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Three components encapsulated nanoparticles: Preparation and photophysical property
⁎Corresponding authors. hqyang@fjnu.edu.cn (Hongqin Yang), yirupeng@fjnu.edu.cn (Yiru Peng)
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Received: ,
Accepted: ,
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.
Abstract
Abstract
Two novel polymeric nanoparticles co-loaded three components, tetra-(4-bromine thiophenol) phthalocyanine zinc/magnesium, gold particles and curcumin, were assembled through hydrophobic interaction and Au—S bonds. The transmission electron microscope images, dynamic light scattering (DLS) and EDS spectra evidenced the formation of the polymeric nanoparticles. The effect between the curcumin and gold nanoparticles on the photophysical and photochemical properties of phthalocyanines in polymeric nanoparticles were investigated by UV–vis and fluorescence spectroscopy. The polymeric nanoparticle co-loaded with three components showed a higher singlet oxygen quantum yield and encapsulation ratios compared with co-loaded with only one component due to the synergistic effect between curcumin and gold nanoparticles within the nanoparticles. Three components encapsulated into a nanoparticle could provide a new strategy to enhance the singlet oxygen quantum yield as well as encapsulation ratio of polymeric nanoparticles.
Keywords
Polymeric nanoparticles
Curcumin
Phthalocyanine
Gold particles
Singlet oxygen quantum yield
Encapsulation ratio
Synergistic effect
1 Introduction
Photodynamic therapy (PDT) has emerged as a promising method for the treatment of cancers and non-cancer disease. Phthalocyanine (Pc) and its metal derivatives (MPcs) have been proposed as a promising second-generation photosensitizer for PDT (Torre et al., 2012; Peer et al., 2007). However, the phthalocyanines with 18 electrons π-conjugation system are liable to aggregate in solution due to their π-π* stacking interactions and hydrophobic interaction (Scalise and Durantini, 2005; Chidawanyika and Nyokong, 2009). The aggregation behaviors of MPcs significantly reduce their solubility, singlet oxygen quantum yields and fluorescence quantum yields, resulting in a decrease in photodynamic therapy efficiency. The introduction of functional substituents on the peripheral/axially position of MPcs could not only increase their solubility but also reduce aggregation to some extent.
The other disadvantage for MPcs is that they lack selective accumulation in the tumor tissues which results in a loss of PDT efficiency and increases toxicity in normal tissues (Sun et al., 2014). Some nanocarrier systems, such as liposomes, polymeric micelles, dendrimers and inorganic nanoparticles, can selectively deliver drugs to tumor tissues via a passive targeting approach through enhanced permeation and retention (EPR) effect (Fu et al., 2002; Sanna and Sechi, 2020) Polymeric micelles have gained great attention due to their inherent advantages such as low toxicity, high stability and small size (<200 nm), which have made them as ideal candidates for delivering phthalocyanines to tumors (Zhang et al., 2014). Some MPcs encapsulated into nanocarrier have been demonstrated to be able to improve the target ability. However the aggregation behavior is very severe when the phthalocyanines are encapsulated into nanocarriers.
Curcumin (Cur) is a yellow-orange plant dye extracted from the rhizomes of the Curcuma Longa (Heger et al., 2014). It is a potential antioxidant, anti-inflammation, antitumor, anti-HIV, and antimicrobial drug (Kunnumakkara et al., 2017). It can also inhibit lipid peroxidation and scavenge superoxide anion, nitric oxide, and hydroxyl radicals. Curcuma could generate singlet oxygen under certain conditions, that is, it produced singlet oxygen in toluene, while in acetonitrile it quenched singlet oxygen upon irradiation (Chignell et al., 1994; Markovi et al., 2019). Cur’s clinical applications have far been limited by low solubility, low bioavailability, rapid metabolism and degradation at physiological pH value (Paunovic et al., 2016). In order to overcome these problems associated with poor solubility and low bioavailability, Cur was encapsulated in a range of copolymer micelles such as poly(ɛ-caprolactone)-based block copolymers, poly(ethylene glycol)-monoacrylate, poly(N-isopropylacrylamide) and poly(N-vinyl-2-pyrrolidone) random copolymers, or poly(poly(ethylene glycol) methyl ether methacrylate, polystyrene block copolymers and alkyne end-functionalized amphiphilic poly(D,L-lactide)-b-poly(N,N-dimethylaminoethyl methacrylate) (Jia et al., 2018; Naksuriya et al., 2014; He et al., 2020). Each of these polymer systems was able to enhance antioxidant activity, intracellular uptake and cytotoxicity of Cur (Naksuriya et al., 2014; Schraufstatter and Bernt, 1949; Hazzah et al., 2016).
