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Review

Recent developments and strategies for the discovery of TACE inhibitors

, , , , , , & show all
Pages 779-801 | Received 10 Nov 2019, Accepted 16 Mar 2020, Published online: 13 Apr 2020

References

  • Wong E, Cohen T, Romi E, et al. Harnessing the natural inhibitory domain to control TNFα Converting Enzyme (TACE) activity in vivo. Sci Rep. 2016;6(1):35598.
  • Kato T, Hagiyama M, Ito A. Renal ADAM10 and 17: their physiological and medical meanings. Front Cell Dev Biol. 2018;6:153.
  • Chemaly M, McGilligan V, Gibson M, et al. Role of tumour necrosis factor alpha converting enzyme (TACE/ADAM17) and associated proteins in coronary artery disease and cardiac events. Arch Cardiovasc Dis. 2017;110:700–711.
  • Klein T, Bischoff R. Active metalloproteases of the A Disintegrin and Metalloprotease (ADAM) family: biological function and structure. J Proteome Res. 2011;10:17–33.
  • Bode W, Gomis-Rüth FX, Stöckler W. Astacins, serralysins, snake venom and matrix metalloproteinases exhibit identical zinc-binding environments (HEXXHXXGXXH and Met-turn) and topologies and should be grouped into a common family, the ‘metzincins’. FEBS Lett. 1993;331:134–140.
  • Moss ML, Minond D. Recent advances in ADAM17 research: a promising target for cancer and inflammation. Mediators Inflamm. 2017;2017:9673537.
  • Moss ML, Sklair-Tavron L, Nudelman R. Drug insight: tumor necrosis factor-converting enzyme as a pharmaceutical target for rheumatoid arthritis. Nat Clin Pract Rheumatol. 2008;4:300–309.
  • Zhou J, Zhang Y, Zhou X, et al. An expeditious one-pot synthesis of 1,6-dideoxy-N-alkylated nojirimycin derivatives and their inhibitory effects on the secretion of IFN-gamma and IL-4. Bioorg Med Chem. 2008;16:1605–1612.
  • Duan JJ, Chen L, Wasserman ZR, et al. Discovery of gamma-lactam hydroxamic acids as selective inhibitors of tumor necrosis factor alpha converting enzyme: design, synthesis, and structure-activity relationships. J Med Chem. 2002;45:4954–4957.
  • Grootveld M, McDermott MF. BMS-561392. Bristol-Myers Squibb. Curr Opin Invest Drugs. 2003;4:598–602.
  • Qian M, Bai SA, Brogdon B, et al. Pharmacokinetics and pharmacodynamics of DPC 333 ((2R)-2-((3R)-3-amino-3{4-[2-methyl-4-quinolinylmethoxy]phenyl}-2-oxopyrrolidinyl)-N-hydroxy-4-methylpentanamide)), a potent and selective inhibitor of tumor necrosis factor alpha-converting enzyme in rodents, dogs, chimpanzees, and humans. Drug Metab Dispos. 2007;35:1916–1925.
  • Clary L. Novel benzenesulphonamide compounds, method for synthesizing same, and the use thereof in medicine as well as in cosmetics. WO2011/001088. 2011.
  • Thabet MM, Huizinga TW. Drug evaluation: apratastat, a novel TACE/MMP inhibitor for rheumatoid arthritis. Curr Opin Invest Drugs. 2006;7: 1014–1019.
  • Moss ML, Jin SLC, Milla ME, et al. Cloning of a disintegrin metalloproteinase that processes precursor tumor-necrosis factor -alpha. Nature. 1997;385:733–736.
  • Murumkar PR, Giridhar R, Yadav MR. 3D-quantitative structure-activity relationship studies on benzothiadiazepinehydroxamates as inhibitors of tumor necrosis factor-alpha converting enzyme. Chem Biol Drug Des. 2008;71:363–373.
