Peptydowe związki makrocykliczne : nowe perspektywy w diagnostyce i terapii chorób

• Autorzy: Wądrzyk Magdalena , Miśkiewicz Julia , Kasperkiewicz-Wasilewska Paulina

Identyfikatory

DOI

10.53584/wiadchem.2024.11.1

Warianty tytułu

EN

Peptide macrocyclic compounds : new perspectives in diagnostic and disease treatment

• Języki publikacji: PL

Abstrakty

PL

In recent years macrocyclic peptides have drawn much interest due to their beneficial physiochemical properties and potential medical applications. The goal of this review is to summarize the advantages and drawbacks of macrocyclic peptides and provide examples of their use as therapeutic agents. Macrocyclic peptides are characterized by better stability, selectivity and resistance to degradation than their linear counterparts, but on the other hand, macrocyclic peptide synthesis has low efficiency due to possible side reactions and difficulties with solubility of linear precursors. Macrocyclic peptides might also be more immunogenic than their linear counterparts. Macrocyclic peptides have been found as an promising group of molecules for innovative medicine and, to date, they are used as antimicrobial drugs which are effective against both bacteria and fungi. As macrocyclic peptides are highly selective, they also serve a role in cancer therapies and diagnostics. Patented macrocyclic peptides act as a scaffold for the search and optimization of specific inhibitors of cell signaling pathways used by cancer cells to avoid cell death. The presence of peptide ringsin the structure of macrocyclic peptides makesthem analogs of hormones, such as somatostatin and insulin. As a result, macrocyclic peptides could prove to be a good basis for the development of hormonal drugs with extended duration of action. Aside from their role in medicine macrocyclic peptides might also be used in the field of chemical biology as selective and specific chemical probes which would allow for the visualization and imagining of various molecular targets.

Słowa kluczowe

PL

peptydy makrocykliczne; proteazy; terapie celowane; antybiotyki; syntetyczne hormony

EN

macrocyclic peptide; protease; target therapies; antibiotics; synthetic hormones

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2024
• Tom: [Z] 78, 11-12
• Strony: 1405--1445
• Opis fizyczny: Bibliogr. 112 poz., rys.

Twórcy

autor

Wądrzyk Magdalena

• Katedra Chemii Biologicznej i Bioobrazowania, Wydział Chemiczny Politechniki Wrocławskiej, ul. Na Grobli 15, 50-421 Wrocław

• https://orcid.org/0000-0002-9880-3375

autor

Miśkiewicz Julia

• Katedra Chemii Biologicznej i Bioobrazowania, Wydział Chemiczny Politechniki Wrocławskiej, ul. Na Grobli 15, 50-421 Wrocław

• https://orcid.org/0009-0007-2332-5122

autor

Kasperkiewicz-Wasilewska Paulina

• Katedra Chemii Biologicznej i Bioobrazowania, Wydział Chemiczny Politechniki Wrocławskiej, ul. Na Grobli 15, 50-421 Wrocław

