Carroll AR, Lamb J, Moni R, Guymer GP, Forster PI, Quinn RJ (2008) Myrtucmmulones F-I, phloroglucinols with thyrotropin-releasing hormone receptor-2 binding affinity from the seeds of Corymbia scabrida. J Nat Prod 71:1564–1568. https://doi.org/10.1021/np800247u

Article  CAS  PubMed  Google Scholar 

Charpentier M, Jauch J (2017) Metal catalysed versus organocatalysed stereoselective synthesis: the concrete case of myrtucommulones. Tetrahedron 73:6614–6623. https://doi.org/10.1016/j.tet.2017.10.011

Article  CAS  Google Scholar 

Dean RA, Fam HK, An J, Choi K, Shimizu Y, Jones SJ, Boerkoel CF, Interthal H, Pfeifer TA (2014) Identification of a putative tdp1 inhibitor (CD00509) by in vitro and cell-based assays. J Biomol Screen 19:1372–1382. https://doi.org/10.1177/1087057114546551

Article  CAS  PubMed  Google Scholar 

Do PM, Varanasi L, Fan S, Li C, Kubacka I, Newman V, Chauhan K, Daniels SR, Boccetta M, Garrett MR, Li R, Martinez LA (2012) Mutant p53 cooperates with ETS2 to promote etoposide resistance. Genes Dev 26:830–845. https://doi.org/10.1101/gad.181685.111

Article  CAS  PubMed  PubMed Central  Google Scholar 

Hatano M, Goto Y, Izumiseki A, Akakura M, Ishihara K (2015) Boron tribromide-assisted chiral phosphoric acid catalyst for a highly enantioselective Diels-Alder reaction of 1,2-dihydropyridines. J Am Chem Soc 137:13472–13475. https://doi.org/10.1021/jacs.5b08693

Article  CAS  PubMed  Google Scholar 

Herzog BH, Devarakonda S, Govindan R (2021) Overcoming chemotherapy resistance in SCLC. J Thorac Oncol 16:2002–2015. https://doi.org/10.1016/j.jtho.2021.07.018

Article  CAS  PubMed  Google Scholar 

Kankanala J, Marchand C, Abdelmalak M, Aihara H, Pommier Y, Wang Z (2016) Isoquinoline-1,3-diones as selective inhibitors of tyrosyl DNA phosphodiesterase II (TDP2). J Med Chem 59:2734–2746. https://doi.org/10.1021/acs.jmedchem.5b01973

Article  CAS  PubMed  PubMed Central  Google Scholar 

Kankanala J, Ribeiro CJA, Kiselev E, Ravji A, Williams J, Xie J, Aihara H, Pommier Y, Wang Z (2019) Novel deazaflavin analogues potently inhibited tyrosyl DNA phosphodiesterase 2 (TDP2) and strongly sensitized cancer cells toward treatment with topoisomerase II (TOP2) poison etoposide. J Med Chem 62:4669–4682. https://doi.org/10.1021/acs.jmedchem.9b00274

Article  CAS  PubMed  PubMed Central  Google Scholar 

Kiselev E, Ravji A, Kankanla J, Xie J, Wang Z, Pommier Y (2020) Novel deazaflavin tyrosyl-DNA phosphodiesterase 2 (TDP2) inhibitors. DNA Repair 85:102747. https://doi.org/10.1016/j.dnarep.2019.102747

Article  CAS  PubMed  Google Scholar 

Komulainen E, Pennicott L, Le Grand D, Caldecott KW (2019) Deazaflavin inhibitors of TDP2 with cellular activity can affect etoposide influx and/or efflux. ACS Chem Biol 14:1110–1114. https://doi.org/10.1021/acschembio.9b00144

Article  CAS  PubMed  PubMed Central  Google Scholar 

Kont YS, Dutta A, Mallisetty A, Mathew J, Minas T, Kraus C, Dhopeshwarkar P, Kallakury B, Mitra S, Üren A, Adhikari S (2016) Depletion of tyrosyl DNA phosphodiesterase 2 activity enhances etoposide-mediated double-strand break formation and cell killing. DNA Repair 43:38–47. https://doi.org/10.1016/j.dnarep.2016.04.009

