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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Review Article

A Comprehensive Review of the Benzimidazole Scaffold as a Potential Nucleus for Anti-Ulcer Activity

Author(s): Kuldeep Singh*, Bharat Bhushan, Ajit Kumar Varma, Ravi Shekhar, Rajeev Kumar Sharma, Niladry Sekhar Ghosh, Ekta Pandey, Sunam Saha, Shivendra Kumar, Avinash Kumar Mishra and Mohit Agrawal

Volume 21, Issue 6, 2024

Published on: 23 January, 2024

Page: [493 - 504] Pages: 12

DOI: 10.2174/0115701786267759231121070546

Price: $65

Abstract

The benzimidazole scaffold is a promising nucleus for developing novel therapeutic agents for ulcer treatment. Its unique chemical structure provides desirable pharmacological properties, such as excellent bioavailability, metabolic stability, and low toxicity, making it an attractive candidate for ulcer treatment. Several benzimidazole derivatives have shown significant anti-ulcer activity in preclinical and clinical studies, acting through multiple pathways, including inhibition of gastric acid secretion, suppression of gastric inflammation, and promotion of mucosal protection. Some benzimidazole derivatives have also demonstrated anti-Helicobacter pylori activity, suggesting their potential for eradicating bacteria associated with ulcer formation. However, challenges such as poor solubility and limited selectivity remain. Various approaches, such as prodrug design and formulation optimization, have been explored to overcome these issues and improve the therapeutic profile of benzimidazole derivatives. Overall, the benzimidazole scaffold holds great promise as a nucleus for developing novel anti-ulcer agents. Further research and optimization efforts are needed to harness its full potential and translate it into effective treatments for ulcers. With continued advancements in medicinal chemistry and drug design, benzimidazole-based compounds may offer new therapeutic options for patients suffering from ulcers and related gastrointestinal disorders. Hence, this review highlights the knowledge about benzimidazole scaffold, the mechanism of ulcer formation, and various benzimidazole derivatives with anti-ulcer activity, which can be further studied in pre-clinical and clinical trials.

[1]
Walia, R.; Hedaitullah, M.; Naaz, S.F.; Iqbal, K.; Lamba, H.S. Int. J. Res. Pharm. Chem., 2011, 1(3), 565-574.
[2]
Singh, N.; Pandurangan, A.; Rana, K.; Anand, P.; Ahamad, A.; Tiwari, A.K. Int. Curr. Pharm. J., 2012, 1(5), 110-118.
[http://dx.doi.org/10.3329/icpj.v1i5.10284]
[3]
Malfertheiner, P.; Chan, F.K.L.; McColl, K.E.L. Lancet, 2009, 374(9699), 1449-1461.
[http://dx.doi.org/10.1016/S0140-6736(09)60938-7] [PMID: 19683340]
[4]
Lanas, A.; Chan, F.K.L. Peptic ulcer disease. Lancet, 2017, 390(10094), 613-624.
[http://dx.doi.org/10.1016/S0140-6736(16)32404-7] [PMID: 28242110]
[5]
Patil, A.; Ganguly, S.; Surana, S. Rasayan J. Chem., 2008, 1(3), 447-460.
[6]
Barker, H.A.; Smyth, R.D.; Weissbach, H.; Toohey, J.I.; Ladd, J.N.; Volcani, B.E. J. Biol. Chem., 1960, 235(2), 480-488.
[http://dx.doi.org/10.1016/S0021-9258(18)69550-X] [PMID: 13796809]
[7]
Wright, J.B. January 29, the chemistry of the Benzimidazoles; Research Laboratories, The Upjohn Company: Kalamazoo, MI, 1951.
[8]
Phillip, M. J. Chem. Soc. C, 1951, 1143-1145.
[9]
Remick, AE Electronic interpretations of organic chemistry, 1949.
[10]
Walia, R. IJRPC, 2011, 1(3), 565-574.
