Document Type : Original Article


Department of Applied Chemistry, Faculty of Science, Malayer University, Malayer, 65174, Iran


In the current work, the density functional theory (DFT) and time-dependent density functional theory (TD-DFT) at ωB97XD/Lanl2DZ level of theory was accomplished to study the effects of Cu and Ni decorated on Boron nitride nanocage (B12N12) on the interaction of 8-hydroxyquinoline (8-HQ) drug as a novel candidate for drug delivery. The adsorption energy and thermodynamic results demonstrated that the adsorption of 8-HQ drug from O and N sites on the surface of nanocage was more favorable than other sites, and with decorating Cu and Ni atoms, the adsorption process of the 8-HQ drug was exothermic and spontaneous on the nanocage surface. The gap energy and global hardness values of the Ni and Cu decorated B12N12 nanocage was smaller than the pristine B12N12 nanocage, so the conductivity and reactivity of nanocage in this state was more than that the other states. The atom in molecule (AIM), reduced density gradient plots (RDG), and electron localized function (ELF) results confirmed that the nature of bonding between 8-HQ drugs with B12N12 nanocage was partially covalent or electrostatic. The UV-visible results revealed that with decorating Cu and Ni atoms, the optical properties of the system alter significantly from pure state. The results of this study can be used to make a novel sensitive sensor and novel drug delivery carriers for the 8-HQ drug.

Graphical Abstract

The drug delivery appraisal of Cu and Ni decorated B12N12 nanocage for an 8-hydroxyquinoline drug: A DFT and TD-DFT computational study


Main Subjects


In recent years, one of the most important challenges of the drug industry is to increase the therapeutic efficacy of the drug and deliver it accurately and completely to the target cells in the body. Various methods and combinations have been used to solve this issue. One of the newest methods is to use safe nanoparticles to deliver the drug to the target cells. Among the studied nanomaterials, Boron nitride nanocage (B12N12) has received more attention due to the physical and chemical properties, nonlinear optical features, oxidation resistance, inherent no cytotoxicity, and its wide application in the construction of electrical, magnetic, and imaging systems [16]. The theoretical results of Seifert et al. [7] demonstrated that B12N12 is more stable than other BN nanocages such as B16N16 and B28N28 nanocages and it is suitable for various interactions.

In 2004, Oku and coworker [8] were able to experimentally synthesize the B12N12 nanocage and identify it by mass spectroscopic methods. They showed that the B12N12 nanocage is composed of tetragonal and hexagonal rings and is semiconductor. The recent researches showed that the B12N12 has a high potential for adsorbing and interacting various compounds.

The interaction of B12N12 nanocage with NH3 [9], carbon monoxide [1012], carbon dioxide [13], nitrogen dioxide, nitrogen monoxide, and methane [1416], hydrogen and hydrogen sulfide [1719], hydrogen cyanide [20], tabun molecule [21], cyanogen halides [22], formic Acid [23], O3 and SO2 [24], hydrogen abstraction of methanimine [25], Methanol [26], methylamine [27], phosgene [2829], pyridine [30], pyrrole [31], SCN-[32], sulfur mustard chemical [33], halogen molecules [34], and Methanol dehydrogenation [35] were investigated through theoretical computational methods. The results of these studies demonstrated that the B12N12 nanocage has an excellent performance in adsorbing and characterizing these compounds in the environment and system. Moreover, extensive research has been conducted in the field of drug interaction with B12N12 nanocage, which is very important in the process of targeted drug delivery and the preparation of a drug-selective sensor. Abdolahi et al. [36] found that the interaction of the celecoxib drug with B12N12 nanocage is non-covalent and this nanocage is a good candidate for delivery and carrier of celecoxib drug. On the other study Soltani et al. [37] indicated that the interaction B12N12 nanocage with 5AVA drug is exothermic and B12N12 nanocage is a useful compound for delivery of 5AVA drug. Zhu et al. [38] computational results confirmed that the interaction of 5-aminosalicylic acid drug with B12N12, Al B11N12, and GaB11N12 nanocage is electrostatic and doped atoms (Al and Ga) increase the interaction drug with nanocage. In another study, Farmanzadeh et al. [39] displayed that the adsorption of amantadine drug on B12N12 nanocage in both gas and solvent is chemically type. Vessally et al. [40] reported that the Al doped B12N12 nanocage has a more potential for delivery and carrier of aspirin drug in bio systems. The 8-hydroxyquinoline (8-HQ) drug is widely used for the treatment of neuroprotection, anticancer, anti-HIV, antibacterial, and antifungal. The 8-HQs drug has shown interesting properties as a fungicide, bactericide antituberculosis agents, antineoplastic activity, metal-related diseases, and ant proliferative [4145]. Following our previous works [4655], in this project, we intend to study the interaction and adsorption of 8-HQ drug with pristine, Cu and Ni decorated B12N12 nanocage to evaluate its efficiency in identifying the drug and its delivery properties. By using the outputs of this study, it can be suggested the sensitive sensors or delivery for 8-HQs drug.

