Abstract
Nanodiamonds (NDs) have emerged as a very useful material for drug-carrier applications in nanomedicine. Herein, we prepared cisplatin-like structures on the surface of the NDs to investigate their potential use as anticancer drugs. Cis-diamminediiodoplatinum(II)-modified NDs have been prepared by the coordination of [PtI4]2− to amine-modified NDs. Subsequent halogen exchange of the iodine ligands with chloride ions resulted in the formation of cis-diamminedichloroplatinum(II)-modified NDs, 100% exchange occurred as detected by XPS analysis. Another cisplatin-like ND derivative has been constructed, where the platinum is anchored onto the NDs via an amine-capped silane linker. This was achieved by grafting (3-aminopropyl)trimethoxysilane (APTMES) onto the NDs, followed by coordination of the [PtI4]2− Pt-precursor and halogen exchange with Cl− to produce cis-diamminedichlorodoplatinum(II)-silane-modified NDs. Since the Pt is three methylene groups away from the ND support, it is more flexible to move and participate in reactions than the platinum of the cis-diamminedichloroplatinum(II)-modified NDs, which results in its improved IC50 value of 2.6 µml against HeLa cancer cells vs. the 6.5 µml of diamminedichloroplatinum(II)-modified NDs.
Similar content being viewed by others
References
Ahmed AI, Perevedentseva EV, Karmenyan A, Cheng CL (2019) Spectroscopy of nanodiamond surface: investigation and applications. In: Yang N (ed) Novel aspects of diamond: from growth to applications. Springer, Berlin, pp 363–413. https://doi.org/10.1007/978-3-030-12469-4_11
Aldossary SA (2019) Review on pharmacology of cisplatin: clinical use, toxicity and mechanism of resistance of cisplatin. Biomed Pharmacol J 12(1): 07–15. https://doi.org/10.13005/npj/1608
Andersen SM, Dhiman R, Skou E (2015) X-ray photoelectron spectroscopy investigation on electrochemical degradation of proton exchange membrane fuel cell electrodes. J Power Sources 282:87–94. https://doi.org/10.1016/j.poweour.2015.02.004
Basu A, Krishnamurthy S (2010) Cellular responses to cisplatin-induced DNA damage. J Nucleic Acids 2010:1–16
Benson SW (1965) III - Bond energies. J Chem Educ 42(9):502. https://doi.org/10.1021/ed042p502
Botha E, Landman M, van Rooyen PH, Erasmus E (2018) Electronic properties of ferrocenyl-terpyridine coordination complexes: an electrochemical and X-ray photoelectron spectroscopic approach. Inorg Chim Acta 482: 514–521. http://linkinghub.elsevier.com/retrieve/pii/S0020169317318029
Butler JS, Sadler PJ (2013) Targeted delivery of platinum-based anticancer complexes. Curr Opin Chem Biol 17(2):175–188. https://doi.org/10.1016/j.cbpa.2013.01.004
Canaria CA et al (2002) Characterization of the carbon–silicon stretch in methylated porous silicon—observation of an anomalous isotope shift in the FTIR spectrum. Inorg Chem Commun 5(8):560–564. https://doi.org/10.1016/S1387-7003(02)00465-3
Chen Q et al (2018) Platinum(iv) prodrugs with long lipid chains for drug delivery and overcoming cisplatin resistance. Chem Commun 54(42):536–537. https://doi.org/10.1039/C8CC02791A
Cleare MJ, Hoeschele JD (1973) Studies on the antitumor activity of group VIII transition metal complexes. Part I. Platinum (II) complexes. Bioinorg Chem 2(3):187–210
Dai Z, Wang Z (2020) Photoactivatable platinum-based anticancer drugs: mode of photoactivation and mechanism of action. Molecules 25(21):5167. https://doi.org/10.3390/molecules25215167
Dasari S, Tchounwou PB (2014) Cisplatin in cancer therapy: molecular mechanisms of action. Eur J Pharmacol 740:364–378. https://doi.org/10.1016/j.ejphar.2014.07.025
Dhar S, Kolishetti N, Lippard SJ, Farokhzad OC (2011) Targeted delivery of a cisplatin prodrug for safer and more effective prostate cancer therapy in vivo. Proc Natl Acad Sci 108(5):1850–1855. https://doi.org/10.1073/pnas.1011379108
Dhara SC (1970) A rapid method for the synthesis of cis-[Pt(NH3)2Cl2]. Indian J Chem 8:193
Dolmatov VYu (2007) Corrections to the article by VYu Dolmatov ‘detonation synthesis nanodiamonds: synthesis, structure, properties and applications.’ Russ Chem Rev 76:339–360
