Investigating the potential of monocyclic B9N9 and C18 rings for the electrochemical sensing, and adsorption of carbazole-based anti-cancer drug derivatives: DFT-based first-principle study

Yumna Niamat; Junaid Yaqoob; Muhammad Usman Khan; Riaz Hussain; Mazhar Amjad Gilani; Abrar Ul Hassan; Tansir Ahamad

doi:10.1007/s00894-024-06049-1

Investigating the potential of monocyclic B₉N₉ and C₁₈ rings for the electrochemical sensing, and adsorption of carbazole-based anti-cancer drug derivatives: DFT-based first-principle study

J Mol Model. 2024 Jul 3;30(8):245. doi: 10.1007/s00894-024-06049-1.

Authors

Yumna Niamat¹, Junaid Yaqoob^{2

3}, Muhammad Usman Khan⁴, Riaz Hussain¹, Mazhar Amjad Gilani⁵, Abrar Ul Hassan^{6

7}, Tansir Ahamad⁸

Affiliations

¹ Department of Chemistry, University of Okara, Okara, -56300, Pakistan.
² Department of Chemistry, University of Okara, Okara, -56300, Pakistan. [email protected].
³ Department of Chemistry, COMSATS University Islamabad, Lahore Campus, Lahore, 54600, Pakistan. [email protected].
⁴ Department of Chemistry, University of Okara, Okara, -56300, Pakistan. [email protected].
⁵ Department of Chemistry, COMSATS University Islamabad, Lahore Campus, Lahore, 54600, Pakistan.
⁶ Lunan Research Institute, Beijing Institute of Technology, 888 Zhengtai Road, Tengzhou, 277599, China.
⁷ School of Materials Science and Engineering, Beijing Institute of Technology, Beijing, 100081, China.
⁸ Department of Chemistry, College of Science, King Saud University, 11451, Riyadh, Saudi Arabia.

PMID: 38960925
DOI: 10.1007/s00894-024-06049-1

Abstract

Context: For the first time, the use of monocyclic rings C₁₈ and B₉N₉ as sensors for the sensing of carbazole-based anti-cancer drugs, such as tetrahydrocarbazole (THC), mukonal (MKN), murrayanine (MRY), and ellipticine (EPT), is described using DFT simulations and computational characterization. The geometries, electronic properties, stability studies, sensitivity, and adsorption capabilities of C₁₈ and B₉N₉ counterparts towards the selected compounds confirm that the analytes interact through active cavities of the C₁₈ and B₉N₉ rings of the complexes.

Methods: Based on the interaction energies, the sensitivity of surfaces towards EPT, MKN, MRY, and THC analytes is observed. The interaction energy of EPT@B₉N₉, MKN@B₉N₉, MRY@B₉N_9, and THC@B₉N₉ complexes are observed - 20.40, - 19.49, - 20.07, and - 18.27 kcal/mol respectively which is more exothermic than EPT@C₁₈, MKN@C₁₈, MRY@C₁₈, and THC@C₁₈ complexes are - 16.37, - 13.97, - 13.96, and - 11.39 kcal/mol respectively. According to findings from the quantum theory of atoms in molecules (QTAIM) and the reduced density gradient (RDG), dispersion forces play a significant role in maintaining the stability of these complexes. The electronic properties including FMOs, density of states (DOS), natural bond orbitals (NBO), charge transfer, and absorption studies are carried out. In comparison of B₉N₉ and C₁₈, the analyte recovery time for C₁₈ is much shorter (9.91 × 10^-11 for THC@C₁₈) than that for B₉N₉ shorter recovery time value of 3.75 × 10^-9 for EPT@B₉N₉. These results suggest that our reported sensors B₉N₉ and C₁₈ make it faster to detect adsorbed molecules at room temperature. The sensor response is more prominent in B₉N₉ due to its fine energy gap and high adsorption energy. Consequently, it is possible to think of these monocyclic systems as a potential material for sensor applications.

Keywords: B9N9 and C18 rings; Carbazole-based anti-cancer drugs; DFT; QTAIM; Reduced density gradient; Sensing.

MeSH terms

Adsorption
Antineoplastic Agents* / chemistry
Carbazoles* / chemistry
Density Functional Theory*
Electrochemical Techniques / methods
Models, Molecular
Molecular Structure

Substances

Carbazoles
Antineoplastic Agents
carbazole

Grants and funding

Researchers Supporting Project number (RSP2024R6)/King Saud University, Riyadh, Saudi Arabia.