Aromatic sulphonamides of aziridine-2-carboxylic acid derivatives as novel PDIA1 and PDIA3 inhibitors

References

• Hemminki K, Ludlum DB. Covalent modification of DNA by antineoplastic agent. J Natl Cancer Inst. 1984;73(5):1021–1028.
   PubMedGoogle Scholar
• Akhtar R, Naqvi SAR, Zahoor AF, Saleem S. Nucleophilic ring opening reactions of aziridines. Mol Divers. 2018;22(2):447–501.
   PubMed Web of Science ®Google Scholar
• Gaitonde M. A spectrophotometric method for the direct determination of cysteine in the presence of other naturally occurring amino acids. Biochem J. 1967;104(2):627–633.
   PubMed Web of Science ®Google Scholar
• Morodor L, Musiol HJ, Scharf R. Aziridine-2-carboxylic acid A reactive amino acid unit for a new class of cysteine proteinase inhibitors. FEBS Lett. 1992;299(1):51–53.
   PubMed Web of Science ®Google Scholar
• Leite I, Andrianov V, Zelencova-Gopejenko D, Loza E, Kazhoka-Lapsa I, Domracheva I, Stoyak M, Chlopicki S, Kalvins I. Aziridine-2-carboxylic acid derivatives and its open-ring isomers as a novel PDIA1 inhibitors. Chem Heterocycl Comp. 2021;57(11):1086–1106.
   Web of Science ®Google Scholar
• Aleksis R, Jaudzems K, Ivanova J, Žalubovskis R, Kalvinsh I, Liepinsh E. Reactivity of aziridine-2-carboxamide (leakadine) with nucleophiles in aqueous solutions. Chem Heterocycl Comp. 2014;49(11):1589–1598.
   Web of Science ®Google Scholar
• Ali Khan H, Mutus B. Protein disulfide isomerase a multifunctional protein with multiple physiological roles. Front Chem. 2014;2:70.
   PubMed Web of Science ®Google Scholar
• Kozlov G, Määttänen P, Thomas DY, Gehring K. A structural overview of the PDI family of proteins. FEBS J. 2010;277(19):3924–3936.
   PubMed Web of Science ®Google Scholar
• Xu S, Sankar S, Neamati N. Protein disulfide isomerase: a promising target for cancer therapy. Drug Discov Today. 2014;19(3):222–240.
   PubMed Web of Science ®Google Scholar
• Benham AM. The protein disulfide isomerase family: key players in health and disease. Antioxid Redox Signal. 2012;16(8):781–789.
   PubMed Web of Science ®Google Scholar
• Stojak M, Milczarek M, Kurpinska A, Suraj-Prazmowska J, Kaczara P, Wojnar-Lason K, Banach J, Stachowicz-Suhs M, Rossowska J, Kalviņš I, et al. Protein disulphide isomerase A1 is involved in the regulation of breast cancer cell adhesion and transmigration via lung microvascular endothelial cells. Cancers (Basel). 2020;12(10):2850.
   PubMed Web of Science ®Google Scholar
• Wu Y, Essex DW. Vascular thiol isomerases in thrombosis: the yin and yang. J Thromb Haemost. 2020;18(11):2790–2800.
   PubMed Web of Science ®Google Scholar
• Keller R. The computer aided resonance assignment tutorial. Goldau, Switzerland: Cantina Verlag; 2004.
   Google Scholar
• Williamson MP. Using chemical shift perturbation to characterise ligand binding. Prog Nucl Magn Reson Spectrosc. 2013;73:1–16.
   PubMed Web of Science ®Google Scholar
• Nadir UK, Singh A. Synthesis of functionalized N ‐arylsulfonyl aziridines from α,β‐unsaturated esters, amides, ketones, and nitriles using N, N ‐dichloroarylsulfonamides as nitrogen source. Synth Commun. 2004;34(7):1337–1347.
