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New ferrocene integrated amphiphilic guanidines: Synthesis, spectroscopic elucidation, DFT calculation and in vitro α-amylase and α-glucosidase inhibition combined with molecular docking approach.

ABSTRACT: Three N, N', N″-trisubstituted ferrocenyl guanidines (MG-10, MG-12 and MG-14) were synthesized, characterized by several analytical methods such as FT-IR, ¹H and ¹³C NMR, elemental analysis and UV-visible spectroscopy. These compounds have long chain aliphatic groups therefore their aliphatic nature has been evaluated by determining their critical micelle concentration (CMC). CMC point decreases from 0.036 mM to 0.013 mM with increase in the aliphatic chain length. The quantum mechanical parameters such as the energy of frontier molecular orbitals (E_HOMO and E_LUMO) and the Mulliken charge distribution on the optimized structures were determined using a DFT/B3LYP method combined with the 6-31G (d,p) basis set in the gas phase. The in vitro antidiabetic activity of synthesized compounds showed that MG-12 has IC₅₀value 23.10 μg/mL against α-amylase while MG-10 has IC₅₀value 27.32 μg/mL against α-glucosidase with the respective standard Acarbose (IC₅₀value 20.12 μg/mL). Theoretical docking analysis demonstrated that MG-10 and MG-12 interacted with α-amylase by 3 types of interaction, including hydrogen bonds, hydrophobic interactions and electrostatic interactions.

SUBMITTER: Zubair S

PROVIDER: S-EPMC10102212 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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New ferrocene integrated amphiphilic guanidines: Synthesis, spectroscopic elucidation, DFT calculation and in vitro α-amylase and α-glucosidase inhibition combined with molecular docking approach.

Zubair Shumaila S Badshah Amin A Patujo Jahangeer J Khan Mehmand M Raheel Ahmad A Asghar Faiza F Imtiaz Shamila S

Heliyon 20230328 4

Three N, N', N″-trisubstituted ferrocenyl guanidines (MG-10, MG-12 and MG-14) were synthesized, characterized by several analytical methods such as FT-IR, <sup>1</sup>H and <sup>13</sup>C NMR, elemental analysis and UV-visible spectroscopy. These compounds have long chain aliphatic groups therefore their aliphatic nature has been evaluated by determining their critical micelle concentration (CMC). CMC point decreases from 0.036 mM to 0.013 mM with increase in the aliphatic chain length. The quan ...[more]

PMID: 37064477

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Dataset Information

New ferrocene integrated amphiphilic guanidines: Synthesis, spectroscopic elucidation, DFT calculation and in vitro α-amylase and α-glucosidase inhibition combined with molecular docking approach.

Publications

New ferrocene integrated amphiphilic guanidines: Synthesis, spectroscopic elucidation, DFT calculation and in vitro α-amylase and α-glucosidase inhibition combined with molecular docking approach.

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