Abstract
An aspirin-ligated cisplatin derivative, biasplatin, was prepared from acetylsalicylic anhydride and oxoplatin in DMF. Biasplatin was synthesized from oxoplatin and aspirin anhydride as starting materials by a substitution reaction of hydroxo leaving groups in its axial position. The obtained biasplatin was fully characterized by FTIR, 1HNMR, 13CNMR, and ESI mass spectroscopy. Biasplatin entrapped into MIL-101(Fe) by suspended in DMF and stirring for 72 h at ambient temperature, known as biasplatin@MIL-101(Fe). The slow release of biasplatin and biasplatin@MIL-101(Fe) was conducted in PBS solution pH 7.20, 37 °C as media and measured by UV–Vis spectrophotometer. The release of biasplatin without loaded into MIL-101(Fe) is persistent for 3%, and biasplatin@MIL-101(Fe) is 0.05% over 72 h. A significant slow release of biasplatin@MIL-101(Fe) only 1% compared with time release of biasplatin without loaded into MIL-101(Fe).
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References
Adkins D, Ley J, Michel L, Wildes TM, Thorstad W, Gay HA, Daly M, Rich J, Paniello R, Uppaluri R, Jackson R, Trinkaus K, Nussenbaum B (2016) nab-Paclitaxel, cisplatin, and 5-fluorouracil followed by concurrent cisplatin and radiation for head and neck squamous cell carcinoma. Oral Oncol 61:1–7. https://doi.org/10.1016/j.oraloncology.2016.07.015
Ahmad Z, Majeed S, Shah A (2018) In vitro release and cytocoxicity of cisplatin loaded methoxy poly (ethylene glycol)-block-poly (glutaminc acid) nanoparticles against human breast cancer cell lines. J Drug Deliv Sci Technol 43:85–93. https://doi.org/10.1016/j.jddst.2017.09.016
Alderden RA, Hall MD, Hambley TW (2006) The discovery and development of cisplatin. J Chem Educ 83:728–734. https://doi.org/10.1021/ed083p728
Amable L (2016) Cisplatin resistance and opportunities for precision medicine. Pharmacol Res 106:27–36. https://doi.org/10.1016/j.phrs.2016.01.001
Anon (n.d.) Promega (online) https://www.promega.de/resources/product-guides-and-selectors/protocols-and-applications-guide/buffers-for-biochemical-reactions/. Accessed 15 Nov 2017
Arafath A, Adam F, Razali MR, Hassan LEA, Ahamed MBK, Majid AMSA (2017) Synthesis, characterization and anticancer studies of Ni(II), Pd(II) and Pt(II) complexes with Schiff base derived from N-methylhydrazinecarbothioamide and 2-hydroxy-5-methoxy-3-nitrobenzaldehyde. J Mol Struct 1130:791–798. https://doi.org/10.1016/j.molstruc.2016.10.099
Budd JS, Allen K, Walsh A, Bell PRF (1993) The effectiveness of low dose slow release aspirin as an antiplatelet agent. J R Soc Med 86:261–263
Catanzaro D, Nicolosi S, Cocetta V, Salvalaio M, Pagetta A, Ragazzi E, Montopoli M, Pasut G (2018) Cisplatin liposome and 6-amino nicotinamide combination to overcome drug resistance in ovarian cancer cells. Oncotarget 9:16847–16860. https://doi.org/10.18632/oncotarget.24708
Cheng Q, Shi H, Wang H, Min Y, Wang J, Liu Y (2014) The ligation of aspirin to cisplatin demonstrates significant synergistic effects on tumor cells. Chem Commun 50:7427–7480. https://doi.org/10.1039/c4cc00419a
Cheng Q, Shi H, Wang H, Wang J, Liu Y (2016) Asplatin enhances drug efficacy by altering the cellular response. Metallomics 8:672–678. https://doi.org/10.1039/c6mt00066e
Clissold SP (1986) Aspirin and related derivatives of salicylic acid. ADIS Drug Information Service, Auckland
Escola A, Crespo M, Lopez C, Quirante J, Jayaraman A, Polat IH, Badia J, Baldoma L, Cascante M (2016) On the stability and biological behaviour of cyclometallated Pt(IV) complexes with halido and aryl ligands in the axial positions. Bioorg Med Chem 24:5804–5815. https://doi.org/10.1016/j.bmc.2016.09.037
Filippousi M, Turner S, Leus K, Siafaka PI, Tseligka ED, Vandichel M, Nanaki SG, Vizirianakis IS, Bikiaris DN, Van Der Voort P, Van Tendeloo G (2016) Biocompatible Zr-based nanoscale MOFs coated with modified poly (ε-caprolactone) as anticancer drug carriers. Int J Pharm 509:208–218. https://doi.org/10.1016/j.ijpharm.2016.05.048
Fu Q, Xu J, Ladewig K, Henderson TMA, Qiao GG (2015) Degradable cross-linked polymer vesicles for the efficient delivery of platinum drugs. Polym Chem 6:35–44. https://doi.org/10.1039/c4py01123f
He C, Lu K, Liu D, Lin W (2014) Nanoscale metal-organic frameworks for the co-delivery of cisplatin and pooled siRNAs to enhance therapeutic efficacy in drug-resistant ovarian cancer cells. J Am Chem Soc 136:5181–5184. https://doi.org/10.1021/ja4098862
He C, Liu D, Lin W (2015) Self-assembled nanoscale coordination polymers carrying siRNA and cisplatin for effective treatment of resistant ovarian cancer. Biomaterials 36:124–133. https://doi.org/10.1016/j.biomaterials.2014.09.017
Horcajada P, Serre C, Vallet-Regí M, Sebban M, Taulelle F, Férey G (2006) Metal-organic frameworks as efficient materials for drug delivery. Angew Chem Int Ed 45:5974–5978. https://doi.org/10.1002/anie.2006.01878
Jing Y, Haitao X, Jingsi Q, Zhen-liang X (2016) Layered metal-organic framework [Zn2(bpda)(chdc2)]∝ for aqueous encapsulation and sensitization of visible-emitting rare-earth cations. Mater Lett 168:203–206. https://doi.org/10.1016/j.matlet.2016.01.080
Juhász M, Takahashi S, Fujii T (2011) Temperature-resolved thermal analysis of cisplatin by evolved gas analysis-mass spectrometry. J Anal Appl Pyrolysis 91:114–118. https://doi.org/10.1016/j.jaap.2011.01.009
Lestari WW, Arvinawati M, Martien R, Kusumaningsih T (2018) Green and facile synthesis of MOF and nano MOF containing zinc(II) and benzen 1,3,5-tri carboxylate and its study in ibuprofen slow-release. J Matchemphys 204:141–162. https://doi.org/10.1016/j.matchemphys.2017.10.034
Liu Y, Shi H, Min Y, Cheng Q (2013) Preparation method of complex of aspirin-platinum for treating tumor. PatentPak CN 102942594 A 20130227
Liu D, Lu K, Poon C, Lin W (2014) Metal-Organic frameworks as sensory materials and imaging agents. Inorg Chem 53:1916–1924. https://doi.org/10.1021/ic402194c
Mocniak KA, Kubajewska I, Spilllane DEM, Williams GR, Morris RE (2015) Incorporation of cisplatin into the metal-organic frameworks UiO66-NH2 and UiO66–encapsulation vs conjugation. RSC Adv 5:83648–83656. https://doi.org/10.1039/c5ra14011k
Otera J (2003) Esterification. Methods, reactions and applications. Wiley, Weinheim
Pathak RK, Marrache S, Choi JH, Berding TB, Dhar S (2014) The prodrug Platin-A: simultaneous release of cisplatin and aspirin. Angew Chem Int Ed 53:1963–1967. https://doi.org/10.1002/anie.201308899
Santiago-Portillo A, Navalón S, Cirujano FG, Xamena FXL, Alvaro M, Garcia H (2015) MIL-101 as reusable solid catalyst for autoxidation of benzylic hydrocarbons in the absence of additional oxidizing reagents. ACS Catal 5:3216–3224. https://doi.org/10.1021/acscatal.5b00411
Scarano W, de Souza P, Stenzel MH (2015) Dual-drug delivery of curcumin and platinum drugs in polymeric micelles enhances the synergistic effects: a double act for the treatment of multidrug-resistant cancer. Biomater Sci 3:163–174. https://doi.org/10.1039/c4bm00272e
Shi Y, Liu S, Kerwood DJ, Goodisman J, Dabrowiak JC (2012) Pt(IV) complexes as prodrugs for cisplatin. J Inorg Biochem 107:6–14. https://doi.org/10.1016/j.jinorgbio.2011.10.012
Singco B, Liu LH, Cheng YT, Shih YH, Huang HY, Lin CH (2016) Approaches to drug delivery: confinement of aspirin in MIL-100(Fe) and aspirin in the de novo synthesis of metal-organic frameworks. Micropor Mesopor Mater 223:254–260. https://doi.org/10.1016/j.micromeso.2015.08.017
Tang J, Yang M, Yang M, Wang J, Dong W, Wang G (2015) Heterogeneous Fe-MIL-101 catalysts for efficient one-pot four-component coupling synthesis of highly substituted pyrroles. New J Chem 39:4919–4923. https://doi.org/10.1039/C5NJ00632E
Tao Z, Xie Y, Goodisman J, Asefa T (2010) Isomer-dependent adsorption and release of cis- and trans-platin anticancer drugs by mesoporous silica nanoparticles. Langmuir 26:8914–8924. https://doi.org/10.1021/1a904695a
Taylor-Pashow KML, Rocca JD, Xie Z, Tran S, Lin W (2009) Postsynthetic modifications if iron-carboxylate nanoscale metal-organic frameworks for imaging and drug delivery. J Am Chem Soc 131:14261–14263. https://doi.org/10.1021/ja906198y
Theiner S, Varbanov HP, Galanski M, Egger AE, Berger W, Hefferer P, Keppler BK (2015) Comparative in vitro and in vivo pharmacological investigation of platinum(IV) complexes as novel anticancer drug candidates for oral application. J Biol Inorg Chem 20:89–99. https://doi.org/10.1007/s00775-014-1214-6
Wang X, Lu X, Wu L, Chen J (2015) 3D metal-organic framework as highly efficient biosensing platform for ultrasensitive and rapid detection of bisphenol A. Biosens Bioelectron 65:295–301. https://doi.org/10.1016/j.bios.2014.10.010
Wexselblatt E, Raveendran R, Salameh S, Friedman-Ezra A, Yavin E, Gibson D (2015) On the stability of Pt(IV) pro-drugs with haloaceto ligands in the axial positions. Chem Eur J 21:3108–3114. https://doi.org/10.1002/chem.201405467
Xiao H, Qi R, Liu S, Hu X, Duan T, Zheng Y, Huang Y, Jing X (2011) Biodegradable polymer-cisplatin(IV) conjugate as a pro-drug of cisplatin(II). Biomaterials 32:7732–7739. https://doi.org/10.1016/j.biomaterials.2011.06.072
Xiao H, Li W, Qi R, Yan L, Wang R, Liu S, Zheng Y, Xie Z, Huang Y, Jing X (2012) Co-delivery of daunomycin and oxaliplatin by biodegradable polymers for safer and more efficacious combination therapy. J Control Release 163:304–314. https://doi.org/10.1016/j.conrel.2012.06.004
Xu J, Shimakoshi H, Hisaeda Y (2015) Development of metal-organic framework (MOF)-B12 system as new bio-inspired heterogeneous catalyst. J Organomet Chem 782:89–95. https://doi.org/10.1016/j.jorganchem.2014.11.015
Yachnin JR, Wallin I, Lewensohn R, Sirzén F, Ehrsson H (1998) The kinetics and cytotoxicity of cisplatin and its monohydrated complex. Cancer Lett 132:175–180. https://doi.org/10.1016/s0304-3835(98)00175-x
Acknowledgements
This work was supported by Erasmus + Mobility Programme associated with Institute für Anorganische Chemie Universität Leipzig Germany and Ministry of Research, Technology and Higher Education of The Republic of Indonesia (RISTEK DIKTI), in the scheme International Research Collaboration (PKLN) project No. 474/UN27.21/PP/2018 and Fundamental Research Grant project No. 719/UN27.21/PN/2019 (Kementerian Riset Teknologi Dan Pendidikan Tinggi Republik Indonesia). The author wishes to thank Sara Durini Ph.D. and Prof. Dr. Dr. hc. mult. Evamarie Hey-Hawkins for their helpful assistance and suggestion during research stay at Institute für Anorganische Chemie Universität Leipzig Germany, and we would like to thank Rafaella Precker (Institute für Anorganische Chemie, Universität Leipzig, Germany) for providing MIL-101(Fe).
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Rosari, V.A., Lestari, W.W. & Firdaus, M. Synthesis of aspirin-ligated cisplatin derivatives and its slow release study over MIL-101(Fe). Chem. Pap. 74, 2733–2741 (2020). https://doi.org/10.1007/s11696-020-01114-4
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DOI: https://doi.org/10.1007/s11696-020-01114-4