[11]
Podunavac-Kuzmanovic, S.O.; Cvetkovic, D.M. J. Serb. Chem. Soc., 2007, 72(5), 459-466.
[http://dx.doi.org/10.2298/JSC0705459P]
[12]
Flemström, G.; Turnberg, L.A. In: Clinics in gastroenterology; 13th ed; Isenberg, J.I.; Johansson, C., Eds.; W B Saunders Company: London, Philadelphia, Toronto, 1984, pp. 327-354.
[13]
Kato, I.; Nomura, A.M.Y.; Stemmermann, G.N.; Chyou, P.H. Am. J. Epidemiol., 1992, 135(5), 521-530.
[http://dx.doi.org/10.1093/oxfordjournals.aje.a116319] [PMID: 1570818]
[14]
Rosenstock, S.; Jørgensen, T.; Bonnevie, O.; Andersen, L. Gut, 2003, 52(2), 186-193.
[http://dx.doi.org/10.1136/gut.52.2.186] [PMID: 12524398]
[15]
Levenstein, S. Psychosom. Med., 2002, 64(5), 767-772.
[http://dx.doi.org/10.1097/01.PSY.0000024230.11538.C6] [PMID: 12271107]
[16]
Peters, M.N.; Richardson, C.T. Gastroenterology, 1983, 84(1), 114-119.
[http://dx.doi.org/10.1016/S0016-5085(83)80174-7] [PMID: 6847839]
[17]
Noach, L.A.; Bosma, N.B.; Jansen, J.; Hoek, F.J.; Van Deventer, S.J.H.; Tytgat, G.N.J. Scand. J. Gastroenterol., 1994, 29(5), 425-429.
[http://dx.doi.org/10.3109/00365529409096833] [PMID: 8036458]
[18]
Barchi, A.; Miraglia, C.; Violi, A.; Cambiè, G.; Nouvenne, A.; Capasso, M.; Leandro, G.; Meschi, T. De’ Angelis, G.L.; Di Mario, F. Acta Biomed., 2018, 89(8-S), 40-43.
[http://dx.doi.org/10.23750/abm.v89i8-S.7917] [PMID: 30561417]
[19]
Crowe, S.E.; Alvarez, L.; Dytoc, M.; Hunt, R.H.; Muller, M.; Sherman, P.; Patel, J.; Jin, Y.; Ernst, P.B. Gastroenterology, 1995, 108(1), 65-74.
[http://dx.doi.org/10.1016/0016-5085(95)90009-8] [PMID: 7806065]
[20]
Karttunen, R. Clin. Exp. Immunol., 2008, 83(3), 396-400.
[http://dx.doi.org/10.1111/j.1365-2249.1991.tb05650.x] [PMID: 1900743]
[21]
Dixon, M.F. Best Pract. Res. Clin. Gastroenterol., 2000, 14(1), 27-40.
[http://dx.doi.org/10.1053/bega.1999.0057] [PMID: 10749087]
[22]
Wallace, J.L.; Vong, L. Curr. Opin. Investig. Drugs, 2008, 9(11), 1151-1156.
[http://dx.doi.org/10.1254/jpssuppl.WCP2018.0_CL-24] [PMID: 18951293]
[23]
Darling, R.L.; Romero, J.J.; Dial, E.J.; Akunda, J.K.; Langenbach, R.; Lichtenberger, L.M. Gastroenterology, 2004, 127(1), 94-104.
[http://dx.doi.org/10.1053/j.gastro.2004.04.003] [PMID: 15236176]
[24]
Lichtenberger, L.M.; Zhou, Y.; Dial, E.J.; Raphael, R.M. J. Pharm. Pharmacol., 2010, 58(11), 1421-1428.
[http://dx.doi.org/10.1211/jpp.58.10.0001] [PMID: 17132203]
[25]
Mashita, Y.; Taniguchi, M.; Yokota, A.; Tanaka, A.; Takeuchi, K. Digestion, 2006, 73(2-3), 124-132.
