Synthesis and Antitumor Properties of Temozolomide-Based Platinum(Ⅳ) Complexes
- Corresponding author: Hong-Ke LIU, liuhongke@njnu.edu.cn Zhi SU, zhisu@njnu.edu.cn
Citation: Yan SU, Meng-Meng WANG, Hong-Ke LIU, Zhi SU. Synthesis and Antitumor Properties of Temozolomide-Based Platinum(Ⅳ) Complexes[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(3): 430-440. doi: 10.11862/CJIC.2022.044
Louis D N, Perry A, Reifenberger G, Deimling A, Figarella-Branger D, Cavenee W K, Ohgaki H, Wiestler O D, Kleihues P, Ellison D W. The 2016 World Health Organization Classification of Tumors of the Central Nervous System: A Summary[J]. Acta Neuropathol., 2016,131(6):803-820. doi: 10.1007/s00401-016-1545-1
Giese A, Bjerkvig R, Berens M E, Westphal M. Cost of Migration: Invasion of Malignant Gliomas and Implications for Treatment[J]. J. Clin. Oncol., 2003,21(8):1624-1636. doi: 10.1200/JCO.2003.05.063
Affronti M L, Heery C R, Herndon J E, Rich J N, Reardon D A, Desjardins A, Vredenburgh J J, Friedman A H, Bigner D D, Friedman H S. Overall Survival of Newly Diagnosed Glioblastoma Patients Receiving Carmustine Wafers Followed by Radiation and Concurrent Temozolomide plus Rotational Multiagent Chemotherapy[J]. Cancer, 2009,115(15):3501-3511. doi: 10.1002/cncr.24398
de Souza R M, Shaweis H, Han C, Sivasubramaniam V, Brazil L, Beaney R, Sadler G, Al-Sarraj S, Hampton T, Logan J, Hurwitz V, Bhangoo R, Gullan R, Ashkan K. Erratum: Has the Survival of Patients with Glioblastoma Changed over the Years?[J]. Br. J. Cancer, 2016,114(2):146-150. doi: 10.1038/bjc.2015.421
Stupp R, Taillibert S, Kanner A, Read W, Steinberg D M, Lhermitte B, Toms S, Idbaih A, Ahluwalia M S, Fink K, Di Meco F, Lieberman F, Zhu J J, Stragliotto G, Tran D D, Brem S, Hottinger A F, Kirson E D, Lavy-Shahaf G, Weinberg U, Kim C Y, Paek S H, Nicholas G, Bruna J, Hirte H, Weller M, Palti Y, Hegi M E, Ram Z. Effect of Tumor-Treating Fields plus Maintenance Temozolomide vs Maintenance Temozolomide Alone on Survival in Patients With Glioblastoma: A Randomized Clinical Trial[J]. JAMA - J. Am. Med. Assoc., 2017,318(23):2306-2316. doi: 10.1001/jama.2017.18718
Furnari F B, Fenton T, Bachoo R M, Mukasa A, Stommel J M, Stegh A, Hahn W C, Ligon K L, Louis D N, Brennan C, Chin L, DePinho R A, Cavenee W K. Malignant Astrocytic Glioma: Genetics, Biology, and Paths to Treatment[J]. Genes Dev., 2007,21(21):2683-2710. doi: 10.1101/gad.1596707
Fan C H, Liu W L, Cao H, Wen C, Chen L, Jiang G. O6-Methylgua-nine DNA Methyltransferase as a Promising Target for the Treatment of Temozolomide-Resistant Gliomas[J]. Cell Death Dis., 2013,4(10)e876. doi: 10.1038/cddis.2013.388
Hirose Y, Berger M S, Pieper R O. p53 Effects both the Duration of G2 & M Arrest and the Fate of Temozolomide-Treated Human Glioblas- toma Cells[J]. Cancer Res., 2001,61(5):1957-1963.
Friedman H S, Kerby T, Calvert H. Temozolomide and Treatment of Malignant Glioma[J]. Clin. Cancer Res., 2000,6(7):2585-2597.
