Synthesis, Characterization, and Evaluation of Antifungal Activity of 1-Butyl-3-hexyl-1 H-imidazol-2(3 H)-selenone by Surface-Enhanced Raman Spectroscopy

Noor Ul Huda; Muhammad Wasim; Haq Nawaz; Muhammad Irfan Majeed; Muhammad Rizwan Javed; Nosheen Rashid; Muhammad Adnan Iqbal; Anam Tariq; Ahmad Hassan; Muhammad Waseem Akram; Faisal Jamil; Muhammad Imran

doi:10.1021/acsomega.3c05436

Synthesis, Characterization, and Evaluation of Antifungal Activity of 1-Butyl-3-hexyl-1 H-imidazol-2(3 H)-selenone by Surface-Enhanced Raman Spectroscopy

ACS Omega. 2023 Sep 21;8(39):36460-36470. doi: 10.1021/acsomega.3c05436. eCollection 2023 Oct 3.

Affiliations

¹ Department of Chemistry, University of Agriculture Faisalabad, Faisalabad 38000, Pakistan.
² Department of Bioinformatics and Biotechnology, Government College University Faisalabad (GCUF), Faisalabad 38000, Pakistan.
³ Department of Chemistry, University of Education, Faisalabad Campus, Faisalabad 38000, Pakistan.
⁴ Department of Biochemistry, Government College University Faisalabad (GCUF), Faisalabad 38000, Pakistan.
⁵ Department of Chemistry, Faculty of Science, King Khalid University, P.O. Box 9004, Abha 61413, Saudi Arabia.

Abstract

In the present research work, a selenium N-heterocyclic carbene (Se-NHC) complex/adduct was synthesized and characterized by using different analytical methods including FT-IR, ¹HNMR, and ¹³CNMR. The antifungal activity of the Se-NHC complex against Aspergillus flavus (A. flavus) fungus was investigated with disc diffusion assay. Moreover, the biochemical changes occurring in this fungus due to exposure of different concentrations of the in-house synthesized compound are characterized by surface-enhanced Raman spectroscopy (SERS) and are illustrated in the form of SERS spectral peaks. SERS analysis yields valuable information about the probable mechanisms responsible for the antifungal effects of the Se-NHC complex. As demonstrated by the SERS spectra, this Se-NHC complex caused denaturation and conformational changes in the proteins as well as decomposition of the fungal cell membrane. The SERS spectra were analyzed using two chemometric tools such as principal component analysis (PCA) and partial least-squares discriminant analysis (PLS-DA). The fungal samples' SERS spectra were differentiated using PCA, while various groups of spectra were discriminated with ultrahigh sensitivity (98%), high specificity (99.7%), accuracy (100%), and area under the receiver operating characteristic curve (87%) using PLS-DA.