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Related Concept Videos

Pore Transport and Ion-Pair Transport01:17

Pore Transport and Ion-Pair Transport

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Pore transport and ion-pair formation are critical mechanisms for the absorption and distribution of drugs in the body.
Pore transport, also known as convective transport, is a process where small molecules like urea, water, and sugars rapidly cross cell membranes as though there were channels or pores in the membrane. Although direct microscopic evidence is limited  but the concept of pores or channels is widely accepted based on physiological evidence. Despite the lack of direct...
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Carrier-mediated transport is a pivotal process in drug absorption, particularly for lipid-insoluble drugs, and encompasses facilitated diffusion and active transport. Facilitated diffusion allows drugs to move along their concentration gradient without energy expenditure, while active transport utilizes ATP to drive drug movement against this gradient.
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Drug Absorption Mechanism: Carrier-Mediated Membrane Transport01:19

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Certain large, lipid-insoluble drug molecules that resemble amino acids, peptides, or glucose, require specialized carrier proteins to facilitate their diffusion across cell membranes. This transport can occur through either facilitated diffusion, which does not require energy input, or active transport, which does require energy input.
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Amines to Amides: Acylation of Amines01:19

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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Updated: Mar 27, 2026

Thermostabilization, Expression, Purification, and Crystallization of the Human Serotonin Transporter Bound to S-citalopram
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MATE Transporter-Dependent Export of Hydroxycinnamic Acid Amides.

Melanie Dobritzsch1, Tilo Lübken2, Lennart Eschen-Lippold2

  • 1Department of Stress and Developmental Biology, Leibniz Institute of Plant Biochemistry, D-06120 Halle (Saale), Germany Interdisciplinary Centre for Crop Plant Research, Martin Luther University Halle-Wittenberg, D-06120 Halle (Saale), Germany.

The Plant Cell
|January 9, 2016
PubMed
Summary

Arabidopsis thaliana uses coumaroylagmatine to inhibit Phytophthora infestans spore germination. Transgenic potato plants engineered with Arabidopsis genes can secrete this compound, enhancing plant defense against late blight.

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Area of Science:

  • Plant Pathology
  • Plant Biochemistry
  • Molecular Plant-Microbe Interactions

Background:

  • Arabidopsis thaliana employs multilayered defenses against Phytophthora infestans, the pathogen causing potato late blight.
  • Surface-localized secondary metabolites play a crucial role in controlling pathogen entry.

Purpose of the Study:

  • Investigate the role of surface-localized metabolites in controlling P. infestans entry into Arabidopsis.
  • Identify specific compounds and genetic factors involved in plant defense at the leaf surface.

Main Methods:

  • Untargeted metabolite profiling of P. infestans incubated on Arabidopsis leaves.
  • In vitro assays to assess the activity of identified metabolites on P. infestans.
  • Mutant analyses to determine genes involved in metabolite biosynthesis and transport.
  • Genetic engineering of potato plants to express Arabidopsis defense-related genes.

Main Results:

  • Coumaroylagmatine, a hydroxycinnamic acid amide, was identified as a key metabolite secreted into the P. infestans inoculum.
  • Coumaroylagmatine demonstrated inhibitory activity against P. infestans spore germination in vitro.
  • The p-coumaroyl-CoA:agmatine N4-p-coumaroyl transferase (ACT) and MATE transporter DTX18 were identified as crucial for coumaroylagmatine biosynthesis and secretion.
  • Transgenic potato plants expressing ACT and DTX18 exhibited enhanced secretion of hydroxycinnamic acid amides, conferring resistance to P. infestans.

Conclusions:

  • Secreted hydroxycinnamic acid amides, like coumaroylagmatine, contribute to plant defense by inhibiting pathogen spore germination at the leaf surface.
  • The ACT and DTX18 genes from Arabidopsis can be utilized to engineer enhanced resistance in crops like potato.
  • DTX18 functions as a specific transporter for hydroxycinnamic acid amides, facilitating their extracellular accumulation for defense.