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Mini-Reviews in Medicinal Chemistry

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ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

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Review Article

New Development of Novel Berberine Derivatives against Bacteria

Author(s): Faisal Jamshaid, Jun Dai* and Li Xi Yang

Volume 20, Issue 8, 2020

Page: [716 - 724] Pages: 9

DOI: 10.2174/1389557520666200103115124

Price: $65

Abstract

Many berberine derivatives have been synthesized for their antibacterial activity in the past years. In order to elucidate their new Structural Activity Relationship (SAR), the recently synthesized berberine derivatives are reviewed. The newly synthesized berberine derivatives are reported in this review with novel modifications on the berberine structure at various positions. It is hoped that this article would help scientists to design and synthesize new berberine derivatives with high potency and a broad spectrum of antimicrobial activities, more effectiveness and lower toxicity for improved antimicrobial therapy. These berberine derivatives could be developed as novel antibacterial agents to treat patients with infectious diseases, especially caused by resistant bacteria.

Keywords: Antimicrobial therapy, oregon grape, tree turmeric, traditional medicine, lipopolysaccharide, antidepressant.

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[1]
Zhang, S.; Chang, J.; Damu, G.; Geng, R.; Zhou, C. Berberine azoles as antimicrobial agents: Synthesis, biological evaluation and their interactions with human serum albumin. MedChemComm, 2013, 5, 839-846.
[http://dx.doi.org/10.1039/c3md00032j]
[2]
Grycová, L.; Dostál, J.; Marek, R. Quaternary protoberberine alkaloids. Phytochemistry, 2007, 68(2), 150-175.
[http://dx.doi.org/10.1016/j.phytochem.2006.10.004]
[3]
Zhang, S.L.; Chang, J.J.; Damu, G.L.V.; Fang, B.; Zhou, X.D.; Geng, R.X.; Zhou, C.H. Novel berberine triazoles: synthesis, antimicrobial evaluation and competitive interactions with metal ions to human serum albumin. Bioorg. Med. Chem. Lett., 2013, 23(4), 1008-1012.
[http://dx.doi.org/10.1016/j.bmcl.2012.12.036] [PMID: 23312473]
[4]
Peng, X.; Cai, G.; Zhou, C. Recent developments in azole compounds as antibacterial and antifungal agents. Curr. Top. Med. Chem., 2013, 13, 1963-2010.
[http://dx.doi.org/10.2174/15680266113139990125] [PMID: 23895097]
[5]
Zhou, C.H.; Wang, Y. Recent researches in triazole compounds as medicinal drugs. Curr. Med. Chem., 2012, 19(2), 239-280.
[http://dx.doi.org/10.2174/092986712803414213] [PMID: 22320301]
[6]
Rosato, A.; Piarulli, M.; Corbo, F.; Muraglia, M. Carone, Vilali, M.; Vilali, C. In vitro synergistic action of certain combinations of gentamicin and essential oils. Curr. Med. Chem., 2010, 17, 3289-3295.
[http://dx.doi.org/10.2174/092986710792231996] [PMID: 20666717]
[7]
Zhou, L.; Peng, X.; Damu, G.; Geng, R.; Zhou, C. Comprehensive review in current developments of imidazole-based medicinal chemistry. Med. Res. Rev., 2014, 34, 340-437.
[http://dx.doi.org/10.1002/med.21290] [PMID: 23740514]
[8]
Schoenbart, B.; Ellen, S. Traditional Chinese medicine for the Digestive System, http://health.howstuffworks.com/wellness/ natural-medicine/chinese/traditional-chinese-medicine-for-the-digestive-system.htm2007.
[9]
Otsuka, H.; Fujimura, H.; Sawada, T.; Goto, M. Studies on antiinflammatory agents. II. Anti-inflammatory constituents from Rhizome of Coptis japonica Makino. J. Pharm. Soc. Jpn., , 1981, 101, 883-890.
[http://dx.doi.org/10.1248/yakushi1947.101.10_883]
[10]
The Japanes Pharmacopoeia, 13th ed; YakujiNippo: Tokyo, 1996, Vol. 766, pp. 228-229.
[11]
Zhang, S.; Chang, J.; Damu, G.; Geng, R.; Zhou, C. Design, synthesis and biological evaluation of berberine-benzimidazole hybrids as new type of potentially DNA-targeting antimicrobial agents. Bioorg. Eur. J. Med. Chem., 2016, 122, 205-215.
[12]
Zhang, S.; Chang, J.; Damu, G.; Geng, R.; Zhou, C. Berberine azoles as antimicrobial agents: Synthesis, biological evaluation and their interactions with human serum albumin. MedChemComm, 2013, 4, 839-846.
[13]
Chu, H.; Jin, G.; Friedman, E.; Zhen, X. Recent development in studies of tetrahydroprotoberberines: mechanism in antinociception and drug addiction. Cell. Mol. Neurobiol., 2008, 28(4), 491-499.
[http://dx.doi.org/10.1007/s10571-007-9179-4] [PMID: 17710533]
[14]
Kuo, C.L.; Chi, C.W.; Liu, T.Y. The anti-inflammatory potential of berberine in vitro and in vivo. Cancer Lett., 2004, 203(2), 127-137.
[http://dx.doi.org/10.1016/j.canlet.2003.09.002] [PMID: 14732220]
[15]
Gautam, R.; Jachak, S.M. Recent developments in anti-inflammatory natural products. Med. Res. Rev., 2009, 29(5), 767-820.
[http://dx.doi.org/10.1002/med.20156] [PMID: 19378317]
[16]
Zhou, X.; Chen, M.; Zheng, Z.; Zhu, G.; Jiang, Z.; Bai, L. Synthesis and evaluation of novel 12-aryl berberine analogues with hypoxia-inducible factor-1 inhibitory activity. RSC Advances, 2007, 7, 26921-26929.
[17]
Wang, Y.X.; Pang, W.Q.; Zeng, Q.X.; Deng, Z.S.; Fan, T.Y.; Jiang, J.D.; Deng, H.B.; Song, D.Q. Synthesis and biological evaluation of new berberine derivatives as cancer immunotherapy agents through targeting IDO1. Eur. J. Med. Chem., 2018, 143, 1858-1868.
[http://dx.doi.org/10.1016/j.ejmech.2017.10.078] [PMID: 29133053]
[18]
Xi, L.; Zhi-Yi, Y.; Xiao-Jin, Y.; Fan, L.; Jing-Fei, J.; Xuan, Y.; Xiu-Wei, Y.; Dong-Ming, X.; Li-Jun, D.Effects of Angelica dahurica on obesity and fatty liver in mice. Chin. J. Nat. Med., 2016, 14, 641-652.
[PMID: 27667509]
[19]
Mistry, B.; Keum, Y.; Kim, D. Synthesis, antioxidant and anticancer screenings of berberine-indole conjugates. Res. Chem. Intermed., 2016, 42, 3241-3256.
[http://dx.doi.org/10.1007/s11164-015-2208-x]
[20]
Singh, A.; Duggal, S.; Kaur, N.; Singh, J. Alkaloid with wide spectrum of pharmacological activities. J. Nat. Prod., 2010, 3, 64-75.
[21]
Wongbutdee, J. Physiological effects of berberine. Thai Pharm. Health Sci. J., 2009, 4, 78-83.
[22]
Zhang, S.; Wang, X.; Yin, W.; Liu, Z.; Zhou, M.; Xiao, D.; Liu, Y.; Peng, D. Synthesis and hypoglycemic activity of 9-O-(lipophilic group substituted) berberine derivatives. Bioorg. Med. Chem. Lett., 2016, 26(19), 4799-4803.
[http://dx.doi.org/10.1016/j.bmcl.2016.08.027] [PMID: 27561717]
[23]
Li, R.; Wu, J.; He, Y.; Hai, L.; Wu, Y. Synthesis and in vitro evaluation of 12-(substituted aminomethyl) berberrubine derivatives as anti-diabetics. Bioorg. Med. Chem. Lett., 2014, 24(7), 1762-1765.
[http://dx.doi.org/10.1016/j.bmcl.2014.02.032] [PMID: 24613165]
[24]
Li, H.; Cai, X.; Li, X. The new applications and the side effects of Rhizoma Coptidis in clinic. Med. J. Chin. People’s Armed Police Forces, 2008, 19, 661-663.
[25]
Liu, Y.; Hao, H.; Xie, H.; Lai, L.; Wang, Q.; Liu, C.; Wang, G. Extensive intestinal first-pass elimination and predominant hepatic distribution of berberine explain its low plasma levels in rats. Drug Metab. Dispos., 2010, 38, 1779-1784.
[http://dx.doi.org/10.1124/dmd.110.033936] [PMID: 20634337]
[26]
Ma, B.L.; Yao, M.K.; Zhong, J.; Ma, Y.M.; Gao, C.L.; Wu, J.S.; Qiu, F.R.; Wang, C.H.; Wang, X.H. Increased systemic exposure to rhizoma coptidis alkaloids in lipopolysaccharide-pretreated rats attributable to enhanced intestinal absorption. Drug Metab. Dispos., 2012, 40(2), 381-388.
[http://dx.doi.org/10.1124/dmd.111.041152] [PMID: 22086980]
[27]
Lee, Y.H.; Kim, D.; Lee, M.J.; Kim, M.J.; Jang, H.S.; Park, S.H.; Lee, J.M.; Lee, H.Y.; Han, B.S.; Son, W.C.; Seok, J.H.; Lee, J.K.; Jeong, J.; Kang, J.S.; Kang, J.K. Subchronic toxicity study of Coptidis rhizoma in rats. J. Ethnopharmacol., 2014, 152(3), 457-463.
[http://dx.doi.org/10.1016/j.jep.2014.01.011] [PMID: 24486210]
[28]
Wang, G.; Jin, J.; Zeng, J.; Shi, R.; Dai, Y.; Li, J.W.Y.; Wang, T.; Ma, Y. Involvement of P-glycoprotein and multidrug and toxin extrusion protein 1 in hepatic and renal berberine efflux in mice; RSC Adv, 2017, pp. 34801-34809.
[29]
Zou, K.; Li, Z.; Zhang, Y.; Zhang, H.Y.; Li, B.; Zhu, W.L.; Shi, J.Y.; Jia, Q.; Li, Y.M. Advances in the study of berberine and its derivatives: a focus on anti-inflammatory and anti-tumor effects in the digestive system. Acta Pharmacol. Sin., 2017, 38(2), 157-167.
[http://dx.doi.org/10.1038/aps.2016.125] [PMID: 27917872]
[30]
Huang, Z.J.; Zeng, Y.; Lan, P.; Sun, P.H.; Chen, W.M. Advances in structural modifications and biological activities of berberine: an active compound in traditional Chinese medicine. Mini Rev. Med. Chem., 2011, 11(13), 1122-1129.
[http://dx.doi.org/10.2174/138955711797655362] [PMID: 22353221]
[31]
Wang, J.; Yang, T.; Chen, H.; Xu, Y.; Yu, L.; Liu, T.; Tang, J.; Yi, Z.; Yang, C.; Xue, W.; Yang, F. The synthesis and antistaphylococcal activity of 9, 13-disubstituted berberine derivatives. Eur. J. Med. Chem., 2017, 127, 424-433.
[32]
Fan, T.; Hu, X.; Tang, S.; Liu, X.; Wang, Y.; Deng, H.; You, X.; Jiang, J.; Li, Y.; Song, D. Discovery and development of 8-substituted cycloberberine derivatives as novel antibacterial agents against MRSA. ACS Med. Chem. Lett., 2018, 9(5), 484-489.
[http://dx.doi.org/10.1021/acsmedchemlett.8b00094] [PMID: 29795764]
[33]
Iwasa, K.; Kamigauchi, M.; Ueki, M.; Taniguchi, M. Antibacterial activity and structure-activity relationships of berberine analogs. Eur. J. Med. Chem., 1996, 31, 469-478.
[http://dx.doi.org/10.1016/0223-5234(96)85167-1]
[34]
Iwasa, K.; Kamigauchi, M.; Sugiura, M.; Nanba, H. Antimicrobial activity of some 13-alkyl substituted protoberberinium salts. Planta Med., 1997, 63(3), 196-198.
[http://dx.doi.org/10.1055/s-2006-957651] [PMID: 9225598]
[35]
Iwasa, K.; Nanba, H.; Lee, D.U.; Kang, S.I. Structure-activity relationships of protoberberines having antimicrobial activity. Planta Med., 1998, 64(8), 748-751.
[http://dx.doi.org/10.1055/s-2006-957572] [PMID: 9933992]
[36]
Jeyakkumar, P.; Liu, H.B.; Gopala, L.; Cheng, Y.; Peng, X.M.; Geng, R.X.; Zhou, C.H. Novel benzimidazolyl tetrahydroprotoberberines: Design, synthesis, antimicrobial evaluation and multi-targeting exploration. Bioorg. Med. Chem. Lett., 2017, 27(8), 1737-1743.
[http://dx.doi.org/10.1016/j.bmcl.2017.02.071] [PMID: 28302402]
[37]
Parraga, J.; Cabedo, N.; Andujar, S.; Moreno, L.; Galan, A.; Angelina, E.; Enriz, R.D. IVORRA, M.D.; Sanz, M.J; Cortes, D. 2,3,9- and 2,3,11-Trisubstituted tetrahydroprotoberberines as D2 dopaminergic ligands. Eur. J. Med. Chem., 2013, 68, 150-166.
[PMID: 23974015]
[38]
Yu, H.J.; Chen, Y.; Yu, L.; Hao, Z.F.; Zhou, L.H. Synthesis, visible light photocleavage, antiproliferative and cellular uptake properties of ruthenium complex [Ru(phen)2(mitatp)]2+. Eur. J. Med. Chem., 2012, 55, 146-154.
[http://dx.doi.org/10.1016/j.ejmech.2012.07.014] [PMID: 22841281]
[39]
Fang, X.J.; Jeyakkumar, P.; Avula, S.R.; Zhou, Q.; Zhou, C.H. Design, synthesis and biological evaluation of 5-fluorouracil-derived benzimidazoles as novel type of potential antimicrobial agents. Bioorg. Med. Chem. Lett., 2016, 26(11), 2584-2588.
[http://dx.doi.org/10.1016/j.bmcl.2016.04.036] [PMID: 27117429]
[40]
Gao, W.W.; Gopala, L.; Bheemanaboina, R.R.Y.; Zhang, G.B.; Li, S.; Zhou, C.H. Discovery of 2-aminothiazolyl berberine derivatives as effectively antibacterial agents toward clinically drug-resistant Gram-negative Acinetobacter baumanii. Eur. J. Med. Chem., 2018, 146, 15-37.
[http://dx.doi.org/10.1016/j.ejmech.2018.01.038] [PMID: 29396362]
[41]
Childress, E.S.; Kharel, Y.; Brown, A.M.; Bevan, D.R.; Lynch, K.R.; Santos, W.L. Transforming sphingosine kinase 1 inhibitors into dual and sphingosine kinase 2 selective inhibitors: Design, Synthesis, and in Vivo activity. J. Med. Chem., 2017, 60(9), 3933-3957.
[http://dx.doi.org/10.1021/acs.jmedchem.7b00233] [PMID: 28406646]
[42]
Cui, S.F.; Wang, Y. LV, J.S.; Damu, G.LV.; Zhou, C.H. Recent advances in application of thiazole compounds. Sci. China B Chem., 2012, 42, 1105-1131.
[43]
Rouf, A.; Tanyeli, C. Bioactive thiazole and benzothiazole derivatives. Eur. J. Med. Chem., 2015, 97, 911-927.
[http://dx.doi.org/10.1016/j.ejmech.2014.10.058] [PMID: 25455640]
[44]
Geronikaki, A.A.; Pitta, E.P.; Liaras, K.S. Thiazoles and thiazolidinones as antioxidants. Curr. Med. Chem., 2013, 20(36), 4460-4480.
[http://dx.doi.org/10.2174/09298673113209990143] [PMID: 23834182]
[45]
Cui, S.F.; Addla, D.; Zhou, C.H. Novel 3-aminothiazolquinolones: Design, synthesis, bioactive evaluation, SARs, and preliminary antibacterial mechanism. J. Med. Chem., 2016, 59, 4488-4510.
[http://dx.doi.org/10.1021/acs.jmedchem.5b01678]
[46]
Cheng, Y.; Avula, S.R.; Gao, W.W.; Addla, D.; Tangadanchu, V.K.R.; Zhang, L.; Lin, J.M.; Zhou, C.H. Multi-targeting exploration of new 2-aminothiazolyl quinolones: Synthesis, antimicrobial evaluation, interaction with DNA, combination with topoisomerase IV and penetrability into cells. Eur. J. Med. Chem., 2016, 124, 935-945.
[http://dx.doi.org/10.1016/j.ejmech.2016.10.011] [PMID: 27769037]
[47]
Iwasa, K.; Lee, D.U.; Kang, S.I.; Wiegrebe, W. Antimicrobial activity of 8-alkyl- and 8-phenyl-substituted berberines and their 12-bromo derivatives. J. Nat. Prod., 1998, 61(9), 1150-1153.
[http://dx.doi.org/10.1021/np980044+] [PMID: 9748388]

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