Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.3K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
3.3K
Phase I Reactions: Reductive Reactions01:27

Phase I Reactions: Reductive Reactions

154
Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...
154
Nitrosation of Enols01:19

Nitrosation of Enols

2.4K
The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
2.4K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

3.2K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
3.2K
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

2.7K
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
2.7K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Development and Validation of a Novel and Cost-Effective RP-HPLC Method for the Separation of an Isomeric Impurity in Cariprazine Hydrochloride, an Antipsychotic Agent.

Biomedical chromatography : BMC·2026
Same author

Monitoring Molecular Interactions with Cell Membranes Using Time-Dependent Second Harmonic Generation Microscopy.

Biochemistry·2025
Same author

Influence of Temperature on Molecular Adsorption and Transport at Liposome Surfaces Studied by Molecular Dynamics Simulations and Second Harmonic Generation Spectroscopy.

The journal of physical chemistry. B·2021
Same author

Molecular Adsorption and Transport at Liposome Surfaces Studied by Molecular Dynamics Simulations and Second Harmonic Generation Spectroscopy.

The journal of physical chemistry. B·2019
Same author

Characteristics of ovarian cancer detection by a near-infrared fluorescent probe activated by human NAD(P)H: quinone oxidoreductase isozyme 1 (hNQO1).

Oncotarget·2017
Same author

Cascade Reaction-Based, Near-Infrared Multiphoton Fluorescent Probe for the Selective Detection of Cysteine.

Analytical chemistry·2017

Related Experiment Video

Updated: May 11, 2025

Synthesis of Stimuli-responsive Nanogels using Aqueous One-step Crosslinking and Co-nanopolymerization
06:26

Synthesis of Stimuli-responsive Nanogels using Aqueous One-step Crosslinking and Co-nanopolymerization

Published on: January 24, 2025

843

Redox-responsive liposomes aimed at nitroreductase for contents release.

Brajadulal Ghosh1, Robin L McCarley1

  • 1Department of Chemistry, Louisiana State University, Baton Rouge, LA, USA.

Journal of Liposome Research
|April 17, 2025
PubMed
Summary

Novel redox-sensitive liposomes failed to release drugs due to azo bond formation. However, adding a nitro-containing organic group enabled 45% drug release, suggesting a modified approach for targeted cancer therapy.

Keywords:
DOPEN-DOPEStimuli responsiveazoazoxy

More Related Videos

A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles
09:57

A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

Published on: December 23, 2016

8.8K
Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds
08:23

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

Published on: February 16, 2022

3.7K

Related Experiment Videos

Last Updated: May 11, 2025

Synthesis of Stimuli-responsive Nanogels using Aqueous One-step Crosslinking and Co-nanopolymerization
06:26

Synthesis of Stimuli-responsive Nanogels using Aqueous One-step Crosslinking and Co-nanopolymerization

Published on: January 24, 2025

843
A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles
09:57

A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

Published on: December 23, 2016

8.8K
Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds
08:23

Chemiluminescence-based Assays for Detection of Nitric Oxide and its Derivatives from Autoxidation and Nitrosated Compounds

Published on: February 16, 2022

3.7K

Area of Science:

  • Biomedical Engineering
  • Drug Delivery Systems
  • Nanotechnology

Background:

  • Developing stimuli-responsive liposomes for targeted cancer therapy is crucial.
  • Redox-sensitive liposomes aim to release drugs specifically in tumor microenvironments.
  • Nitroreductase (NTR) is often overexpressed in tumor tissues, making it a target for drug release mechanisms.

Purpose of the Study:

  • To construct and evaluate novel N-DOPE liposomes designed for redox-triggered drug release in malignant tumors.
  • To investigate the mechanism of payload release from N-DOPE liposomes in response to nitroreductase.
  • To identify factors influencing the efficacy of redox-sensitive liposomes as drug carriers.

Main Methods:

  • Synthesis of N-DOPE liposomes with a redox-active 4-nitrobenzyl formate head group.
  • Testing drug release using calcein as a model payload under various conditions (Na₂S₂O₄, NTR, temperature, aerobic/anaerobic).
  • Spectroscopic methods to analyze the formation of azo bonds and understand the reduction pathway.

Main Results:

  • N-DOPE liposomes did not release encapsulated calcein payload under tested conditions, even with Na₂S₂O₄ and NTR.
  • Azo bond formation was identified as the inhibitory factor preventing complete nitro group reduction to amine, thus blocking payload release.
  • Addition of an organic group containing nitro during reduction with Na₂S₂O₄ led to a 45% release of liposomal content.

Conclusions:

  • The designed N-DOPE liposomes, as initially hypothesized, did not achieve complete payload release due to azo bond formation.
  • The formation of an azo bond impedes the intended 1,6 elimination mechanism for drug release.
  • Modifying the reduction process by adding a nitro-containing organic group shows potential for achieving partial drug release, warranting further investigation for optimized drug delivery.