Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene

Numan Yüksel

doi:10.17714/gumusfenbil.1752525

TR EN

Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene

Öz

In this work, the adsorption and sensing behavior of a calixarene macrocycle toward three β-lactam anti-biotics was probed by density functional theory (DFT). All calculations were carried out with the B3LYP hybrid functional using the 6-31G(d,p) basis set. The simulations demonstrate that the calix[4]arene scaffold exhibits a pronounced sensing response exclusively for floxacillin: its sensor response factor is roughly six orders of magnitude greater than those obtained for ampicillin and penicillin. Additionally, analysis of frontier orbitals shows a 16.4% contraction of the HOMO–LUMO gap upon floxacillin binding, a perturbation that is visually evident in the density of states profile. Taken together, these findings establish calix[4]arene as a viable electronic sensor for floxacillin under ambient conditions.

Anahtar Kelimeler

Anti-biotic, Calix[4]arene, DFT, Sensor

Kaynakça

Al-Tawarh, W. M., Altarawneh, R. M., Al-Trawneh, S. A., Alshahateet, S. F., & Al-Taweel, S. (2023). An effective calix[4]arene-based adsorbent for tetracycline removal from water systems: Kinetic, isotherm, and thermodynamic studies. Journal of Chemical Research. https://doi.org/10.1177/17475198231187600
Becke, A. D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38, 3098. https://doi.org/10.1103/PhysRevA.38.3098
Demir, S., & Fellah, M. F. (2020). A DFT study on Pt doped (4,0) SWCNT: CO adsorption and sensing. Applied Surface Science, 504. https://doi.org/10.1016/j.apsusc.2019.144141
Eno, E. A., Louis, H., Unimuke, T. O., Gber, T. E., Mbonu, I. J., Ndubisi, C. J., & Adalikwu, S. A. (2022). Reactivity, stability, and thermodynamics of para-methylpyridinium-based ionic liquids: Insight from DFT, NCI, and QTAIM. Journal of Ionic Liquids, 2, 100030. https://doi.org/10.1016/j.jil.2022.100030
Fellah, M. F., & Onal, I. (2013). A DFT study on the [VO]1+–ZSM-5 cluster: direct methanol oxidation to formaldehyde by N2O. Physical Chemistry Chemical Physics, 15(33), 13969-13977. https://doi.org/10.1039/C3CP51637G
Fellah, M. F. (2019). Pt doped (8,0) single wall carbon nanotube as hydrogen sensor: A density functional theory study. International Journal of Hydrogen Energy 44(49), 27010-27021. https://doi.org/10.1016/j.ijhydene.2019.08.169
Foresman, J. B., & Frisch, A. (Eds). (1996). Exploring Chemistry with Electronic Structure Methods (2nd ed.). Gaussian Inc., Pittsburgh.
Frisch, M. J., et al. (2013). Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford CT.
Hokmabadi, F., Zadmard, R., Jalali, M. R., & Abaee, M. S. (2022). Synthesis and characterization of a new reusable calix[4]arene-bonded silica gel sorbent for antidiabetic drugs. RSC Advances, 12, 25123-25132. https://doi.org/10.1039/D2RA04530C
Khan, M. S., & Khan, M. S. (2012). Comparative theoretical study of iron and magnesium incorporated porphyrin induced carbon nanotubes and their interaction with hydrogen molecule. Physica E: Low-dimensional Systems and Nanostructures, 44, 1857-1861. https://doi.org/10.1016/j.physe.2012.05.010