[http://dx.doi.org/10.1159/000094098] [PMID: 16804302]
[26]
Mavrova, A.T.; Anichina, K.K.; Vuchev, D.I.; Tsenov, J.A.; Denkova, P.S.; Kondeva, M.S.; Micheva, M.K. Eur. J. Med. Chem., 2006, 41(12), 1412-1420.
[http://dx.doi.org/10.1016/j.ejmech.2006.07.005] [PMID: 16996654]
[27]
Bansal, Y.; Silakari, O. Bioorg. Med. Chem., 2012, 20(21), 6208-6236.
[http://dx.doi.org/10.1016/j.bmc.2012.09.013] [PMID: 23031649]
[28]
Carcanague, D.; Shue, Y.K.; Wuonola, M.A.; Uria-Nickelsen, M.; Joubran, C.; Abedi, J.K.; Jones, J.; Kühler, T.C. J. Med. Chem., 2002, 45(19), 4300-4309.
[http://dx.doi.org/10.1021/jm020868v] [PMID: 12213071]
[29]
Grassi, A.; Ippen, J.; Bruno, M.; Thomas, G. Eur. J. Pharmacol., 1991, 195(2), 251-259.
[http://dx.doi.org/10.1016/0014-2999(91)90543-Y] [PMID: 1908386]
[30]
Lindberg, P.; Nordberg, P.; Alminger, T.; Brändström, A.; Wallmark, B. J. Med. Chem., 1986, 29(8), 1327-1329.
[http://dx.doi.org/10.1021/jm00158a001] [PMID: 3016260]
[31]
Li, B.; Liu, Y.; Zhang, L.; Guo, X.; Wen, C.; Zhang, F.; Luo, X.; Xia, Y. FASEB J., 2021, 35(11), e21942.
[http://dx.doi.org/10.1096/fj.202100695RR] [PMID: 34670018]
[32]
Mohamed, N.A.; Abd El-Ghany, N.A.; Abdel-Aziz, M.M. Int. J. Biol. Macromol., 2021, 181, 956-965.
[http://dx.doi.org/10.1016/j.ijbiomac.2021.04.095] [PMID: 33878358]
[33]
El-Nezhawy, A.O.H.; Biuomy, A.R.; Hassan, F.S.; Ismaiel, A.K.; Omar, H.A. Bioorg. Med. Chem., 2013, 21(7), 1661-1670.
[http://dx.doi.org/10.1016/j.bmc.2013.01.070] [PMID: 23453216]
[34]
Handa, O.; Naito, Y.; Yoshikawa, T. Inflamm. Res., 2010, 59(12), 997-1003.
[http://dx.doi.org/10.1007/s00011-010-0245-x] [PMID: 20820854]
[35]
El-Dash, Y.; Khalil, N.A.; Ahmed, E.M.; Hassan, M.S.A. Bioorg. Chem., 2021, 107, 104610.
[http://dx.doi.org/10.1016/j.bioorg.2020.104610] [PMID: 33454504]
[36]
Veerasamy, R.; Roy, A.; Karunakaran, R.; Rajak, H. Pharmaceuticals, 2021, 14(7), 663.
[http://dx.doi.org/10.3390/ph14070663] [PMID: 34358089]
[37]
Chu, T.H.; Huang, S.T.; Yang, S.F.; Li, C.J.; Lin, H.W.; Weng, B.C.; Yang, S.M.; Huang, S.C.; Wu, J.C.; Chang, Y.C.; Wen, Z.H.; Chen, Y.M.A.; Wu, W.J.; Kung, M.L.; Tai, P.H.; Wu, D.C.; Tai, M.H. Oncogene, 2019, 38(37), 6461-6477.
[http://dx.doi.org/10.1038/s41388-019-0886-3] [PMID: 31332288]
[38]
Sathyanarayana, R.; Poojary, B.; Srinivasa, S.M.; Merugumolu, V.K.; Chandrashekarappa, R.B.; Rangappa, S. J. Indian Chem. Soc., 2022, 19(4), 1301-1317.