Article  CAS  PubMed  Google Scholar 

Kossmann BR, Abdelmalak M, Lopez S, Tender G, Yan C, Pommier Y, Marchand C, Ivanov I (2016) Discovery of selective inhibitors of tyrosyl-DNA phosphodiesterase 2 by targeting the enzyme DNA-binding cleft. Bioorg Med Chem Lett 26:3232–3236. https://doi.org/10.1016/j.bmcl.2016.05.065

Article  CAS  PubMed  PubMed Central  Google Scholar 

Ledesma FC, El KSF, Zuma MC, Osborn K, Caldecott KW (2009) A human 5’-tyrosyl DNA phosphodiesterase that repairs topoisomerase-mediated DNA damage. Nature 461:674–678. https://doi.org/10.1038/nature08444

Mansoori B, Mohammadi A, Davudian S, Shirjang S, Baradaran B (2017) The different mechanisms of cancer drug resistance: a brief review. Adv Pharm Bull 7:339–348. https://doi.org/10.15171/apb.2017.041

Marchand C, Abdelmalak M, Kankanala J, Huang SY, Kiselev E, Fesen K, Kurahashi K, Sasanuma H, Takeda S, Aihara H, Wang Z, Pommier Y (2016) Deazaflavin inhibitors of tyrosyl-DNA phosphodiesterase 2 (TDP2) specific for the human enzyme and active against cellular TDP2. ACS Chem Biol 11:1925–1933. https://doi.org/10.1021/acschembio.5b01047

Article  CAS  PubMed  PubMed Central  Google Scholar 

Nicoletti R, Ferranti P, Caira S, Misso G, Castellano M, Di Lorenzo G, Caraglia M (2014) Myrtucommulone production by a strain of Neofusicoccum australe endophytic in myrtle (Myrtus communis). World J Microbiol Biotechnol 30:1047–1052. https://doi.org/10.1007/s11274-013-1523-x

Article  CAS  PubMed  Google Scholar 

Pommier Y, Huanga SY, Gao R, Das BB, Murai J, Marchand C (2014) Tyrosyl-DNA-phosphodiesterases (TDP1 and TDP2). DNA Repair 23:114–129. https://doi.org/10.1016/j.dnarep.2014.03.020

Article  CAS  Google Scholar 

Raoof A, Depledge P, Hamilton NM, Hamilton NS, Hitchin JR, Hopkins GV, Jordan AM, Maguire LA, McGonagle AE, Mould DP, Rushbrooke M, Small HF, Smith KM, Thomson GJ, Turlais F, Waddell ID, Waszkowycz B, Watson AJ, Ogilvie DJ (2013) Toxoflavins and deazaflavins as the first reported selective small molecule inhibitors of tyrosyl-DNA phosphodiesterase II. J Med Chem 56:6352–6370. https://doi.org/10.1021/jm400568p

Article  CAS  PubMed  Google Scholar 

Ribeiro CJA, Kankanala J, Shi K, Kurahashi K, Kiselev E, Ravji A, Pommier Y, Aihara H, Wang Z (2018) New fluorescence-based high-throughput screening assay for small molecule inhibitors of tyrosyl-DNA phosphodiesterase 2 (TDP2). Eur J Pharm Sci 118:67–79. https://doi.org/10.1016/j.ejps.2018.03.021

Article  CAS  PubMed  PubMed Central  Google Scholar 

Ribeiro CJA, Kankanala J, Xie J, Williams J, Aihara H, Wang Z (2019) Triazolopyrimidine and triazolopyridine scaffolds as TDP2 inhibitors. Bioorg Med Chem Lett 29:257–261. https://doi.org/10.1016/j.bmcl.2018.11.044

