A computational study on the usability of amino acid-functionalised nitrogen-doped graphene oxides as temperature-responsive drug delivery systems

References

• Siegel RL, Miller KD, Jemal A. (2015). Cancer statistics, 2015. CA Cancer J Clin 65:5–29.
   PubMed Web of Science ®Google Scholar
• Luo Z, Ding X, Hu Y, et al. (2013). Engineering a hollow nanocontainer platform with multifunctional molecular machines for tumor-targeted therapy in vitro and in vivo. ACS Nano 7:10271–84.
   Google Scholar
• Zhao F, Zhao Y, Liu Y, et al. (2011). Cellular uptake, intracellular trafficking, and cytotoxicity of nanomaterials. Small 7:1322–37.
   PubMed Web of Science ®Google Scholar
• Gurunathan S, Kim J-H. (2016). Synthesis, toxicity, biocompatibility, and biomedical applications of graphene and graphene-related materials. Int J Nanomedicine 11:1927–45.
   PubMed Web of Science ®Google Scholar
• Yang K, Feng L, Liu Z. (2016). Stimuli responsive drug delivery systems based on nano-graphene for cancer therapy. Adv Drug Deliv Rev 105:228–41.
   PubMed Web of Science ®Google Scholar
• Nergiz SZ, Gandra N, Tadepalli S, Singamaneni S. (2014). Multifunctional hybrid nanopatches of graphene oxide and gold nanostars for ultraefficient photothermal cancer therapy. ACS Appl Mater Interf 6:16395–402.
   PubMed Web of Science ®Google Scholar
• Zhang B, Wang Y, Zhai G. (2016). Biomedical applications of the graphene-based materials. Mater Sci Eng C Mater Biol Appl C 61:953–64.
   PubMed Web of Science ®Google Scholar
• Thomas RG, Moon M, Lee S, Jeong YY. (2015). Paclitaxel loaded hyaluronic acid nanoparticles for targeted cancer therapy: in vitro and in vivo analysis. Int J Biol Macromol 72:510–18.
   PubMed Web of Science ®Google Scholar
• Shim G, Kim M-G, Park JY, Oh Y-K. (2016). Graphene-based nanosheets for delivery of chemotherapeutics and biological drugs. Adv Drug Deliv Rev 105:205–27.
   PubMed Web of Science ®Google Scholar
• Kim M-G, Shon Y, Miao W, et al. (2016). Biodegradable graphene oxide and polyaptamer DNA hybrid hydrogels for implantable drug delivery. Carbon N Y 105:14–22.
   Web of Science ®Google Scholar
• Kiew SF, Kiew LV, Lee HB, et al. (2016). Assessing biocompatibility of graphene oxide-based nanocarriers: A review. J Control Release 226:217–28.
   PubMed Web of Science ®Google Scholar
• Yang H, Bremner DH, Tao L, et al. (2016). Carboxymethyl chitosan-mediated synthesis of hyaluronic acid-targeted graphene oxide for cancer drug delivery. Carbohydr Polym 135:72–8.
   PubMed Web of Science ®Google Scholar
• Gao P, Liu M, Tian J, et al. (2016). Improving the drug delivery characteristics of graphene oxide based polymer nanocomposites through the “one-pot” synthetic approach of single-electron-transfer living radical polymerization. Appl Surf Sci 378:22–9.
   Web of Science ®Google Scholar
• Pan Q, Lv Y, Williams GR, et al. (2016). Lactobionic acid and carboxymethyl chitosan functionalized graphene oxide nanocomposites as targeted anticancer drug delivery systems. Carbohydr Polym 151:812–20.
   PubMed Web of Science ®Google Scholar
• Xie M, Lei H, Zhang Y, et al. (2016). Non-covalent modification of graphene oxide nanocomposites with chitosan/dextran and its application in drug delivery. RSC Adv 6:9328–37.