  • Murumkar PR, Gupta SD, Zambre VP, et al. Development of predictive 3D-QSAR CoMFA and CoMSIA models for beta-aminohydroxamic acid-derived tumor necrosis factor-alpha converting enzyme inhibitors. Chem Biol Drug Des. 2009;73:97–107.
  • DasGupta S, Murumkar PR, Giridhar R, et al. Studies on novel 2-imidazolidinones and tetrahydropyrimidin-2(1H)-ones as potential TACE inhibitors: design, synthesis, molecular modeling, and preliminary biological evaluation. Bioorg Med Chem. 2009;17:3604–3617.
  • Murumkar PR, Zambre VP, Yadav MR. Development of predictive pharmacophore model for in silico screening, and 3D QSAR CoMFA and CoMSIA studies for lead optimization, for designing of potent tumor necrosis factor alpha converting enzyme inhibitors. J Comput Aided Mol Des. 2010;24:143–156.
  • Sengupta P, Puri CS, Chokshi HA, et al. Synthesis, preliminary biological evaluation and molecular modeling of some new heterocyclic inhibitors of TACE. Eur J Med Chem. 2011;46:5549–5555.
  • Murumkar PR, Sharma MK, Shinde AC, et al. Three-dimensional quantitative structure–activity relationship CoMFA/CoMSIA on pyrrolidine-based tartrate diamides as TACE inhibitors. Med Chem Res. 2013;22:4192–4201.
  • Murumkar PR, Sharma MK, Giridhar R, et al. Virtual screening-based identification of lead molecules as selective TACE inhibitors. Med Chem Res. 2015;24:226–244.
  • DasGupta S, Murumkar PR, Giridhar R, et al. Current perspective of TACE inhibitors: a review. Bioorg Med Chem. 2009;17:444–459.
  • Murumkar PR, DasGupta S, Chandani SR, et al. Novel TACE inhibitors in drug discovery: a review of patented compounds. Expert Opin Ther Pat. 2010;20:31–57.
  • Yadav MR, Gupta SD, Murumkar PR, et al. Small molecule selective TACE inhibitors: potential therapeutic agents. Adv Med Biol. 2010;3:77–116.
  • Yadav MR, Murumkar PR, Zambre VP. Advances in studies on collagenase inhibitors. Exp Suppl. 2012;103:83–135.
  • Murumkar PR, Giridhar R, Yadav MR. Novel methods and strategies in the discovery of TACE inhibitors. Expert Opin Drug Discov. 2013;8:157–181.
  • Nuti E, Casalini F, Santamaria S, et al. Selective Arylsulfonamide inhibitors of ADAM-17: hit optimization and activity in ovarian cancer cell models. J Med Chem. 2013;56:8089–8103.
  • Nuti E, Casalini F, Avramova SI. Potent arylsulfonamide inhibitors of tumor necrosis factor-alpha converting enzyme able to reduce activated leukocyte cell adhesion molecule shedding in cancer cell models. J Med Chem. 2010;53:2622–2635.
  • Rossello A, Nuti E, Maresca A. ADAMs and ADAMts selective synthetic inhibitors. In drug design of zinc-enzyme inhibitors: functional, structural, and disease applications. In: CT S, Winum JY, editors. Wiley series in drug discovery and development. Hoboken, NJ: John Wiley and sons; 2009. p. 591–645.
  • Fisher JF, Mobashery S. Recent advances in MMP inhibitor design. Cancer Metastasis Rev. 2006;25:115–136.
  • Georgiadis D. Yiotakis A specific targeting of metzincin family members with small-molecule inhibitors: progress toward a multifarious challenge. Bioorg Med Chem. 2008;16:8781–8794.
  • Condon JS, Joseph-McCarthy D, Levin JI, et al. Identification of potent and selective TACE inhibitors via the S1 pocket. Bioorg Med Chem Lett. 2007;17:34–39.
