Discovery of dual tubulin-NEDDylation inhibitors with antiproliferative activity

References

• Zhong C, Kayamori K, Koide S, Shinoda D, Oshima M, Nakajima-Takagi Y, Nagai Y, Mimura N, Lennox W, Sheedy J. Efficacy of tubulin polymerization inhibitor in myelodysplastic syndrome. Blood 2020;136(1):35–35.
   Google Scholar
• Hong Y, Zhu YY, He Q, Gu SX. Indole derivatives as tubulin polymerization inhibitors for the development of promising anticancer agents. Bioorg Med Chem 2021;55:116597.
   PubMed Web of Science ®Google Scholar
• Qi J, Dong H, Huang J, Zhang S, Niu L, Zhang Y, Wang J. Synthesis and biological evaluation of N-substituted 3-oxo-1,2,3,4-tetrahydro-quinoxaline-6-carboxylic acid derivatives as tubulin polymerization inhibitors. Eur J Med Chem 2018;143:8–20.
   PubMed Web of Science ®Google Scholar
• Yang H, An B, Li X, Zeng W. Evaluation of 4-phenylamino-substituted naphthalene-1,2-diones as tubulin polymerization inhibitors. Bioorg Med Chem Lett 2018;28(18):3057–3063.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Yang JJ, Li P, Hou YH, Huang SN, Tippin MA, Pham V, Song L, Zi X, Xue WL, et al. Bioactive heterocycles containing a 3,4,5-trimethoxyphenyl fragment exerting potent antiproliferative activity through microtubule destabilization. Eur J Med Chem 2018;157:50–61.
   PubMed Web of Science ®Google Scholar
• Donthiboina K, Anchi P, Sri Ramya PV, Karri S, Srinivasulu G, Godugu C, Shankaraiah N, Kamal A. Synthesis of substituted biphenyl methylene indolinones as apoptosis inducers and tubulin polymerization inhibitors. Bioorg Chem 2019;86:210–223.
   PubMed Web of Science ®Google Scholar
• Liu W, He M, Li Y, Peng Z, Wang G. A review on synthetic chalcone derivatives as tubulin polymerisation inhibitors. J Enzyme Inhib Med Chem 2022;37(1):9–38.
   PubMed Web of Science ®Google Scholar
• Han S, Shin H, Oh JW, Oh YJ, Her NG, Nam DH. The protein neddylation inhibitor MLN4924 suppresses patient-derived glioblastoma cells via inhibition of ERK and AKT signaling. Cancers 2019;11(12):1849.
   PubMed Web of Science ®Google Scholar
• Yu Q, Jiang Y, Sun Y. Anticancer drug discovery by targeting cullin neddylation. Acta Pharm Sin B (5)2020;10:746–765.
   PubMed Web of Science ®Google Scholar
• Hammill JT, Bhasin D, Scott DC, Min J, Chen Y, Lu Y, Yang L, Kim HS, Connelly MC, Hammill C, et al. Discovery of an orally bioavailable inhibitor of defective in cullin neddylation 1 (DCN1)-mediated cullin neddylation. J Med Chem 2018;61(7):2694–2706.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Song J, Zhu T, Pang XJ, Wang SH, Zhang YB, Wu BW, Wang JW, Zi X, Zhang SY, et al. Discovery of novel tertiary amide derivatives as NEDDylation pathway activators to inhibit the tumor progression in vitro and in vivo. Eur J Med Chem 2020;192:112153.
   PubMed Web of Science ®Google Scholar
• Song J, Liu Y, Yuan XY, Liu WB, Li YR, Yu GX, Tian XY, Zhang YB, Fu XJ, Zhang SY, et al. Discovery of 1,2,4-triazine dithiocarbamate derivatives as NEDDylation agonists to inhibit gastric cancers. Eur J Med Chem 2021;225:113801.
   PubMed Web of Science ®Google Scholar
• Li Z, Ding J, Chen C, Chang J, Huang B, Geng Z, Wang Z. Dual-target cancer theranostic for glutathione S-transferase and hypoxia-inducible factor-1α inhibition. Chem Commun (Camb). 2017;53(92):12406–12409.