[http://dx.doi.org/10.1007/s13738-021-02381-y]
[39]
Boonstra, J.; Post, J.A. Gene, 2004, 337, 1-13.
[http://dx.doi.org/10.1016/j.gene.2004.04.032] [PMID: 15276197]
[40]
Zhang, Y.; Tocchetti, C.G.; Krieg, T.; Moens, A.L. Free Radic. Biol. Med., 2012, 53(8), 1531-1540.
[http://dx.doi.org/10.1016/j.freeradbiomed.2012.07.010] [PMID: 22819981]
[41]
Dumont, M.; Beal, M.F. Free Radic. Biol. Med., 2011, 51(5), 1014-1026.
[http://dx.doi.org/10.1016/j.freeradbiomed.2010.11.026] [PMID: 21130159]
[42]
Reuter, S.; Gupta, S.C.; Chaturvedi, M.M.; Aggarwal, B.B. Free Radic. Biol. Med., 2010, 49(11), 1603-1616.
[http://dx.doi.org/10.1016/j.freeradbiomed.2010.09.006] [PMID: 20840865]
[43]
Arora, R.K.; Kaur, N.; Bansal, Y.; Bansal, G. Acta Pharm. Sin. B, 2014, 4(5), 368-375.
[http://dx.doi.org/10.1016/j.apsb.2014.07.001] [PMID: 26579406]
[44]
Tanaka, J.; Iida, H.; Abe, M.; Yuda, Y.; Inoue, S.; Okabe, S. Arzneimittelforschung, 2011, 54(4), 221-229.
[http://dx.doi.org/10.1055/s-0031-1296963] [PMID: 15146935]
[45]
Kovalev, G.V.; Spasor, A.A.; Bakumov, P.A.; Reshetov, M.E.; Anisimova, V.A. Zhurnal. HF Farmatsevticheskii Zhurnal, 1990, 24(2), 127-130.
[46]
Kubo, K.; Oda, K.; Kaneko, T.; Satoh, H.; Nohara, A. Chem. Pharm. Bull., 1990, 38(10), 2853-2858.
[http://dx.doi.org/10.1248/cpb.38.2853] [PMID: 2076571]
[47]
Braendstroem, A.E.; Sunden, P.; Elisabeth, G. World Patent No. 9119712, 1991.
[48]
Kiyoaki, K.; Tamaka, T.; Hiroko, O.; Fumiya, H.; Yasukatsu, Y.; Fukio, K. Eur Patent No. 457331, 1991.
[49]
Katsura, Y.; Inoue, Y.; Nishino, S.; Tomoi, M.; Takasugi, H. Chem. Pharm. Bull., 1992, 40(7), 1818-1822.
[http://dx.doi.org/10.1248/cpb.40.1818] [PMID: 1356644]
[50]
Bernhard, K.; Gerhard, G.; Joerg, S.B.; Wolfgang, O. World Patent No.9501351, 1995.
[51]
Yamada, S.; Goto, T.; Shimanuki, E.; Narita, S. Chem. Pharm. Bull., 1994, 42(3), 718-720.
[http://dx.doi.org/10.1248/cpb.42.718] [PMID: 8004722]
[52]
Kohl, B.; Sturm, E.; Senn-Bilfinger, J.; Simon, W.A.; Krueger, U.; Schaefer, H.; Rainer, G.; Figala, V.; Klemm, K. J. Med. Chem., 1992, 35(6), 1049-1057.
[http://dx.doi.org/10.1021/jm00084a010] [PMID: 1313110]
[53]
Terashima, K.; Shimamura, H.; Kawase, A.; Tanaka, Y.; Uenishi, K.; Kimura, I.; Ishizuka, Y.; Sato, M. Chem. Pharm. Bull. (Tokyo), 1995, 43(1), 166-168.
