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Research Article

Virtual Screening Approach for the Discovery of Selective 5α-Reductase Type II Inhibitors for Benign Prostatic Hyperplasia Treatment

ORCID Icon, ORCID Icon, , & ORCID Icon
Pages 2149-2163 | Received 02 Mar 2023, Accepted 24 Oct 2023, Published online: 13 Nov 2023

References

  • Wang JL , LiuHL , ZhouZL , ChenWH , HoY. Discovery of novel 5α-reductase type II inhibitors by pharmacophore modelling, virtual screening, molecular docking and molecular dynamics simulations. Mol. Simul.41(4), 287–297 (2015).
  • Aggarwal S , TharejaS , VermaA , BhardwajTR , KumarM. An overview on 5α-reductase inhibitors. Steroids75(2), 109–153 (2010).
  • Guarna A , BelleC , MachettiFet al. 19-Nor-10-azasteroids: a novel class of inhibitors for human steroid 5α-reductases 1 and 2. J. Med. Chem.40, 1112–1129 (1997).
  • Canguven O , BurnettAL. The effect of 5 α-reductase inhibitors on erectile function. J. Androl.29, 514–523 (2008).
  • Kulig K , MalawskaB. Trends in the development of new drugs for treatment of benign prostatic hyperplasia. Curr. Med. Chem.13, 3395–3416 (2006).
  • Thorpe A , NealD. Benign prostatic hyperplasia. Lancet361, 1359–1367 (2003).
  • Salem OI , FrotscherM , SchererCet al. Novel 5α-reductase inhibitors: synthesis, structure−activity studies, and pharmacokinetic profile of phenoxybenzoylphenyl acetic acids. J. Med. Chem.49, 748–759 (2006).
  • Rassweiler J , TeberD , KuntzR , HofmannR. Complications of transurethral resection of the prostate (TURP) – incidence, management, and prevention. Eur. Urol.50, 969–980 (2006).
  • Andersson S , RussellDW. Structural and biochemical properties of cloned and expressed human and rat steroid 5 alpha-reductases. Proc. Natl Acad. Sci.87, 3640–3644 (1990).
  • Li X , ChenC , SinghSM , LabrieF , LabrieF. The enzyme and inhibitors of 4-ene-3-oxosteroid 5α-oxidoreductase. Steroids60, 430–441 (1995).
  • Luo J , DunnTA , EwingCM , WalshPC , IsaacsWB. Decreased gene expression of steroid 5 alpha-reductase 2 in human prostate cancer: implications for finasteride therapy of prostate carcinoma. Prostate57, 134–139 (2003).
  • Finn DA , Beadles-BohlingAS , BeckleyEHet al. A new look at the 5α-reductase inhibitor finasteride. CNS Drug. Rev.12, 53–76 (2006).
  • Gormley GJ , StonerE , BruskewitzRCet al. The effect of finasteride in men with benign prostatic hyperplasia. N. Engl. J. Med.327, 1185–1191 (1992).
  • Hirosumi J , NakayamaO , ChidaNet al. FK143, a novel nonsteroidal inhibitor of steroid 5α-reductase: (2) in vivo effects on rat and dog prostates. J. Steroid Biochem. Mol. Biol.52, 365–373 (1995).
  • Sawada K , OkadaS , GoldenPet al. 4-(1-Benzoylindol-3-yl) butyric acids and FK143: novel nonsteroidal inhibitors of steroid 5α-reductase (II). Chem. Pharm. Bull. (Tokyo)47, 481491 (1999).
  • Lesuisse D , GourvestJF , AlbertEet al. Biphenyls as surrogates of the steroidal backbone. Part 2: discovery of a novel family of non-steroidal 5-α-reductase inhibitors. Bioorg. Med. Chem. Lett.11, 1713–1716 (2001).
  • Baston E , SalemOI , HartmannRW. Cyclohex-1-ene carboxylic acids: synthesis and biological evaluation of novel inhibitors of human 5α reductase. Arch. Pharm.336, 31–38 (2003).