   Web of Science ®Google Scholar
• Tian J, Luo Y, Huang L, et al. (2016). Pegylated folate and peptide-decorated graphene oxide nanovehicle for in vivo targeted delivery of anticancer drugs and therapeutic self-monitoring. Biosens Bioelectron 80:519–24.
   PubMed Web of Science ®Google Scholar
• Yu H, Yang P, Jia Y, et al. (2016). Regulation of biphasic drug release behavior by graphene oxide in polyvinyl pyrrolidone/poly(ɛ-caprolactone) core/sheath nanofiber mats. Coll Surf B Biointerf 146:63–9.
   PubMed Web of Science ®Google Scholar
• Kim JO, Thapa RK, Choi JY, et al. (2016). Receptor-targeted, drug-loaded, functionalized graphene oxides for chemotherapy and photothermal therapy. Int J Nanomed 11:2799–813.
   PubMed Web of Science ®Google Scholar
• Jiang T, Sun W, Zhu Q, et al. (2015). Furin-mediated sequential delivery of anticancer cytokine and small-molecule drug shuttled by graphene. Adv Mater 27:1021–8.
   PubMed Web of Science ®Google Scholar
• Hu Q, Sun W, Wang C, Gu Z. (2016). Recent advances of cocktail chemotherapy by combination drug delivery systems. Adv Drug Deliv Rev 98:19–34.
   PubMed Web of Science ®Google Scholar
• Guo L, Shi H, Wu H, et al. (2016). Prostate cancer targeted multifunctionalized graphene oxide for magnetic resonance imaging and drug delivery. Carbon N Y 107:87–99.
   Web of Science ®Google Scholar
• Siriviriyanun A, Popova M, Imae T, et al. (2015). Preparation of graphene oxide/dendrimer hybrid carriers for delivery of doxorubicin. Chem Eng J 281:771–81.
   Web of Science ®Google Scholar
• Xu H, Fan M, Elhissi AM, et al. (2015). PEGylated graphene oxide for tumor-targeted delivery of paclitaxel. Nanomedicine 10:1247–62.
   Google Scholar
• Nasrollahi F, Varshosaz J, Khodadadi AA, et al. (2016). Targeted delivery of docetaxel by use of transferrin/poly(allylamine hydrochloride)-functionalized graphene oxide nanocarrier. ACS Appl Mater Interf 8:13282–93.
   PubMed Web of Science ®Google Scholar
• Wei Y, Zhou F, Zhang D, et al. (2016). A graphene oxide based smart drug delivery system for tumor mitochondria-targeting photodynamic therapy. Nanoscale 8:3530–8.
   PubMed Web of Science ®Google Scholar
• An B, Lin Y-S, Brodsky B. (2016). Collagen interactions: drug design and delivery. Adv Drug Deliv Rev 97:69–84.
   PubMed Web of Science ®Google Scholar
• Ramezanpour M, Leung SSW, Delgado-Magnero KH, et al. (2016). Computational and experimental approaches for investigating nanoparticle-based drug delivery systems. Biochim Biophys Acta 1858:1688–709.
   PubMed Web of Science ®Google Scholar
• Barnard AS. (2016). Challenges in modelling nanoparticles for drug delivery. J Phys Condens Matter 28:023002.
   PubMed Web of Science ®Google Scholar
• Groh CM, Hubbard ME, Jones PF, et al. (2014). Mathematical and computational models of drug transport in tumours. J R Soc Interface 11:20131173.
   PubMed Web of Science ®Google Scholar
• Ahmed S, Vepuri SB, Kalhapure RS, et al. (2016). Interactions of dendrimers with biological drug targets: reality or mystery – a gap in drug delivery and development research. Biomater Sci 4:1032–50.
   PubMed Web of Science ®Google Scholar
• Grebner C, Iegre J, Ulander J, et al. (2016). Binding mode and induced fit predictions for prospective computational drug design. J Chem Inf Model 56:774–87.
   PubMed Web of Science ®Google Scholar
• Shi C, Yuan D, Nangia S, et al. (2014). A structure–property relationship study of the well-defined telodendrimers to improve hemocompatibility of nanocarriers for anticancer drug delivery. Langmuir 30:6878–88.
