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Related Concept Videos

Elements and Compounds01:27

Elements and Compounds

105.3K
Pure substances consist of only one type of matter. A pure substance can be an element or a compound. An element consists of only one type of atom, while a compound consists of two or more types of atoms held together by a chemical bond.
Elements
Elements are classified as atomic or molecular based on the nature of their basic units. They are unique forms of matter with specific chemical and physical properties that cannot break down into smaller substances by ordinary chemical reactions. There...
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Periodic Classification of the Elements04:00

Periodic Classification of the Elements

59.6K
The periodic table arranges atoms based on increasing atomic number so that elements with the same chemical properties recur periodically. When their electron configurations are added to the table, a periodic recurrence of similar electron configurations in the outer shells of these elements is observed. Because they are in the outer shells of an atom, valence electrons play the most important role in chemical reactions. The outer electrons have the highest energy of the electrons in an atom...
59.6K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

7.0K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
7.0K
Classification of Elements and Compounds02:54

Classification of Elements and Compounds

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Pure substances consist of only one type of matter. A pure substance can be an element or a compound. An element consists of only one type of atom, while a compound consists of two or more types of atoms held together by a chemical bond. Elements are classified as atomic or molecular based on the nature of their basic units.
Compounds are pure substances composed of two or more elements in fixed, definite proportions. Compounds are classified as ionic or molecular (covalent) based on the bonds...
73.4K
Key Elements for Plant Nutrition02:35

Key Elements for Plant Nutrition

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Like all living organisms, plants require organic and inorganic nutrients to survive, reproduce, grow and maintain homeostasis. To identify nutrients that are essential for plant functioning, researchers have leveraged a technique called hydroponics. In hydroponic culture systems, plants are grown—without soil—in water-based solutions containing nutrients. At least 17 nutrients have been identified as essential elements required by plants. Plants acquire these elements from the...
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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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Hydroponics: A Versatile System to Study Nutrient Allocation and Plant Responses to Nutrient Availability and Exposure to Toxic Elements
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Heterocycles: Versatile control elements in bioactive macrocycles.

Harjeet S Soor1, Solomon D Appavoo1, Andrei K Yudin1

  • 1Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto M5S 3H6, Canada.

Bioorganic & Medicinal Chemistry
|May 9, 2018
PubMed
Summary
This summary is machine-generated.

Macrocyclic peptides offer therapeutic advantages but struggle with cell entry. This review explores how incorporating heterocycles into macrocycles can enhance their properties for drug development.

Keywords:
Cellular membrane permeabilityConformationHeterocyclesMacrocyclesPeptides

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Area of Science:

  • Medicinal Chemistry
  • Chemical Biology
  • Drug Discovery

Background:

  • Macrocyclic peptides are promising therapeutics due to enhanced stability and bioavailability compared to linear peptides.
  • A key limitation of macrocyclic peptides is their poor lipophilicity, hindering cellular membrane penetration and access to intracellular targets.
  • Existing strategies to improve cell permeability include bicyclic scaffolds, d-amino acids, and N-methylation, primarily through conformational control.

Purpose of the Study:

  • To review the impact of heterocycle incorporation on the conformational stability and properties of macrocyclic peptides.
  • To highlight the less-explored structural consequences of introducing heterocycles into macrocyclic frameworks.
  • To provide insights into novel strategies for enhancing macrocyclic peptide therapeutics.

Main Methods:

  • Literature review of key examples involving heterocycle incorporation into macrocyclic structures.
  • Analysis of conformational changes induced by heterocycles in macrocyclic peptides.
  • Discussion of how heterocycles affect physicochemical properties relevant to drug development.

Main Results:

  • Heterocycle incorporation significantly influences the conformational landscape of macrocyclic peptides.
  • These structural modifications can modulate properties such as stability and potentially cell permeability.
  • The study identifies specific instances where heterocycles have been successfully employed to fine-tune macrocycle characteristics.

Conclusions:

  • Heterocycle incorporation represents a valuable, yet underexplored, strategy for optimizing macrocyclic peptide therapeutics.
  • Understanding these structural consequences is crucial for designing next-generation macrocyclic drugs with improved efficacy.
  • Further investigation into heterocycle-containing macrocycles could unlock new therapeutic potentials.