  • Azzouni F , GodoyA , LiY , MohlerJ. The 5 alpha-reductase isozyme family: a review of basic biology and their role in human diseases. Adv. Urol.2012,978531 (2012).
  • Robitaille J , LangloisVS. Consequences of steroid-5α-reductase deficiency and inhibition in vertebrates. Gen. Comp. Endocrinol.290, 113400 (2020).
  • Marks LS . 5α-Reductase: history and clinical importance. Rev. Urol.6(Suppl. 9), S11–S21 (2004).
  • Schmidt LJ , TindallDJ. Steroid 5 alpha-reductase inhibitors targeting BPH and prostate cancer. J. Steroid Biochem. Mol. Biol.125, 32–38 (2011).
  • Liss MA , ThompsonIM. Prostate cancer prevention with 5-alpha reductase inhibitors: concepts and controversies. Curr. Opin. Urol.28, 42–45 (2018).
  • Tian G , ChenSY , FacchineKL , PrakashSR. Chemical mechanism of the covalent modification of 5. alpha.-reductases by finasteride as probed by secondary tritium isotope effects. J. Am. Chem. Soc.117, 2369–2370 (1995).
  • Bull HG , Garcia-CalvoM , AnderssonSet al. Mechanism-based inhibition of human steroid 5α-reductase by finasteride: enzyme-catalyzed formation of NADP− dihydrofinasteride, a potent bisubstrate analog inhibitor. J. Am. Chem. Soc.118(10), 2359–2365 (1996).
  • Wambier CG , GorenA , Vaño-GalvánSet al. Androgen sensitivity gateway to COVID-19 disease severity. Drug Dev. Res.81(7), 771–776 (2020).
  • Samuel RM , MajdH , RichterMNet al. Androgen signalling regulates SARS-CoV-2 receptor levels and is associated with severe COVID-19 symptoms in men. Cell Stem Cell27(6), 876–889 (2020).
  • Drury JE , DiCostanzo L , PenningTM , ChristiansonDW. Inhibition of human steroid 5β-reductase (AKR1D1) by finasteride and structure of the enzyme-inhibitor complex. J. Biol. Chem.284, 19786–19790 (2009).
  • Yao Z , XuY , ZhangM , JiangS , NicklausMC , LiaoC. Discovery of a novel hybrid from finasteride and epristeride as 5α-reductase inhibitor. Bioorg. Med. Chem. Lett.21, 475–478 (2011).
  • Wright NP , WalesJK. An unusual case of hermaphroditism-A 46, XX/69, XXY chimera. J. Pediatr. Endocrinol. Metab.17, 905–908 (2004).
  • Xiao Q , WangL , SupekarSet al. Structure of human steroid 5α-reductase 2 with the anti-androgen drug finasteride. Nat. Commun.11(1), 1–11 (2020).
  • Way2drug . www.way2drug.com/passtargets/
  • Güner OF , WaldmanM , HoffmannR , KimJH. Strategies for database mining and pharmacophore development. In: Pharmacophore Perception, Development, and Use in Drug Design, IUL BIotechnology Series.GünerOF ( Ed.). International University Line, La Jolla, CA, USA, 213–236 (2000).
  • John S , ThangapandianS , SakkiahS , LeeKW. Potent BACE-1 inhibitor design using pharmacophore modeling, in silico screening and molecular docking studies. BMC Bioinform.12, 1–11 (2011).
  • Ismail MA , Aboul-EneinMN , AbouzidKA , AbouEl Ella DA , IsmailNS. ACE inhibitors hypothesis generation for selective design, synthesis and biological evaluation of 3-mercapto-2-methyl-propanoyl-pyrrolidine-3-imine derivatives as antihypertensive agents. Bioorg. Med. Chem.17(10), 3739–3746 (2009).
  • National Cancer Institute . The NCI transcriptional pharmacodynamics workbench. https://tpwb.nci.nih.gov
  • National Cancer Institute . Downloadable structure files of NCI open database compounds. https://cactus.nci.nih.gov/download/nci/