• https://orcid.org/0000-0002-1291-047X

Bibliografia

• [1] J. L. Lau and M. K. Dunn, Bioorg Med Chem, 2018, 26, 2700.
• [2] L. Wang, N. Wang, W. Zhang, X. Cheng, Z. Yan, G. Shao, X. Wang, R. Wang and C. Fu, Sig Transduct Target Ther, 2022, 7, 1.
• [3] T. A. F. Cardote and A. Ciulli, Chem Med. Chem, 2016, 11, 787.
• [4] M. Miliński, P. Najgebauer, R. Balwierz, U. Skotnicka-Graca and M. A. Staś, Farm Pol, 2022, 78, 326.
• [5] M. Muttenthaler, G. F. King, D. J. Adams and P. F. Alewood, Nat Rev Drug Discov, 2021, 20, 309
• [6] A. A. Vinogradov, Y. Yin and H. Suga, J Am Chem Soc, 2019, 141, 4167.
• [7] H. Y. Chow, Y. Zhang, E. Matheson and X. Li, Chem Rev, 2019, 119, 9971.
• [8] H. C. Hayes, L. Y. P. Luk and Y. H. Tsai, Org Biomol Chem, 2021, 19, 3983.
• [9] C. A. Lipinski, B. W. Dominy and P. J. Feeney, Adv Drug Deliv Rev, 2001, 46, 3.
• [10] P. G. Dougherty, A. Sahni and D. Pei, Chem Rev, 2019, 119, 10241.
• [11] S. Liras and K. F. McClure, ACS Med Chem Lett, 2019, 10, 1026.
• [12] D. A. Price, H. Eng, K. A. Farley, G. H. Goetz, Y. Huang, Z. Jiao, A. S. Kalgutkar, N. M. Kablaoui, B. Khunte, S. Liras, C. Limberakis, A. M. Mathiowetz, R. B. Ruggeri, J. M. Quan and Z. Yang, Org Biomol Chem, 2017, 15, 2501.
• [13] L. Gentilucci, R. De Marco and L. Cerisoli, Curr Pharm Des, 2010, 16, 3185.
• [14] B. Khatri, V. R. Nuthakki and J. Chatterjee, Methods Mol Biol, 2019, 2001, 17.
• [15] X. Ji, A. L. Nielsen and C. Heinis, Angew Chem Int Ed, 2024, 63, 8251.
• [16] S. Hess, Y. Linde, O. Ovadia, E. Safrai, D. E. Shalev, A. Swed, E. Halbfinger, T. Lapidot, I. Winkler, Y. Gabinet, A. Faier, D. Yarden, Z. Xiang, F. P. Portillo, C. Haskell-Luevano, C. Gilon and A. Hoffman, J Med Chem, 2008, 51, 1026.
• [17] G. Bhardwaj, V. Khipple Mulligan, C. D. Bahl, J. M. Gilmore, P. J. Harvey, O. Cheneval, G. W. Buchko, S. V S R K Pulavarti, Q. Kaas, A. Eletsky, P.-S. Huang, W. A. Johnsen, P. Jr Greisen, G. J. Rocklin, Y. Song, T. W. Linsky, A. Watkins, S. A. Rettie, X. Xu, L. P. Carter, R. Bonneau, J. M. Olson, E. Coutsias, C. E. Correnti, T. Szyperski, D. J. Craik and D. Baker, Nature, 2016, 538, 329.
• [18] S. J. Bogdanowich-Knipp, S. Chakrabarti, T. D. Williams, R. K. Dillman and T. J. Siahaan, J Pept Res, 1999, 53, 530.
• [19] L. K. Buckton, M. N. Rahimi and S. R. McAlpine, Chem-Eur J, 2021, 27, 1487.
• [20] J. Yang, Q. Zhu, Y. Wu, X. Qu, H. Liu, B. Jiang, D. Ge and X. Song, Front. Oncol., 2022, 12, 2171.
• [21] D. P. Fairlie, J. D. A. Tyndall, R. C. Reid, A. K. Wong, G. Abbenante, M. J. Scanlon, D. R. March, D. A. Bergman, C. L. L. Chai and B. A. Burkett, J Med Chem, 2000, 43, 1271.