Gold nanoparticles (Au) have been widely applied in imaging, biosensors, medicine, photothermal therapy (PTT) cancers (Jia et al., 2020). Conjugated Aus with phthalocyanines could improve the phthalocyanine's drug delivery efficiency, modulate its photophysical properties and enhance the singlet oxygen quantum yield (Chen et al., 2018; Nyokong, 2007).
In order to improve the uptake and cytotoxicity of phthalocyanines, increase their encapsulation ratio and reduce the aggregation of phthalocyanine in nanoparticles, three components, curcumin, tetra-(4-bromine thiophenol) phthalocyanine zinc (II)/magnesium (II) and Aus were co-loaded to form polymeric nanoparticles using poly (ethylene glycol)-β-poly(caprolactone) (MPEG5000-PCL2000) (PP) as a nanocarrier. The hydrophobic interaction between the tetra-(4-bromine thiophenol) phthalocyanine zinc (II)/magnesium (II) and curcumin could enhance encapsulation ratio and the Au-S bonds between the tetra-(4-bromine thiophenol) phthalocyanine zinc (II)/magnesium (II) and Aus could disperse the phthalocyanines and reduce their aggregation behaviors. The photophysical properties of three components encapsulated nanoparticles were studied for the first time.
2 Experimental
The equipment, materials, photochemical and photophysical formulas, and parameters used in this study were given as supplementary materials.
2.1 Preparation of gold nanoparticles (Aus)
Gold nanoparticles were prepared according to the method given in the literature (Frens, 1973). Gold nanoparticles were prepared by citrate reduction of HAuCl4. Briefly, 100 mL aqueous solution was added to a round bottom flask which contained 1 mM HAuCl4 with vigorously stirring. Then, 10 mL of trisodium citrate (38.8 mM) was added rapidly to the mixture. The mixture was boiled for 15 min, during this time solution of mixture color changed from pale yellow to wine red. The solution was cooled to room temperature with continuously stirring. Then 0.5 mL of ammonia water (20–30% v/v) containing 11-mercaptoundecanoic acid (0.0230 g, 10 mM) was added and the mixture was stirred overnight. The sizes of the gold nanoparticles were imaged by TEM analysis.
2.2 The synthesis of tetra-(4-bromine thiophenol) phthalocyanine zinc (II)/magnesium (II) (ZnPcBr and MgPcBr)
2.2.1 Synthesis of 4-(4-bromothiophenol) phthalonitrile (D-Br)
A mixture of 4-nitrobenzonitrile (1.7313 g, 10.0 mmol), 4-bromothiophenol (1.9293 g, 10.0 mmol), anhydrous K2CO3 (4.1462 g, 30.0 mmol) and N, N-dimethylformamide (DMF) (25 mL) was stirred at room temperature for 72 h. The reacted product was poured into ice water. The precipitate was filtered and washed with distilled water until the filtrate was neutralized. The precipitate was purified by silica gel column chromatographic method using dichloromethane as eluent. The filtrate was collected, and the solvent was evaporated. The residue was dried and a white solid (D-Br) was obtained in yield of 92.9%. IR: υmax, cm −1: 3440, 3090, 2570, 2230 (C≡N), 1580, 1470, 825, 525. 1H NMR (400 MHz, DMSO‑d6, ppm): 7.98 (d, J = 8 Hz, 1H; H4), 7.94 (d, J = 4 Hz, 1H; H5), 7.71–7.74 (m, 2H; H2), 7.50–7.54 (m, 2H; H1), 7.46–7.49 (m, 1H; H3). ESI-MS for C14H7BrN2S: calcd.: 315; found:315 [M].