   PubMed Web of Science ®Google Scholar
• Shi C, Guo D, Xiao K, et al. (2015). A drug-specific nanocarrier design for efficient anticancer therapy. Nat Commun 6:7449.
   PubMed Web of Science ®Google Scholar
• Liu J-Q, Li X-F, Gu C-Y, et al. (2015). A combined experimental and computational study of novel nanocage-based metal-organic frameworks for drug delivery. Dalt Trans 44:19370–82.
   PubMed Web of Science ®Google Scholar
• Barraza LF, Jiménez VA, Alderete JB. (2015). Effect of PEGylation on the structure and drug loading capacity of PAMAM-G4 dendrimers: a molecular modeling approach on the complexation of 5-fluorouracil with native and PEGylated PAMAM-G4. Macromol Chem Phys 216:1689–701.
   Web of Science ®Google Scholar
• Mohammed AAK, Burger SK, Ayers PW. (2014). Drug release by pH-responsive molecular tweezers: atomistic details from molecular modeling. J Comput Chem 35:1545–51.
   PubMed Web of Science ®Google Scholar
• Metwally AA, Hathout RM. (2015). Computer-assisted drug formulation design: novel approach in drug delivery. Mol Pharm 12:2800–10.
   PubMed Web of Science ®Google Scholar
• Kavousanakis ME, Kalogeropoulos NG, Hatziavramidis DT. (2014). Computational modeling of drug delivery to the posterior eye. Chem Eng Sci 108:203–12.
   Web of Science ®Google Scholar
• Stanzione F, Jayaraman A. (2015). Computational design of oligopeptide containing poly(ethylene glycol) brushes for stimuli-responsive drug delivery. J Phys Chem B 119:13309–20.
   PubMed Web of Science ®Google Scholar
• Duncan GA, Bevan MA, Brannon-Peppas L, et al. (2015). Computational design of nanoparticle drug delivery systems for selective targeting. Nanoscale 7:15332–40.
   PubMed Web of Science ®Google Scholar
• Geetha P, Sivaram AJ, Jayakumar R, Gopi Mohan C. (2016). Integration of in silico modeling, prediction by binding energy and experimental approach to study the amorphous chitin nanocarriers for cancer drug delivery. Carbohydr Polym 142:240–9.
   PubMed Web of Science ®Google Scholar
• Fahrenholtz SJ, Moon TY, Franco M, et al. (2015). A model evaluation study for treatment planning of laser-induced thermal therapy. Int J Hyperth 31:705–14.
   PubMed Web of Science ®Google Scholar
• Trujillo M, Bon J, José Rivera M, et al. (2016). Computer modelling of an impedance-controlled pulsing protocol for RF tumour ablation with a cooled electrode. Int J Hyperth 32:931–9.
   PubMed Web of Science ®Google Scholar
• Singh S, Repaka R. (2017). Temperature-controlled radiofrequency ablation of different tissues using two-compartment models. Int J Hyperth 33:122–34.
   PubMed Web of Science ®Google Scholar
• Deshazer G, Prakash P, Merck D, Haemmerich D. (2017). Experimental measurement of microwave ablation heating pattern and comparison to computer simulations. Int J Hyperth 33:74–82.
   PubMed Web of Science ®Google Scholar
• Wei Q, Tong X, Zhang G, et al. (2015). Nitrogen-doped carbon nanotube and graphene materials for oxygen reduction reactions. Catalysts 5:1574–1602.
   Google Scholar
• Lin TT, Lv QF. (2015). Preparation and application of nitrogen-doped graphene. J Function Mater 5:7–12.
   Google Scholar
• Lu Y, Huang Y, Zhang M, Chen Y. (2014). Nitrogen-doped graphene materials for supercapacitor applications. J Nanosci Nanotechnol 14:1134–44.
   PubMed Web of Science ®Google Scholar
• Rao CNR, Gopalakrishnan K, Govindaraj A. (2014). Synthesis, properties and applications of graphene doped with boron, nitrogen and other elements. Nano Today 9:324–343.
   Web of Science ®Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, et al. (2009). Gaussian 9. Wallingford, CT: Gaussian, Inc.
   Google Scholar
• Gill PMW, Johnson BG, Pople JA, Frisch MJ. (1992). The performance of the Becke–Lee–Yang–Parr (B-LYP) density functional theory with various basis sets. Chem Phys Lett 197:499–505.
   Web of Science ®Google Scholar
• Becke AD. (1993). Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–52.
   Web of Science ®Google Scholar
• Rassolov VA, Ratner MA, Pople JA, et al. (2001). 6-31G* basis set for third-row atoms. J Comput Chem 22:976–84.
   Web of Science ®Google Scholar
• Trott O, Olson AJ. (2010). AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 31:455–61.
   PubMed Web of Science ®Google Scholar
• Morris GM, Huey R, Lindstrom W, et al. (2009). AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem 30:2785–91.
   PubMed Web of Science ®Google Scholar
• Case DA, Berryman JT, Betz RM, et al. (2012). AMBER12. San Francisco: University of California.
   Google Scholar
• Wang J, Wolf RM, Caldwell JW, et al. (2004). Development and testing of a general amber force field. J Comput Chem 25:1157–74.
   PubMed Web of Science ®Google Scholar
• Mahoney MW, Jorgensen WL. (2000). A five-site model for liquid water and the reproduction of the density anomaly by rigid, nonpolarizable potential functions. J Chem Phys 112:8910–22.
   Web of Science ®Google Scholar
• Allen MP, Tildesley DJ, Computer simulation of liquids. Oxford: Clarendon Press; 1987.
   Google Scholar
• Yoneya M, Berendsen HJC, Hirasawa K (1994). A non-iterative matrix method for constraint molecular dynamics simulations. Mol Simul 13:395–405.
   Web of Science ®Google Scholar
• Humphrey W, Dalke A, Schulten K. (1996). VMD: visual molecular dynamics. J Mol Graph 14:33–8.
   PubMed Web of Science ®Google Scholar
• Wei D, Liu Y, Wang Y, et al. (2009). Synthesis of N-doped graphene by chemical vapor deposition and its electrical properties. Nano Lett 9:1752–8.
   PubMed Web of Science ®Google Scholar
• Hildebrandt B, Wust P, Ahlers O, et al. (2002). The cellular and molecular basis of hyperthermia. Crit Rev Oncol Hematol 43:33–56.
   PubMed Web of Science ®Google Scholar
• van der Zee J. (2002). Heating the patient: a promising approach?. Ann Oncol 13:1173–84.
   PubMed Web of Science ®Google Scholar
• Yu L, Ren N, Yang K, et al. (2016). Photo/pH dual-responsive biocompatible poly(methacrylic acid)-based particles for triggered drug delivery. J Appl Polym Sci 133:44003.
   Google Scholar
• Mao J, Li Y, Wu T, et al. (2016). A simple dual-pH responsive prodrug-based polymeric micelles for drug delivery. ACS Appl Mater Interf 8:17109–17.
   PubMed Web of Science ®Google Scholar
• Zhao H, Li Q, Hong Z. (2016). Paclitaxel-loaded mixed micelles enhance ovarian cancer therapy through extracellular pH-triggered PEG detachment and endosomal escape. Am Chem Soc 13:2411–22.
   Google Scholar
• Kneepkens E, Fernandes A, Nicolay K, Grüll H. (2016). Iron(III)-based magnetic resonance–imageable liposomal T1 contrast agent for monitoring temperature-induced image-guided drug delivery. Invest Radiol 51:735–45.
   PubMed Web of Science ®Google Scholar
• Panja S, Dey G, Bharti R, et al. (2016). Tailor-made temperature-sensitive micelle for targeted and on-demand release of anticancer drugs. Am Chem Soc 8:12063–74.
   Google Scholar