Areny jako proleki

• Autorzy: Guzik U. , Hupert-Kocurek K. , Nieć A. , Wojcieszyńska D.

Warianty tytułu

EN

Arenes as prodrugs

• Języki publikacji: PL

Abstrakty

EN

Nowadays, improvement of physicochemical, biopharmaceutical and pharmacokinetic properties of pharmacologically active compounds is connected with development of prodrugs. Prodrugs are defined as pharmaceutical compounds inactive in their parent form and converted either chemically or enzymatically to the active derivative in the organism. A lot of prodrugs are aromatic compounds because of benzene ring reactivity. There are two main classes of prodrugs. In the carrier-linked prodrugs, the active drug is linked to a carrier through bioreversible covalent bond removed by enzymatic or chemical reactions. The second class comprises bioprecursor prodrugs that are modified in the body to induce the functional groups. Additionally, based on the site of prodrugs conversion into their active forms, they are classified into two groups: prodrugs metabolized intracellulary and prodrugs metabolized extracellulary. Chemical or enzymatic transformation of prodrugs may occur through their reduction, decarboxylation, oxidative deamination, cyclization, phosphorylation and/or hydrolysis. These reactions enable to overcome different barriers in drug delivery through changes in aqueous solubility, chemical instability and insufficient oral adsorption. It may also cause prolonged duration of drug action. Moreover, the prodrugs strategy allows achieving brain and tumor specific targeting. Summarizing, the designing of the prodrugs seems to be one of the most promising strategies to enhance the therapeutic effect of drugs and reduction of their negative side effects.

Słowa kluczowe

PL

prolek; związki aromatyczne; aktywacja proleku

EN

prodrug; aromatic compounds; prodrugs activation

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2015
• Tom: [Z] 69, 3-4
• Strony: 255--269
• Opis fizyczny: Bibliogr. 43 poz., schem., tab.

Twórcy

autor

Guzik U.

• Katedra Biochemii, Wydział Biologii i Ochrony Środowiska, Uniwersytet Śląski w Katowicach ul. Jagiellońska 28, 40-032 Katowice

autor

Hupert-Kocurek K.

• Katedra Biochemii, Wydział Biologii i Ochrony Środowiska, Uniwersytet Śląski w Katowicach ul. Jagiellońska 28, 40-032 Katowice

autor

Nieć A.

• Katedra Biochemii, Wydział Biologii i Ochrony Środowiska, Uniwersytet Śląski w Katowicach ul. Jagiellońska 28, 40-032 Katowice

autor

Wojcieszyńska D.

• Katedra Biochemii, Wydział Biologii i Ochrony Środowiska, Uniwersytet Śląski w Katowicach ul. Jagiellońska 28, 40-032 Katowice