  • Ismail MAH , ToddMH , BarkerS , AbouEl Ella DA , AbouzidKAM , ToubarRA. Design and synthesis of new tetrazolyl- and carboxy-biphenylylmethyl-quinazolin-4-one derivatives as angiotensin II AT1 receptor antagonists. J. Med. Chem.49, 1526–1535 (2006).
  • Ismail NS , ElzahabiHS , SabryP , BaseliousFN , AbdelMalakAS , HannaF. A study of the allosteric inhibition of HCV RNA-dependent RNA polymerase and implementing virtual screening for the selection of promising dual-site inhibitors with low resistance potential. J. Recept. Sig. Transd.37(4), 341–354 (2017).
  • Elhefnawi M , ElGamacyM , FaresM. Multiple virtual screening approaches for finding new hepatitis C virus RNA-dependent RNA polymerase inhibitors: structure-based screens and molecular dynamics for the pursue of new poly pharmacological inhibitors. BMC Bioinformatics13, 1–21 (2012).
  • Krammer A , KirchhoffPD , JiangX , VenkatachalamCM , WaldmanM. LigScore: a novel scoring function for predicting binding affinities. J. Mol. Graph. Model.23, 395–407 (2005).
  • Muegge I . PMF scoring revisited. J. Med. Chem.49, 5895–5902 (2006).
  • Wei D , JiangX , ZhouLet al. Discovery of multitarget inhibitors by combining molecular docking with common pharmacophore matching. J. Med. Chem.51, 7882–7888 (2008).
  • Lakshmi PJ , KumarBV , NayanaRS. Design, synthesis, and discovery of novel non-peptide inhibitor of caspase-3 using ligand based and structure based virtual screening approach. Bioorg. Med. Chem.17, 6040–6047 (2009).
  • Yang SY . Pharmacophore modeling and applications in drug discovery: challenges and recent advances. Drug Discov. Today15, 444–450 (2010).
  • Faragalla J , BremnerJ , BrownD , GriffithR , HeatonA. Comparative pharmacophore development for inhibitors of human and rat 5-α-reductase. J. Mol. Graph. Model.22, 83–92 (2003).
  • Chen GS , ChangCS , KanWM , ChangCL , WangKC , ChernJW. Novel lead generation through hypothetical pharmacophore three-dimensional database searching: discovery of isoflavonoids as nonsteroidal inhibitors of rat 5α-reductase. J. Med. Chem.44, 3759–3763 (2001).
  • Sprague PW . Automated chemical hypothesis generation and database searching with Catalyst®. Perspect. Drug. Discov.3, 1–20 (1995).
  • Tsai HH , ZanuyD , HaspelNet al. The stability and dynamics of the human calcitonin amyloid peptide DFNKF. Biophys. J.87, 146–158 (2004).
  • Thangapandian S , JohnS , SakkiahS , LeeKW. Ligand and structure based pharmacophore modeling to facilitate novel histone deacetylase 8 inhibitor design. Eur. J. Med. Chem.45, 4409–4417 (2010).
  • Mandour AA , NassarIF , AbdelAal MTet al. Synthesis, biological evaluation and in silico studies of new CDK2 inhibitors based on pyrazolo[3,4-d]pyrimidine and pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine scaffold with apoptotic activity. J. Enzyme Inhib. Med. Chem.37(1), 1957–1973 (2022).
  • Nassar IF , AalMT , El-SayedWAet al. Discovery of pyrazolo [3, 4-d] pyrimidine and pyrazolo [4, 3-e][1, 2, 4] triazolo [1, 5-c] pyrimidine derivatives as novel CDK2 inhibitors: synthesis, biological and molecular modeling investigations. RSC Adv.12(23), 14865–14882 (2022).
  • Hagras M , MandourAA , MohamedEAet al. Design, synthesis, docking study and anticancer evaluation of new trimethoxyphenyl pyridine derivatives as tubulin inhibitors and apoptosis inducers. RSC Adv.11(63), 39728–39741 (2021).

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