• [22] T. A. Hill, N. E. Shepherd, F. Diness and D. P. Fairlie, Angew Chem Int Ed, 2014, 53, 13020.
• [23] A. L. Jochim and P. S. Arora, ACS Chem Biol, 2010, 5, 919.
• [24] M. A. T. Blaskovich, J Med Chem, 2016, 59, 10807.
• [25] B. Khatri, V. R. Nuthakki and J. Chatterjee, Methods Mol Biol, 2019, 2001, 17.
• [26] D. S. Kemp and J. Rebek, J Am Chem Soc, 1970, 92, 5792.
• [27] A. S. De Groot and D. W. Scott, Trends Immunol, 2007, 28, 482.
• [28] Immunogenicity Assessment for Therapeutic Protein Products, FDA, CDER, CBER, 2014, [online]Clinical/Medical, [dostęp:12.09.2024]. Dostępny w internecie: https://www.fda.gov/regulatory-information/search-fda-guidance-documents/immunogenicity-assessment-therapeutic-protein-productsFda, Cder and pritzlaffo, .
• [29] Clinical Pharmacology Considerations for Peptide Drug Products, FDA, CDER, 2023, [online], Clinical Pharmacology, [dostęp dnia: 12.09.2024]. Dostępny online: https://www.fda.gov/regulatory-information/search-fda-guidance-documents/clinical-pharmacology-considerations-peptide-drug-products
• [30] H. Zhang and S. Chen, RSC Chem Biol, 2022, 3, 18.
• [31] Y. Y. Syed, Drugs, 2023, 83, 833.
• [32] M. Hoenigl, R. Sprute, M. Egger, · Amir Arastehfar, · Oliver, A. Cornely, R. Krause, C. Lass-Flörl, J. Prattes, A. Spec, · George, R. Thompson, N. Wiederhold, · Jeffrey and D. Jenks, Drugs, 2021, 81, 1703
• [33] M. Szymański, S. Chmielewska, U. Czyżewska, M. Malinowska and A. Tylicki, J Enzyme Inhib Med Chem, 2022, 37, 876.
• [34] G. Pirri, A. Giuliani, S. F. Nicoletto, L. Pizzuto and A. C. Rinaldi, Cent Eur J Biol, 2009, 4, 258.
• [35] M. A. T. Blaskovich, J Med Chem, 2016, 59, 10807.
• [36] Y. Mast and W. WohllebenInt J Med Microbiol, 2014, 304, 44.
• [37] A. A. Sy-Cordero, C. J. Pearce and N. H. Oberlies, J. Antibiot, 2012, 65, 541.
• [38] A. J. Flint and A. P. Davis, Org Biomol Chem, 2022, 20, 7694.
• [39] P. Kumar Reddy Kalluru Kalluru, S. Gundakaram, M. Mamilla, S. Goutham Reddy Yartha, S. Dabbara, S. Teja Lingam, K. Naik Gugulothu, M. Gangannapalle and P. Kumar Thada, Ann Med Surg (Lond), 2024, 86,4575.
• [40] O. Yushchuk, B. Ostash, A. W. Truman, F. Marinelli and V. Fedorenko, Appl Microbiol Biotechnol, 2020, 104, 3279.
• [41] S. Biondi, E. Chugunova and M. Panunzio, in Studies in Natural Products Chemistry, Elsevier B.V., 2016, 50, 249.
• [42] A. Luther, C. Bisang and D. Obrecht, Bioorg Med Chem, 2018, 26, 2850.
• [43] J. Barberán, A. de la Cuerda and L. C. Barberán, Rev Espa Quimioter, 2021, 34, 26.
• [44] A. Y. Chen, M. J. Zervos and J. A. Vazquez, Int J Clin Pract, 2007, 61, 853.
• [45] H. Aldemir, S. Shu, F. Schaefers, H. Hong, R. Richarz, S. Harteis, M. Einsiedler, T. M. Milzarek, S. Schneider and T. A. M. Gulder, Chemistry, 2022, 28, 3389.
• [46] P. A. Smith, M. F. T. Koehler, H. S. Girgis, D. Yan, Y. Chen, Y. Chen, J. J. Crawford, M. R. Durk, R. I. Higuchi, J. Kang, J. Murray, P. Paraselli, S. Park, W. Phung, J. G. Quinn, T. C. Roberts, L. Rougé, J. B. Schwarz, E. Skippington, J. Wai, M. Xu, Z. Yu, H. Zhang, M.-W. Tan and C. E. Heise, Nature, 2018, 561, 189.
• [47] Y. Zhang, D. Zhang, W. Zhao, H. Li, Z. Lu, B. Guo, X. Meng, X. Zhou and Y. Yang, J Med Chem, 2024, 67, 6585.
• [48] N. A. Schilling, A. Berscheid, J. Schumacher, J. S. Saur, M. C. Konnerth, S. N. Wirtz, J. M. Beltrán-Beleña, A. Zipperer, B. Krismer, A. Peschel, H. Kalbacher, H. Brötz-Oesterhelt, C. Steinem and S. Grond, Angewandte Chemie, 2019, 58, 9234.
• [49] S. Roa, L. Avalle, H. Zhang, Y. Zhang, L. Wang, Q. Lei, D. Wang and K. Sun, Front. Cell Dev Biol, 2020, 8, 672.
• [50] S. Shaabani, H. P. S. Huizinga, R. Butera, A. Kouchi, K. Guzik, K. Magiera-Mularz, T. A. Holak and A. Dömling, Expert Opin Ther Pat, 2018, 28, 665.
• [51] W. Uzar, B. Kaminska, H. Rybka, L. Skalniak, K. Magiera-Mularz and R. Kitel, Expert Opin Ther Pat, 2024, 34, 627.
• [52] Q. Miao, W. Zhang, K. Zhang, H. Li, J. Zhu and S. Jiang, RSC Adv, 2021, 11, 23270.
• [53] B. A. Seigal, W. H. Connors, A. Fraley, R. M. Borzilleri, P. H. Carter, S. L. Emanuel, J. Fargnoli, K. Kim, M. Lei, J. G. Naglich, M. E. Pokross, S. L. Posy, H. Shen, N. Surti, R. Talbott, Y. Zhang and N. K. Terrett, J Med Chem, 2015, 58, 2855.
• [54] Z. D. Crees, M. P. Rettig, R. G. Jayasinghe, K. Stockerl-Goldstein, S. M. Larson, I. Arpad, G. A. Milone, M. Martino, P. Stiff, D. Sborov, D. Pereira, I. Micallef, G. Moreno-Jiménez, G. Mikala, M. Liz Paciello Coronel, U. Holtick, J. Hiemenz, M. H. Qazilbash, N. Hardy, T. Latif, I. García-Cadenas, A. Vainstein-Haras, E. Sorani, I. Gliko-Kabir, I. Goldstein, D. Ickowicz, L. Shemesh-Darvish, S. Kadosh, F. Gao, M. A. Schroeder, R. Vij and J. F. DiPersio, Nat Med, 2023, 29, 869.
• [55] S. M. Hoy, Drugs, 2023, 83, 1635.
• [56] J. D. Hainsworth, J. A. Reeves, J. R. Mace, E. J. Crane, O. Hamid, J. R. Stille, A. Flynt, S. Roberson, J. Polzer and E. R. Arrowsmith, Target Oncol, 2016, 11, 643.
• [57] R. Salgia, R. W. Weaver, M. McCleod, J. R. Stille, S. B. Yan, S. Roberson, J. Polzer, A. Flynt, E. Raddad, V. L. Peek, S. R. Wijayawardana, S. L. Um, S. Gross, M. C. Connelly, C. Morano, M. Repollet, R. Sanders, K. Baeten, D. D’Haese and D. R. Spigel, Invest New Drugs, 2017, 35, 334.
• [58] B. S. Cho, Z. Zeng, H. Mu, Z. Wang, S. Konoplev, T. McQueen, M. Protopopova, J. Cortes, J. R. Marszalek, S. Bin Peng, W. Ma, R. E. Davis, D. E. Thornton, M. Andreeff and M. Konopleva, Blood, 2015, 126, 222.
• [59] S.-B. Peng, X. Zhang, D. Paul, L. M. Kays, W. Gough, J. Stewart, M. T. Uhlik, Q. Chen, Y.-H. Hui, M. J. Zamek-Gliszczynski, J. A. Wijsman, K. M. Credille and L. Zeng Yan, Mol Cancer Ther, 2017, 8, 94619.
• [60] M. Boehm, K. Beaumont, R. Jones, A. S. Kalgutkar, L. Zhang, K. Atkinson, G. Bai, J. A. Brown, H. Eng, G. H. Goetz, B. R. Holder, B. Khunte, S. Lazzaro, C. Limberakis, S. Ryu, M. J. Shapiro, L. Tylaska, J. Yan, R. Turner, S. S. F. Leung, M. Ramaseshan, D. A. Price, S. Liras, M. P. Jacobson, D. J. Earp, ⊥ R Scott Lokey, A. M. Mathiowetz and E. Menhaji-Klotz, J Med Chem, 2017, 60, 9653.
• [61] K. D. Rasmussen and K. Helin, Genes Dev , 2016, 30, 733.
• [62] K. Šimelis, H. Saraç, E. Salah, K. Nishio, T. E. McAllister, T. P. Corner, A. Tumber, R. Belle, C. J. Schofield, H. Suga and A. Kawamura, Bioorg Med Chem, 2024, 99, 117597.
• [63] F. H. Al-Awadhi, L. A. Salvador-Reyes, L. A. Elsadek, R. Ratnayake, Q. Y. Chen and H. Luesch, ACS Chem Neurosci, 2020, 11, 1937.
• [64] G. Poli, R. Di Fabio, L. Ferrante, V. Summa and M. Botta, Chem Med Chem, 2017, 12, 1917.
• [65] M. Borgini, C. Zamperini, F. Poggialini, L. Ferrante, V. Summa, M. Botta and R. Di Fabio, ACS Med Chem Lett, 2020, 11, 846.
• [66] J. R. Diamond, T. M. Pitts, D. Ungermannova, C. G. Nasveschuk, G. Zhang, A. J. Phillips, S. M. Bagby, J. Pafford, B. W. Yacob, T. P. Newton, J. J. Tentler, B. Gittleman, S. J. Hartman, J. A. Demattei, J. D. Winkler, M. K. Wendt, W. P. Schiemann, S. G. Eckhardt, X. Liu and A. D. Piscopio, Mol Cancer Ther, 2022, 21, 397.
• [67] P. R. Watson, S. Gupta, P. Hosseinzadeh, B. P. Brown, D. Baker and D. W. Christianson, ACS Chem Biol, 2023, 18, 959.
• [68] J. Koehbach and D. J. Craik, Trends Pharmacol Sci, 2019, 40, 517.
• [69] N. L. Daly and D. J. Craik, Curr Opin Chem Biol, 2011, 15, 362.
• [70] C. Jennings, J. West, C. Waine, D. Craik and M. Anderson, Proc Natl Acad Sci USA, 2001, 98, 10614-9.
• [71] A. G. Poth, Y. H. Huang, T. T. Le, M. W. Kan and D. J. Craik, Int J Pharm, 2019, 565, 437.
• [72] L. Mehta, R. Dhankhar, P. Gulati, R. K. Kapoor, A. Mohanty and S. Kumar, J Pept Sci, 2020, 26, e3246.
• [73] J. List, J. Gattringer, S. Huszarek, S. Marinovic, H. A. Neubauer, P. Kudweis, E. M. Putz, R. Hellinger and D. Gotthardt, Biomed pharmacother, 2024, 177, 117057.
• [74] A. Stengel and Y. Taché, Ann N Y Acad Sci, 2019, 1455, 98.
• [75] P. Marbach, W. Bauer, U. Briner, W. Doepfner, T. Petcher, J. Pless Hormone Res, 1988, 29, 54.
• [76] M. Theodoropoulou and G. K. Stalla, Front Neuroendocrinol, 2013, 34, 228.
• [77] M. Bolanowski, M. Kałużny, · Przemysław Witek and · Aleksandra Jawiarczyk-Przybyłowska, Rev Endocr Metab Disord, 2022, 23, 601.
• [78] M. Bolanowski, M. Kałużny, · Przemysław Witek and · Aleksandra Jawiarczyk-Przybyłowska, Rev Endocr Metab Disord, 2022, 23, 601.
• [79] R. M. Paragliola and R. Salvatori, Front Endocrinol (Lausanne), 2018, 9, 00078.
• [80] U. Plöckinger, U. Hoffmann, M. Geese, A. Lupp, M. Buchfelder, J. Flitsch, P. Vajkoczy, W. Jakob, W. Saeger, S. Schulz and C. Dohrmann, Eur J Endocrinol, 2012, 166, 223.
• [81] W. M. I. De Boon, M. J. Van Esdonk, F. E. Stuurman, N. R. Biermasz, L. Pons, I. Paty and J. Burggraaf, J Clin endocrinol Metab, 2018, 104, 883.
• [82] H. A. Halem, U. Hochgeschwender, J. K. Rih, R. Nelson, G. A. Johnson, A. Thiagalingam and M. D. Culler, Endocrinology, 2020, 161, 101.
• [83] T. Cuny, T. Graillon, · Célines Defilles, · Rakesh Datta, S. Zhang, D. Figarella-Branger, · Henry Dufour, G. Mougel, · Thierry Brue, T. Landsman, H. A. Halem, · Michael, D. Culler, A. Barlier and A. Saveanu, Pituitary, 2021, 24, 351.
• [84] B. L. Furman, Lispro insulin in: xPharm: The Comprehensive Pharmacology Reference, Elsevier, 2007.
• [85] G. B. Bolli, F. Porcellati, P. Lucidi, C. G. Fanelli and D. R. Owens, Metabolism, 2022, 126, 154935.
• [86] J. Leohr, C. Kazda , R. Liu, S Reddy, M.A. Dellva, M. Matzopoulos, M.T. Loh, T. Hardy, O. Klein, C. Kapitza, Diabetes Obes Metab, 2022, 24, 187.
• [87] J. Kildegaard, S. T. Buckley, R. H. Nielsen, G. K. Povlsen, T. Seested, U. Ribel, H. B. Olsen, S. Ludvigsen, C. B. Jeppesen, H. H. F. Refsgaard, K. M. Bendtsen, N. R. Kristensen, S. Hostrup and J. Sturis, Pharm Res, 2019, 36, 2578.
• [88] J J. Rosenstock and S. Del Prato, Metabolism, 2022, 126, 4924.
• [89] K. K. Niloy and T. L. Lowe, Adv Drug Deliv Rev, 2023, 203, 115121.
• [90] H. A. Blair, BioDrugs, 2024, 38, 717.
• [91] T. B. Kjeldsen, F. Ek Hubálek, C. U. Hjørringgaard, T. M. Tagmose, E. Nishimura, C. E. Stidsen, T. Porsgaard, C. Fledelius, H. H. F. Refsgaard, S. Gram-Nielsen, H. Naver, L. Pridal, T. Hoeg-Jensen, C. B. Jeppesen, V. Manfè, S. Ludvigsen, I. Lautrup-Larsen and P. Madsen, J Med Chem, 2021, 64, 00257.
• [92] N. Jouini, J. Cardinale and T. L. Mindt, Chem Med Chem, 2022, 17, 00091.
• [93] X. Zhou, J. Jiang, X. Yang, T. Liu, J. Ding, S. Nimmagadda, M. G. Pomper, H. Zhu, J. Zhao, Z. Yang and N. Li, J Nucl Med., 2022, 63, 536.
• [94] D. Kumar, A. Lisok, E. Dahmane, M. McCoy, S. Shelake, S. Chatterjee, V. Allaj, P. Sysa-Shah, B. Wharram, W. G. Lesniak, E. Tully, E. Gabrielson, E. M. Jaffee, J. T. Poirier, C. M. Rudin, J. V. S. Gobburu, M. G. Pomper and S. Nimmagadda, J Clin Invest, 2019, 129, 616.
• [95] S. L. Cytryn, N. Pandit-Taskar, M. A. Lumish, S. B. Maron, P. Gu, G. Y. Ku, J. F. Chou, M. Capanu, A. Antoine, D. Loegel, L. Feder, S. Philemond, S. K. Lyashchenko, J. S. Lewis, V. Paroder, A. Srivastava, L. H. Tang, H. Schoder and Y. Y. Janjigian, J Nucl Med, 2024, 65, 722.
• [96] Y. Shimizu, T. Suzuki, T. Yoshikawa, I. Endo and T. Nakatsura, Front Oncol, 2019, 9, 00248.
• [97] F. Lin, R. Clift, T. Ehara, H. Yanagida, S. Horton, A. Noncovich, M. Guest, D. Kim, K. Salvador, S. Richardson, T. Miller, G. Han, A. Bhat, K. Song and G. Li, J Nucl Med., 2024, 65, 586.
• [98] K. Suzuki, T. Ui, A. Nagano, A. Hino and Y. Arano, Sci Rep, 2019, 9, 15284.
• [99] D. Kwon, J. Lozada, Z. Zhang, J. Zeisler, R. Poon, C. Zhang, Á. Roxin, K. S. Lin, D. Perrin and F. Benard, Mol Pharm, 2021, 18, 187.
• [100] T. Peng, X. Wang, Z. Li, L. Bi, J. Gao, M. Yang, Y. Wang, X. Yao, H. Shan and H. Jin, Mol Pharm, 2021, 18, 3638.
• [101] J. Lau, D. Kwon, E. Rousseau, Z. Zhang, J. Zeisler, C. F. Uribe, H. T. Kuo, C. Zhang, K. S. Lin and F. Bénard, Mol Pharm, 2019, 16, 4688.
• [102] H. Leupe, S. Ahenkorah, J. Dekervel, M. Unterrainer, E. Van Cutsem, C. Verslype, F. Cleeren and C. M. Deroose, J Nucl Med, 2023, 64, 835.
• [103] R. S. Gamage, D. H. Li, C. L. Schreiber and B. D. Smith, ACS Omega, 2021, 6, 30130.
• [104] L. Yuan, W. Lin, Y. Yang and H. Chen, J Am Chem Soc, 2012, 134, 1200.
• [105] S. K. Shaw, W. Liu, C. F. A. Gómez Durán, C. L. Schreiber, M. de L. Betancourt Mendiola, C. Zhai, F. M. Roland, S. J. Padanilam and B. D. Smith, Chem - Euro Jl, 2018, 24, 13821.
• [106] K. Chen, L.-P. Yap, R. Park, X. Hui, K. Wu, D. Fan, X. Chen and P. S. Conti, Amino Acids, 2012, 42, 1329.
• [107] F. Bianying, G. Linjie, W. Lihua, L. Fan, L. Jianxin, G. Jimin, F. Chunhai and H. Qing, Anal Chem, 2013, 85, 7732.
• [108] D. W. Hwang, N. Bahng, K. Ito, S. Ha, M. Y. Kim, E. Lee, H. Suga and D. S. Lee, Cancer Lett, 2017, 385, 144.
• [109] J. R. Sierra and M. S. Tsao, Ther Adv Med Oncol, 2011, 3, S21.
• [110] R. Subiros-Funosas, V. Cheuk, L. Ho, N. D. Barth, L. Mendive-Tapia, M. Pappalardo, X. Barril, R. Ma, C.-B. Zhang, B.-Z. Qian, M. Sintes, O. Ghashghaei, R. Lavilla and M. Vendrell, Chem Sci, 2019, 11, 1368.
• [111] S. Shao, Z. Li, H. Cheng, S. Wang, N. G. Perkins, P. Sarkar, W. Wei and M. Xue, J Am Chem Soc, 2018, 140, 13586.
• [112] J. M. Leth, E. A. Newcombe, A. L. Grønnemose, J. T. Jørgensen, K. Qvist, A. S. Clausen, L. Bruhn, S. Knudsen, A. Kjaer, B. B. Kragelund, T. Jørgen, D. Jørgensen and M. Ploug, Sci Rep, 2023, 13, 17248.