Najnowsze kierunki poszukiwań cząsteczek o aktywności przeciwprątkowej

• Autorzy: Płoszaj P. , Piwowar A. , Ryng S.

Warianty tytułu

EN

Recent research of compounds with antitubercular activity

• Języki publikacji: PL

Abstrakty

EN

Tuberculosis (TB) caused by Mycobacterium tuberculosis (MTB) remains a leading cause of morbidity and mortality in developing countries [1]. With the discovery of chemotherapeutic agents in the 1940s and implementation of directly- -observed therapy short course (DOTS) in the 1980s, it was believed that TB would decline globally. Although a declining trend was observed in most developed countries, this was not evident in other parts of the world [2]. In addition, the rate of successful treatment has been compromised in recent years due to the increasing prevalence of multidrug-resistant (MDR-) and extensively drug-resistant TB ( XDR-TB) strains [3]. Accordingly, significant efforts have been made to discover and develop new treatment modalities against TB. This article serves as a summary of the most recent developments in search for novel anti-tubercular compounds. Here we focus on reviewing the results of basic research and clinical trials obtained in 2015 including: a) the phase IV clinical trials conducted for newly developed: bedaquiline, delamanid, clofazimine (previously registered for treatment of leprosis) b) phase III for fixed-dose combination of existing drugs: pretomanid – moxifloxacin – pyrazinamide) and c) the phase II clinical trials for sutezolid, AZD5847 and SQ109 [4]. All newly developed compounds used in these studies have been briefly characterized and their synthesis pathways fully described. In addition we review the most recent and promising results on nicotinic acid hydrazides, thienyl-pirimidines imidazole- -thiadiazole-benzimidazole and benzocoumarine derivatives presenting their synthesis pathways, most active chemical structures and their potential applications. Throughout this paper the ultimate direction for new drug development strategies, in search for the anti-tubercular agents, have been reviewed.

Słowa kluczowe

PL

gruźlica; związki przeciwprątkowe; lekoodporność prątków; badania kliniczne

EN

tuberculosis; anti-tubercular compounds; drug-resistant tuberculosis; clinical tests

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2016
• Tom: [Z] 70, 1-2
• Strony: 35--56
• Opis fizyczny: Bibliogr. 87 poz., tab., schem.

Twórcy

autor

Płoszaj P.

• Katedra i Zakład Chemii Organicznej, Uniwersytet Medyczny im. Piastów Śląskich ul. Borowska 211 A, 50-556 Wrocław

autor

Piwowar A.

• Katedra i Zakład Toksykologii, Uniwersytet Medyczny im. Piastów Śląskich ul. Borowska 211, 50-556 Wrocław

autor

Ryng S.

• Katedra i Zakład Chemii Organicznej, Uniwersytet Medyczny im. Piastów Śląskich ul. Borowska 211 A, 50-556 Wrocław

