) under specific light conditions to aid in the visualization of cancerous tissues.

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Aminolevulinic acid is approved for visualizing malignant glioma tissue in adults during surgery.

Answer: True

Explanation: The source material states that Aminolevulinic acid is approved for visualizing malignant glioma tissue in adult patients during surgical procedures.

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Intraoperative use of Aminolevulinic acid in glioma surgery has been shown to potentially increase residual tumor volume.

Answer: False

Explanation: The intraoperative use of Aminolevulinic acid in glioma surgery has been demonstrated to potentially *decrease* the volume of residual tumor and improve progression-free survival, not increase it.

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The US FDA approved aminolevulinic acid hydrochloride for glioma surgery visualization in the year 2007.

Answer: False

Explanation: The US FDA approved aminolevulinic acid hydrochloride for visualizing malignant glioma tissue during surgery in the year 2017, not 2007.

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Aminolevulinic acid facilitates intra-operative cancer delineation because it is metabolized into protoporphyrin IX (PpIX), which fluoresces under specific light.

Answer: True

Explanation: The mechanism described is accurate: Aminolevulinic acid is converted to fluorescent protoporphyrin IX (PpIX) within cancer cells, enabling surgeons to visualize these tissues under specific illumination.

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Fluorescence-guided surgery using Aminolevulinic acid has only shown success in brain gliomas.

Answer: False

Explanation: The source indicates that fluorescence-guided surgery using Aminolevulinic acid has demonstrated success in various cancer types, including brain gliomas, bladder cancer, and oral squamous cell carcinoma, not exclusively brain gliomas.

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Protoporphyrin IX accumulates in cancer cells treated with Aminolevulinic acid because these cells have an overactive ferrochelatase enzyme.

Answer: False

Explanation: Protoporphyrin IX accumulates in cancer cells treated with Aminolevulinic acid because these cells typically exhibit *reduced or absent* activity of the ferrochelatase enzyme, which is responsible for incorporating iron into PpIX to form heme.

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The accumulation of protoporphyrin IX in cancer cells, induced by Aminolevulinic acid, makes them more susceptible to photodynamic therapy due to its cytotoxic effects upon light activation.

Answer: True

Explanation: The preferential accumulation of protoporphyrin IX in cancer cells, induced by Aminolevulinic acid, enhances their susceptibility to photodynamic therapy due to PpIX's ability to generate cytotoxic reactive oxygen species when activated by light.

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What is the primary medical application of Aminolevulinic acid described in the text?

Answer: Photodynamic detection and surgery of cancer.

Explanation: The primary medical application detailed for Aminolevulinic acid pertains to its use in the photodynamic detection and surgical treatment of cancer.

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How does Aminolevulinic acid contribute to photodynamic therapy (PDT)?

Answer: It acts as a precursor to a photosensitizer molecule.

Explanation: Aminolevulinic acid serves as a precursor that is converted intracellularly into protoporphyrin IX, which then functions as the photosensitizer in photodynamic therapy.

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In which specific type of cancer is Aminolevulinic acid indicated for visualizing malignant tissue during surgery in adults?

Answer: Malignant glioma

Explanation: Aminolevulinic acid is specifically indicated for adults to visualize malignant tissue during surgery for malignant glioma.

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What benefit has been observed from the intraoperative use of Aminolevulinic acid in malignant glioma treatment?

Answer: Reduced volume of residual tumor and extended progression-free survival.

Explanation: Studies indicate that the intraoperative application of Aminolevulinic acid in malignant glioma treatment can lead to a reduction in residual tumor volume and an extension of progression-free survival.

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The US FDA approved aminolevulinic acid hydrochloride for use in glioma surgery in which year?

Answer: 2017

Explanation: The U.S. Food and Drug Administration (FDA) approved aminolevulinic acid hydrochloride for the visualization of malignant glioma tissue during surgery in the year 2017.

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How does Aminolevulinic acid enable surgeons to better delineate malignant tissues during surgery?

Answer: By being metabolized into fluorescent protoporphyrin IX (PpIX) within cancer cells.

Explanation: Aminolevulinic acid is converted into protoporphyrin IX (PpIX) within cancer cells. This PpIX exhibits fluorescence under specific light wavelengths, thereby allowing surgeons to precisely identify and delineate malignant tissues.