Erasmus E (2018) X-ray photoelectron spectroscopy: charge transfer in fe 2p peaks and inner-sphere reorganization of ferrocenyl-containing chalcones. J Electron Spectrosc Relat Phenom 223:84–88. https://doi.org/10.1016/j.elspec.2018.01.004
Faklaris O et al (2008) Detection of single photoluminescent diamond nanoparticles in cells and study of the internalization pathway. Small 4(12):2236–2239. https://doi.org/10.1002/smll.200800655
Fokin AA, Schreiner PR (2009) Band gap tuning in nanodiamonds: first principle computational studies. Mol Phys 107(8–12):823–830
Gabizon A (2001) Stealth liposomes and tumor targeting: one step further in the quest for the magic bullet. Clin Cancer Res Off J Am Assoc Cancer Res 7:223–225
Gerber SJ, Erasmus E (2018a) Electronic effects of metal hexacyanoferrates: an XPS and FTIR study. Mater Chem Phys 203:73–81. https://doi.org/10.1016/j.matchemphys.2017.09.029
Gerber SJ, Erasmus E (2018) Surfactant-stabilized nano-metal hexacyanoferrates with electrocatalytic and heterogeneous catalytic applications. Transit Met Chem 43(5):409–420. https://doi.org/10.1007/s11243-018-0228-2
Ghosh S (2019) Cisplatin: the first metal based anticancer drug. Bioorganic Chem 88:102925. https://doi.org/10.1016/j.bioorg.2019.102925
Guan B, Zou F, Zhi J (2010) Nanodiamond as the PH-responsive vehicle for an anticancer drug. Small 6(14):1514–1519. https://doi.org/10.1002/smll.200902305
Gulaczyk I et al (2020) The NH 2 scissors band of methylamine. Can J Phys 98(6):560–566. https://doi.org/10.1139/cjp-2019-0469
Heacock RA, Marion L (1956) The infrared spectra of secondary amines and their salts. Can J Chem 34(12):1782–1795
Kang X et al (2015) Advances in drug delivery system for platinum agents based combination therapy. Cancer Biol Med 12(4):362–374
Karasawa T, Steyger PS (2015) An integrated view of cisplatin-induced nephrotoxicity and ototoxicity. Toxicol Lett 237(3):219–227. https://doi.org/10.1016/j.toxlet.2015.06.012
Kenny RG, Chuah SW, Crawford A, Marmion CJ (2017) Platinum(IV) prodrugs - a step closer to Ehrlich’s vision? Eur J Inorg Chem 12:1596–1612. https://doi.org/10.1002/ejic.201601278
Kopecek J (2000) HPMA copolymer–anticancer drug conjugates: design, activity, and mechanism of action. Eur J Pharm Biopharm 50(1):61–81. https://doi.org/10.1016/s0939-6411(00)00075-8
Krueger A (2008) The structure and reactivity of nanoscale diamond. J Mater Chem 18(13):1485. https://doi.org/10.1039/b716673g
Lee ES, Na K, Bae YH (2005) Doxorubicin loaded PH-sensitive polymeric micelles for reversal of resistant MCF-7 tumor. J Control Release 103(2):405–418. https://doi.org/10.1016/j.jconrel.2004.12.018
Li X, Liu Y, Tian H (2018) Current developments in Pt(IV) prodrugs conjugated with bioactive ligands. Bioinorg Chem Appl 2018:1–18. https://doi.org/10.1155/2018/8276139
Li C et al (2019) Recent progress in drug delivery. Acta Pharm Sin B 9(6):1145–1162. https://doi.org/10.1016/j.apsb.2019.08.003
Lin-Vien D, Colthup N, Fateley W, Grasselli J (1991) The handbook of infrared and raman characteristic frequencies of organic molecules. Elsevier, Amsterdam
Martinho N, Santos TCB, Florindo HF, Silva LC (2019) Cisplatin-membrane interactions and their influence on platinum complexes activity and toxicity. Front Physiol 9. https://doi.org/10.3389/fphys.2018.01898/full
Mochalin VN et al (2011) Covalent incorporation of aminated nanodiamond into an epoxy polymer network. ACS Nano 5(9):7494–7502. https://doi.org/10.1021/nn2024539
Mochalin VN, Shenderova O, Ho D, Gogotsi Y (2012) The properties and applications of nanodiamonds. Nat Nanotechnol 7(1):11–23. https://doi.org/10.1038/nnano.2011.209
Morenc M et al (2017) Detonation nanodiamond particles modified by non-steroidal anti-inflammatory drugs in vitro examination. Eng Biomater 20(140):12–20
Moreno-Castilla C, López-Ramón MV, Carrasco-Marı́n F (2000) Changes in surface chemistry of activated carbons by wet oxidation. Carbon 38(14):1995–2001. https://doi.org/10.1016/S0008-6223(00)00048-8
Mu W, Chu Q, Liu Y, Zhang N (2020) A review on nano-based drug delivery system for cancer chemoimmunotherapy. Nano-Micro Lett 12(1):142. https://doi.org/10.1007/s40820-020-00482-6
