206
Views
23
CrossRef citations to date
0
Altmetric
Original Research

New Isatin–Indole Conjugates: Synthesis, Characterization, and a Plausible Mechanism of Their in vitro Antiproliferative Activity

ORCID Icon, ORCID Icon, , , & ORCID Icon
Pages 483-495 | Published online: 03 Feb 2020

References

  • JemalA, BrayF, CenterMM, et al. Global cancer statistics. CA Cancer J Clin. 2011;61(2):69–90. doi:10.3322/caac.v61:221296855
  • JayashreeB, NigamS, PaiA, et al. Targets in anticancer research-a review. Indian J Exp Biol. 2015;53:489–507.26349312
  • EmamiS, DadashpourS. Current developments of coumarin-based anti-cancer agents in medicinal chemistry. Eur J Med Chem. 2015;102:611–630. doi:10.1016/j.ejmech.2015.08.03326318068
  • ZwickE, BangeJ, UllrichA. Receptor tyrosine kinase signalling as a target for cancer intervention strategies. Endocr Relat Cancer. 2001;8(3):161–173. doi:10.1677/erc.0.008016111566607
  • NewmanDJ, CraggGM. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J Nat Prod. 2012;75(3):311–335. doi:10.1021/np200906s22316239
  • LuoF, GuJ, ChenL, et al. Systems pharmacology strategies for anticancer drug discovery based on natural products. Mol Biosyst. 2014;10(7):1912–1917. doi:10.1039/c4mb00105b24802653
  • SwathiK, SarangapaniM. Synthesis and screening of biologically significant 5 hydroxy isatin derivatives for antioxidant activity. Adv Exp Med Biol. 2015;822:129–137.25416982
  • SharmaPK, BalwaniS, MathurD, et al. Synthesis and anti-inflammatory activity evaluation of novel triazolyl-isatin hybrids. J Enzyme Inhib Med Chem. 2016;31(6):1520–1526. doi:10.3109/14756366.2016.115101527146339
  • Gil-TurnesMS, HayME, FenicalW. Symbiotic marine bacteria chemically defend crustacean embryos from a pathogenic fungus. Science. 1989;246(4926):116–118. doi:10.1126/science.27812972781297
  • VineK, MatesicL, LockeJ, et al. Cytotoxic and anticancer activities of isatin and its derivatives: a comprehensive review from 2000-2008. Anticancer Agents Med Chem. 2009;9(4):397–414. doi:10.2174/187152061090904039719442041
  • AttiaMI, EldehnaWM, AfifiSA, et al. New hydrazonoindolin-2-ones: synthesis, exploration of the possible anti-proliferative mechanism of action and encapsulation into PLGA microspheres. PLoS One. 2017;12(7):e0181241. doi:10.1371/journal.pone.018124128742842
  • MotzerRJ, HutsonTE, TomczakP, et al. Sunitinib versus interferon alfa in metastatic renal-cell carcinoma. N Eng J Med. 2007;356(2):115–124. doi:10.1056/NEJMoa065044
  • GriffithR, BrownM, McCluskeyA, et al. Small molecule inhibitors of protein kinases in cancer-how to overcome resistance. Mini Rev Med Chem. 2006;6(10):1101–1110. doi:10.2174/13895570677856018417073710
  • GarofaloA, NaumovaE, ManentiL, et al. The combination of the tyrosine kinase receptor inhibitor SU6668 with paclitaxel affects ascites formation and tumor spread in ovarian carcinoma xenografts growing orthotopically. Clin Cancer Res. 2003;9(9):3476–3485.12960140
  • KrishnegowdaG, GowdaAP, TagaramHRS, et al. Synthesis and biological evaluation of a novel class of isatin analogs as dual inhibitors of tubulin polymerization and Akt pathway. Bioorg Med Chem. 2011;19(20):6006–6014. doi:10.1016/j.bmc.2011.08.04421920762
  • LakhdarS, WestermaierM, TerrierF, et al. Nucleophilic reactivities of indoles. J Org Chem. 2006;71(24):9088–9095. doi:10.1021/jo061433917109534
  • DissLB, RobinsonSD, WuY, et al. Age-related changes in melatonin release in the murine distal colon. ACS Chem Neurosci. 2013;4(5):879–887. doi:10.1021/cn400061723631514
  • de SaA, FernandoR, BarreiroEJ, et al. From nature to drug discovery: the indole scaffold as a ‘privileged structure’. Mini Rev Med Chem. 2009;9(7):782–793. doi:10.2174/13895570978845264919519503
  • AhmadA, A SakrW, Wahidur RahmanK. Anticancer properties of indole compounds: mechanism of apoptosis induction androle in chemotherapy. Curr Drug Targets. 2010;11(6):652–666. doi:10.2174/13894501079117092320298156
  • AkkoçMK, YükselMY, Durmazİ, et al. Design, synthesis, and biological evaluation of indole-based 1, 4-disubstituted piperazines as cytotoxic agents. Turk J Chem. 2012;36(4):515–525.