  • Li NG, Shi ZH, Tang YP. Discovery of selective small molecular TACE inhibitors for the treatment of rheumatoid arthritis. Curr Med Chem. 2012;19:2924–2956.
  • Guo Q, Wang Y, Xu D, et al. Rheumatoid arthritis: pathological mechanisms and modern pharmacologic therapies. Bone Res. 2018;6:15.
  • Ouvry G, Berton Y, Bhurruth-Alcor Y. Identification of novel TACE inhibitors compatible with topical application. Bioorg Med Chem Lett. 2017;27:1848–1853.
  • Aubert J. Utilization of TACE inhibitors for the treatment of acne. WO2009/004247. 2010.
  • Boiteau JG, Ouvry G, Arlabosse JM. Discovery and process development of a novel TACE inhibitor for the topical treatment of psoriasis. Bioorg Med Chem. 2018;26:945–956.
  • Tu G, Xu W, Huang H. Progress in the development of matrix metalloproteinase inhibitors. Curr Med Chem. 2008;15:1388–1395.
  • Rosner KE, Guo Z, Orth P. the discovery of novel tartrate-based TNF-alpha converting enzyme (TACE). Bioorg Med Chem Lett. 2010;20:1189–1193.
  • Guardiani C, Procacci P. The conformational landscape of tartrate-based inhibitors of the TACE enzyme as revealed by Hamiltonian replica exchange simulation. Phys Chem Chem Phys. 2013;15:9186–9196.
  • Dai C, Li D. Popovici-Muller J.2-(2-Aminothiazol-4-yl)pyrrolidine-based tartrate diamides as potent, selective and orally bioavailable TACE inhibitors. Bioorg Med Chem Lett. 2011;21:3172–3176.
  • Banchelli M, Guardiani C, Tenori E, et al. Chemical-physical analysis of a tartrate model compound for TACE inhibition. Phys Chem Chem Phys. 2013;15:18881–18893.
  • Li D, Popovici-Muller J, Belanger DB. Structure and activity relationships of tartrate-based TACE inhibitors. Bioorg Med Chem Lett. 2010;20:4812–4815.
  • Banchelli M, Guardiani C, Sandberg RB, et al. Media effects in modulating the conformational equilibrium of a model compound for tumor necrosis factor converting enzyme inhibition. J Mol Struct. 2015;1091:65–73.
  • Ren S, Hesk D, McNamara P. Synthesis of [3H], [13C3, 15N], and [14C]SCH900567: an inhibitor of TNF-α (tumor necrosis factor alpha) converting enzyme (TACE). J Labelled Comp Radiopharm. 2014;57:632–636.
  • Yu W, Guo Z, Orth P, et al. Discovery and SAR of hydantoin TACE inhibitors. Bioorg Med Chem Lett. 2010;20:1877–1880.
  • Yu W, Tong L, Kim SH. Biaryl substituted hydantoin compounds as TACE inhibitors. Bioorg Med Chem Lett. 2010;20:5286–5289.
  • Shankar B. Compounds for the treatment of inflammatory disorders. WO/2010/0366638 . 2010.
  • Tong L, Kim SH, Rosner K. Fused bi-heteroaryl substituted hydantoin compounds as TACE inhibitors. Bioorg Med Chem Lett. 2017;27:3037–3042.
  • Rautio J, Kumpulainen H, Heimbach T, et al. Prodrugs: design and clinical applications. Nat Rev Drug Discovery. 2008;7:255–270.
  • Tong L, Kim SH, Chen L. Development of a prodrug of hydantoin based TACE inhibitor. Bioorg Med Chem Lett. 2017;27:3704–3708.
  • Pu Y, Cao D, Xie C. Anti-arthritis effect of a novel quinazoline derivative through inhibiting production of TNF-α mediated by TNF-α converting enzyme in murine collagen-induced arthritis model. Biochem Biophys Res Commun. 2015;462:288–293.