[http://dx.doi.org/10.1248/cpb.43.166] [PMID: 7895305]
[54]
Jain, K.S.; Shah, A.K.; Bariwal, J.; Shelke, S.M.; Kale, A.P.; Jagtap, J.R.; Bhosale, A.V. Bioorg. Med. Chem., 2007, 15(3), 1181-1205.
[http://dx.doi.org/10.1016/j.bmc.2006.07.068] [PMID: 17150362]
[55]
Kaun, Y.E.; Kwon, C.J.; Yun, C.S.; Kyu, K.S. World Patent No. 9700875, 1997.
[56]
Cotton, H.; Elebring, T.; Larsson, M.; Li, L.; Sörensen, H.; von Unge, S. Tetrahedron Asymmetry, 2000, 11(18), 3819-3825.
[http://dx.doi.org/10.1016/S0957-4166(00)00352-9]
[57]
Hirashima, S.; Suzuki, T.; Ishida, T.; Noji, S. J. Med. Chem., 2006, 49, 4721-4736.
[http://dx.doi.org/10.1021/jm060269e] [PMID: 16854079]
[58]
Hirashima, S.; Oka, T.; Ikegashira, K.; Noji, S.; Yamanaka, H.; Hara, Y.; Goto, H.; Mizojiri, R.; Niwa, Y.; Noguchi, T.; Ando, I.; Ikeda, S.; Hashimoto, H. Bioorg. Med. Chem. Lett., 2007, 17(11), 3181-3186.
[http://dx.doi.org/10.1016/j.bmcl.2007.03.027] [PMID: 17383878]
[59]
Hwu, J.R.; Singha, R.; Hong, S.C.; Chang, Y.H.; Das, A.R.; Vliegen, I.; De Clercq, E.; Neyts, J. Antiviral Res., 2008, 77(2), 157-162.
[http://dx.doi.org/10.1016/j.antiviral.2007.09.003] [PMID: 17977606]
[60]
Beaulieu, P.L.; Dansereau, N.; Duan, J.; Garneau, M.; Gillard, J.; McKercher, G.; LaPlante, S.; Lagacée, L.; Thauvette, L.; Kukolj, G. Bioorg. Med. Chem. Lett., 2010, 20(6), 1825-1829.
[http://dx.doi.org/10.1016/j.bmcl.2010.02.003] [PMID: 20185309]
[61]
Goulet, S.; Poupart, M.A.; Gillard, J.; Poirier, M.; Kukolj, G.; Beaulieu, P.L. Bioorg. Med. Chem. Lett., 2010, 20(1), 196-200.
[http://dx.doi.org/10.1016/j.bmcl.2009.10.136] [PMID: 19945870]
[62]
Kosaka, N.; Tanaka, H.; Tomaru, A.; Ishii, A.; Shuto, K. Jpn. J. Pharmacol., 1994, 65(4), 305-312.
[http://dx.doi.org/10.1254/jjp.65.305] [PMID: 7990267]
[63]
Yamada, S.; Goto, T.; Yuasa, S.; Yamaguchi, T.; Kogi, K. Yakugaku Zasshi, 1996, 116(8), 657-670.
[http://dx.doi.org/10.1248/yakushi1947.116.8_657] [PMID: 8831267]
[64]
Hiroshi, S.; Koji, T.; Akito, K.; Yasuhiro, I.; Isami, K.; Asyoshi, K. Chem. Pharm. Bull., 1995, 43, 166-168.
[65]
Ung, K.S.; Yeon, K.D.; Ju, C.G.; Kol, H.S.; Jun, P.S. Hoon, NS World Patent No. 9523140, 1995.
[66]
Elof, B.A.; Kerstin, S.I.; Hijelte, T. Inaera, L World Patent No. 9515962, 1995.
[67]
Kaun, Y.E.; Kwon, C.J.; Yun, C.S. Kyu, KS World Patent No. 9700875, 1997.