Details of computational method

In the current study, the pristine, Ni and Cu decorated B12N12 nanocage are denoted with A, B, and C notation. The activated sites of 8-HQ drug adsorption on the nanocage surface are determined by a (for O site), and b (for N site) symbol (see Figure 1).

First, all possible complexes are considered for adsorbing 8-HQ drug on the surface of the B12N12, Ni, and Cu& B12N12 nanocages (see Figure 1), and all above complexes are optimized at ωB97XD/Lanl2DZ level of density functional theory (DFT) by using Gaussian 09 package [56]. The frequency analysis demonstrated that there was no imaginary frequency for these compounds. The optimization criteria for all studied complexes are Max Force=0.00038 Hartree and Max displacement=0.00015 Bohr. By applying equations of 1‒4 the adsorption energy (Eads), ∆G, ∆H, and ∆S for all complexes of 8-HQ drug with the B12N12, Cu, and Ni& B12N12 nanocages are calculated, as listed in Table 1.

Figure 1. All complexes of 8-HQ with B12N12, Cu& B12N12, and Ni& B12N12 nanocages named with A-a to C-b complexes

Table 1. Adsorption energy (Eads), thermodynamic parameters of 8-HQ with B12N12, Cu& B12N12, and Ni& B12N12 nanocages for A-a to C-d complexes










d(bond) (Å)





































Where, the E8-HQ /nanocage complex, G8-HQ/nanocage complex, H8-HQ/nanocage complex, and S8-HQ/nanocage complex are the total electronic energy, Gibbs free energy, enthalpy, and entropy of 8-HQ drug with pristine, Cu, and Ni decorated B12N12 nanocage complex, respectively. The E8-HQ, Enanocage, G8-HQ, Gnanocage, H8-HQ, Hnanocage, S8-HQ, and Snanocage are the total electronic energy, Gibbs free energy, enthalpy, and entropy of isolated 8-HQ drug, pristine, or Cu and Ni decorated B12N12 nanocage, respectively. The base set superposition error values for all complexes is in the range 0.005‒0.021 eV. The HOMO-LUMO energies, DOS plots, gap energy, electrochemical potential, global hardness, and total charge transfer parameter [5761] for all drugs and nanocage complexes are estimated (see Table 2). The bonding nature between drug and nanocage can be determined by reduced density parameters (RDG), molecular electrostatic potential (MEP), and atoms in molecules (AIM) theory.

Results and Discussion

The geometrical, and adsorption parameters

The optimized geometrical structures of interaction 8-HQ drug from N, O, C2, and C6 sites with B12N12, Ni, and Cu & B12N12 nanocages are displayed in Figure 1, as it can be seen the interaction of 8-HQ drug from electrostatic sites (N and O) is more probable than C2 and C6 sites. The bond distance (d) between 8-HQ… nanocage at the A-a and A-b models are 1.62 and 1.63 Å. It is noticeable that with decorating Cu and Ni atoms, 8-HQ drug bind to the metal surface simultaneously from nitrogen and oxygen sites, moreover the Ni atom attaches to the B and N atoms of the B12N12 nanocage. The B‒N bond lengths for tetragonal and hexagonal rings of B12N12 nanocage are 1.434 to 1.510 Å, respectively, and it is in agreement with other reports [36]. The stable site for adsorbing 8-HQ and decorating Cu and Ni atoms is B21 site. The bond lengths B21-N6, and B21-N7 in the pristine (A), Cu decorated (B), and Ni decorated (C) is 1.434 (1.510), 1.459 (1.637), and 1.448(1.602) Å, respectively. The B21-N6, and B21-N7 bond length in the A-a, A-b, B-a, B-b, C-a, and C-b complexes are (1.492, 1.607 Å), (1.521, 1.595 Å), (1.475, 1.757 Å), (1.482, 1.734 Å), (1.469, 1.895 Å), and (1.467, 1.900 Å), respectively. As you can see with decorating Ni and Cu atoms, the bond length of B21-N7 alters sharply and so the electrical properties of the complex change significantly. These results suggest that Ni and Cu atoms play a catalytic role in this process and increase drug-nanocage interaction.