  • Wu D, Gu Q1, Zhao N. Structure-based rational design of peptide hydroxamic acid inhibitors to target tumor necrosis factor-α converting enzyme as potential therapeutics for hepatitis. J Drug Target. 2015;23:936–942.
  • Berman HM, Westbrook J, Feng Z, et al. The protein data bank. Nucleic Acids Res. 2000;28:235–242.
  • Wang Z, L W, Fan R. Molecular design and structural optimization of potent peptide hydroxamate inhibitors to selectively target human ADAM metallopeptidase domain 17. Comput Biol Chem. 2016;61:15–22.
  • Qiu Z, Yan M, Li Q, et al. Definition of peptide inhibitors from a synthetic peptide library by targeting gelatinase B/matrix metalloproteinase-9 (MMP-9) and TNF-α converting enzyme (TACE/ADAM-17).J. J Enzyme Inhib Med Chem. 2012;27:533–540.
  • Udechukwu MC, Tsopmo A, Mawhinney H, et al. Inhibition of ADAM17/TACE activity by zinc-chelating rye secalin-derived tripeptides and analogues. RSC Adv. 2017;7:26361–26369.
  • Bandarage UK, Wang T, Come JH. Novel thiol-based TACE inhibitors. Part 2: rational design, synthesis, and SAR of thiol-containing aryl sulfones. Bioorg Med Chem Lett. 2008;18:44–48.
  • Leung CH, Liu LJ, Lu L, et al. A metal-based tumour necrosis factor-alpha converting enzyme inhibitor. Chem Commun. 2015;51:3973–3976.
  • Srour N, Lebel A, McMahon S, et al. TACE/ADAM-17 maturation and activation of sheddase activity require proprotein convertase activity. FEBS Lett. 2003;554:275–283.
  • Wong E, Maretzky T, Peleg Y, et al. The functional maturation of A Disintegrin And Metalloproteinase (ADAM) 9, 10 and 17 requires processing at a newly identified proprotein convertase (PC) cleavage site. J Biol Chem. 2015;290:12135–12146.
  • Gonzales PE, Solomon A, Miller AB, et al. Inhibition of the tumor necrosis factor-alpha converting enzyme by its pro domain. J Biol Chem. 2004;279:31638–31645.
  • Matthews AL, Noy PJ, Reyat JS, et al. Regulation of A Disintegrin And Metalloproteinase (ADAM) family sheddases ADAM10 and ADAM17: the emerging role of tetraspanins and rhomboids. Platelets. 2017;28:333–341.
  • Moroy G, Martiny VY, Vayer P, et al. Toward in silico structure-based ADMET prediction in drug discovery. Drug Discov Today. 2012;17:44–55.
  • Sliwoski G, Kothiwale S, Meiler J. Computational methods in drug discovery. Pharmacol Rev. 2014;66:334–395.
  • Feng WF, Zhao YB, Huang W, et al. Molecular modeling and biological effects of peptidomimetic inhibitors of TACE activity. J Enzyme Inhib Med Chem. 2010;25:459–466.
  • Murumkar PR, Le L, Truong TN, et. al. Determination of structural requirements of influenza neuraminidase type A inhibitors and binding interaction analysis with the active site of A/H1N1 by 3D-QSAR CoMFA and CoMSIA modeling. Med Chem Commun. 2011;2:710–719.
  • Liu S, Liu S, Wang Y. The P2/P2ʹ sites affect the substrate cleavage of TNF-α converting enzyme (TACE). Mol Immunol. 2014;62:122–128.
  • Baker NA, Sept D, Joseph S, et al. Electrostatics of nanosystems: application to microtubules and the ribosome. Proc Natl Acad Sci USA. 2001;98:10037–10041.
  • Lambert MH, Blackburn RK, Seaton TD. Substrate specificity and novel selective inhibitors of TNF-alpha converting enzyme (TACE) from two-dimensional substrate mapping. Comb Chem High Throughput Screen. 2005;8:327–339.
