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In Vitro Study of Antiviral Properties of Compounds Based on Tetrahydropyran Derivative of closo-Decaborate Anion with Amino Acid Ester Residues against Influenza Virus A/IIV-Orenburg/83/2012(H1N1)pdm09
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In Vitro Study of Antiviral Properties of Compounds Based on Tetrahydropyran Derivative of closo-Decaborate Anion with Amino Acid Ester Residues against Influenza Virus A/IIV-Orenburg/83/2012(H1N1)pdm09
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In Vitro Study of Antiviral Properties of Compounds Based on Tetrahydropyran Derivative of closo-Decaborate Anion with Amino Acid Ester Residues against Influenza Virus A/IIV-Orenburg/83/2012(H1N1)pdm09
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Journal Article
In Vitro Study of Antiviral Properties of Compounds Based on Tetrahydropyran Derivative of closo-Decaborate Anion with Amino Acid Ester Residues against Influenza Virus A/IIV-Orenburg/83/2012(H1N1)pdm09
2025
Overview
Based on the substituted derivative of the decahydro-
closo
-decaborate anion (Ph
4
P)
2
[B
10
H
9
O(CH
2
)
5
COOH] obtained by opening the tetrahydropyran substituent in the anion [B
10
H
9
O(CH
2
)
5
]
–
, compounds of the general formula Na
2
[B
10
H
9
O(CH
2
)
6
C(O)X], where X = Trp-OMe (
1
), His-OMe (
2
), Met-OMe (
3
), Pld-OMe (
4
), containing various amino acid substituents attached to the pendant carboxyl group, were synthesized. The compounds were isolated as sodium salts. The residues of L-tryptophan (Na
2
1
) and L-histidine (Na
2
2
) contained aromatic heterocyclic groups indole and imidazole, respectively, as a side group. In turn, compounds Na
2
3
and Na
2
4
contained substituted alkanes as a side group: L-methionine (Na
2
3
) contained a methyl ethyl sulfide group, and compound Na
2
4
contained the residue of an aliphatic synthetic amino acid, in which the side group was represented by γ-butyrolactam (2-oxopyrrolidin-3-yl) (Pld-OMe). Compounds Na
2
1
and Na
2
2
were found to exhibit dose-dependent antiviral activity against the influenza virus strain A/IIV-Orenburg/83/2012(H1N1)pdm09 in vitro. IC
50
for compound Na
2
1
was found to be 5.0 μg/mL, and for compound Na
2
2
it was found to be 10.0 μg/mL. Molecular docking of the M2 protein pore and ligands
1
and
2
was performed. It was found that the most probable arrangement of molecules in the pore of the M2 channel is associated with the location of the heterocycle inside the pore of the M2 channel in the region of the residues His37–Trp41, with the arrangement being more favorable for
1
rather than for
2
. This fact explains some difference in the concentrations of suppression of viral reproduction for Na
2
1
and Na
2
2
. For compounds Na
2
3
and Na
2
4
, antiviral activity was not detected.
