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Related Concept Videos

Prodrugs01:30

Prodrugs

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Prodrugs are a class of pharmaceutical compounds that undergo a biotransformation process within the body to be converted into a pharmacologically active drug. Prodrugs are designed to improve the therapeutic properties of the parent drug, such as enhancing bioavailability, increasing stability, or reducing toxicity. The concept of prodrugs revolves around modifying the chemical structure of the original drug to make it more effective or convenient for administration.
Prodrugs help overcome...
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Peroxisomes01:24

Peroxisomes

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Peroxisomes are specialized organelles present in fungi, plant, and animal cells. It can vary in number, size, morphology, and activity depending on the type of tissue and the nutritional state of the cell. For example, cells with active lipid metabolism, such as adipocytes, neurons, and hepatocytes, have more peroxisomes than other cells in the body. Besides their primary role in breaking down complex organic molecules, peroxisomes can also synthesize specific macromolecules and participate in...
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Drug Metabolism: Phase I Reactions01:17

Drug Metabolism: Phase I Reactions

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A phase I reaction is a biochemical process that introduces a functionally reactive polar group to a substance. This transformation predominantly occurs in the liver, facilitated by the cytochrome P450 system of hemoproteins situated in the lipophilic endoplasmic reticulum of cells. The metabolite generated through this process can have varying polarities. If it is sufficiently polar, it can be easily excreted in the urine due to its water compatibility. However, if the metabolite is nonpolar,...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Redox Reactions01:24

Redox Reactions

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Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...
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Electron Transport Chain: Complex I and II01:46

Electron Transport Chain: Complex I and II

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The mitochondrial electron transport chain (ETC) is the main energy generation system in the eukaryotic cells. However, mitochondria also produce cytotoxic reactive oxygen species (ROS) due to the large electron flow during oxidative phosphorylation. While Complex I is one of the primary sources of superoxide radicals, ROS production by Complex II is uncommon and may only be observed in cancer cells with mutated complexes.
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Updated: Sep 5, 2025

Preparation and Characterization of Lipophilic Doxorubicin Pro-drug Micelles
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Preparation and Characterization of Lipophilic Doxorubicin Pro-drug Micelles

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Modified peroxamide-based reactive oxygen species (ROS)-responsive doxorubicin prodrugs.

Mina Jafari1, Vishnu Sriram1, Gurdat Premnauth2

  • 1Chemical Engineering Program, Department of Chemical and Environmental Engineering, University of Cincinnati, Cincinnati, OH 45221, United States.

Bioorganic Chemistry
|July 5, 2022
PubMed
Summary

Researchers developed novel doxorubicin prodrugs that are sensitive to reactive oxygen species (ROS). The OH-mOX-Dox prodrug effectively targets breast cancer cells with minimal toxicity to normal cells, showing promise for cancer therapy.

Keywords:
DoxorubicinReactive oxygen speciesStimuli-responsive prodrug

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Synthesis of Aptamer-PEI-g-PEG Modified Gold Nanoparticles Loaded with Doxorubicin for Targeted Drug Delivery
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Using In Vitro Live-cell Imaging to Explore Chemotherapeutics Delivered by Lipid-based Nanoparticles
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Area of Science:

  • Biochemistry
  • Pharmacology
  • Oncology

Background:

  • Reactive oxygen species (ROS) are crucial for intracellular signaling.
  • Elevated ROS levels in the tumor microenvironment present therapeutic opportunities.
  • ROS-responsive prodrugs offer targeted cancer treatment strategies.

Purpose of the Study:

  • To design and synthesize novel peroxamide-based ROS-responsive prodrugs of doxorubicin.
  • To evaluate the ROS sensitivity and anti-cancer efficacy of these novel prodrugs.
  • To assess the targeted delivery and reduced toxicity of the developed prodrugs.

Main Methods:

  • Synthesis of modified peroxamide-based doxorubicin prodrugs.
  • In vitro evaluation of ROS sensitivity and specificity using cancer cell lines.
  • Assessment of anti-proliferation effects on breast cancer cell lines (MDA-MB-468, MDA-MB-231) and normal breast cells (MCF-12A).
  • Investigation of cytotoxicity enhancement with l-buthionine sulfoximine (BSO) and X-ray irradiation.

Main Results:

  • The OH-mOX-Dox prodrug demonstrated stable and highly specific ROS sensitivity.
  • OH-mOX-Dox exhibited potent anti-proliferation activity against MDA-MB-468 and MDA-MB-231 cells.
  • Minimal toxicity was observed in the normal breast cell line MCF-12A.
  • Cytotoxicity was significantly enhanced by elevated ROS levels induced by BSO and X-ray irradiation.

Conclusions:

  • Novel peroxamide-based doxorubicin prodrugs with specific ROS-responsiveness were successfully developed.
  • The OH-mOX-Dox prodrug shows significant potential for targeted breast cancer therapy.
  • Combined treatment strategies involving ROS induction can enhance the efficacy of OH-mOX-Dox.