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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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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).
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Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

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sp3d and sp3d 2 Hybridization
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Updated: Oct 26, 2025

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H2pyhox - Octadentate Bis(pyridyloxine).

Lily Southcott1,2, Xiaozhu Wang1, Neha Choudhary1,2

  • 1Medicinal Inorganic Chemistry Group, Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada.

Inorganic Chemistry
|July 26, 2021
PubMed
Summary

A new chelating ligand, H2pyhox, was synthesized for radiometals like Copper-64 and Indium-111. This versatile ligand shows promise for radiopharmaceutical applications due to its robust coordination and kinetic inertness.

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Area of Science:

  • Radiochemistry
  • Coordination Chemistry
  • Medicinal Chemistry

Background:

  • Development of novel chelating agents is crucial for radiometal complexation in nuclear medicine.
  • Existing ligands may have limitations in coordinating a wide range of radiometals or exhibit insufficient kinetic stability.
  • The 8-hydroxyquinoline (oxine) scaffold is a known chelator, but modifications can enhance its versatility.

Purpose of the Study:

  • To synthesize and characterize a new versatile chelating ligand, H2pyhox, for intermediate size and softness radiometals.
  • To evaluate the coordination properties of H2pyhox with various metal ions, including radiometals.
  • To assess the stability and suitability of H2pyhox-metal complexes for radiopharmaceutical applications.

Main Methods:

  • Synthesis of the H2pyhox ligand incorporating pyridine and oxine moieties.
  • Structural analysis of metal complexes (Cu2+, La3+, In3+) to understand ligand adaptation.
  • UV-Vis spectroscopy to determine protonation and formation constants.
  • Radiolabeling studies with 111In3+ and 64Cu2+ under varying conditions.
  • Stability assays (serum, protein, ligand challenge) for radiometal complexes.

Main Results:

  • H2pyhox was successfully synthesized and characterized.
  • Structural studies confirmed the ligand's ability to accommodate metal ions of different sizes and charges.
  • Protonation and formation constants were determined, indicating strong metal binding.
  • Efficient radiolabeling of 111In3+ and 64Cu2+ was achieved under mild conditions (<15 min, RT, pH 6).
  • H2pyhox demonstrated the first successful radiolabeling of 225Ac3+ with an oxinate ligand, albeit at higher concentrations and mild heating.
  • Radiometal complexes ([111In]In-H2pyhox and [64Cu]Cu-H2pyhox) exhibited kinetic inertness in challenge assays.

Conclusions:

  • H2pyhox is a versatile chelating ligand capable of coordinating intermediate size and softness radiometals.
  • The ligand demonstrates robustness and kinetic inertness, making it suitable for radiopharmaceutical development.
  • H2pyhox represents a promising new scaffold for chelating a range of medically relevant radiometals, including challenging ones like 225Ac3+.