1,982
Views
0
CrossRef citations to date
0
Altmetric
Brief Reports

Design, synthesis and biological evaluation of novel diosgenin–benzoic acid mustard hybrids with potential anti-proliferative activities in human hepatoma HepG2 cells

, ORCID Icon, , , , , , , , & show all
Pages 1299-1314 | Received 07 Feb 2022, Accepted 19 Apr 2022, Published online: 02 Jun 2022

References

  • Newman DJ, Cragg GM. Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J Nat Prod 2020;83:1299–803.
  • Zolottsev VA, Latysheva АS, Pokrovsky VS, et al. Promising applications of steroid сonjugates for cancer research and treatment. Eur J Med Chem 2021;210:113089.
  • Nahar L, Sarker SD. A review on steroid dimers: 2011–2019. Steroids 2020;164:108736.
  • Ma LW, Wang HJ, Wang J, et al. Novel steroidal 5α,8α-endoperoxide derivatives with semicarbazone/thiosemicarbazone side-chain as apoptotic inducers through an intrinsic apoptosis pathway: design, synthesis and biological studies. Molecules 2020;25:1209.
  • Liao WL, Lin JY, Shieh JC, et al. Induction of G2/M phase arrest by diosgenin via activation of Chk1 kinase and Cdc25C regulatory pathways to promote apoptosis in human breast cancer cells. Int J Mol Sc 2019;21:172.
  • Li SY, Shang J, Mao XM, et al. Diosgenin exerts anti-tumor effects through inactivation of cAMP/PKA/CREB signaling pathway in colorectal cancer. Eur J Pharmacol 2021;908:174370.
  • Mao XM, Zhou P, Li SY, et al. Diosgenin suppresses cholangiocarcinoma cells via inducing cell cycle arrest and mitochondria-mediated apoptosis. Onco Targets Ther 2019;12:9093–104.
  • Long C, Chen J, Zhou H, et al. Diosgenin exerts its tumor suppressive function via inhibition of Cdc20 in osteosarcoma cells. Cell Cycle 2019;18:346–58.
  • Liu YL, Zhou ZJ, Yan JZ, et al. Diosgenin exerts antitumor activity via downregulation of skp2 in breast cancer cells. BioMed Res Int 2020;2020:8072639–10.
  • Singh RK, Kumar S, Prasad DN, et al. Therapeutic journey of nitrogen mustard as alkylating anticancer agents: historic to future perspectives. Eur J Med Chem 2018;151:401–33.
  • Yan X, Song JL, Yu MX, et al. Synthesis of flavonoids nitrogen mustard derivatives and study on their antitumor activity in vitro. Bioorg Chem 2020;96:103613.
  • Martín-Cámara O, Arribas M, Wells G, et al. Multitarget hybrid fasudil derivatives as a new approach to the potential treatment of amyotrophic lateral sclerosis. J Med Chem 2022;65:1867–1882.
  • Pandey AR, Rai D, Singh SP, et al. Synthesis and evaluation of galloyl conjugates of flavanones as BMP-2 upregulators with promising bone anabolic and fracture healing properties. J Med Chem 2021;64:12487–505.
  • Harrison JR, Brand S, Smith V, et al. A molecular hybridization approach for the design of potent, highly selective, and brain-penetrant N-myristoyltransferase inhibitors. J Med Chem 2018;61:8374–89.
  • Zhang L, Xu LJ, Chen HH, et al. Structure-based molecular hybridization design of Keap1-Nrf2 inhibitors as novel protective agents of acute lung injury. Eur J Med Chem 2021;222:113599.
  • Hou QQ, Lin X, Lu X, et al. Discovery of novel steroidal-chalcone hybrids with potent and selective activity against triple-negative breast cancer. Bioorg Med Chem 2020;28:115763.