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Which of the following is NOT mentioned as a type of cancer where fluorescence-guided surgery using Aminolevulinic acid has shown success?

Answer: Pancreatic cancer

Explanation: The source lists brain and spine gliomas, bladder cancer, and oral squamous cell carcinoma as examples where fluorescence-guided surgery with Aminolevulinic acid has been successful. Pancreatic cancer is not mentioned in this context.

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Why does protoporphyrin IX (PpIX) tend to accumulate in cancer cells treated with Aminolevulinic acid?

Answer: Cancer cells have reduced or absent activity of the enzyme ferrochelatase.

Explanation: The accumulation of protoporphyrin IX in cancer cells treated with Aminolevulinic acid is primarily due to the reduced or absent activity of the ferrochelatase enzyme within these cells, which normally converts PpIX into heme.

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What is the role of protoporphyrin IX (PpIX) in fluorescence-guided surgery after Aminolevulinic acid administration?

Answer: It fluoresces under specific light, enabling visualization of malignant tissues.

Explanation: Following administration of Aminolevulinic acid, its metabolite protoporphyrin IX (PpIX) accumulates in malignant tissues and exhibits fluorescence under specific light wavelengths, thereby facilitating surgical visualization.

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Pharmaceutical Aspects

Aminolevulinic acid is marketed under trade names such as Levulan and Ameluz.

Answer: True

Explanation: The provided information indicates that Aminolevulinic acid is available commercially under trade names including Levulan and Ameluz.

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Aminolevulinic acid can only be administered topically for medical treatments.

Answer: False

Explanation: The source indicates that Aminolevulinic acid can be administered topically or taken orally, not exclusively topically.

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In Canada and the United States, Aminolevulinic acid is available over-the-counter without a prescription.

Answer: False

Explanation: Aminolevulinic acid is classified as prescription-only (Rx-only) in Canada and the United States, not available over-the-counter.

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Common side effects of Aminolevulinic acid include improved vision and reduced fatigue.

Answer: False

Explanation: The potential side effects listed in the source material are adverse effects such as liver damage, nerve problems, and hyperthermia, not improved vision or reduced fatigue.

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Which of the following is NOT listed as a trade name for Aminolevulinic acid?

Answer: HemeMax

Explanation: Based on the provided information, Levulan, NatuALA, and Ameluz are identified as trade names for Aminolevulinic acid. HemeMax is not listed among them.

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Which routes of administration are mentioned for Aminolevulinic acid?

Answer: Topical and oral.

Explanation: The provided information indicates that Aminolevulinic acid can be administered topically or taken orally.

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What is the legal status of Aminolevulinic acid in the European Union?

Answer: Prescription-only (Rx-only).

Explanation: Aminolevulinic acid is classified as prescription-only (Rx-only) in the European Union, as well as in Canada and the United States.

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Potential side effects associated with Aminolevulinic acid administration include all of the following EXCEPT:

Answer: Improved cognitive function

Explanation: The documented potential side effects include liver damage, nerve problems, and hyperthermia. Improved cognitive function is not listed as a side effect.

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Applications in Plant Science

Feeding external Aminolevulinic acid to plants typically results in improved chlorophyll production without any negative effects.

Answer: False

Explanation: While controlled low doses can be beneficial, providing excessive external Aminolevulinic acid to plants can lead to the accumulation of toxic intermediates, such as protochlorophyllide, potentially causing negative effects.

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Spraying plants with controlled, low doses of Aminolevulinic acid can help protect them from stress and promote growth.

Answer: True

Explanation: The application of Aminolevulinic acid at controlled, low concentrations (e.g., up to 150 mg/L) has been observed to confer stress resistance and promote growth in plants.

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What is a potential negative consequence if plants are given external Aminolevulinic acid?

Answer: They can accumulate toxic levels of protochlorophyllide.

Explanation: Exogenous application of Aminolevulinic acid to plants can lead to the accumulation of protochlorophyllide, a chlorophyll precursor, potentially causing phytotoxicity if the downstream pathway cannot process it efficiently.

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Controlled spraying of Aminolevulinic acid on plants at low doses (up to 150 mg/L) is suggested to have what effect?

Answer: Protect plants from stress and promote growth.

Explanation: Application of Aminolevulinic acid at controlled low concentrations has been shown to enhance plant resilience against stress factors and stimulate growth.

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