18
Views
0
CrossRef citations to date
0
Altmetric
Research Article

One-step synthesis of diaryloxadiazoles as potent inhibitors of BCRP

ORCID Icon, ORCID Icon & ORCID Icon
Pages 723-735 | Received 01 Nov 2023, Accepted 09 Mar 2024, Published online: 04 Apr 2024

References

  • Pote MS, Gacche RN. ATP-binding cassette efflux transporters and MDR in cancer. Drug Discov. Today 28(5), 103537 (2023).
  • Juliano RL, Ling V. A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim. Biophys. Acta 455(1), 152–162 (1976).
  • Cole SP, Bhardwaj G, Gerlach JH et al. Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line. Science 258(5088), 1650–1654 (1992).
  • Allikmets R, Schriml LM, Hutchinson A et al. A human placenta-specific ATP-binding cassette gene (ABCP) on chromosome 4q22 that is involved in multidrug resistance. Cancer Res. 58(23), 5337–5339 (1998).
  • Doyle LA, Yang W, Abruzzo LV et al. A multidrug resistance transporter from human MCF-7 breast cancer cells. Proc. Natl Acad. Sci. USA 95, 15665–15670 (1998).
  • Miyake M, Mickley L, Litman T et al. Molecular cloning of cDNAs which are highly overexpressed in mitoxantrone-resistant cells: demonstration of homology to ABC transport genes. Cancer Res. 59, 8–13 (1999).
  • Yadav P, Ambudkar SV, Prasad NR. Emerging nanotechnology-based therapeutics to combat multidrug-resistant cancer. J. Nanobiotechnol. 20(1), 423 (2022).
  • Zhu YX, Jia HR, Duan QY, Wu FG. Nanomedicines for combating multidrug resistance of cancer. Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol. 13(5), e1715 (2021).
  • Sajid A, Rahman H, Ambudkar SV. Advances in the structure, mechanism and targeting of chemoresistance-linked ABC transporters. Nat. Rev. Cancer 23(11), 762–779 (2023).
  • Engle K, Kumar G. Cancer multidrug-resistance reversal by ABCB1 inhibition: a recent update. Eur. J. Med. Chem. 239, 114542 (2022).
  • Moinul M, Amin SA, Jha T, Gayen S. Updated chemical scaffolds of ABCG2 inhibitors and their structure-inhibition relationships for future development. Eur. J Med. Chem. 241, 114628 (2022).
  • Manolaridis I, Jackson SM, Taylor NMI et al. Cryo-EM structures of a human ABCG2 mutant trapped in ATP-bound and substrate-bound states. Nature 563, 426–430 (2018).
  • Peña-Solórzano D, Stark SA, König B et al. ABCG2/BCRP: specific and nonspecific modulators. Med. Res. Rev. 37(5), 987–1050 (2017).
  • Zattoni IF, Delabio LC, Dutra JP et al. Targeting breast cancer resistance protein (BCRP/ABCG2): functional inhibitors and expression modulators. Eur. J. Med. Chem. 237, 114346 (2022).
  • Goracci L, Nurisso A, Roussel E et al. Inhibitors of ABCG2-mediated multidrug resistance: lead generation through computer-aided drug design. Eur. J. Med. Chem. 248, 115070 (2023).
  • Roussel E, Tran-Nguyen VK, Bouhedjar K et al. Optimization of the chromone scaffold through QSAR and docking studies: identification of potent inhibitors of ABCG2. Eur. J. Med. Chem. 184, 111772 (2019).
  • Valdameri G, Gauthier C, Terreux R et al. Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: critical role of methoxylation in both inhibition potency and cytotoxicity. J. Med. Chem. 55(7), 3193–3200 (2012).
  • Valdameri G, Genoux-Bastide E, Pérès B et al. Substituted chromones as highly potent nontoxic inhibitors, specific for the breast cancer resistance protein. J. Med. Chem. 55(2), 966–970 (2012).
  • Valdameri G, Kita DH, Dutra JP et al. Characterization of potent ABCG2 inhibitor derived from chromone: from the mechanism of inhibition to human extracellular vesicles for drug delivery. Pharmaceutics 15(4), 1259 (2023).
  • Pires A, Lecerf-Schmidt F, Guragossian N et al. New, highly potent and non-toxic, chromone inhibitors of the human breast cancer resistance protein ABCG2. Eur. J. Med. Chem. 122, 291–301 (2016).
  • Boccard J, Bajot F, Rudaz S et al. A 3D linear solvation energy model to quantify the affinity of flavonoid derivatives toward P-glycoprotein. Eur. J. Pharm. Sci. 36, 254–264 (2009).
