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Related Concept Videos

Structure-Activity Relationships and Drug Design01:28

Structure-Activity Relationships and Drug Design

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Drug design is a dynamic field that involves discovering and developing new medications based on specific biological targets. This process heavily relies on structure-activity relationships (SAR) and quantitative structure-activity relationships (QSAR) to guide the design and optimization of efficient drugs.
SAR studies the intricate relationship between a drug's chemical structure and biological activity. It focuses on understanding how modifications to a drug's structure can influence...
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Carboxylic Acid Derivatives: Overview01:15

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Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
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Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
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Relative Reactivity of Carboxylic Acid Derivatives01:13

Relative Reactivity of Carboxylic Acid Derivatives

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Carboxylic acid derivatives such as acid halides, anhydrides, esters, and amides undergo nucleophilic acyl substitution reactions with varying degrees of reactivity.
A key factor in assessing the reactivity of the acid derivatives is the basicity of the substituent or the leaving group. The lower the basicity of the leaving group, the higher the reactivity of the derivative. The basicity of the leaving group follows this order:
Halide ions < Acyloxy ions < Alkoxy ions < Amine ions
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Local Anesthetics: Chemistry and Structure-Activity Relationship01:27

Local Anesthetics: Chemistry and Structure-Activity Relationship

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Local anesthetics (LAs) are drugs that induce a temporary loss of sensation in a limited body area, preventing pain. Cocaine was the first local anesthetic discovered in the late 19th century. Cocaine is a benzoic acid ester obtained from the leaves of coca shrubs and was often used for its psychotropic effects. Cocaine was first isolated in 1860 by Albert Niemann. Sigmund Freud studied the physiological actions of cocaine. Carl Koller later introduced it into clinical practice in 1884 as a...
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Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

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Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
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Structure-activity relationship read-across and transcriptomics for branched carboxylic acids.

Shengde Wu1, Corie Ellison1, Jorge Naciff1

  • 1Global Product Stewardship, The Procter and Gamble Company, Mason, Ohio 45040, USA.

Toxicological Sciences : an Official Journal of the Society of Toxicology
|December 30, 2022
PubMed
Summary
This summary is machine-generated.

This study used transcriptomics and PBPK models to assess chemical similarity for branched carboxylic acids, comparing them to valproic acid (VPA). Results show specific alkyl substituents elicit similar profiles to VPA, improving chemical read-across predictions.

Keywords:
2-ethylhexanoic acidbranched-alkyl carboxylic acidsread-acrossstructure-activity relationship (SAR)valproic acid

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Area of Science:

  • Toxicology and Pharmacology
  • Computational Chemistry
  • Genomics

Background:

  • Valproic acid (VPA) is a known developmental toxicant.
  • Read-across is a method used to predict the toxicity of chemicals based on data from similar substances.
  • Understanding chemical similarity is crucial for accurate toxicity assessments.

Purpose of the Study:

  • To support read-across for branched carboxylic acids using valproic acid (VPA) as a comparator.
  • To evaluate the utility of transcriptomics, toxicokinetics, and PBPK models in chemical similarity assessments.
  • To investigate the influence of alkyl chain branching on transcriptional profiles and internal dosimetry.

Main Methods:

  • Chemical similarity evaluations were performed.
  • Transcriptional profiling was conducted in four cell types using the L1000 platform.
  • In vitro toxicokinetic data were integrated into physiologically based pharmacokinetic (PBPK) models.
  • Molecular docking was used to explore potential mechanisms of action.

Main Results:

  • Transcriptional profiling revealed that 2-ethylhexanoic acid (EHA) and 2-propylnonanoic acid (PNA) exhibited profiles similar to VPA.
  • Other tested chemicals showed distinct transcriptional profiles, suggesting limitations for read-across.
  • PBPK modeling indicated that increasing branched chain length decreased predicted plasma Cmax.
  • Molecular docking provided a potential mechanistic link between VPA and observed transcriptional changes.

Conclusions:

  • Transcriptomics and PBPK modeling can enhance the accuracy of read-across for branched carboxylic acids.
  • The position and length of alkyl substituents significantly influence chemical similarity and toxicological profiles.
  • This approach supports a more refined application of read-across in chemical safety assessments.