Bibliografia

• [1] A. Abu-Jaish, S. Jumaa, R. Karaman, Prodrug overview [w:] Prodrugs design – a new era, R. Karaman (Red.), Nova Publisher, USA, 2014.
• [2] P.K. Halen, P.R. Murumkar, R. Giridhar, M.R. Yadav, Mini-Rev. Med. Chem., 2009, 9, 124.
• [3] J.B. Zawilska, J. Wojcieszak, A.B. Olejniczak, Pharmacol. Rep., 2013, 65, 1.
• [4] W. Chen, Y. Han, X. Peng, Chem. Eur. J., 2014, 20, 7410.
• [5] M. Grzybek, P. Wyrozumska, K. Sdebelska, A.F. Sikorski, Med. Weter., 2002, 58, 420.
• [6] B. Testa, Curr. Opin. Chem Biol., 2009, 13, 338.
• [7] O. Tredan, A.B. Garbens, A.S. Lalani, I.F. Tannock, Cancer Res., 2009, 69, 940.
• [8] R. Musiol, M. Serda, J. Polanski, Curr. Pharm. Des., 2011, 17, 3548.
• [9] V.J. Stella, Prodrugs: challenges and rewards, part I, Springer, New York 2007.
• [10] B. Testa, Biochem. Pharmacol, 2004, 68, 2097.
• [11] KUEI-MENG WU: „A new classification of prodrugs: regulatory perspectives”-Pharmaceuticals, 2(3), 77-81 (2009).
• [12] J. Choi, H.R.B. Raghavendran, N.Y. Sung, J.H. Kim, B.S. Chun, D.H. Ahn, H.S. Choi, K.W. Kang, J.W. Lee, Chem. Biol. Interact., 2010, 183, 249.
• [13] D.N. Croft, J.H.P. Cuddigan, C. Sweetland, Br. Med. J., 1972, 3, 545.
• [14] F.M. Williams, U. Moore, R.A. Seymour, E.M. Mutch, E. Nicholson, P. Wright, H. Wynne, P.G. Blain, M.D. Rawlins, Br. J. Clin. Pharmacol., 1989, 28, 703.
• [15] H.D. Tabba, M.E. Abdel-Hamid, M.M. Al-Arab, M.M. Hasan, S. Abu-Lafi, N.M. Najib, Int. J. Pharm., 1989, 54, 57.
• [16] F. Yang, Z.Y. Ma, Y. Zhang, G.Q. Li, M. Li, J.K. Qin, O. Lockridge, H. Liang, Eur. J. Pharm. Biopharm., 2013, 84, 549.
• [17] D.G. Waller, C.F. George, Br. J. Clin. Pharmacol., 1989, 28, 497.
• [18] K. Lingertat-Walsh, S.E. Walker, S. Law, M. Abesamis, P. Sales, Can. J. Hosp. Pharm., 2006, 59, 194.
• [19] S. Nikfar, R. Rahimi, A. Rezaie, M. Abdollahi, Dig. Dis. Sci., 2009, 54, 1157.
• [20] J. Rautio, H. Kumpulainen, T. Heimbach, R. Oliyai, D. Oh, T. Järvinen, J. Savolainen, Nat. Rev. Drug. Discov., 2008, 7, 255.
• [21] H. Uchino, Y. Kanai, D.K. Kim, M.F. Wempe, A. Chairoungdua, E. Morimoto, M.W. Anders, H. Endou, Mol. Pharmacol., 2002, 61, 729.
• [22] Ch.L. Wang, Y.B. Fan, H.H. Lu, T.H. Tsai, M.Ch. Tsai, H.P. Wang, J. Biomed. Sci., 2010, 17, 71.
• [23] G.T. Mah, A.M. Tejani, V.M. Musini, Cochrane Database Syst. Rev., 2009, 4, 1.
• [24] I.A.A. Ibrahim, N. Shahzad, F.S. Al-Joudi, S.S. Al-Ghamdi, M.A. Alshagga, N.M. Hammodi, Clin. Exp. Pharmacol., 2013, 3, 136.
• [25] M.J. Kasten, Med. Prak., 2000, 10, 71.
• [26] I. Paternotte, H.J. Fan, P. Screve, M. Claesen, P.M. Tulkens, E. Sonveaux, Bioorg. Med. Chem., 2001, 9, 493.
• [27] P.H.J. Houba, E. Boven, I.H. Van Der Meulen-Muileman, R.G.G. Leenders, J.W. Scheeren, H.M. Pinedo, H.J. Haisma, Br. J. Cancer, 2001, 84, 550.
• [28] J.M. Brown, W.R. Wilson, Nat. Rev. Cancer, 2004, 4, 437.
• [29] W.A. Denny, Lancet Oncol., 2000, 1, 25.
• [30] Y. Jounaidi, D.J. Waxman, Cancer Res., 2000, 60, 3761.
• [31] J.P. Celli, B.Q. Spring, I. Rizvi, C.L. Evans, K.S. Samkoe, S. Verma, B.W. Pogue, T. Hasan, Chem. Rev., 2010, 110, 2795.
• [32] B. Moses, Y. You, Med. Chem., 2013, 3, 192.
• [33] A.P. Castano, T.N. Demidova, M.R. Hamblin, Photodiagn. Photodyn. Ther., 2004, 1, 279.
• [34] T.J. Dougherty, C.J. Gomer, B.W. Henderson, G. Jori, D. Kessel, M. Korbelik, J. Moan, Q. Peng, J. Natl. Cancer Inst., 1998, 90, 889.
• [35] P. Cramers, M. Ruevekamp, H. Oppelaar, O. Dalesio, P. Baas, F.A. Stewart, Br. J. Cancer, 2003, 88, 283.
• [36] C.P. Leamon, J.A. Reddy, Adv. Drug Deliv. Rev., 2004, 56, 1127.
• [37] R.J. Lee, S. Wang, P.S. Low, BBA-Mol. Cell Res., 1996, 1312, 237.
• [38] M. Szwed, A. Marczak, A. Rogalska, A. Matusiak, Z. Jóźwiak, Nowotwory-J. Oncol., 2010, 60, 442.
• [39] B. Piątkowska-Jakubas, A. Nowakowska-Kopera, A.B. Skotnicki, Acta Haematol. Pol., 2005, 36, 5.
• [40] B.S. Anand, J.M. Hill, S.Dey, K. Maruyama, P.S. Bhattacharjee, M.E. Myles, Y.E. Nashed, A.K. Mitra, Invest. Ophthalmol. Vis. Sci., 2003, 44, 2529.
• [41] R. Karaman, K.K. Dajani, A. Qtait, M. Khamis, Chem. Biol. Drug Des., 2012, 79, 819.
• [42] W.H. Miller, R.L. Miller, Biochem. Pharmacol., 1982, 31, 3879.
• [43] Ch. Vanpouille, A. Lisco, M. Derudas, E. Saba, J.Ch. Grivel, B. Brichacek, F. Scrimieri, R. Schinazi, D. Schols, Ch. McGuigan, J. Balzarini, L. Margolis, J. Infect. Dis., 2010, 201, 635.