  • Kerru N, Singh P, Koorbanally N, et al. Recent advances (2015–2016) in anticancer hybrids. Eur J Med Chem 2017;142:179–212.
  • Sun JN, Wang JS, Wang XY, et al. Design and synthesis of β-carboline derivatives with nitrogen mustard moieties against breast cancer. Bioorg Med Chem 2021;45:116341.
  • Xu YZ, Gu XY, Peng SJ, et al. Design, synthesis and biological evaluation of novel sesquiterpene mustards as potential anticancer agents. Eur J Med Chem 2015;94:284–97.
  • Han T, Tian KT, Pan HQ, et al. Novel hybrids of Brefeldin A and nitrogen mustards with improved antiproliferative selectivity: design, synthesis and antitumor biological evaluation. Eur J Med Chem 2018;150:53–63.
  • Acharya PC, Bansal R. Synthesis of androstene oxime-nitrogen mustard bioconjugates as potent antineoplastic agents. Steroids 2017;123:73–83.
  • Zhang JL, Wang XM, Yang JF, et al. Novel diosgenin derivatives containing 1,3,4-oxadiazole/thiadiazole moieties as potential antitumor agents: design, synthesis and cytotoxic evaluation. Eur J Med Chem 2020;186:111897.
  • Wang XD, Sun YY, Zhao C, et al. 12-Chloracetyl-PPD, a novel dammarane derivative, shows anti-cancer activity via delay the progression of cell cycle G2/M phase and reactive oxygen species-mediate cell apoptosis. Eur J Pharmacol 2017;798:49–56.
  • Ma LW, Zhang JL, Guo LN, et al. Design and synthesis of diosgenin derivatives as apoptosis inducers through mitochondria-related pathways. Eur J Med Chem 2021;217:113361.
  • Wang WB, Li C, Chen Z, et al. Novel diosgenin-amino acid-benzoic acid mustard trihybrids exert antitumor effects via cell cycle arrest and apoptosis. J Steroid Biochem Mol Biol 2022;216:106038.
  • Ma LW, Chen Z, Li J, et al. DP from Euphorbia fischeriana S. mediated apoptosis in leukemia cells via the PI3k/Akt signaling pathways. J Ethnopharmacol 2021;279:113889.
  • Schrodinger, LLC. Glide. New York, NY: Schrodinger, LLC; 2016
  • Bruncko M, Oost TK, Belli BA, et al. Studies leading to potent, dual inhibitors of Bcl-2 and Bcl-xL. J Med Chem 2007;50:641–62.
  • Wolfram RK, Fischer L, Kluge R, et al. Homopiperazine-rhodamine B adducts of triterpenoic acids are strong mitocans. Eur J Med Chem 2018;155:869–79.
  • Gao X, Li J, Wang MY, et al. Novel enmein-type diterpenoid hybrids coupled with nitrogen mustards: Synthesis of promising candidates for anticancer therapeutics. Eur J Med Chem 2018;146:588–98.
  • Sikka S, Shanmugam MK, Siveen KS, et al. Diosgenin attenuates tumor growth and metastasis in transgenic prostate cancer mouse model by negatively regulating both NF-κB/STAT3 signaling cascades. Eur J Pharmacol 2021;906:174274.
  • Guo WH, Chen YJ, Gao JS, et al. Diosgenin exhibits tumor suppressive function via down-regulation of EZH2 in pancreatic cancer cells. Cell Cycle 2019;18:1745–58.
  • Wang FF, Shi C, Yang Y, et al. Medicinal mushroom Phellinus igniarius induced cell apoptosis in gastric cancer SGC-7901 through a mitochondria-dependent pathway. Biomed Pharmacother 2018;102:18–25.
  • Sattler M, Liang H, Nettesheim D, et al. Structure of Bcl-xL-Bak peptide complex: recognition between regulators of apoptosis. Science 1997;275:983–6.
  • Ashkenazi A, Fairbrother WJ, Leverson JD, et al. From basic apoptosis discoveries to advanced selective BCL-2 family inhibitors. Nat Rev Drug Discov 2017;16:273–84.