  • MacDonoughMT, StreckerTE, HamelE, et al. Synthesis and biological evaluation of indole-based, anti-cancer agents inspired by the vascular disrupting agent 2-(3′-hydroxy-4′-methoxyphenyl)-3-(3″,4″,5″-trimethoxybenzoyl)-6-methoxyindole (OXi8006). Bioorg Med Chem. 2013;21(21):6831–6843. doi:10.1016/j.bmc.2013.07.02823993969
  • AlmagroL, Fernández-PérezF, PedreñoM. Indole alkaloids from catharanthus roseus: bioproduction and their effect on human health. Molecules. 2015;20(2):2973–3000. doi:10.3390/molecules2002297325685907
  • BradnerW. Mitomycin C: a clinical update. Cancer Treat Rev. 2001;27(1):35–50. doi:10.1053/ctrv.2000.020211237776
  • Singh SidhuJ, SinglaR, JaitakV, JaitakV. Indole derivatives as anticancer agents for breast cancer therapy: a review. Anticancer Agents Med Chem. 2016;16(2):160–173. doi:10.2174/1871520615666150520144217
  • SravanthiT, ManjuS. Indoles-a promising scaffold for drug development. Eur J Pharm Sci. 2016;91:1–10. doi:10.1016/j.ejps.2016.05.02527237590
  • ChadhaN, SilakariO. Indoles as therapeutics of interest in medicinal chemistry: bird’s eye view. Eur J Med Chem. 2017;134:159–184. doi:10.1016/j.ejmech.2017.04.00328412530
  • AlmutairiMS, HassanES, KeetonAB, et al. Antiproliferative activity and possible mechanism of action of certain 5-methoxyindole tethered C-5 functionalized isatins. Drug Des Devel Ther. 2019;13:3069. doi:10.2147/DDDT
  • SangY-L, ZhangW-M, LvP-C, et al. Indole-based, antiproliferative agents targeting tubulin polymerization. Curr Top Med Chem. 2016;17(2):120–137. doi:10.2174/1568026616666160530154812
  • SongY-L, DongY-F, YangT, et al. Synthesis and pharmacological evaluation of novel bisindolylalkanes analogues. Bioorg Med Chem. 2013;21(24):7624–7627. doi:10.1016/j.bmc.2013.10.03424262885
  • GianniniG, MarziM, Di MarzoM, et al. Exploring bis-(indolyl) methane moiety as an alternative and innovative CAP group in the design of histone deacetylase (HDAC) inhibitors. Bioorg Med Chem Lett. 2009;19(10):2840–2843. doi:10.1016/j.bmcl.2009.03.10119359173
  • HaddachM, MichauxJ, SchwaebeMK, et al. Discovery of CX-6258. A potent, selective, and orally efficacious pan-pim kinases inhibitor. ACS Med Chem Lett. 2012;3(2):135–139. doi:10.1021/ml200259q24900437
  • XiaY, FanC-D, ZhaoB-X, et al. Synthesis and structure–activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells. Eur J Med Chem. 2008;43:2347–2353. doi:10.1016/j.ejmech.2008.01.02118313806
  • ZhangD, WangG, ZhaoG, et al. Synthesis and cytotoxic activity of novel 3-(1H-indol-3-yl)-1H-pyrazole-5-carbohydrazide derivatives. Eur J Med Chem. 2011;46:5868–5877. doi:10.1016/j.ejmech.2011.09.04922000925
  • PieczonkaAM, StrzelczykA, SadowskaB, et al. Synthesis and evaluation of antimicrobial activity of hydrazones derived from 3-oxido-1H-imidazole-4-carbohydrazides. Eur J Med Chem. 2013;64:389–395. doi:10.1016/j.ejmech.2013.04.02323648974
  • GediyaLK, NjarVC. Promise and challenges in drug discovery and development of hybrid anticancer drugs. Expert Opin Drug Discov. 2009;4(11):1099–1111. doi:10.1517/1746044090334170523480431
  • MishraS, SinghP, SinghP. Hybrid molecules: the privileged scaffolds for various pharmaceuticals. Eur J Med Chem. 2016;124:500–536. doi:10.1016/j.ejmech.2016.08.03927598238
  • KerruN, SinghP, KoorbanallyN, et al. Recent advances (2015–2016) in anticancer hybrids. Eur J Med Chem. 2017;142:179–212. doi:10.1016/j.ejmech.2017.07.03328760313
  • Al-WabliR, ZakariaA, AttiaM. Synthesis, spectroscopic characterization and antimicrobial potential of certain new isatin-indole molecular hybrids. Molecules. 2017;22(11):1958. doi:10.3390/molecules22111958
  • Abdel-AzizHA, EldehnaWM, KeetonAB, et al. Isatin-benzoazine molecular hybrids as potential antiproliferative agents: synthesis and in vitro pharmacological profiling. Drug Des Devel Ther. 2017;11:2333. doi:10.2147/DDDT
  • GrauzdytėD, PukalskasA, ViranaickenW, et al. Protective effects of phyllanthus phillyreifolius extracts against hydrogen peroxide induced oxidative stress in HEK293 cells. PLoS One. 2018;13(11):e0207672. doi:10.1371/journal.pone.020767230444889
  • AlmutairiMS, GhabbourHA, AttiaMI. Crystal structure of methyl 1H-indole-2-carboxylate, C10H9NO2. Z Krist-New Cryst St. 2017;232(3):431–432.
