Investigation of the Interaction of Benzo(a)Pyrene and Fluoranthene with Cucurbit[n]urils (n = 6-8): Experimental and Molecular Dynamic Study.

Autor: Elbashir AA; Department of Chemistry, College of Science, King Faisal University, Al-Ahsa 31982, Saudi Arabia.; Department of Chemistry, Faculty of Science, University of Khartoum, Khartoum 11114, Sudan., Alfadil AA; Department of Chemistry, Faculty of Science, University of Khartoum, Khartoum 11114, Sudan.; Department of Chemistry, College of Science, Sultan Qaboos University, P.O. Box 36, Al-Khoud 123, Oman.; Department of Chemical Laboratories, College of Science, Sudan University of Science and Technology, Khartoum 11115, Sudan., Suliman FO; Department of Chemistry, College of Science, Sultan Qaboos University, P.O. Box 36, Al-Khoud 123, Oman., Alnajjar AO; Department of Chemistry, College of Science, King Faisal University, Al-Ahsa 31982, Saudi Arabia.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2023 Jan 23; Vol. 28 (3). Date of Electronic Publication: 2023 Jan 23.
DOI: 10.3390/molecules28031136
Abstrakt: The inclusion complexes of cucurbit[n]uril, CB[n] (n = 6-8), with poly aromatic hydrocarbon (PAH) Benzo(a)Pyrene (BaP), and fluoranthene (FLT) were investigated carefully in aqueous media. Fluorescence and 1 H NMR spectroscopy were used to characterize and investigate the inclusion complexes that were prepared in the aqueous media. The most predominant complexes of both guests with hosts were the 1:1 guest: host complexes. Stability constants of 2322 ± 547 M -1 , 7281 ± 689 M -1 , 3566 ± 473 M -1 were obtained for the complexes of BaP with CB[6], CB[7], and CB[8], respectively. On the other hand, stability constants of 5900.270 ± 326 M -1 , 726.87 ± 78 M -1 , 3327.059 ± 153 M -1 were obtained for the complexes of FLT with CB[6], CB[7], and CB[8], respectively. Molecular dynamic (MD) simulations were used to study the mode and mechanism of the inclusion process and to monitor the stability of these complexes in aqueous media at an atomistic level. Analysis of MD trajectories has shown that both BaP and FLT form stable inclusion complexes with CB[7] and CB[8] in aqueous media throughout the simulation time, subsequently corroborating the experimental results. Nevertheless, the small size of CB[6] prohibited the encapsulation of the two PAHs inside the cavity, but stable exclusion complex was observed between them. The main driving forces for the stability of these complexes are the hydrophobic forces, van der Waals interactions, electrostatic effect, the π····π and C-H···π interaction. These results suggest that BaP and FLT can form stable complexes with CB[n] (n = 6-8) in solution.
Competing Interests: The authors declare no conflict of interest.
Databáze: MEDLINE
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