The Eads values of all studied complexes (Table 1) are negative and exothermic.

The trend of increasing Eads in models a, and b is as follows: C-a (‒54.90 Kcal/mol)> B-a (‒41.22 Kcal/mol)> A-a (‒23.28 Kcal/mol), and C-b (‒61.18 Kcal/mol)> B-a (‒40.66 Kcal/mol)> A-a (‒40.03 Kcal/mol). As result, the C-b adsorption complex is the most favorable, and Ni decorated plays a very good role in the adsorption process. By examining the results of thermodynamic parameters, it is observed that the ∆G and ∆H values of the A-a to C-b complexes are negative, and process spontaneous in a thermodynamic approach. Comparisons of the thermodynamic parameters values confirmed that the interaction of 8-HQ drug with Ni & B12N12 nanocage is the most favorable. Therefore, the Ni & B12N12 nanocage can be an appropriate suggestion for targeted delivery 8-HQ drug in the body. From output of thermodynamic calculation, the IR spectrum of all studied complexes is calculated and is displayed in Figure S3 (Supplementary data). In the IR spectrum of studied complexes, a sharp peak with high absorption intensity in the 1400‒1500 cm-1 is observed for C‒N bond stretching, and another peak has lower intensity.


To investigate the electrical behavior of the 8-HQ drug & B12N12 nanocage complex, the structures of HOMO and LUMO orbitals along with quantum parameters are calculated and the results are presented in Figure 2 and Table 2.

Figure 2 displays that in the Cu decorated B12N12 nanocage, the orbital structures of HOMO and LUMO of 8-HQ drug & B12N12 nanocage complex is separated into α and β spin due to the alone electron of valance layer of Cu. In the HOMO-LUMO orbitals figures, it can be seen that the highest HOMO density is concentrated on the nanocage surface, so this surface is more suitable for attacking electrophilicity species. While the highest LUMO density is concentrated on the 8-HQ drug surface, this area is suitable for a nucleophilicity attack. On the other hand, in the cellular environment, the drug part tends more towards negatively charged particles, while the nanocage tends towards to positively charged particles. This factor may play an important role in drug behavior therapy.

According to Table 2, the amount of Egap values are in range of 1.353 to 4.235 eV. Therefore, with adsorbing 8-HQ drug and decorating Cu & Ni atoms, the conductivity of B12N12 nanocage enhances. This result suggests that the Cu & Ni decorated B12N12 nanocage can be a sensitive sensor for the 8-HQ drug. The Egap amount for the alpha spin of B-a, and B-b models is lower than other models. Global hardness (η) is one of the useful parameters that can be used for determine the activity of a compound. The smaller values of η indicate that the compound is more active. This result indicates that the activity of 8-HQ drug with Ni & B12N12 nanocage complex is more than other studied systems. Thus, this property is more appropriate in the drug delivery phenomenon and therapeutic properties. The values of electrochemical potential for A-a to C-b complexes are negative and all studied complexes are stable in thermodynamic viewpoint. On the other hand, the ∆N and ρNBO values are positive, as result 8-HQ drug has a donor electron role in this system. The density of states (DOS) and partial density of state plots of studied complexes are determined by GaussSum software, as displayed in Figure 3.