   Web of Science ®Google Scholar
• Lapinsky DJ, Bergmeier SC. A Suzuki cross-coupling route to substituted aziridines. Tetrahedron Lett. 2001;42(49):8583–8586.
   Web of Science ®Google Scholar
• Smith AB, Kim DS. A general, convergent strategy for the construction of indolizidine alkaloids: total syntheses of (−)-indolizidine 223AB and alkaloid (−)-205B. J Org Chem. 2006;71(7):2547–2557.
   PubMed Web of Science ®Google Scholar
• Baldwin JE, Spivey AC, Schofield CJ, Sweeney JB. Amino acid synthesis via ring opening of N-sulphonyl aziridine-2-carboxylate esters with organometallic reagents. Tetrahedron. 1993;49(28):6309–6330.
   Web of Science ®Google Scholar
• Smith AM, Chan J, Oksenberg D, Urfer R, Wexler DS, Ow A, Gao L, McAlorum A, Huang SG. A high-throughput turbidometric assay for screening inhibitors of protein disulfide isomerase activity. J Biomol Screen. 2004;9(7):614–620.
   PubMedGoogle Scholar
• Watanabe MM, Laurindo FRM, Fernandes DC. Methods of measuring protein disulfide isomerase activity: a critical overview. Front Chem. 2014;2:73.
   PubMed Web of Science ®Google Scholar
• Kemmink J, Darby NJ, Creighton TE, Dijkstra K, Scheek RM. Nuclear magnetic resonance characterization of the N-terminal thioredoxin-like domain of protein disulfide isomerase. Protein Sci. 1995;4(12):2587–2593.
   PubMed Web of Science ®Google Scholar
• Kemmink J, Darby NJ, Dijkstra K, Nilges M, Creighton TE. Structure determination of the N-terminal thioredoxin-like domain of protein disulfide isomerase using multidimensional heteronuclear 13C/15N NMR spectroscopy. Biochemistry. 1996;35(24):7684–7691.
   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
• Stokes WS, Casati S, Strickland J, Paris M. Neutral red uptake cytotoxicity tests for estimating starting doses for acute oral toxicity tests. Curr Protoc Toxicol. 2008;36:20.4.1–20.4.20.
   Google Scholar
• ICCVAM. Test method valuation report (TMER): in vitro cytotoxicity test methods for estimating starting doses for acute oral systemic toxicity tests. Research Triangle Park (NC): NIH Publication; 2006.
   Google Scholar
• ICCVAM. 2006a, Background review document: in vitro basal cytotoxicity test methods for estimating acute oral systemic toxicity. Research Triangle Park (NC): National Institute for Environmental Health Sciences.
   Google Scholar
• OECD, Guidelines 420. Acute oral toxicity − fixed dose procedure. OECD guidelines for testing of chemicals. Paris, France: OECD; 2001. p. 1.
   Google Scholar
• Wietrzyk J, Chodyński M, Fitak H, Wojdat E, Kutner A, Opolski A. Antitumor properties of diastereomeric and geometric analogs of vitamin D3. Anticancer Drugs. 2007;18(4):447–457.
   PubMed Web of Science ®Google Scholar
• Pawlak A, Ziolo E, Fiedorowicz A, Fidyt K, Strzadala L, Kalas W. Long-lasting reduction in clonogenic potential of colorectal cancer cells by sequential treatments with 5-azanucleosides and topoisomerase inhibitors. BMC Cancer. 2016;16(1):893.
   PubMedGoogle Scholar
• Milczarek M, Psurski M, Kutner A, Wietrzyk J. Vitamin D analogs enhance the anticancer activity of 5-fluorouracil in an in vivomouse colon cancer model. BMC Cancer. 2013;13(1):294.
   PubMedGoogle Scholar
• Kramkowski K, Leszczynska A, Mogielnicki A, Chlopicki S, Fedorowicz A, Grochal E, Mann B, Brzoska T, Urano T, Motterlini R, et al. Antithrombotic properties of water-soluble carbon monoxide-releasing molecules. Arterioscler Thromb Vasc Biol. 2012;32(9):2149–2157.
