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Abstract <p>A series of novel boron–amino acid conjugates (Ph<sub>4</sub>P)<sub>2</sub>[B<sub>12</sub>H<sub>11</sub>O(CH<sub>2</sub>)<sub>2</sub>O(CH<sub>2</sub>)<sub>3</sub>C(O)R] (R is HisOMe, TrpOMe) has been synthesized based on the [B<sub>12</sub>H<sub>12</sub>]<sup>2–</sup> cluster anion functionalized with a carboxyalkyl spacer obtained via 1,4-dioxane ring opening and formation of the corresponding acid (Ph<sub>4</sub>P)<sub>2</sub>[B<sub>12</sub>H<sub>11</sub>O(CH<sub>2</sub>)<sub>2</sub>O(CH<sub>2</sub>)<sub>3</sub>COOH]. The resulting compounds contain residues of L-histidine and L-tryptophan methyl esters, linked to the boron cluster through an alkoxy spacer. The formation of the target compounds was confirmed by IR and NMR spectroscopies, ESI MS and elemental analysis. Biological evaluation of the sodium salts revealed dose-dependent antiviral activity against a rimantadine-resistant strain of influenza virus A/IIV-Orenburg/83/2012 in vitro. The IC<sub>50</sub> values were determined to be 5.0 µg/mL for the tryptophan derivative and 10.0 µg/mL for the histidine derivative. These findings highlight the potential of boron–amino acid conjugates based on the [B<sub>12</sub>H<sub>12</sub>]<sup>2–</sup> platform for the development of targeted antiviral agents.</p>

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Derivatives of the closo-Dodecaborate [B12H12]2– Anion with L-Histidine and L-Tryptophan Residues Linked via an Alkoxy Spacer: Synthesis and Antiviral Activity against Influenza A(H1N1)pdm09 Strain

  • 期刊论文

  • 发表日期：

    2025年12月1日

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  • T. M. Garaev,
  • I. I. Yudin,
  • T. V. Grebennikova,
  • E. Yu. Matveev,
  • E. A. Eshtukova-Shcheglova,
  • I. E. Sokolov,
  • V. V. Avdeeva,
  • K. Yu. Zhizhin,
  • N. T. Kuznetsov

摘要

Abstract

A series of novel boron–amino acid conjugates (Ph4P)2[B12H11O(CH2)2O(CH2)3C(O)R] (R is HisOMe, TrpOMe) has been synthesized based on the [B12H12]2– cluster anion functionalized with a carboxyalkyl spacer obtained via 1,4-dioxane ring opening and formation of the corresponding acid (Ph4P)2[B12H11O(CH2)2O(CH2)3COOH]. The resulting compounds contain residues of L-histidine and L-tryptophan methyl esters, linked to the boron cluster through an alkoxy spacer. The formation of the target compounds was confirmed by IR and NMR spectroscopies, ESI MS and elemental analysis. Biological evaluation of the sodium salts revealed dose-dependent antiviral activity against a rimantadine-resistant strain of influenza virus A/IIV-Orenburg/83/2012 in vitro. The IC50 values were determined to be 5.0 µg/mL for the tryptophan derivative and 10.0 µg/mL for the histidine derivative. These findings highlight the potential of boron–amino acid conjugates based on the [B12H12]2– platform for the development of targeted antiviral agents.