Kobko, N., & Dannenberg, J. (2001). Effect of basis set superposition error (BSSE) upon ab initio calculations of organic transition states. Journal of Physical Chemistry A 105(10), 1944-50. https://doi.org/10.1021/jp001970b
Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B, 37, 785. https://doi.org/10.1103/PhysRevB.37.785
Lefebvre, C., Rubez, G., Khartabil, H., Boisson, J. C., Contreras-Garcia, J., Hénon, E. (2017). Accurately extracting the signature of intermolecular interactions present in the NCI plot of the reduced density gradient versus electron density. Physical Chemistry Chemical Physics, 19, 17928-17936. https://doi.org/10.1039/C7CP02110K
Li, L., & Zhao, J. (2020). Defected boron nitride nanosheet as an electronic sensor for 4-aminophenol: A density functional theory study. Journal of Molecular Liquids, 306. https://doi.org/10.1016/j.molliq.2020.112926
Li, X., Yin, Z., Zhai, Y., Kang, W., Shi, H., & Li, Z. (2020). Magnetic solid-phase extraction of four β-lactams using polypyrrole-coated magnetic nanoparticles from water samples by micellar electrokinetic capillary chromatography analysis. Journal of Chromatography A, 1610, 460541. https://doi.org/10.1016/j.chroma.2019.460541
Li, Y., Shi, M., Xia, M., & Wang, F. (2021). The enhanced adsorption of ampicillin and amoxicillin on modified montmorillonite with dodecyl dimethyl benzyl ammonium chloride: experimental study and density functional theory calculation. Advanced Powder Technology, 32(10), 3465-3475. https://doi.org/10.1016/j.apt.2021.08.001
Lu, T., Chen, & F. (2012). Multiwfn: A multifunctional wavefunction analyzer. Journal of computational chemistry, 33, 580-592. https://doi.org/10.1002/jcc.22885
Mishal, B. H., Das, S., Mahajan, V. N., Dharne, M. S., Joshi, R. S., & Giri, A. P. (2024). An adsorption based downstream processing approach for penicillin v from a penicillium chrysogenum bioncl I22 culture filtrate. ACS Omega, 9(24), 25859–25869. https://doi.org/10.1021/acsomega.4c00251
O’Boyle, N. M., Tenderholt, A. L., & Langner, K. M. (2007). cclib: A library for package-independent computational chemistry algorithms. Journal of Computational Chemistry, 29(5), 839-845. https://doi.org/10.1002/jcc.20823
Pearson, R. G. (2005). Chemical hardness and density functional theory. Journal of Chemical Sciences, 117, 369-377. https://doi.org/10.1007/BF02708340
Peng, S., Cho, K., Qi, P., & Dai, H. (2004). Ab initio study of CNT NO2 gas sensor. Chemical Physics Letters, 387(4-6), 271-276. https://doi.org/10.1016/j.cplett.2004.02.026
Sundaram, S. M., Gurusamy, A., & Kumarasamy, M. (2024). Green synthesis of biochar from miscanthus sinensis plant and characterized by the adsorption of antibiotics biochar from aqueous solution. Iranian Journal of Chemistry and Chemical Engineering, 43(2), 610-620. https://doi.org/10.30492/ijcce.2024.562763.5613
Tri, N. N., Ho, D. Q., Carvalho, A. J. P., Nguyen, M. T., & Trung, N. T. (2021). Insights into adsorptive interactions between antibiotic molecules and rutile-TiO2 (110) surface. Surface Science, 703, 121723. https://doi.org/10.1016/j.susc.2020.121723
Wang, Q., Sun, Y., Zhao, S., Bai, C., Cong, Z., Dong, Y., & Wang, T. (2023). Metallo-β-lactamases immobilized by magnetic zeolitic imidazolate frameworks-8 for degradation of β-lactam antibiotics in an aqueous environment. RSC Advances, 13, 34884-34890. https://doi.org/10.1039/D3RA05973A
Woodward, Z., Brooks, P., Smith, B. M., Wallis, M., & Ogbourne, S. M. (2018). Adsorption and leachable contamination of flucloxacillin, cyclosporin and amiodarone following delivery through an intravenous administration set. Pharmaceutical Research, 35(121). https://doi.org/10.1007/s11095-018-2409-2
Yuksel, N., Köse, A., & Fellah, M. F. (2020). A Density Functional Theory study of molecular hydrogen adsorption on Mg site in OFF type zeolite cluster. International Journal of Hydrogen Energy, 45(60), 34983-34992. https://doi.org/10.1016/j.ijhydene.2020.02.110
Yuksel, N., Köse, A., & Fellah, M. F. (2021). The supramolecularly complexes of calix[4]arene derivatives toward favipiravir antiviral drug (used to treatment of COVID-19): a DFT study on the geometry optimization, electronic structure and infrared spectroscopy of adsorption and sensing. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 101, 77-89. https://doi.org/10.1007/s10847-021-01087-1