In the DOS plots, it is shown that with decorating Cu and Ni atoms, the number and intensity of peaks is more that pristine B12N12 nanocage, which indicates that the optical property of the system increase. Due to appearing a small peak in the gap area the Egap of drug and nanocage complexes decrease from a pure state. The PDOS plots reveal that the highest interaction of the orbitals occur in the HOMO region. In the A-a, B-a, A-b, and B-b models, models the most interaction in HOMO region is observed for 2p orbital of C and N atoms of 8-HQ drug with N atoms of nanocage, while the interaction of the 3p orbital of C, N, and O atoms of the 8-HQ drug with B atoms of nanocage in the LUMO region is more than other atoms. In C-a and C-b models, in the HOMO and LUMO regions, the most interaction is observed between 2p and 3p orbitals of N and C atoms of drug with the same orbitals of nanocage atoms.

AIM analyses

The theory atom in molecule of the Bader [62] is one of the most important and practical techniques that is applied to determine the nature of binding between various materials. By using AIM theory the ρ, HBCP, VBCP, GBCP, and ∇2ρ(r), at the bond critical point of 8-HQ drug with B12N12 and Cu&B12N12, Ni&B12N12 nanocage complexes are calculated and outcomes are reported in Table 3. Based on the AIM theory, the strong covalent bond is indicated with ∇2ρ(r) <0 and HBCP<0 values, the strong electrostatic bond is displayed with ∇2ρ(r) >0 and HBCP>0 values, and partially covalent bond is determined with HBCP<0 and ∇2ρ(r) >0 values [6365].

Figure 2. HOMO-LUMO orbital structures for A-a to C-b complexes

Table 2. Quantum parameters of 8-HQ with B12N12, Cu& B12N12, and Ni& B12N12 nanocages for A-a to C-d complexes





























































(Eg= ELUMO‒EHOMO), (μ= (EHOMO+ELUMO)/2), (η= (ELUMO‒EHOMO)/2), and (ΔN= ‒μ/η)

Figure 3. DOS and PDOS plots for A-a to C-b complexes

Table 3. Topological parameters of AIM of 8-HQ with B12N12, Cu& B12N12, and Ni& B12N12 nanocages for A-a to C-d complexes



-G(r) / V(r)






















































The calculated results of Table 3 revealed that the values of ∇2ρ(r) and HBCP for all adsorption models except the C-a model are positive and negative, respectively. Thus, the interaction of 8-HQ drug with B12N12 and Cu & B12N12, Ni & B12N12 nanocage complexes except C-a model is a partially covalent bond type. In the C-a model, the ∇2ρ(r) and HBCP values are negative, so the interaction between drug and nanocage is strong covalent bond. ELF (Electron localization function) is another functional parameter in which the determination of the electrons’ concentration in the region between two compounds. If its value is less than 0.5 it indicates delocalization electron between two compounds and type of bonding is partial covalent, and if it is between 0.5 to 1, it indicates a localization electron between two compounds and nature of bonding is covalent. Examination of the results shows that the ELF value for all models except C-a model is less than 0.5 and the nature of the bond is partial covalent or electrostatic type and for C-a model is greater than 0.5 and indicates the nature of the covalent bond.

RDG scatter plots

To better understand the nature of non‒covalent interaction between 8-HQ drug with B12N12 and Cu&B12N12, Ni& B12N12 nanocages, RDG (reduced density gradient) diagrams are very suitable that are extracted based on the following equation [66]:

In this scatter diagram, the product of sign of λ2 and ρ(r) (electron density) is applied to determine the different types of interactions between two compounds. The RDG scatter graphs for A-a to C-b complexes are determined, as depicted in Figure 4.

In the RDG scatter graphs, the blue (λ2<0), green (λ2=0) and red (λ2 >0) colors indicate the attractive, van der Walls, and repulsive interactions. A close inspection of the RDG scatter graphs reveal that the RDG density for all studied complex is shown in the blue (λ2<0) region. Therefore, the interactions between 8-HQ drug with nanocage is electrostatic or hydrogen bond type. The most density of RDG in the red (λ2 >0) is related to the steric effects between O and N atoms of 8-HQ drug with nanocage. The analysis of RDG graphs confirms that the interaction of 8-HQ drug with B12N12, Cu&B12N12, and Ni& B12N12 nanocages except C-a model is electrostatic type.

MEP plots

A valuable method to study the charge distributions and nucleophilic or electrophilic properties of molecule is MEP [67]. In the MEP plots, red and blue colors indicate the nucleophilic (positive charge) and electrophilic (negative charge) of molecule surface, respectively.