Article  CAS  PubMed  Google Scholar 

Shaheen F, Ahmad M, Khan SN, Hussain SS, Anjum S, Tashkhodjaev B, Turgunov K, Sultankhodzhaev MN, Choudhary MI, Atta-ur-Rahman (2006) New α-glucosidase inhibitors and antibacterial compounds from Myrtus communis L. Eur J Org Chem 10:2371–2377. https://doi.org/10.1002/ejoc.200500936

Article  CAS  Google Scholar 

Wang P, Elsayed MSA, Plescia CB, Ravji A, Redon CE, Kiselev E, Marchand C, Zeleznik O, Agama K, Pommier Y, Cushman M (2017) Synthesis and biological evaluation of the first triple inhibitors of human topoisomerase 1, tyrosyl–DNA phosphodiesterase 1 (Tdp1), and tyrosyl–DNA phosphodiesterase 2 (Tdp2). J Med Chem 60:3275–3288. https://doi.org/10.1021/acs.jmedchem.6b01565

Article  CAS  PubMed  PubMed Central  Google Scholar 

Wiechmann K, Müller H, Huch V, Hartmann D, Werz O, Jauch J (2015) Synthesis and biological evaluation of novel myrtucommulones and structural analogues that target mPGES-1 and 5-lipoxygenase. Eur J Med Chem 101:133–149. https://doi.org/10.1016/j.ejmech.2015.06.001

Article  CAS  PubMed  Google Scholar 

Wu Y, Chen M, Wang WJ, Li NP, Ye WC, Wang L (2020) Phloroglucinol derivatives from Myrtus communis ‘Variegata’ and their antibacterial activities. Chem Biodivers 17:e2000292. https://doi.org/10.1002/cbdv.202000292

Article  CAS  PubMed  Google Scholar 

Yang H, Zhu XQ, Wang W, Chen Y, Hu Z, Zhang Y, Hu DX, Yu LM, Agama K, Pommier Y, An LK (2021) The synthesis of furoquinolinedione and isoxazoloquinolinedione derivatives as selective tyrosyl-DNA phosphodiesterase 2 (TDP2) inhibitors. Bioorg Chem 111:104881. https://doi.org/10.1016/j.bioorg.2021.104881

Article  CAS  PubMed  PubMed Central  Google Scholar 

Yu LM, Hu Z, Chen Y, Ravji A, Lopez S, Plescia CB, Yu Q, Yang H, Abdelmalak M, Saha S, Agama K, Kiselev E, Marchand C, Pommier Y, An LK (2018) Synthesis and structure-activity relationship of furoquinolinediones as inhibitors of tyrosyl-DNA phosphodiesterase 2 (TDP2). Eur J Med Chem 151:777–796. https://doi.org/10.1016/j.ejmech.2018.04.024

Article  CAS  PubMed  PubMed Central  Google Scholar 

Zeng Z, Cortés-Ledesma F, El Khamisy SF, Caldecott KW (2011) TDP2/TTRAP is the major 5′-tyrosyl DNA phosphodiesterase activity in vertebrate cells and is critical for cellular resistance to topoisomerase II-induced DNA damage. J Biol Chem 286:403–409. https://doi.org/10.1074/jbc.M110.181016

Article  CAS  PubMed  Google Scholar 

Zhang Y, He XZ, Yang H, Liu HY, An LK (2021) Robustadial A and B from Eucalyptus globulus Labill. and their anticancer activity as selective tyrosyl-DNA phosphodiesterase 2 inhibitors. Phyther Res 35:5282–5289. https://doi.org/10.1002/ptr.7207

Article  CAS  Google Scholar 

Zhang Y, Yang H, Wang FT, Peng X, Liu HY, Li QJ, An LK (2022) Discovery, enantioselective synthesis of myrtucommulone E analogues as tyrosyl-DNA phosphodiesterase 2 inhibitors and their biological activities. Eur J Med Chem 238:114445. https://doi.org/10.1016/j.ejmech.2022.114445

Article  CAS  PubMed  Google Scholar