Bibliografia

• [1] Global Tuberculosis Report 2014, WHO.
• [2] V.K. Chadha, Indian J. Tuberc., 2009, 56(1), 30.
• [3] I. Abubakar, M. Zignol, D. Falzon, M. Raviglione, L. Ditiu, S. Masham, I. Adetifa, N. Ford, H. Cox, S.D. Lawn, B.J. Marais, T.D. McHugh, P. Mwaba, M. Bates, M. Lipman, L. Zijenah, S. Logan, R. McNerney, A. Zumla, K. Sarda, P. Nahid, M. Hoelscher, M. Pletschette, Z.A. Memish, P. Kim, R. Hafner, S. Cole, G.B. Migliori, M. Maeurer, M. Schito, A. Zumla, Lancet Infect. Dis., 2013, 13(6), 529.
• [4] http://www.newtbdrugs.org/project.php?id=202745.
• [5] K. Todar, Mycobacterium tuberculosis and Tuberculosis, Todar’s Online Textbook of Bacteriology 2009.
• [6] Tuberculosis, Fact Sheet 104. WHO Report 2015.
• [7] D. Michałowska-Mitczuk, Postępy Farmakoterapii. Farmakoterapia gruźlicy, 2009, 65 (1), 51.
• [8] R. Loddenkemper, D. Sagabiel, A. Brendel. Eur. Respir. J., 2002, 36, 66.
• [9] M. Zignol, M.S. Hosseini, A. Wright, C.L. Weezenbeek, P. Nunn, C.J. Watt, B.G. Williams, C. Dye, J. Infect. Dis., 2006, 194(4), 479.
• [10] H. Tomioka, K. Namba, Kekkaku, 2006, 81, 753.
• [11] K. Andries, P. Verhasselt, J. Guillemont, H.W. Gohlmann, J.M. Neefs, H. Winkler, J. Van Gestel, P. Timmerman, M. Zhu, E. Lee, P. Williams, D. de Chaffoy, E. Huitric, S. Hoffner, E. Cambau, C. Truffot-Pernot, N. Lounis, V. Jarlier, Science, 2005, 14, 223.
• [12] A.K. Kakkar, N. Dahiya, Tuberculosis (Edinb), 2014, 94(4), 357.
• [13] Provisional CDC Guidelines for the Use and Safety Monitoring of Bedaquiline Fumarate (Sirturo) for the Treatment of Multidrug-Resistant Tuberculosis, MMWR Recomm. Rep. 2013, 62, 1.
• [14] J. Guillemont, Quinoline derivatives and their use as mycobacterial inhibitors, WO/2004/011436 (2004).
• [15] N. Lounis, J. Guillemont, N. Veziris, A. Koul, V. Jarlier, K. Andries, Med. Mal. Infect., 2010, 40(7), 383.
• [16] Y.S. Kwon, B.H. Jeong, W.J. Koh, Curr. Opin. Pulm. Med., 2014, 20(3), 280.
• [17] S.G. Franzblau, J.F. O’Sullivan, Antimicrob. Agents Chemother., 1988, 32, 1583.
• [18] C. Jagannath, M.V. Reddy, S. Kailasam, Am. J. Respir. Crit. Care Med., 1995, 151, 1083.
• [19] N.E. Morrison, G.M. Marley, Int. J. Lepr. Other Mycobact. Dis., 1976, 44(1-2), 133.
• [20] J.L. Arbiser, S.L. Moschella, J. Am. Acad. Dermatol., 1995, 32(2 Pt 1), 241.
• [21] T. Wu, S.J. Levine, M.G. Lawrence, C. Logun, C.W. Angus, J.H. Shelhamer, J. Clin. Invest., 1994, 93(2), 571.
• [22] X.W. Gui, H.P. Xiao, Z.Y. Hu, Z.L. Cui, J. Wang, J.M. Lu, Zhonghua Jie He He Hu Xi Za Zhi, 2011, 34(8), 579.
• [23] Z. Zhang, T. Li, G. Qu, Y. Pang, Y. Zhao, Int. J. Antimicrob. Agents, 2015, 45(1), 71.
• [24] M. Gopal, N. Padayatchi, J.Z. Metcalfe, M.R. O’Donnell, Int. J. Tuberc. Lung. Dis., 2013, 17, 1001.