According to the MEP plots in Figure 5, the positive charge is localized around the 8-HQ drug surface and this site is suitable for attacking to the negative site of biological cellule in the body. The decoration of Cu and Ni atoms alter the distribution of positive and negative charges around the drug and nanocage and cause the effect of drug on the target cell increase.

UV˗ visible spectrum

To understand of UV-visible spectrum and behavior of molecules in the exited state the TD-DFT calculated method is used at ωB97XD/Lanl2DZ level [68]. Thus, we considered 20 exited states to determine UV-visible spectra and transition states for all studied complexes. The UV-visible spectrums are displayed in Figure 6, and also the transition states parameters are listed in Table 4.

The values of the λmax for A-a, and A-b complexes are demonstrated in the 282.01 and 234.78 nm with f=0.974 and 0.275 for transition states S0→S5 and S0→S30.

Figure 4. RDG scatter and plots for A-a to C-b complexes

Figure 5. MEP plots for A-a to C-b complexes

Table 4. The exited energy of UV-visible parameters 8-HQ with B12N12, Cu & B12N12, and Ni & B12N12 nanocages for A-a to C-d complexes

Figure 6. UV-visible plots for A-a to C-b complexes

While in the B-a and B-b complexes, a peak in the λmax of 1265.21 and 1258.02 nm in f=0.1076 and 0.1703 is observed for transmissions S0→S1, and one peak is observed at the wavelengths of 382.48 and 378.65 nm with f=0.0377 and 0.0428 for transfers S0→S13 and S0→S13, respectively. The first peak is in the visible region and the second is in the ultraviolet region. With decorating Ni atom in the C-a, and C-b complexes, two peaks are also observed in the λmax of 471.06 and 477.75 nm with f=0.1011 and 0.0469 for transfers S0→S6 and S0→S4, respectively. These peaks are in the visible area, and other peaks appear at 298.67 and 309.93 nm with f = 0.0649 and 0.0493 for transitions S0→S4 and S0→S17 are in the ultraviolet region. Therefore, with decorating of Cu and Ni atoms, the optical behavior of the 8-HQ drug and B12P12 nanocage complexes change significantly which is prominent in identifying the drug position in the body.


The interaction of 8-HQ drug with B12N12, Cu & B12N12, and Ni & B12N12 nanocages are investigated at the ωB97XD/Lanl2DZ level of DFT theory. The Eads of the complex of 8-HQ drug with B12N12 and Cu & B12N12, Ni & B12N12 nanocages are exothermic and the trend of it as follows: C-a (-54.90 Kcal/mol)> B-a (-41.22 Kcal/mol)> A-a (-23.28 Kcal/mol), and C-b (-61.18 Kcal/mol)> B-a (-40.66 Kcal/mol)> A-a (-40.03 Kcal/mol). The Egap and η values of 8-HQ drug and Cu and Ni atoms decorated B12N12 nanocage complexes are lower than pure states and the conductivity and reactivity of the complexes are more than the pure nanocage. The computational results of AIM, RDG, and ELF demonstrate that the bonding nature 8-HQ drug with B12N12, Cu & B12N12, and Ni & B12N12 nanocages is partially covalent or electrostatic. The TD-DFT results indicate that the optical properties of the 8-HQ drug with B12N12, Cu & B12N12, and Ni & B12N12 nanocages complexes alter significantly from pure state and this feature is remarkable for tracking the drug in the body. The computational results of this study suggest that Ni & B12N12 is an excellent carrier for targeted drug delivery to target cells.

Disclosure Statement

No potential conflict of interest was reported by the authors.


This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

Authors' contributions

All authors contributed to data analysis, drafting, and revising of the paper and agreed to be responsible for all the aspects of this work.

Supporting Information

Figures S1- S3 are depicted in supplementary data.

How to cite this manuscript: Hourinaz Darougari, Mahdi Rezaei-Sameti. The drug delivery appraisal of Cu and Ni decorated B12N12 nanocage for an 8-hydroxyquinoline drug: A DFT and TD-DFT computational study. Asian Journal of Nanoscience and Materials, x(x) 2022, xx-xx. DOI: 10.26655/AJNANOMAT.2022.3.3

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