2.2.2 Synthesis of tetra-(4-bromine thiophenol) phthalocyanine zinc (II) (ZnPcBr)
A mixture of D-Br (1.5760 g, 5.00 mM), zinc acetate dihydrate (0.2772 g, 1.25 mM), n-Pentanol (5 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (35 μL) was stirred at 140 °C for 24 h. After the mixture being cooled to room temperature, anhydrous ethanol (30 mL) was added, and then the mixture was filtered. The residue was soluble in dichloromethane and was further purified twice by silica gel column chromatography using acetone and dichloromethane (v: v = 1: 10) as eluents. The filtrate was collected and the solvent was evaporated. The residue was dried under vacuum. A blue powder was obtained in yield of was 6.0%. Analysis calcd for C56H28Br4N8S4Zn (%) C, 50.72; H, 2.13; Br, 24.10; N, 8.45; S, 9.67; Zn, 4.93; found: C, 51.72; H, 2.03; Br, 25.01; N, 9.35; S, 9.34; Zn, 4.73. IR: υmax, cm −1: 3440, 2930, 1590, 1470, 1383, 825, 541. 1H NMR (400 MHz, CDCl3, ppm): 8.95–9.01 (t, J = 12 Hz, 4H), 8.82 (s, 4H), 7.95–8.00 (t, J = 8 Hz, 4H), 7.57–7.72, ESI-MS for C56H28Br4N8S4Zn(m/z): calcd.: 1326.13; found: 1326.27 [M].
2.2.3 Synthesis of tetra-(4-bromine thiophenol) phthalocyanine zinc (II)/magnesium (II) (MgPcBr)
The process for synthesis of MgPcBr was similar to that of ZnPcBr. The dark blue solid was obtained in yield of 12.5%. Analysis calcd for C56H28Br4N8S4Mg (%) C, 52.34; H, 2.20; Br, 24.87; N, 8.72; S, 9.98; Mg,1.89; found: C, 52.10; H, 2.30; Br, 25.21; N, 9.15; S 9.21; Mg,1.73. IR: υmax, cm −1: 3440, 2923 1595 (Ar—H), 1518, 1470, 1388 ,815, 742, 525, 8.93 (s, 4H;), 8.12–8.52 (q, 4H;), 7.95–8.02 (q, 4H;), 7.73–7.78 (t, J = 8 Hz, 8H), 7.64–7.69 (t, J = 8 Hz, 8H), ESI-MS for C56H28Br4N8S4Mg(m/z): calcd.: 1285; found: 1285 [M].
2.3 Synthesis of polymeric nanoparticles
The polymeric nanoparticles were prepared by a solvent-dialysis method (Danafar, 2016). For preparation of MgPcBr@PP or ZnPcBr@PP: MgPcBr or ZnPcBr (1 mL, 1 × 10–4 M) DMF solution was mixed with 5 mg methoxy poly (ethylene glycol)-β-poly(caprolactone) (MPEG5000-PCL2000) (PP), the mixture was ultrasonic for 5 min, 9 mL of deionized water was added dropwise and the mixture was stirred at room temperature for 30 min to obtain MgPcBr@PP or ZnPcBr@PP.
Preparation of Cur@PP and Au@PP: 9.4 mL of deionized water was added dropwise into a mixing solution containing PP (0.5 mL, 10 mg/mL) and Cur (0.1 mL, 1 × 10−3 M) in DMF, and the mixure was stirred at room temperature for 30 min to obtain Cur@PP; 8.6 mL of deionized water was added dropwise into a mixture solution containing PP (0.5 mL, 10 mg/mL) and Au (0.8 mL, 1 × 10-4 M) in water with stirring at room temperature for 30 min to obtain Au@PP.
Preparing MgPcBr/Cur/Au@PP or ZnPcBr/Cur/Au@PP: A DMF solution containing MgPcBr or ZnPcBr (1 mL, 1 × 10−4 M) and Cur (0.1 mL, 1 × 10−3 M) was mixed with 5 mg PP, and then the mixture was ultrasonic for 5 min. Au (0.8 mL, 1 × 10-4 M) water solution was added into the mixture, and 8.1 mL of deionized water was also added dropwise with stirring at room temperature for 30 min to obtain MgPcBr/Cur/Au@PP or ZnPcBr/Cur/Au@PP.
These polymeric nanoparticles were dialyzed against deionized water at room temperature for 24 h using a dialysis membrane with a 7000 Da molecular weight cut-off (MWCO). After dialysis, the solutions were collected and filtered with 0.22 µm membrane to remove the free Cur, MgPcBr, ZnPcBr and Aus.