[68]
Yong, Y.H.; Jong, C.K.; Mansik, C.; Gyu, K.S. Soo, CW World Patent No. 9703077, 1997.
[69]
Shabajee, N.; Lamb, E.J.; Sturgess, I.; Sumathipala, R.W. BMJ, 2008, 337(jul10 3), a425.
[http://dx.doi.org/10.1136/bmj.39505.738981.BE] [PMID: 18617497]
[70]
Kromer, W.; Krüger, U.; Huber, R.; Hartmann, M.; Steinijans, V.W. Pharmacology, 1998, 56(2), 57-70.
[http://dx.doi.org/10.1159/000028183] [PMID: 9494064]
[71]
Shin, J.M.; Sachs, G. Gastroenterology, 2002, 123(5), 1588-1597.
[http://dx.doi.org/10.1053/gast.2002.36593] [PMID: 12404233]
[72]
Cheer, S.M.; Prakash, A.; Faulds, D.; Lamb, H.M. Drugs, 2003, 63(1), 101-133.
[http://dx.doi.org/10.2165/00003495-200363010-00006] [PMID: 12487624]
[73]
Lazzaroni, M.; Porro, G.B. Drugs, 2009, 69(1), 51-69.
[http://dx.doi.org/10.2165/00003495-200969010-00004] [PMID: 19192936]
[74]
Bianchi Porro, G.; Lazzaroni, M.; Imbesi, V.; Montrone, F.; Santagada, T. Dig. Liver Dis., 2000, 32(3), 201-208.
[http://dx.doi.org/10.1016/S1590-8658(00)80821-X] [PMID: 10975769]
[75]
Landes, B.D.; Petite, J.P.; Flouvat, B. Clin. Pharmacokinet., 1995, 28(6), 458-470.
[http://dx.doi.org/10.2165/00003088-199528060-00004] [PMID: 7656504]
[76]
Robinson, M.; Sahba, B.; Avner, D.; Jhala, N.; Greski-Rose, P.A.; Jennings, D.E. Aliment. Pharmacol. Ther., 1995, 9(1), 25-31.
[http://dx.doi.org/10.1111/j.1365-2036.1995.tb00347.x] [PMID: 7766740]
[77]
Robinson, M.; Campbell, D.R.; Sontag, S.; Sabesin, S.M. Dig. Dis. Sci., 1995, 40(3), 590-597.
[http://dx.doi.org/10.1007/BF02064376] [PMID: 7895551]
[78]
Barradell, L.B.; Faulds, D.; McTavish, D. Drugs, 1992, 44(2), 225-250.
[http://dx.doi.org/10.2165/00003495-199244020-00007] [PMID: 1382017]
[79]
Gremse, D.A. Expert Opin. Pharmacother., 2001, 2(10), 1663-1670.
[http://dx.doi.org/10.1517/14656566.2.10.1663] [PMID: 11825309]
[80]
Dekkers, B. Aliment. Pharmacol. Ther., 1999, 13(1), 49-57.
[81]
Breiter, J.R.; Riff, D.; Humphries, T. J. Am. J. Gastroenterol., 2000, 95(4), 936-942.
[http://dx.doi.org/10.1111/j.1572-0241.2000.01933.x] [PMID: 10763941]
[82]
Cloud, M.L.; Enas, N.; Humphries, T.J.; Bassion, S.; Group, T.R.S. Dig. Dis. Sci., 1998, 43(5), 993-1000.
[http://dx.doi.org/10.1023/A:1018822532736] [PMID: 9590413]
[83]
Stack, W.A.; Knifton, A.; Thirlwell, D.; Cockayne, A.; Jenkins, D.; Hawkey, C.J.; Atherton, J.C. Am. J. Gastroenterol., 1998, 93(10), 1909-1913.
[http://dx.doi.org/10.1111/j.1572-0241.1998.00582.x] [PMID: 9772054]
[84]
Fujisaki, H.; Oketani, K.; Nagakawa, J.; Takenaka, O.; Yamanishi, Y. Jpn. J. Pharmacol., 1998, 76(3), 279-288.
[http://dx.doi.org/10.1254/jjp.76.279] [PMID: 9593221]
[85]
Williams; Pounder. Aliment. Pharmacol. Ther., 1999, 13, 3-10.
[http://dx.doi.org/10.1046/j.1365-2036.1999.00019.x]
[86]
Besancon, M.; Simon, A.; Sachs, G.; Shin, J.M. J. Biol. Chem., 1997, 272(36), 22438-22446.
[http://dx.doi.org/10.1074/jbc.272.36.22438] [PMID: 9278394]
[87]
Patil, A.; Ganguly, S.; Surana, S. J. Chem. Sci., 2010, 122(3), 443-450.
[http://dx.doi.org/10.1007/s12039-010-0052-5]
[88]
Chang, C.S.; Liu, J.F.; Lin, H.J.; Lin, C.D.; Tang, C.H.; Lu, D.Y.; Sing, Y.T.; Chen, L.Y.; Kao, M.C.; Kuo, S.C.; Lai, C.H. Eur. J. Med. Chem., 2012, 48, 244-254.
[http://dx.doi.org/10.1016/j.ejmech.2011.12.021] [PMID: 22217866]
[89]
Bariwal, J.B.; Shah, A.K.; Kathiravan, M.K.; Somani, R.S.; Jagtap, J.R.; Jain, K.S.; Indian, J. Pharm. Educ. Res., 2008, 42, 225-231.
[90]
Nicole, B.; Timur, G.; Jean, L.; Michele, L.; Marie, T.J. Eur Patent No. 385850, 1990.
[91]
Uchida, M.; Chihiro, M.; Morita, S.; Yamashita, H.; Yamasaki, K.; Kanbe, T.; Yabuuchi, Y.; Nakagawa, K. Chem. Pharm. Bull., 1990, 38(6), 1575-1586.
[http://dx.doi.org/10.1248/cpb.38.1575] [PMID: 2170036]
[92]
Asano, S.; Yoshida, A.; Yashiro, H.; Kobayashi, Y.; Morisato, A.; Ogawa, H.; Takeguchi, N.; Morii, M. J. Biol. Chem., 2004, 279(14), 13968-13975.
[http://dx.doi.org/10.1074/jbc.M308934200] [PMID: 14699149]
[93]
Keeling, D.J.; Fallowfield, C.; Underwood, A.H. Biochem. Pharmacol., 1987, 36(3), 339-344.
[http://dx.doi.org/10.1016/0006-2952(87)90291-7] [PMID: 3028428]
[94]
Besancon, M.; Shin, J.M.; Mercier, F.; Munson, K.; Miller, M.; Hersey, S.; Sachs, G. Biochemistry, 1993, 32(9), 2345-2355.
[http://dx.doi.org/10.1021/bi00060a028] [PMID: 8382947]
[95]
Shin, J.M.; Cho, Y.M.; Sachs, G. J. Am. Chem. Soc., 2004, 126(25), 7800-7811.
[http://dx.doi.org/10.1021/ja049607w] [PMID: 15212527]
[96]
Shin, J.M.; Sachs, G. Biochem. Pharmacol., 2004, 68(11), 2117-2127.
[http://dx.doi.org/10.1016/j.bcp.2004.07.035] [PMID: 15498502]
[97]
Katashima, M.; Yamamoto, K.; Tokuma, Y.; Hata, T.; Sawada, Y.; Iga, T. Eur. J. Drug Metab. Pharmacokinet., 1998, 23(1), 19-26.
[http://dx.doi.org/10.1007/BF03189822] [PMID: 9625268]
[98]
Sachs, G.; Shin, J.M.; Howden, C.W. Aliment. Pharmacol. Ther., 2006, 23(S2), 2-8.
[http://dx.doi.org/10.1111/j.1365-2036.2006.02943.x] [PMID: 16700898]

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