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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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Acid–Base Equilibria: Activity-Based Definition of pH01:10

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For an ideal solution, the pH is defined as the negative logarithm of the hydrogen ion concentration. For a non-ideal solution, an accurate measurement of the pH must consider the negative logarithm of the hydrogen ion activity rather than concentration. In such a solution, the pH can be more accurately defined as the negative logarithm of a product of the hydrogen ion concentration and its activity coefficient.
In solutions of very low ionic strength—for example, pure water—the...
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IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

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Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic...
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Structures of Aldehydes and Ketones01:04

Structures of Aldehydes and Ketones

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Vanillin—a flavoring agent in vanilla, cinnamaldehyde—a molecule responsible for the distinct smell of cinnamon, and acetone—a strong-smelling ingredient in nail polish removers, all belong to a class of carbonyl compounds called aldehydes and ketones (Figure 1). Although both aldehydes and ketones contain the characteristic carbonyl (C=O) bond, their chemical structures vary with respect to the groups directly attached to the carbonyl carbon.
In aldehydes (Figures 1a and 1b), the...
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Common Names of Aldehydes and Ketones01:11

Common Names of Aldehydes and Ketones

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Some common aldehydes and ketones are popularly known by their common names used historically and predate the IUPAC nomenclature.   
Common names of aldehydes are derived from the names of their corresponding acid. For instance, the two-carbon aldehyde–acetaldehyde derives its name from the corresponding acid–acetic acid. Similarly, formaldehyde derives its name from formic acid and benzaldehyde from benzoic acid.
Aliphatic ketones are named by suffixing the word “ketone” to the...
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Protecting Groups for Aldehydes and Ketones: Introduction01:23

Protecting Groups for Aldehydes and Ketones: Introduction

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Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
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Application of AlDeSense to Stratify Ovarian Cancer Cells Based on Aldehyde Dehydrogenase 1A1 Activity
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Mapping Aldehyde Dehydrogenase 1A1 Activity using an [18 F]Substrate-Based Approach.

Raul Pereira1,2, Thibault Gendron3, Chandan Sanghera1,2

  • 1Centre for Advanced Biomedical Imaging, University College London, Paul O'Gorman Building, 72 Huntley Street, London, WC1E 6DD, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 7, 2018
PubMed
Summary

Researchers developed a novel imaging agent to detect aldehyde dehydrogenase (ALDH) activity in cancer. This first-in-class radiotracer shows promise for non-invasively assessing ALDH1A1, a marker linked to cancer metastasis and survival.

Keywords:
[18F]fluorinationaldehyde dehydrogenasecancerradiochemistryradiolabeling

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Metabolic Mapping: Quantitative Enzyme Cytochemistry and Histochemistry to Determine the Activity of Dehydrogenases in Cells and Tissues
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Area of Science:

  • Medicinal Chemistry
  • Radiochemistry
  • Molecular Imaging
  • Cancer Biology

Background:

  • Aldehyde dehydrogenases (ALDHs) are enzymes crucial for aldehyde oxidation.
  • Elevated ALDH expression in cancer correlates with metastasis and poor patient survival.
  • Non-invasive imaging of ALDH activity in vivo is currently limited.

Purpose of the Study:

  • To synthesize and biologically evaluate novel ALDH1A1-isozyme-selective chemical probes.
  • To develop a PET imaging agent for non-invasive assessment of ALDH activity in cancer.

Main Methods:

  • Synthesis of ALDH1A1-selective probes based on an aromatic aldehyde and a fluorinated pyridine ring.
  • In vitro evaluation of compound affinity and isozyme selectivity.
  • 18F-fluorination of the lead compound for positron emission tomography (PET) studies.
  • In vitro cellular uptake and trapping studies in colorectal tumor cells.
  • In vivo PET imaging in animal models to assess biodistribution and tumor uptake.

Main Results:

  • N-ethyl-6-(fluoro)-N-(4-formylbenzyl)nicotinamide 4b demonstrated high affinity and selectivity for ALDH1A1 in vitro.
  • The 18F-labeled tracer, [18F]4b, was effectively taken up and trapped by colorectal tumor cells via ALDH-mediated oxidation.
  • In vivo PET imaging showed high uptake of [18F]4b in lungs and liver, with clearance via the urinary tract.
  • In vivo oxidation of [18F]4b was observed, potentially impacting tissue penetration.

Conclusions:

  • A first-in-class ALDH1A1-selective radiotracer, [18F]4b, has been developed.
  • The tracer shows potential for non-invasive imaging of ALDH activity in cancer.
  • Further optimization may be needed to improve tissue penetration due to in vivo oxidation.