  • Kalyan Kumar G, Dhamotharan R, Kulkarni NM, et al. Embelin reduces cutaneous TNF-α level and ameliorates skin edema in acute and chronic model of skin inflammation in mice. Eur J Pharmacol. 2011;662:63–69.
  • Dhanjal JK, Nigam N, Sharma S, et al. Embelin inhibits TNF-α converting enzyme and cancer cell metastasis: molecular dynamics and experimental evidence. BMC Cancer. 2014;14:775.
  • Shoichet BK. Virtual screening of chemical libraries. Nature. 2004;432:862–865.
  • Caporuscio F, Tafi A. Pharmacophore modelling: a forty year old approach and its modern synergies. Curr Med Chem. 2011;18:2543–2553.
  • Liu LJ, Leung KH, Lin S. Pharmacophore modeling for the identification of small-molecule inhibitors of TACE. Methods. 2015;71:92–97.
  • Sarkate AP, Murumkar PR, Lokwani DK, et al. Design of selective TACE inhibitors using molecular docking studies: synthesis and preliminary evaluation of anti-inflammatory and TACE inhibitory activity.SAR. QSAR Environ Res. 2015;26:905–923.
  • Alizadeh AA, Hamzeh-Mivehroud M, Sokouti B, et al. An alignment independent 3-D QSAR study on series of Hydroxamic acid based tumor necrosis factor alpha converting enzyme inhibitors. J Chemometrics. 2016;30:537–547.
  • Speck N, Brandsch C, Schmidt N, et al. The antiatherogenic effect of fish oil in male mice is associated with a diminished release of endothelial ADAM17 and ADAM10 substrates. J Nutr. 2015;145:1218–1226.
  • Sharma M, Mohapatra J, Wagh A, et al. Involvement of TACE in colon inflammation: a novel mechanism of regulation via SIRT-1 activation. Cytokine. 2014;66:30–39.
  • Hirata S, Murata T, Suzuki D, et al. Selective inhibition of ADAM17 efficiently mediates glycoprotein Ibα retention during ex vivo generation of human induced pluripotent stem cell-derived platelets. Stem Cells Transl Med. 2017;6:720–730.
  • Hedemann N, Rogmans C, Sebens S, et al. ADAM17 inhibition enhances platinum efficiency in ovarian cancer. Oncotarget. 2018;9:16043–16058.
  • Geribaldi-Doldán N, Carrasco M, Murillo-Carretero M. Specific inhibition of ADAM17/TACE promotes neurogenesis in the injured motor cortex. Cell Death Dis. 2018;9:862.
  • Tape CJ, Willems SH, Dombernowsky SL. Cross-domain inhibition of TACE ectodomain. Proc Natl Acad Sci USA. 2011;108:5578–5583.
  • Kwok HF, Botkjaer KA, Tape CJ, et al. Development of a ‘mouse and human cross-reactive’ affinity-matured exosite inhibitory human antibody specific to TACE (ADAM17) for cancer immunotherapy. Protein Eng Des Sel. 2014;27:179–190.
  • Rios-Doria J, Sabol D, Chesebrough J, et al. A monoclonal antibody to ADAM17 inhibits tumor growth by inhibiting EGFR and non-EGFR-mediated pathways. Mol Cancer Ther. 2015;14:1637–1649.
  • Peng L, Cook K, Xu L, et al. Molecular basis for the mechanism of action of an anti-TACE antibody. mAbs. 2016;8:1598–1605.
  • Dosch J, Ziemke E, Wan S, et al. Targeting ADAM17 inhibits human colorectal adenocarcinoma progression and tumor-initiating cell frequency. Oncotarget. 2017;8:65090–65099.
  • Saad MI, Rose-John S, Jenkins BJ. ADAM17: an emerging therapeutic target for lung cancer. Cancers (Basel). 2019;11:1218.

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