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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

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Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
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Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

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In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
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Ethers to Alkyl Halides: Acidic Cleavage02:18

Ethers to Alkyl Halides: Acidic Cleavage

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Ethers are generally unreactive and unsuitable for direct nucleophilic substitution reactions since the alkoxy groups are strong bases and, therefore, poor leaving groups. However, ethers readily undergo acidic-cleavage reactions. Ethers can be converted to alkyl halides when heated with strong acids such as HBr and HI in a sequence of two substitution reactions.
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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Solubility03:00

Solubility

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Solution, Solubility, and Solubility Equilibrium
A solution is a homogeneous mixture composed of a solvent, the major component, and a solute, the minor component. The physical state of a solution—solid, liquid, or gas—is typically the same as that of the solvent. Solute concentrations are often described with qualitative terms such as dilute (of relatively low concentration) and concentrated (of relatively high concentration).
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Ion Exchange01:17

Ion Exchange

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Ion exchange chromatography separates charged molecules from a solution by reversibly exchanging them with mobile, or 'active', ions associated with the oppositely charged stationary phase. This method can be used to separate ions, soften and deionize water, and purify solutions. The polymers comprising the ion-exchange column are high-molecular-weight and chemically stable polymers, crosslinked to be porous and essentially insoluble. They are also functionalized with either acidic or...
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Extraction and Characterization of Surfactants from Atmospheric Aerosols
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Acid-cleavable poly(oxazoline) surfactants.

Joseph A Garcia1, Linglan Zhu1, Ashley Vergara Mendez1

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, USA.

Polymer Chemistry
|December 5, 2025
PubMed
Summary
This summary is machine-generated.

New stimuli-responsive nanotherapeutics utilize acid-cleavable surfactants for targeted cancer treatment. These novel poly(oxazoline)-based materials enhance drug delivery and endosomal escape in acidic tumor environments.

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Area of Science:

  • Biomaterials Science
  • Nanotechnology
  • Polymer Chemistry

Background:

  • The acidic tumor microenvironment and late endosomes are key targets for stimuli-responsive nanotherapeutics.
  • Acid-cleavable surfactants, especially those with hydrazone linkages, offer stability and controlled intracellular payload release.
  • Efficient endosomal escape is crucial for effective cancer nanomedicine.

Purpose of the Study:

  • To synthesize and characterize a novel hydrazone-linked poly(oxazoline)-based diblock copolymer surfactant.
  • To evaluate the pH-dependent cleavage behavior of the synthesized surfactant.
  • To demonstrate the utility of this surfactant system for controlled payload release and enhanced endosomal escape.

Main Methods:

  • Synthesis of a poly(oxazoline)-based diblock copolymer surfactant featuring hydrazone linkages.
  • pH-stability studies to determine cleavage rates at different pH values (pH 7.4 vs. pH 5.0).
  • Nanoemulsion preparation and assessment of payload partitioning into cell membrane mimics post-cleavage.

Main Results:

  • The hydrazone-linked polymer exhibited significant pH-dependent cleavage, with 80% remaining at pH 7.4 and only 17% at pH 5.0 after 21 hours.
  • Nanoemulsion payloads partitioned into cell membrane mimics exclusively after surfactant cleavage.
  • Payload release increased from 26% to 47% over 42 hours by manipulating pH conditions.

Conclusions:

  • A viable route for creating poly(oxazoline)-based nanomaterials with controlled release capabilities under biologically relevant conditions was demonstrated.
  • The developed surfactant system shows promise for improving endosomal escape and cancer targeting in nanomedicine.
  • This work provides a foundation for advancing stimuli-responsive nanotherapeutics for cancer treatment.