2.4 The loading capacities and encapsulation efficiencies of polymeric nanoparticles
The loading capacities and encapsulation efficiencies of ZnPcBr/MgPcBr in nanoparticles were determined using a UV/Vis spectrophotometer at a wavelength of 690 nm. The loading capacity (LC) and encapsulation efficiency (EE) were calculated according to the following equations,
2.5 Singlet oxygen quantum yield
The singlet oxygen quantum yields (ΦΔ) of polymeric nanoparticles were calculated according to the following equations,
2.6 Fluorescence lifetimes of polymeric nanoparticles
The fluorescence decay curves of polymeric nanoparticles were determined in water. The decay curves of the emission were fitted using an iterative nonlinear least squares method
3 Results and discussion
The synthetic route of ZnPcBr and MgPcBr was shown in Scheme 1. And the detailed synthetic routes for the preparation of polymeric nanoparticles were shown in Scheme 1.
The synthetic routes of ZnPcBr and MgPcBr.
3.1 Synthesis and characterization of polymeric nanoparticles
The Aus were stable because MUA adsorbed on their surface, which prevented them from aggregation. The morphologies of Aus were characterized by TEM imaging. Aus appeared as sphere with a mean diameter of 15 nm.
The polymeric nanoparticles were prepared by a cosolvent-dialysis method (Scheme 2). The PP could self-assembled to form polymeric nanoparticles in water. The critical micelle concentration (CMC) value of PP at room temperature was found to be 0.011 g/L.
The self-assembled scheme of polymeric nanoparticles.
The morphologies of polymeric nanoparticles were examined by TEM and DLS in water (Fig. 1). The polymeric nanoparticles were spherical with diameters was found to about 16–67 nm and their hydrodynamic sizes were found to be 60–101 nm with a high dispersity in water (Fig. 1). The average sizes of polymeric nanoparticles of TEM images were much smaller than those in water, which could be attributed to the pegylated of poly(caprolactone)(PCL) as well as the swelling of the nanoparticle core. Meanwhile, the average sizes of nanoparticles encapsulation three components possessed bigger sizes than those of encapsulation only one component.
The TEM images (a) and DLS images (b) of polymeric nanoparticles.
The encapsulation efficiencies and loading capacities of polymeric nanoparticles were shown in Table 1. The encapsulation efficiencies of ZnPcBr/Cur/Au@PP and MgPcBr/Cur/Au@PP were obviously higher than those of the MgPcBr@PP and ZnPcBr@PP. However the loading capacities were very similar. These results indicated that Cur could solubilize ZnPcBr and MgPcBr in nanoparticles.
Nanoparticles
EE%
LC%
ΦΔb
τs/nsa
MgPcBr/Cur/Au@PP
77.0 ± 7.7
2.0 ± 0.20
0.01
1.89
ZnPcBr/Cur/Au@PP
82.0 ± 0.8
0.22 ± 0.02
0.02
0.89
MgPcBr@PP
7.1 ± 7.1
1.8 ± 0.20
0.01
5.68
ZnPcBr@PP
7.9 ± 0.8
0.21 ± 0.02
0.01
2.80
Au@PP
6.5 ± 0.3
0.11 ± 0.01
–
3.58
Cur@PP
32.0 ± 0.3
4.5 ± 0.4
0.03
0.34
MgPcBr
–
–
0.22d
5.68c
ZnPcBr
–
–
0.53d
2.80c
3.2 The photophysical properties of polymeric nanoparticles
The UV–vis spectra of the polymeric nanoparticles were shown in Fig. 2. The absorption band of curcumin appeared at 420 nm (Wang et al., 2018). Gold particles exhibited a typical absorption band at 526 nm (Pissuwan et al., 2011). MgPcBr or ZnPcBr showed a B band at 350 nm and a Q band at about 690 nm (Agirtas et al., 2015). The UV/Vis spectra of MgPcBr/Cur/Au@PP and ZnPcBr/Cur/Au@PP provided a conclusive evidence for the existence of the three components; curcumin, gold nanoparticles and MgPcBr or ZnPcBr in polymeric nanoparticles. The Q band absorption spectra of MgPcBr/Cur/Au@PP and MgPcBr@PP appeared at 696 nm, which were red-shifted approximate 6 nm compared with that of free MgPcBr, indicating that it mainly existed as a monomer in the nanoparticles. But the absorption spectra of ZnPcBr/Cur/Au@PP and ZnPcBr@PP were a little different. They mainly existed as dimer at 635 nm. Meanwhile the absorption intensity for the Q bands of MgPcBr/Cur/Au@PP or ZnPcBr/Cur/Au@PP were higher than those of the MgPcBr@PP and ZnPcBr@PP. In this case, ZnPcBr was easier to form aggregates than MgPcBr in the nanoparticles. These different behaviors could be attributed to the encapsulated the gold nanoparticles and curcumin into nanoparticles, which changed the micro-environment of MgPcBr and ZnPcBr, and enhanced encapsulation efficiencies of MgPcBr and ZnPcBr into nanoparticles (Table 1).
UV–vis spectra of ZnPcBr and MgPcBr in DMF and polymeric nanoparticles in water. (a) UV–vis spectra of ZnPcBr and MgPcBr(CZnPcBr and MgPcBr = 10-5 mol/L); (b) UV–vis spectra of polymeric nanoparticles in water(CZnPcBr and MgPcBr = 10-5 mol/L).
The fluorescence spectra of polymeric nanoparticles were also evidenced that the encapsulated of ZnPcBr/MgPcBr, Aus and curcumin into nanoparticles (Fig. 3). Compared with the emission spectra of ZnPcBr@PP and MgPcBr@PP, the emission spectra of MgPcBr/Cur/Au@PP and ZnPcBr/Cur/Au@PP were red-shifted. This result indicated that there is an interaction between the Cur and Aus with MgPcBr or ZnPcBr in polymeric nanoparticles. Compared with ZnPcBr@PP, the fluorescence intensity of ZnPcBr/Cur/Au@PP was enhanced, while the fluorescence intensity of MgPcBr/Cur/Au@PP was quenched compared with MgPcBr@PP.
Fluorescence spectra of ZnPcBr and MgPcBr in DMF and polymeric nanoparticles in water (λex = 610 nm).
According to the above UV/Vis spectra and fluorescence spectra, we proposed the micro-environments of nanoparticles affected the photophysical properties of MgPcBr and ZnPcBr. MgPcBr/Cur/Au@PP, MgPcBr mainly dispersed on the surface of gold nanoparticles through Au-S bonds, therefore, it existed as a monomer in UV/Vis spectra (Fig. 2). While for ZnPcBr/Cur/Au@PP, although ZnPcBr dispersed on the surface of gold nanoparticles through Au-S bonds, d orbitals of Zn(II) central ions of ZnPcBr could coordinate with the bromine/sulfurate/ligands of other ZnPcBr molecules to form face-to face slide dimmers, which aggravated the aggregation of ZnPcBr in the nanoparticles.
Meantime, the fluorescence spectra of free MgPcBr and ZnPcBr and polymeric nanoparticles were showed in Fig. 3. Fluorescence emission peak was observed at 697 nm and 696 nm for ZnPcBr and MgPcBr upon excitation at 619 nm, respectively. The fluorescence intensity of ZnPcBr is higher than that of MgPcBr. When ZnPcBr /MgPcBr was encapsulated into nanoparticles, the intensity of fluorescence of ZnPcBr@PP was greatly quenched, while the intensity of fluorescence of MgPcBr@PP was increased. If we further introducted the Cur and Aus into nanopaticles, the fluorescence emissions of MgPcBr/Cur/Au@PP and ZnPcBr/Cur/Au@PP were red-shift to about 725 nm. An obviously quenched fluorescence intensity was observed for MgPcBr/Cur/Au@PP compared with MgPcBr@PP. However an increased fluorescence intensity for ZnPcBr/Cur/Au@PP was found. Therefore, we concluded that the Cur increased the encapsulation ratio of ZnPcBr/MgPcBr in nanoparticles through solubilization effect while the Aus reduced the aggregation of ZnPcBr/MgPcBr in nano-particles through Au-S bonds. Meanwhile, Aus could quench the fluorescence of ZnPcBr/ MgPcBr to some extent.
The fluorescence decay curves of polymeric nanoparticles were shown in Fig. 4. The fluorescence lifetimes of MgPcBr and ZnPcBr in THF was found to be 6.87 ns and 3.26 ns in DMF, respectively. While fluorescence lifetimes of MgPcBr@PP and ZnPcBr@PP were found to be 5.68 ns and 2.80 ns, which were somewhat shorter than those of the free MgPcBr and ZnPcBr. When the gold nanoparticles and curcumin were further introduced into the nanoparticles, the fluorescence lifetimes of MgPcBr/Cur/Au@PP and ZnPcBr/Cur/Au@PP were further decreased to 1.89 ns and 0.89 ns, repectively. The lifetimes of MgPcBr/Cur/Au@PP and ZnPcBr/Cur/Au@PP were shorter than those of the MgPcBr@PP and ZnPcBr@PP. It could be due to the existence of gold nanoparticles and curcumin in the polymeric nanoparticles, which would quench the fluorescence of the MgPcBr and ZnPcBr through either aggregation or fluorescence resonance energy transfer pathways.
Fluorescence decay curves of ZnPcBr and MgPcBr in DMF and polymeric nanoparticles in water (λex = 405 nm).
The elemental compositions of the polymeric nanoparticles were qualitatively determined using an Energy Dispersive X-ray Spectrometer (EDS) (Fig. 5). These results also evidenced the polymeric nanoparticle co-loaded three components, tetra- ZnPcBr and MgPcBr, Aus and curcumin. The EDS spectra of the MgPcBr@PP and ZnPcBr@PP showed the presence of S, Br, C and Mg or Zn elements, which were the elements of molecule of MgPcBr or ZnPcBr. Moreover, the EDS spectra of the Au@PP and Cur@PP showed the presence of only Au, C, which were the elements of gold particles and curcumin. Upon co-loading three components, gold particles, curcumin and ZnPcBr and MgPcBr into the polymeric micelles, the EDS spectra of MgPcBr/Cur/Au@PP and ZnPcBr/Cur/Au@PP displayed the elements of S, Br, C and Mg or Zn as well as Au.
X-ray spectrometer (EDS) analysis of polymeric nanoparticles.
3.3 Singlet oxygen production ability of polymeric nanoparticles
In order to determine the singlet oxygen quantum yield (ФΔ), the chemical photodegradation of the 9, 10-antracenediyl-bis (methylene) dimalonoic acid (ABDA) in water was monitored (Fig. 6). ABDA was degraded when it reacted with single oxygen which was produced by nanoparticle upon irradiation. The ФΔ values of polymeric nanoparticles were shown in Table 1. The ФΔ values of polymeric nanoparticles were relatively low in water, probably due to the fluorescence of ZnPcBr /MgPcBr was quenched either by the formed aggregation or quenched by gold nanoparticles in of polymeric nanoparticles microenvironment. The ФΔ value of ZnPcBr/Cur/Au@PP was found to 0.02, which is the highest in these nanoparticles.
The absorption spectra of 9,10-antracenediyl-bis (methylene) dimalonoic acid (ABDA) containing polymeric nanoparticles with irradiation at 670 nm.
4 Conclusion
The curcumin, MgPcBr or ZnPcBr and Aus were co-loaded into a copolymer micelle to obtain two novel polymeric nanoparticles. UV–vis spectra, TEM images, DLS as well as EDS evidenced the formation of polymer nanoparticles containing three components. The results suggested that the co-loading of gold nanoparticles and curcumin could change the microenvironment of polymeric nanoparticles and affect the photophysical properties of MgPcBr or ZnPcBr and then enhanced the encapsulation efficiencies of MgPcBr and ZnPcBr into nanoparticles. The three components encapsulated nanoparticles provided a new approach to enhance the singlet oxygen quantum yield as well as the encapsulation ratio of polymeric nanoparticles.
Acknowledgments
This study was supported by the National Key Basic Research Program of China (973 project) (2015CB352006), National Natural Science Foundation of China (21274021,61475036), the Natural Science Foundation of Fujian (2019Y0007, 2018J01814), the Joint Funds of Fujian Provincial Health and Education Research (2019-WJ-23), Scientific research innovation team construction program of Fujian Normal University (IRTL 1702). Special funds of the Central Government Guiding Local Science and Technology Development (2017L3009) and Science and Technology Program of Fuzhou (2017-G-77).
Declaration of Competing Interest
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
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Appendix A
Supplementary material
Supplementary data to this article can be found online at https://doi.org/10.1016/j.arabjc.2021.103023.
Appendix A
Supplementary material
The following are the Supplementary data to this article:
