Hydrophilic Surfaces Turning of Graphene Nano Platelets by 1,3,6-Trihydroxyxanthone: π–π Stacking Interaction Affair in 2-D

https://doi.org/10.22146/ijc.89894

Emmy Yuanita(1*), Sirojuttolibin Sirojuttolibin(2), Ni Komang Tri Dharmayani(3), Maria Ulfa(4), Maulida Septiyana(5), Sudirman Sudirman(6)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Mataram, Jl. Majapahit No. 62, Mataram 83115, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Mataram, Jl. Majapahit No. 62, Mataram 83115, Indonesia
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Mataram, Jl. Majapahit No. 62, Mataram 83115, Indonesia
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Mataram, Jl. Majapahit No. 62, Mataram 83115, Indonesia
(5) Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Mataram, Jl. Majapahit No. 62, Mataram 83115, Indonesia
(6) Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Mataram, Jl. Majapahit No. 62, Mataram 83115, Indonesia
(*) Corresponding Author

Abstract


Graphene nanoplatelet (GNP) has a good potential to be developed as a drug carrier material. In this study, the interaction of GNP with one type of drug, namely 1,3,6-trihydroxyxanthone (THX), has been studied. The results of XRD analysis and FTIR uptake show an excellent interaction between THX and GNP through the π–π stacking channel. This interaction makes the GNP surface more polar and soluble in the aqueous media. THX-graphene shows physical and chemical stabilities, where THX can be released under specific and controlled conditions. The results of this study show the potential of utilizing graphene as a drug carrier material for more specific disease targets with a longer drug release time.

Keywords


trihydroxyxanthones; graphene; π–π stacking; polar surfaces

Full Text:

Full Text PDF


References

[1] Wang, Y., Wang, H., Liu, F., Wu, X., Xu, J., Cui, H., Wu, Y., Xue, R., Tian, C., Zheng, B., and Yao, W., 2020, Flexible printed circuit board based on graphene/polyimide composites with excellent thermal conductivity and sandwich structure, Composites, Part A, 138, 106075.

[2] Gao, F., Liu, K., Cheng, R., and Zhang, Y., 2020, Efficiency enhancement of perovskite solar cells based on graphene-CuInS2 quantum dots composite: The roles for fast electron injection and light harvests, Appl. Surf. Sci., 528, 146560.

[3] Bu, Y., Liang, H., Gao, K., Zhang, B., Zhang, X., Shen, X., Li, H., and Zhang, J., 2020, Wafer-scale fabrication of high-purity reduced graphene oxide films as ultrahigh-frequency capacitors with minimal self-discharge, Chem. Eng. J., 390, 124560.

[4] Wang, D., Zhou, J., Li, J., Jiang, X., Wang, Y., and Gao, F., 2019, Cobalt-boron nanoparticles anchored on graphene as anode of lithium ion batteries, Chem. Eng. J., 360, 271–279.

[5] Lascano, S., Chávez-Vásconez, R., Muñoz-Rojas, D., Aristizabal, J., Arce, B., Parra, C., Acevedo, C., Orellana, N., Reyes-Valenzuela, M., Gotor, F.J., Arévalo, C., and Torres, Y., 2020, Graphene-coated Ti-Nb-Ta-Mn foams: A promising approach towards a suitable biomaterial for bone replacement, Surf. Coat. Technol., 401, 126250.

[6] Shahabi, M., and Raissi, H., 2020, Payload delivery of anticancer drug Tegafur with the assistance of graphene oxide nanosheet during biomembrane penetration: Molecular dynamics simulation survey, Appl. Surf. Sci., 517, 146186.

[7] Song, S., Shen, H., Wang, Y., Chu, X., Xie, J., Zhou, N., and Shen, J., 2020, Biomedical application of graphene: From drug delivery, tumor therapy, to theranostics, Colloids Surf., B, 185, 110596.

[8] Jafari, Z., Rad, A.S., Baharfar, R., Asghari, S., and Esfahani, M.R., 2020, Synthesis and application of chitosan/tripolyphosphate/graphene oxide hydrogel as a new drug delivery system for Sumatriptan Succinate, J. Mol. Liq., 315, 113835.

[9] Ruiyi, L., Zaijun, L., Xiulan, S., Jan, J., Lin, L., Zhiguo, G., and Guangli, W., 2020, Graphene quantum dot-rare earth upconversion nanocages with extremely high efficiency of upconversion luminescence, stability and drug loading towards controlled delivery and cancer theranostics, Chem. Eng. J., 382, 122992.

[10] Georgakilas, V., Tiwari, J.N., Kemp, K.C., Perman, J.A., Bourlinos, A.B., Kim, K.S., and Zboril, R., 2016, Noncovalent functionalization of graphene and graphene oxide for energy materials, biosensing, catalytic, and biomedical applications, Chem. Rev., 116 (9), 5464–5519.

[11] Yu, W., Sisi, L., Haiyan, Y., and Jie, L., 2020, Progress in the functional modification of graphene/graphene oxide: A review, RSC Adv., 10 (26), 15328–15345.

[12] Zhang, J., Xu, Y., Cui, L., Fu, A., Yang, W., Barrow, C., and Liu, J., 2015, Mechanical properties of graphene films enhanced by homo-telechelic functionalized polymer fillers via π–π stacking interactions, Composites, Part A, 71, 1–8.

[13] Alwarappan, S., Boyapalle, S., Kumar, A., Li, C.Z., and Mohapatra, S., 2012, Comparative study of single-, few-, and multilayered graphene toward enzyme conjugation and electrochemical response, J. Phys. Chem. C, 116 (11), 6556–6559.

[14] Haniff Wahid, M., Stroeher, U.H., Eroglu, E., Chen, X., Vimalanathan, K., Raston, C.L., and Boulos, R.A., 2015, Aqueous based synthesis of antimicrobial-decorated graphene, J. Colloid Interface Sci., 443, 88–96.

[15] Chia, J.S.Y., Tan, M.T.T., Khiew, P.S., Chin, J.K., and Siong, C.W., 2015, A bio-electrochemical sensing platform for glucose based on irreversible, non-covalent pi–pi functionalization of graphene produced via a novel, green synthesis method, Sens. Actuators, B, 210, 558–565.

[16] Georgakilas, V., Perman, J.A., Tucek, J., and Zboril, R., 2015, Broad family of carbon nanoallotropes: Classification, chemistry, and applications of fullerenes, carbon dots, nanotubes, graphene, nanodiamonds, and combined superstructures, Chem. Rev., 115 (11), 4744–4822.

[17] Yuanita, E., Pranowo, H.D., Siswanta, D., Swasono, R.T., Mustofa, M., Zulkarnain, A.K., Syahri, J., and Jumina, J., 2018, One-pot synthesis, antioxidant activity and toxicity evaluation of some hydroxyxanthones, Chem. Chem. Technol., 12 (3), 290–295.

[18] Zhang, H., Tan, Y., Zhao, L., Wang, L., Fu, N., Zheng, S., and Shen, X., 2020, Anticancer activity of dietary xanthone α-mangostin against hepatocellular carcinoma by inhibition of STAT3 signaling via stabilization of SHP1, Cell Death Dis., 11 (1), 63.

[19] Yuanita, E., Sudarma, I.M., Sudewiningsih, N.M., Syahri, J., Dharmayani, N.K.T., Sudirman, S., Ulfa, M., and Sumarlan, I., 2020, Antibacterial activity and molecular docking studies of series hydroxyxanthone, AIP Conf. Proc., 2243 (1), 020032

[20] Syahri, J., Yuanita, E., Nurohmah, B.A., Wathon, M.H., Syafri, R., Armunanto, R., and Purwono, B., 2017, Xanthone as antimalarial: QSAR analysis, synthesis, molecular docking and in-vitro antimalarial evaluation, Orient. J. Chem., 33 (1), 29–40.

[21] Vrbanac, J., and Slauter, R., 2017, “Chapter 3 - ADME in Drug Discovery” in A Comprehensive Guide to Toxicology in Nonclinical Drug Development (Second Edition), Eds. Faqi, A.S., Academic Press, Boston, US, 39–67.

[22] Kim, J., Han, J.W., and Yamada, Y., 2021, Heptagons in the basal plane of graphene nanoflakes analyzed by simulated X-ray photoelectron spectroscopy, ACS Omega, 6 (3), 2389–2395.

[23] Zhang, X.F., Liu, S.P., and Shao, X.N., 2013, Noncovalent binding of xanthene and phthalocyanine dyes with graphene sheets: The effect of the molecular structure revealed by a photophysical study, Spectrochim. Acta, Part A, 113, 92–99.

[24] Evans, I.R., Howard, J.A.K., Šavikin-Foduloviç, K., and Menković, N., 2004, Isogentisin (1,3-dihydroxy-7-methoxyxanthone), Acta Crystallogr., Sect. E:Crystallogr. Commun., 60 (9), 1557-1559.

[25] Yu, S., Wang, X., Ai, Y., Tan, X., Hayat, T., Hu, W., and Wang, X., 2016, Experimental and theoretical studies on competitive adsorption of aromatic compounds on reduced graphene oxides, J. Mater. Chem. A, 4 (15), 5654–5662.

[26] Shiva, K., Ramakrishna Matte, H.S.S., Rajendra, H.B., Bhattacharyya, A.J., and Rao, C.N.R., 2013, Employing synergistic interactions between few-layer WS2 and reduced graphene oxide to improve lithium storage, cyclability and rate capability of Li-ion batteries, Nano Energy, 2 (5), 787–793.

[27] Huber, R.G., Margreiter, M.A., Fuchs, J.E., von Grafenstein, S., Tautermann, C.S., Liedl, K.R., and Fox, T., 2014, Heteroaromatic π-stacking energy landscapes, J. Chem. Inf. Model., 54 (5), 1371–1379.

[28] Johra, F.T., Lee, J.W., and Jung, W.G., 2014, Facile and safe graphene preparation on solution based platform, J. Ind. Eng. Chem., 20 (5), 2883–2887.

[29] Janiak, C., 2000, A critical account on π–π stacking in metal complexes with aromatic nitrogen-containing ligands, J. Chem. Soc., Dalton Trans., (21), 3885–3896.

[30] Patel, C.R.P., Tripathi, P., Vishwakarma, A.K., Talat, M., Soni, P.K., Yadav, T.P., and Srivastava, O.N., 2018, Enhanced hydrogen generation by water electrolysis employing carbon nano-structure composites, Int. J. Hydrogen Energy, 43 (6), 3180–3189.

[31] Han, X., Kong, H., Chen, T., Gao, J., Zhao, Y., Sang, Y., and Hu, G., 2021, Effect of π–π stacking interfacial interaction on the properties of graphene/poly(Styrene-b-isoprene-b-styrene) composites, Nanomaterials, 11 (9), 2158.

[32] Zainal-Abidin, M.H., Hayyan, M., Ngoh, G.C., and Wong, W.F., 2020, Doxorubicin loading on functional graphene as a promising nanocarrier using ternary deep eutectic solvent systems, ACS Omega, 5 (3), 1656–1668.

[33] Guo, Y., Luo, X.P., Zhang, Z., Merabia, S., Nomura, M., and Volz, S., 2023, Basal-plane heat transport in graphite thin films, Phys. Rev. B, 107 (19), 195430.

[34] Hornsby, T.K., Kashkooli, F.M., Jakhmola, A., Kolios, M.C., and Tavakkoli, J., 2023, Kinetic modelling of ultrasound-triggered chemotherapeutic drug release from the surface of gold nanoparticles, Sci. Rep., 13 (1), 21301.

[35] Zhan, J., Lei, Z., and Zhang, Y., 2022, Non-covalent interactions of graphene surface: Mechanisms and applications, Chem, 8 (4), 947–979.

[36] Zhan, C., Cerón, M.R., Hawks, S.A., Otani, M., Wood, B.C., Pham, T.A., Stadermann, M., and Campbell, P.G., 2019, Specific ion effects at graphitic interfaces, Nat. Commun., 10 (1), 4858.

[37] Zelepukin, I.V., Griaznova, O.Y., Shevchenko, K.G., Ivanov, A.V., Baidyuk, E.V., Serejnikova, N.B., Volovetskiy, A.B., Deyev, S.M., and Zvyagin, A.V., 2022, Flash drug release from nanoparticles accumulated in the targeted blood vessels facilitates the tumour treatment, Nat. Commun., 13 (1), 6910.

[38] Fernández, A.C.R., and Castellani, N.J., 2020, Dipole moment effects in dopamine/N-doped-graphene systems, Surf. Sci., 693, 121546.



DOI: https://doi.org/10.22146/ijc.89894

Article Metrics

Abstract views : 4451 | views : 2023


Copyright (c) 2025 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.