Neburkova J, Vavra J, Cigler P (2017) Coating nanodiamonds with biocompatible shells for applications in biology and medicine. Curr Opin Solid State Mater Sci 21(1):43–53. https://doi.org/10.1016/j.cossms.2016.05.088
Nishiyama N et al (2003) Novel cisplatin-incorporated polymeric micelles can eradicate solid tumors in mice. Cancer Res 63:8977–8983
OHChoi TCK (2010) Comparison between SiOC thin film by plasma enhance chemical vapor deposition and sio2 thin film by fourier transform infrared spectroscopy. J Korean Phys Soc 56(4):1150–1155. https://doi.org/10.3938/jkps.56.1150
Parrott LK, Erasmus E (2018) Metal hexacyanometallate nanoparticles: spectroscopic investigation on the influence of oxidation state of metals on catalytic activity. Catal Lett 148(7):2008–2018. https://doi.org/10.1007/s10562-018-2411-7
Patra JK et al (2018) Nano based drug delivery systems: recent developments and future prospects. J Nanobiotechnol 16(1):71. https://doi.org/10.1186/s12951-018-0392-8
Perevedentseva E et al (2013) Nanodiamond internalization in cells and the cell uptake mechanism. J Nanopart Res 15(8):1834. https://doi.org/10.1007/s11051-013-1834-8
Qasim M, Lim DJ, Park H, Na D (2014) Nanotechnology for diagnosis and treatment of infectious diseases. J Nanosci Nanotechnol 14(10): 7374–7387. https://doi.org/10.1166/jnn.2014.9578
Rakha SA et al (2014) Comparison of mechanical properties of acid and UV Ozone treated nanodiamond epoxy nanocomposites. J Mater Sci Technol 30(8): 753–758. https://doi.org/10.1016/j.jmst.2013.12.011
Rauti R et al (2019) Properties and behavior of carbon nanomaterials when interfacing neuronal cells: how far have we come? Carbon 143: 430–446. https://doi.org/10.1016/j.carbon.2018.11.026
Santiago D et al (2012) Platinum electrodeposition on unsupported carbon nano-onions. Langmuir 28(49):17202–17210. https://doi.org/10.1021/la3031396
Shenderova OA, McGuire GE (2015) Science and engineering of nanodiamond particle surfaces for biological applications (review). Biointerphases 10(3):030802. https://doi.org/10.1116/1.4927679
Stewart JE (1959) Vibrational spectra of primary and secondary aliphatic amines. J Chem Phys 30(5):1259–1265. https://doi.org/10.1063/1.1730168
Tanida S et al (2012) Mechanisms of cisplatin-induced apoptosis and of cisplatin sensitivity: Potential of BIN1 to act as a potent predictor of cisplatin sensitivity in gastric cancer treatment. Int J Surg Oncol 2012:1–8. https://doi.org/10.1155/2012/862879
Vaijayanthimala V et al (2015) Nanodiamond-mediated drug delivery and imaging: challenges and opportunities. Expert Opin Drug Deliv 12(5):735–749
Vichai V, Kirtikara K (2006) Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat Protoc 1(3):1112–1116
Wang D, Lippard SJ (2005) Cellular processing of platinum anticancer drugs. Nat Rev Drug Discov 4(4):307–320. https://doi.org/10.1038/nrd1691
Xing Y, Dai L (2009) Nanodiamonds for nanomedicine. Nanomedicine 4(2):207–218. https://doi.org/10.2217/17435889.4.2.207
Zhang Y, Rhee KY, Hui D, Park SJ (2018) A critical review of nanodiamond based nanocomposites: synthesis, properties and applications. Compos Part B: Eng 143:19–27. https://doi.org/10.1016/j.compositesb.2018.01.028
Zhao Li et al (2014) Platinum on nanodiamond: a promising prodrug conjugated with stealth polyglycerol, targeting peptide and acid-responsive antitumor drug. Adv Funct Mater 24(34):5348–5357. https://doi.org/10.1002/adfm.201304298
Acknowledgements
The author would like to acknowledge generous financial support from the National Nanoscience Postgraduate Teaching and Training Platform, Sasol, the NRF and UFS during this study.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors have no conflicts of interest to declare.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Fiekkies, J.T.R., Fourie, E. & Erasmus, E. Cisplatin-functionalized nanodiamonds: preparation and characterization, with potential antineoplastic application. Appl Nanosci 11, 2235–2245 (2021). https://doi.org/10.1007/s13204-021-01955-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13204-021-01955-9