   PubMed Web of Science ®Google Scholar
• Shuai W, Wang G, Zhang Y, Bu F, Zhang S, Miller DD, Li W, Ouyang L, Wang Y. Recent Progress on tubulin inhibitors with dual targeting capabilities for cancer therapy. J Med Chem 2021;64(12):7963–7990.
   PubMed Web of Science ®Google Scholar
• Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65(1–2):55–63.
   PubMed Web of Science ®Google Scholar
• Liu YN, Wang JJ, Ji YT, Zhao GD, Tang LQ, Zhang CM, Guo XL, Liu ZP. Design, synthesis, and biological evaluation of 1-methyl-1,4-dihydroindeno[1,2-c]pyrazole analogues as potential anticancer agents targeting tubulin colchicine binding site. J Med Chem 2016;59(11):5341–5355.
   PubMed Web of Science ®Google Scholar
• Gai W, Peng Z, Liu CH, et al. Advances in cancer treatment by targeting the neddylation pathway. Front Cell Dev Biol 2021;9:653882.
   PubMed Web of Science ®Google Scholar
• Quan YP, Cheng LP, Wang TC, Pang W, Wu FH, Huang JW. Molecular modeling study, synthesis and biological evaluation of combretastatin A-4 analogues as anticancer agents and tubulin inhibitors. MedChemComm 2018;9(2):316–327.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Li P, Wu BW, Cui XX, Zhao CB, Zhang SY. Molecular diversity of trimethoxyphenyl-1,2,3-triazole hybrids as novel colchicine site tubulin polymerization inhibitors. Eur J Med Chem 2019;165:309–322.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Fu L, Liu YC, Wang JW, Wang YQ, Han BK, Li XR, Zhang C, Li F, Song J, et al. Structure-activity relationship studies of β-lactam-azide analogues as orally active antitumor agents targeting the tubulin colchicine site. Sci Rep 2017;7(1):12788.
   PubMedGoogle Scholar
• Abulkhair HS, Elmeligie S, Ghiaty A, El‐Morsy A, Bayoumi AH, Ahmed HEA, El‐Adl K, Zayed MF, Hassan MH, Akl EN, et al. In vivo- and in silico-driven identification of novel synthetic quinoxalines as anticonvulsants and AMPA inhibitors. Arch Pharm 2021;354(5):2000449.
   PubMed Web of Science ®Google Scholar
• Abul-Khair H, Elmeligie S, Bayoumi A, et al. Synthesis and evaluation of some new (1,2,4) triazolo(4,3-a)quinoxalin-4(5H)-one derivatives as AMPA receptor antagonists. J Heterocycl Chem 2013;50:1202–1208.
   Web of Science ®Google Scholar
• Fu DJ, Zhang L, Song J, Mao RW, Zhao RH, Liu YC, Hou YH, Li JH, Yang JJ, Jin CY, et al. Design and synthesis of formononetin-dithiocarbamate hybrids that inhibit growth and migration of PC-3 cells via MAPK/Wnt signaling pathways. Eur J Med Chem 2017;127:87–99.
   PubMed Web of Science ®Google Scholar
• Pham V, Rendon R, Le VX, Tippin M, Fu DJ, Le TH, Miller M, Agredano E, Cedano J, Zi X, et al. Gartanin is a novel NEDDylation inhibitor for induction of Skp2 degradation, FBXW2 expression, and autophagy. Mol Carcinog 2020;59(2):193–201.
   PubMed Web of Science ®Google Scholar
• Zhang Z, Heng Y, Cheng W, Pan Y, Ni S, Li H. Reactive oxygen species (ROS)-response nanomedicine through knocking down a novel therapeutic target NEDD8-conjugating enzyme UBC12 (UBE2M) in the treatment of liver cancer. Mater Des 2021;204:109648.
   Web of Science ®Google Scholar
• Heo MJ, Kang SH, Kim YS, Lee JM, Yu J, Kim HR, Lim H, Kim KM, Jung J, Jeong LS, et al. UBC12-mediated SREBP-1 neddylation worsens metastatic tumor prognosis. Int J Cancer 2020;147(9):2550–2563.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Cui XX, Zhu T, Zhang YB, Hu YY, Zhang LR, Wang SH, Zhang SY. Discovery of novel indole derivatives that inhibit NEDDylation and MAPK pathways against gastric cancer MGC803 cells. Bioorg Chem 2021;107:104634.
   PubMed Web of Science ®Google Scholar