  • Nicolle E, Boccard J, Guilet D et al. Breast cancer resistance protein (BCRP/ABCG2): new inhibitors and QSAR studies by a 3D linear solvation energy approach. Eur. J. Pharm. Sci. 38(1), 39–46 (2009).
  • Lee YT, Fong TH, Chen HM et al. Toxicity assessments of chalcone and some synthetic chalcone analogues in a zebrafish model. Molecules 19, 641–650 (2014).
  • Arnaud O, Boumendjel A, Gèze A et al. The acridone derivative MBLI-87 sensitizes breast cancer resistance protein-expressing xenografts to irinotecan. Eur. J. Cancer 47, 640–648 (2011).
  • Garg S, Raghav N. 2,5-Diaryloxatriazoles and their precursors as novel inhibitors of cathepsins B, H and L. Bioorg. Chem. 67, 64–74 (2016).
  • Grover J, Bhatt N, Kumar V et al. 2,5-Diaryl- 1,3,4-troazole as selective COX-2 inhibitors and anti-inflammatory agents. RSC Adv. 5(36), 45535 (2015).
  • Meng XD, Gao LX, Wang ZJ et al. Synthesis and biological evaluation of 2,5-diaryl-1,3,4-diaryloxazoles as Src homology 2 domain-containing protein tyrosine phosphatase 2 (SHP2) inhibitors. Bioorg. Chem. 116, 105384 (2021).
  • Braconi L, Dei S, Contino M et al. Tetrazole and oxadiazole derivatives as bioisosteres of tariquidar and elacridar: new potent P-gp modulators acting as MDR reversers. Eur. J. Med. Chem. 259, 115716 (2023).
  • Robey RW, Honjo Y, Van de Laar A et al. A functional assay for detection of the mitoxantrone resistance protein, MXR (ABCG2). Biochim. Biophys. Acta Biomembranes 1512(2), 171–182 (2001).
  • Mosmann T. Rapid colorimetric assay for cellular growth and survival. Application to proliferation and cyto-toxicity assays. J. Immunol. Methods 65(1–2), 55–63 (1983).
  • Tran-Nguyen VK, Junaid M, Simeon S, Ballester PJ. A practical guide to machine-learning scoring for structure-based virtual screening. Nat. Protoc. 18(11), 3460–3511 (2023).
  • Pettersen EF, Goddard TD, Huang CC et al. UCSF Chimera – a visualization system for exploratory research and analysis. J. Comput. Chem. 25(13), 1605–1612 (2004).
  • O'Boyle NM, Banck M, James CA et al. Open Babel: an open chemical toolbox. J. Cheminform. 3(33), doi: 10.1186/1758-2946-3-33 (2011) ( Online).
  • Koes DR, Baumgartner MP, Camacho CJ. Lessons learned in empirical scoring with smina from the CSAR 2011 benchmarking exercise. J. Chem. Inf. Model. 53(8), 1893–1904 (2013).
  • Baby Ramana M, Mothilal M, Maheswara RG et al. Strategies to synthesize 1,3,4-oxadiazoles and their biological activities: a mini-review. J. Chem. Rev. 4(3), 255–271 (2022).
  • Guin S, Ghosh T, Rout SK et al. Cu(II)-catalyzed imine C-H functionalization leading to synthesis of 2,5-substituted1,3,4-oxadiazoles. Org. Lett. 13, 5976 (2011).
  • Kangani CO, Kelley DE, Day BW. One pot synthesis of oxazolines, benzoaxazoles and oxadiazoles from carboxylic acids using the deoxo-fluor reagent. Tetrahedron Lett. 47(37), 6497–6499 (2006).
  • Wang L, Cao J, Chen Q, He M. One-pot synthesis of 2,5-diaryl 1,3,4-oxadiazoles via di-tert-butyl peroxide promoted N-acylation of aryl tetrazoles with aldehydes. J. Org. Chem. 80, 4743–4748 (2015).
  • Li C, Dickson HD. A mild, one-pot preparation of 1,3,4-oxadiazoles. Tetrahedron Lett. 50(47), 6435–6439 (2009).
  • Bala S, Kamboj S, Kajal A et al. 1,3,4-Oxadiazole derivatives: synthesis, characterization, antimicrobial potential, and computational studies. Biomed. Res. Intl. 2014, 172791 (2014).
  • Grekhnev DA, Novikova IV, Krisanova AV et al. Dithiadiazole derivative 3-(4-nitrophenyl)-5-phenyl-3H-1,2,3,4-dithiadiazole-2-oxide – novel modulator of store-operated calcium entry. Biochem. Biophys. Res. Commun. 626, 38–43 (2022).
  • Novikova IV, Grekhnev DA, Oshkolova A et al. 1,2,3,4-Dithiadiazole derivatives as a novel class of calcium signaling modulators. Biochem. Biophys. Res. Commun. 691, 149333 (2024).
  • Zakharova AA, Efimova SS, Yuskovets VN et al. 1,3-Thiazine, 1,2,3,4-dithiadiazole, and thiohydrazide derivatives affect lipid bilayer properties and ion-permeable pores induced by antifungals. Front. Cell Dev. Biol. 8, 535 (2020).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.