Ayrıntılar

Birincil Dil

İngilizce

Konular

Çevresel Biyojeokimya, Sensör Teknolojisi , Supramoleküler Kimya, Hesaplamalı Kimya, Çevresel ve Sürdürülebilir Süreçler

Bölüm

Araştırma Makalesi

Yazarlar

Numan Yüksel ^*
0000-0003-1268-5775
Türkiye

Yayımlanma Tarihi

15 Aralık 2025

Gönderilme Tarihi

28 Temmuz 2025

Kabul Tarihi

17 Kasım 2025

Yayımlandığı Sayı

Yıl 2025 Cilt: 15 Sayı: 4

DOI

https://doi.org/10.17714/gumusfenbil.1752525

IZ

https://izlik.org/JA72YN48GG

APA

Yüksel, N. (2025). Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene. Gümüşhane Üniversitesi Fen Bilimleri Dergisi, 15(4), 1112-1124. https://doi.org/10.17714/gumusfenbil.1752525

AMA

1.Yüksel N. Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene. Gümüşhane Üniversitesi Fen Bilimleri Dergisi. 2025;15(4):1112-1124. doi:10.17714/gumusfenbil.1752525

Chicago

Yüksel, Numan. 2025. “Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene”. Gümüşhane Üniversitesi Fen Bilimleri Dergisi 15 (4): 1112-24. https://doi.org/10.17714/gumusfenbil.1752525.

EndNote

Yüksel N (01 Aralık 2025) Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene. Gümüşhane Üniversitesi Fen Bilimleri Dergisi 15 4 1112–1124.

IEEE

[1]N. Yüksel, “Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene”, Gümüşhane Üniversitesi Fen Bilimleri Dergisi, c. 15, sy 4, ss. 1112–1124, Ara. 2025, doi: 10.17714/gumusfenbil.1752525.

ISNAD

Yüksel, Numan. “Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene”. Gümüşhane Üniversitesi Fen Bilimleri Dergisi 15/4 (01 Aralık 2025): 1112-1124. https://doi.org/10.17714/gumusfenbil.1752525.

JAMA

1.Yüksel N. Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene. Gümüşhane Üniversitesi Fen Bilimleri Dergisi. 2025;15:1112–1124.

MLA

Yüksel, Numan. “Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene”. Gümüşhane Üniversitesi Fen Bilimleri Dergisi, c. 15, sy 4, Aralık 2025, ss. 1112-24, doi:10.17714/gumusfenbil.1752525.

Vancouver

1.Numan Yüksel. Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene. Gümüşhane Üniversitesi Fen Bilimleri Dergisi. 01 Aralık 2025;15(4):1112-24. doi:10.17714/gumusfenbil.1752525

e-ISSN: 2146-538X Yayın Modeli: Sürekli Yayın Atıf Dizinleri: TR Dizin , SCOPUS

Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene

β-laktam anti-biyotiklerin (penisilin, floksasilin ve ampisilin) kaliks[4]aren üzerine adsorpsiyonunun ve tespitinin yoğunluk fonksiyonel teorisi çalışması

Öz

Anahtar Kelimeler

Density functional theory study of β-lactam anti-biotics (penicillin, floxacillin and ampicillin) detection and adsorption onto calix[4]arene

Öz

Anahtar Kelimeler

Kaynakça

Ayrıntılar

Birincil Dil

Konular

Bölüm

Yazarlar

Yayımlanma Tarihi

Gönderilme Tarihi

Kabul Tarihi

Yayımlandığı Sayı

DOI

IZ

Kaynak Göster