   PubMed Web of Science ®Google Scholar
• Vuori K, Myllylä R, Pihlajaniemi T, Kivirikko KI. Expression and site-directed mutagenesis of human protein disulfide isomerase in Escherichia coli. This multifunctional polypeptide has two independently acting catalytic sites for the isomerase activity. J Biol Chem. 1992;267(11):7211–7214.
   PubMed Web of Science ®Google Scholar
• Gilfix BM, Blank DW, Rosenblatt DS. Novel reductant for determination of total plasma homocysteine. Clin Chem. 1997;43(4):687–688.
   PubMed Web of Science ®Google Scholar
• Xu S, Butkevich AN, Yamada R, Zhou Y, Debnath B, Duncan R, Zandi E, Petasis NA, Neamati N. Discovery of an orally active small-molecule irreversible inhibitor of protein disulfide isomerase for ovarian cancer treatment. Proc Natl Acad Sci USA. 2012;109(40):16348–16353.
   PubMed Web of Science ®Google Scholar
• Jasuja R, Passam FH, Kennedy DR, Kim SH, van Hessem L, Lin L, Bowley SR, Joshi SS, Dilks JR, Furie B, et al. Protein disulfide isomerase inhibitors constitute a new class of antithrombotic agents. J Clin Invest. 2012;122(6):2104–2113.
   PubMed Web of Science ®Google Scholar
• Rancy PC, Thorpe C. Oxidative protein folding in vitro: a study of the cooperation between quiescin-sulfhydryl oxidase and protein disulfide isomerase. Biochemistry. 2008;47(46):12047–12056.
   PubMed Web of Science ®Google Scholar
• Santos GB, Gonzalez-Perilli L, Mastrogiovanni M, Aicardo A, Cerdeira CD, Trostchansky A, Brigagão MRPL. Nitroxide 4-hydroxy-2,2′,6,6′-tetramethylpiperidine 1-oxyl (Tempol) inhibits the reductase activity of protein disulfide isomerase via covalent binding to the Cys 400 residue on CXXC redox motif at the a′active site. Chem Biol Interact. 2017;272:117–124.
   PubMed Web of Science ®Google Scholar
• Stainer AR, Sasikumar P, Bye AP, Unsworth AJ, Holbrook LM, Tindall M, Lovegrove JA, Gibbins JM. The metabolites of the dietary flavonoid quercetin possess potent antithrombotic activity, and interact with aspirin to enhance antiplatelet effects. TH Open. 2019;3(3):e244–e258.
   PubMedGoogle Scholar
• Karala AR, Ruddock LW. Bacitracin is not a specific inhibitor of protein disulfide isomerase. FEBS J. 2010;277(11):2454–2462.
   PubMed Web of Science ®Google Scholar
• Khan MMG, Simizu S, Lai NS, Kawatani M, Shimizu T, Osada H. Discovery of a small molecule PDI inhibitor that inhibits reduction of HIV-1 envelope glycoprotein gp120. ACS Chem Biol. 2011;6(3):245–251.
   PubMed Web of Science ®Google Scholar
• Lovat PE, Corazzari M, Armstrong JL, Martin S, Pagliarini V, Hill D, Brown AM, Piacentini M, Birch-Machin MA, Redfern CPF. Increasing melanoma cell death using inhibitors of protein disulfide isomerases to abrogate survival responses to endoplasmic reticulum stress. Cancer Res. 2008; 68(13):5363–5369.
   PubMed Web of Science ®Google Scholar
• Potashman MH, Duggan ME. Covalent modifiers: an orthogonal approach to drug design. J Med Chem. 2009;52(5):1231–1246.
   PubMed Web of Science ®Google Scholar
• Boike L, Henning NJ, Nomura DK. Advances in covalent drug discovery. Nat Rev Drug Discov. 2022;21(12):881–898.
   PubMed Web of Science ®Google Scholar