Gerson S L. MGMT: Its Role in Cancer Aetiology and Cancer Thera-peutics[J]. Nat. Rev. Cancer, 2004,4(4):296-307. doi: 10.1038/nrc1319
Lee S Y. Temozolomide Resistance in Glioblastoma Multiforme[J]. Genes Dis., 2016,3(3):198-210. doi: 10.1016/j.gendis.2016.04.007
Stupp R, Mason W P, van den Bent M J, Weller M, Fisher B, Taphoorn M J B, Belanger K, Brandes A A, Marosi C, Bogdahn U, Curschmann J, Janzer R C, Ludwin S K, Gorlia T, Allgeier A, Lacombe D, Cairncross J G, Eisenhauer E, Mirimanoff R O. Radio-therapy plus Concomitant and Adjuvant Temozolomide for Glioblas-toma[J]. N. Engl. J. Med., 2005,352(10):987-996. doi: 10.1056/NEJMoa043330
Stupp R, Hegi M E, Mason W P, Bent M J, Taphoorn M J B, Janzer R C, Ludwin S K, Allgeier A, Fisher B, Belanger K, Hau P, Brandes A A, Gijtenbeek J, Marosi C, Vecht C J, Mokhtari K, Wesseling P, Villa S, Eisenhauer E, Gorlia T, Weller M, Lacombe D, Cairncross J G, Mirimanoff R O. Effects of Radiotherapy with Concomitant and Adjuvant Temozolomide versus Radiotherapy Alone on Survival in Glioblastoma in a Randomised Phase Ⅲ Study: 5-Year Analysis of the EORTC-NCIC Trial[J]. Lancet Oncol., 2009,10(5):459-466. doi: 10.1016/S1470-2045(09)70025-7
Rosenberg B, Vancamp L, Trosko J E, Mansour V H. Platinum Com- pounds: A New Class of Potent Antitumour Agents[J]. Nature, 1969,222(5191):385-386. doi: 10.1038/222385a0
Wang X H, Wang X Y, Jin S X, Muhammad N, Guo Z J. Stimuli-Responsive Therapeutic Metallodrugs[J]. Chem. Rev., 2019,119(2):1138-1192. doi: 10.1021/acs.chemrev.8b00209
JIN S X, GUO Z J, WANG X Y. Antitumor Metal Complexes Target-ing Energy Metabolism[J]. Progress in Pharmaceutical Sciences, 2020,44(4):280-293.
Klein A V, Hambley T W. Platinum Drug Distribution in Cancer Cells and Tumors[J]. Chem. Rev., 2009,109(10):4911-4920. doi: 10.1021/cr9001066
Dilruba S, Kalayda G V. Platinum-Based Drugs: Past, Present and Future[J]. Cancer Chemother. Pharmacol., 2016,77(6):1103-1124. doi: 10.1007/s00280-016-2976-z
Galluzzi L, Senovilla L, Vitale I, Michels J, Martins I, Kepp O, Castedo M, Kroemer G. Molecular Mechanisms of Cisplatin Resis-tance[J]. Oncogene, 2012,31(15):1869-1883. doi: 10.1038/onc.2011.384
Galluzzi L, Vitale I, Michels J, Brenner C, Szabadkai G, Harel-Bel-lan A, Castedo M, Kroemer G. Systems Biology of Cisplatin Resis-tance: Past, Present and Future[J]. Cell Death Dis., 2014,5(5)e1257. doi: 10.1038/cddis.2013.428
Wang X Y, Guo Z J. Targeting and Delivery of Platinum-Based Anti-cancer Drugs[J]. Chem. Soc. Rev., 2013,42(1):202-224. doi: 10.1039/C2CS35259A
Oun R, Moussa Y E, Wheate N J. The Side Effects of Platinum-Based Chemotherapy Drugs: A Review for Chemists[J]. Dalton Trans., 2018,47(19):6645-6653. doi: 10.1039/C8DT00838H
Karasawa T, Steyger P S. An Integrated View of Cisplatin-Induced Nephrotoxicity and Ototoxicity[J]. Toxicol. Lett., 2015,237(3):219-227. doi: 10.1016/j.toxlet.2015.06.012
Johnstone T C, Suntharalingam K, Lippard S J. The Next Generation of Platinum Drugs: Targeted Pt Agents, Nanoparticle Delivery, and Pt Prodrugs[J]. Chem. Rev., 2016,116(5):3436-3486. doi: 10.1021/acs.chemrev.5b00597
Wilson J J, Lippard S J. Synthetic Methods for the Preparation of Platinum Anticancer Complexes[J]. Chem. Rev., 2014,114(8):4470-4495. doi: 10.1021/cr4004314
Hall M D, Hambley T W. Platinum Antitumour Compounds: Their Bioinorganic Chemistry[J]. Coord. Chem. Rev., 2002,232(1):49-67.