• [25] T. Dey, G. Brigden, H. Cox, Z. Shubber, G. Cooke, N. Ford, J. Antimicrob. Chemother., 2013, 68(2), 284.
• [26] V.C. Barry, J.G. Belton, M.L. Conalty, J.M. Denneny, D.W. Edward, J.F. O’Sullivan, D. Twomey, F. Winder, Nature, 1957, 179(4568), 1013.
• [27] V.C. Barry, M.L. Belton, M.L. Conalty, J.F. O’Sullivan, H. Ernst, US Pat. 2.948.726 (1960).
• [28] V. Barry, M.L. Belton, J.F. O’Sullivan, J. Chem Soc., 1958, 859.
• [29] M. Matsumoto, H. Hashizume, T. Tomishige, M. Kawasaki, H. Tsubouchi, H. Sasaki, Y. Shimokawa, M. Komatsu. PLoS Med., 2006, 3(11), 466.
• [30] W. Raether, H. Hanel, Parasitol Res., 2003, 90 (1), 19.
• [31] D.R. Ashtekar, R. Costa-Perira, K. Nagrajan, N. Vishvanathan, A.D. Bhatt, W. Rittel, Antimicrob. Agents Chemother., 1993, 37(2), 183.
• [32] Drug Discovery & Development, EMA Recommends Two New Tuberculosis Treatments, 2013
• [33] H. Sasaki, Y. Haraguchi, M. Itotani, H. Kuroda, H. Hashizume, T. Tomishige, M. Kawasaki, M. Matsumoto, M. Komatsu, H. Tsubouchi, J. Med. Chem., 2006, 49(26), 7854.
• [34] S.J. Brickner, Current Pharmaceutical. Design, 1996, 2, 175.
• [35] U. Patel, Y.P. Yan, F.W. Jr Hobbs, J. Kaczmarczyk, A.M. Slee, D.L. Pompliano, M.G. Kurilla, E.V. Bobkova, J. Biol. Chem., 2001, 276(40), 37199.
• [36] K.J. Shaw, M.R. Barbachyn, Ann N Y Acad. Sci., 2011, 1241, 48.
• [37] Charakterystyka produktu leczniczego – linezolid, 2012.
• [38] K.N. Williams, C.K. Stover, T. Zhu, R. Tasneen, S. Tyagi, J.H. Grosset, E. Nuermberger, Antimicrob. Agents Chemother., 2009, 53(4), 1314.
• [39] R.S. Wallis, W. Jakubiec, V. Kumar, G. Bedarida, A. Silvia, D. Paige, T. Zhu, M. Mitton-Fry, L. Ladutko, S. Campbell, PF. Miller, Antimicrob. Agents Chemother., 2011, 55(2), 567.
• [40] G.B. Migliori, B. Eker, M.D. Richardson, G. Sotgiu, J.P. Zellweger, A. Skrahina, J. Ortmann, E. Girardi, H. Hoffmann, G. Besozzi, N. Bevilacqua, D. Kirsten, R. Centis, C. Lange, Eur. Respir. J., 2009, 34(2), 387.
• [41] R.S. Wallis, R. Dawson, S.O. Friedrich, A. Venter, D. Paige, T. Zhu, A. Silvia, J. Gobey, C. Ellery, Y. Zhang, K. Eisenach, P. Miller, A.H. Diacon, PLoS One, 2014, 9(4), 94462.
• [42] M.R. Barbachyn, D.K. Hutchinson, S.J. Brickner, M.H. Cynamon, J.O. Kilburn, S.P. Klemens, S.E. Glickman, K.C. Grega, S.K. Hendges, D.S. Toops, C.W. Ford, G.E. Zurenko, J. Med. Chem., 1996, 39(3), 680.
• [43] B. Villemagne, C. Crauste, M. Flipo, A.R. Baulard, B. Deprez, N. Willand, Eur. J. Med. Chem., 2012, 51, 1.
• [44] V. Balasubramanian, S. Solapure, H. Iyer, A. Ghosh, S. Sharma, P. Kaur, R. Deepthi, V. Subbulakshmi, V. Ramya, V. Ramachandran, M. Balganesh, L. Wright, D. Melnick, SL. Butler, V.K. Sambandamurthy, Antimicrob. Agents Chemother., 2014, 58(1), 495.