  • AlmutairiM, ZakariaA, Al-WabliR, et al. Synthesis, spectroscopic identification and molecular docking of certain N-(2-{[2-(1H-indol-2-ylcarbonyl)hydrazinyl] (oxo)acetyl}phenyl)acetamides and N-[2-(2-{[2-(acetylamino)phenyl](oxo) acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides: new antimicrobial agents. Molecules. 2018;23(5):1043.
  • HaressNG, GhabbourHA, AlmutairiMS, et al. Crystal structure of 5-methoxy-N′-[(3Z)-5-chloro-1-(4-fluorobenzyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]-1H-indole-2-carbohydrazide-DMSO (1/1), C25H18ClFN4O3· C2H6OS. Z Krist-New Cryst St. 2016;231(4):1021–1023.
  • AlmutairiMS, GhabbourHA, HaressNG, et al. Crystal structure of 5-methoxy-N′-[(3Z)-1-benzyl-5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene]-1H-indole-2-carbohydrazide-DMSO (1/1), C27H25FN4O4S. Z Krist-New Cryst St. 2016;231(4):1025–1027.
  • SunG, LuY, ChengY, et al. The expression of BTG1is downregulated in NSCLC and possibly associated with tumor metastasis. Tumor Biol. 2014;35(4):2949–2957. doi:10.1007/s13277-013-1379-6
  • WelburnJP, TuckerJA, JohnsonT, et al. How tyrosine 15 phosphorylation inhibits the activity of cyclin-dependent kinase 2-cyclin A. J Biol Chem. 2007;282(5):3173–3181. doi:10.1074/jbc.M60915120017095507
  • BlajeskiAL, PhanVA, KottkeTJ, et al. G 1 and G 2 cell-cycle arrest following microtubule depolymerization in human breast cancer cells. J Clin Invest. 2002;110(1):91–99. doi:10.1172/JCI1327512093892
  • LiuX, ZhaoP, WangX, et al. Celastrol mediates autophagy and apoptosis via the ROS/JNK and Akt/mTOR signaling pathways in glioma cells. J Exp Clin Cancer Res. 2019;38(1):184. doi:10.1186/s13046-019-1173-431053160
  • RixeO, FojoT. Is cell death a critical end point for anticancer therapies or is cytostasis sufficient? Clin Cancer Res. 2007;13(24):7280–7287. doi:10.1158/1078-0432.CCR-07-214118094408
  • QuaroniA, WandsJ, TrelstadRL, et al. Epithelioid cell cultures from rat small intestine. Characterization by morphologic and immunologic criteria. J Cell Biol. 1979;80(2):248–265. doi:10.1083/jcb.80.2.24888453
  • SouleHD, MaloneyTM, WolmanSR, et al. Isolation and characterization of a spontaneously immortalized human breast epithelial cell line, MCF-10. Cancer Res. 1990;50(18):6075–6086.1975513
  • TodaroGJ, GreenH. Quantitative studies of the growth of mouse embryo cells in culture and their development into established lines. J Cell Biol. 1963;17:299–313. doi:10.1083/jcb.17.2.29913985244
  • KovačevićSZ, JevrićLR, KuzmanovićSOP, et al. Prediction of in-silico ADME properties of 1,2-O-isopropylidene aldohexose derivatives. Iran J Pharm Res. 2014;13(3):899–907.25276190
  • DainaA, MichielinO, ZoeteV. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep. 2017;7:42717. doi:10.1038/srep4271728256516