Jin S X, Hao Y Y, Zhu Z Z, Muhammad N, Zhang Z Q, Wang K, Guo Y, Guo Z J, Wang X Y. Impact of Mitochondrion-Targeting Group on the Reactivity and Cytostatic Pathway of Platinum Complexes[J]. Inorg. Chem., 2018,57(17):11135-11145. doi: 10.1021/acs.inorgchem.8b01707
Shi Y, Liu S A, Kerwood D J, Goodisman J, Dabrowiak J C. Pt Complexes as Prodrugs for Cisplatin[J]. J. Inorg. Biochem., 2012,107(1):6-14. doi: 10.1016/j.jinorgbio.2011.10.012
Arrowsmith J, Jennings S A, Clark A S, Stevens M F G. Antitumor Imidazotetrazines. 41. Conjugation of the Antitumor Agents Mitozolo-mide and Temozolomide to Peptides and Lexitropsins Bearing DNA Major and Minor Groove-Binding Structural Motifs[J]. J. Med. Chem., 2002,45(25):5458-5470.
Huang H Y, Yu B L, Zhang P Y, Huang J J, Chen Y, Gasser G, Ji L N, Chao H. Highly Charged Ruthenium Polypyridyl Complexes as Lysosome-Localized Photosensitizers for Two-Photon Photodynamic Therapy[J]. Angew. Chem. Int. Ed., 2015,54(47):14049-14052. doi: 10.1002/anie.201507800
Huang H Y, Zhang P Y, Yu B L, Chen Y, Wang J Q, Ji L N, Chao H. Targeting Nucleus DNA with a Cyclometalated Dipyridophenazineru-thenium Complex[J]. J. Med. Chem., 2014,57(21):8971-8983. doi: 10.1021/jm501095r
Oldfield S P, Hall M D, Platts J A. Calculation of Lipophilicity of a Large, Diverse Dataset of Anticancer Platinum Complexes and the Relation to Cellular Uptake[J]. J. Med. Chem., 2007,50(21):5227-5237. doi: 10.1021/jm0708275
Bonner W M, Redon C E, Dickey J S, Nakamura A J, Sedelnikova O A, Solier S, Pommier Y. γH2AX and Cancer[J]. Nat. Rev. Cancer, 2008,8(12):957-967. doi: 10.1038/nrc2523
Revet I, Feeney L, Bruguera S, Wilson W, Dong T K, Oh D H, Dankort D, Cleaver J E. Functional Relevance of the Histone γH2Ax in the Response to DNA Damaging Agents[J]. Proc. Natl. Acad. Sci. U. S. A., 2011,108(21):8663-8667. doi: 10.1073/pnas.1105866108
Shieh S Y, Ikeda M, Taya Y, Prives C. DNA Damage-Induced Phos-phorylation of p53 Alleviates Inhibition by MDM2[J]. Cell, 1997,91(3):325-334. doi: 10.1016/S0092-8674(00)80416-X
Wang D, Lippard S J. Cellular Processing of Platinum Anticancer Drugs[J]. Nat. Rev. Drug Discovery, 2005,4(4):307-320. doi: 10.1038/nrd1691
Zhou Z J, Song J B, Nie L M, Chen X Y. Reactive Oxygen Species Generating Systems Meeting Challenges of Photodynamic Cancer Therapy[J]. Chem. Soc. Rev., 2016,45(23):6597-6626. doi: 10.1039/C6CS00271D
WU J, TAO Q, GE C, XUE X L, QIAN Y, LIU H K. Synthesis and Antitumor Properties of Ruthenium-Arene Complexes Based on Nat-ural Product Perillol[J]. Chinese J. Inorg. Chem., 2020,36(7):1223-1232.
Wang F X, Liang J H, Zhang H, Wang Z H, Wan Q, Tan C P, Ji L N, Mao Z W. Mitochondria-Accumulating Rhenium Tricarbonyl Com-plexes Induce Cell Death via Irreversible Oxidative Stress and Gluta-thione Metabolism Disturbance[J]. ACS Appl. Mater. Interfaces, 2019,11(14):13123-13133. doi: 10.1021/acsami.9b01057
Carneiro B A, El-Deiry W S. Targeting Apoptosis in Cancer Therapy[J]. Nat. Rev. Clin. Oncol., 2020,17(7):395-417. doi: 10.1038/s41571-020-0341-y
Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
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