• [45] V. Balasubramanian, S. Solapure, R. Shandil, S. Gaonkar, K.N. Mahesh, J. Reddy, A. Deshpande, S. Bharath, N. Kumar, L. Wright, D. Melnick, S.L. Butler, Antimicrob. Agents Chemother., 2014, 58(7), 4185.
• [46] A. Wookey, P.J. Turner, J.M. Greenhalgh, M. Eastwood, J. Clarke, C. Sefton, Clin. Microbiol. Infect., 2004, 10(3), 247.
• [47] Balasubramanian, D. Melnick, A 14-day multiple ascending dose study: AZD5847 is well tolerated at predicted exposure for treatment of tuberculosis (TB) (Abstract A1-1735). Poster session presented at: 51st Annual Interscience Conference on Antimicrobial Agents and Chemotherapy; 2011.
• [48] M.B. Gravestock, D.G. Acton, M.J. Betts, M. Dennis, G. Hatter, A. McGregor, M.L. Swain, R.G. Wilson, L. Woods, A. Wookey, Bioorg. Med. Chem. Lett., 2003, 13(23), 4179.
• [49] W. Li, A. Upadhyay, F.L. Fontes, E.J. North, Y. Wang, D.C. Crans, A.E. Grzegorzewicz, V. Jones, S.G. Franzblau, R.E. Lee, D.C. Crick, M. Jackson, Antimicrob. Agents Chemother., 2014, 58(11), 6413.
• [50] M. Protopopova, C. Hanrahan, B. Nikonenko, R. Samala, P. Chen, J. Gearhart, L. Einck, C.A. Nacy. J. Antimicrob. Chemother., 2005, 56(5), 968.
• [51] L. Jia, J.E. Tomaszewski, C. Hanrahan, L. Coward, P. Noker, G. Gorman, B. Nikonenko, M. Protopopova, Br. J. Pharmacol., 2005, 144(1), 80.
• [52] V.M. Reddy, T. Dubuisson, L. Einck, R.S. Wallis, W. Jakubiec, L. Ladukto, S. Campbell, C.A. Nacy, J. Antimicrob. Chemother., 2012, 67(5), 1163.
• [53] V.M. Reddy, L. Einck, K. Andries, C.A. Nacy, Antimicrob. Agents Chemother., 2010, 54(7), 2840.
• [54] R.E. Lee, M. Protopopova, E. Crooks, R.A. Slayden, M. Terrot, C.E. 3rd Barry, J. Comb. Chem., 2003, 5(2), 172.
• [55] O.K. Onajole, P. Govender, P.D. van Helden, H.G. Kruger, G.E. Maguire, I. Wiid, T. Govender, Eur. J. Med. Chem., 2010, 45(5), 2075.
• [56] B. Lei, C.J. Wei, S.C. Tu, J. Biol. Chem., 2000, 275(4), 2520.
• [57] E.K. Schroeder, N. de Souza, D.S. Santos, J.S. Blanchard, L.A. Basso, Curr. Pharm. Biotechnol., 2002, 3(3), 197.
• [58] J. Sandy, A. Mushtaq, A. Kawamura, J. Sinclair, E. Sim, E. Noble, M.J. Mol. Biol., 2002, 318, 1071.
• [59] M. Zignol, M. Dara, A.S. Dean, D. Falzon, A. Dadu, K. Kremer, H. Hoffmann, S. Hoffner, K. Floyd, Drug Resist. Updat., 2013, 16(6), 108.
• [60] M. Moore, I.M. Onorato, E. McCray, K.G. Castro, JAMA 1993–1996, 215 (1997), 833.
• [61] M.S.C. Lourencoa, M.L. Ferreirab, M.V.N. Souza, M.A. Peralta, T.R.A. Vasconcelos, M. das Gracas, M.O. Henriques, Eur. J. Med. Chem., 2008, 43, 1344.
• [62] S.H. Cardoso, J.V. de Assis, M.V. de Almeida, M.C.S. Lourenco, F.R.C. Vicente, M.V.N. de Souza, Quim. Nova., 2009, 32, 1557.
• [63] B. Bottari, R. Maccari, F. Monforte, R. Ottana, E. Rotondo, M.G. Vigorita, Bioorg. Med. Chem. Lett., 2000, 10, 657.
• [64] V. Judge, B. Narasimhan, M. Ahuja, D. Sriram, P. Yogeeswari, E.D. Clercq, C. Pannecouque, J. Balzarini. Med. Chem. Res., 2012, 21, 1935.
• [65] W.M. Eldehna, M. Fares, M.M. Abdel-Aziz, H.A. Abdel-Aziz. Molecules, 2015, 20(5), 8800.
• [66] G.E. Wright, J.J. Gambino, J. Med. Chem., 1984, 27(2), 181.
• [67] L.F. Jalander, J.E. Lonnqvist, Heterocycles, 1998, 48, 743.
• [68] N.M. Khalifa, M.A. Al-Omar, G. Amr Ael, A.R. Baiuomy, R.F. Abdel-Rahman, Bioorg. Khim., 2015, 41(2), 218.
• [69] E. Matyugina, A. Khandazhinskaya, L. Chernousova, S. Andreevskaya, T. Smirnova, A. Chizhov, I. Karpenko, S. Kochetkov, L. Alexandrova, Bioorg. Med. Chem., 2012, 20(22), 6680.
• [70] M.H. El-Hamamsy, A.W. Smith, A.S. Thompson, M.D. Threadgill, Bioorg. Med. Chem., 2007, 15(13),4552.
• [71] J. Morgan, R. Haritakul, P.A. Keller, Bioorg. Med. Chem. Lett., 2003, 13(10), 1755.
• [72] E.V. Verbitskiy, E.M Cheprakova, P.A. Slepukhin, M.A. Kravchenko, S.N. Skornyakov, G.L. Rusinov, O.N. Chupakhin, V.N. Charushin, Eur. J. Med. Chem., 2015, 97, 225.
• [73] J. Ramprasad, N. Nayak, U. Dalimba, P. Yogeeswari, D. Sriram, S.K. Peethambar, R. Achur, H.S. Kumar, Eur. J. Med. Chem., 2015, 95, 49.
• [74] F. Hadizadeh1, R. Vosooghi, J. Heterocyc. Chem., 2008, 45, 1.
• [75] S.G. Alegaon, K.R. Alagawadi, P.V. Sonkusare, S.M. Chaudhary, D.H. Dadwe, A.S. Shah, Bioorg. Med. Chem. Lett., 2012, 22(5), 1917.
• [76] S. Talath, A.K. Gadad, Eur. J. Med. Chem., 2006, 41(8), 918.
• [77] A. Foroumadi, A. Sakhteman, Z. Sharifzadeh, N. Mohammadhosseini, B. Hemmateenejad, M.H. Moshafi, M. Vosooghi, M. Amini, A. Shafiee, J. Pharm. Sci., 2007, 15(4), 218.
• [78] S.A. Stanley, S.S. Grant, T. Kawate, N. Iwase, M. Shimizu, C. Wivagg, M. Silvis, E. Kazyanskaya, J. Aquadro, A. Golas, M. Fitzgerald, H. Dai, L. Zhang, DT. Hung, ACS Chem. Biol., 2012, 7(8), 1377.
• [79] M. Pieroni, S.K. Tipparaju, S. Lun, Y. Song, A.W. Sturm, W.R. Bishai, A.P. Kozikowski, Chem. Med. Chem., 2011, 6(2), 334.
• [80] K. Kumar, D. Awasthi, S.Y. Lee, I. Zanardi, B. Ruzsicska, S. Knudson, P.J. Tonge, R.A. Slayden, I. Ojima, J. Med. Chem., 2011, 54(1), 374.
• [81] R.O. O’Kennedy, R.D. Thomes Coumarins, Biol. Appl. Mode Action, Willey, 1997.
• [82] R.S. Keri, K.M. Hosamani, R.V. Shingalapur, M.H. Hugar, Eur. J. Med. Chem., 2010, 45(6), 2597.
• [83] A.H. Abd El-Wahab, Pharmaceuticals (Basel), 2012, 5(7), 745.
• [84] K.M. Amin, F.M. Awadalla, A.A. Eissa, S.M. Abou-Seri, G.S. Hassan, Bioorg. Med. Chem., 2011, 19(20), 6087.
• [85] K.B. Puttaraju, K. Shivashankar, M. Chandra, V.P. Mahendra, P.N. Rasal, V. Vivek, K. Rai, M.B. Chanu, Eur. J. Med. Chem., 2013, 69, 316.
• [86] K.M. Hosamani, D.S. Reddy, H.C. Devarajegowda, RSC Adv., 2015, 5, 11261.
• [87] D.S. Reddy, K.M. Hosamani, H.C. Devarajegowda, Eur. J. Med. Chem., 2015, 101, 705.

Uwagi

Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę.