Abstract
Background: Curcumin is a polyphenol compound extracted from plant turmeric with high pharmacological activities. The clinical application of curcumin is limited due to the shortcomings of poor water solubility, instability, and low bioavailability.
Objective: Modifying the 4', 4''-bit of curcumin is an effective strategy to improve the pharmacological activity of curcumin.
Conclusion: In this review, we focused on the strategy of synthesis, medicinal properties, and structurefunction relationship of 4', 4''-bit modified curcumin derivatives.
Keywords: Curcumin, 4', 4''-bit modified, pharmacological activity, synthesis, derivative, structure-function.
Graphical Abstract
[1]
Agrawal, D.K.; Mishra, P.K. Curcumin and its analogues: Potential anticancer agents. Med. Res. Rev., 2010, 30(5), 818-860.
[http://dx.doi.org/10.1002/med.20188] [PMID: 20027668]
[http://dx.doi.org/10.1002/med.20188] [PMID: 20027668]
[2]
Ashrafizadeh, M.; Zarrabi, A.; Hashemi, F.; Moghadam, E.R.; Hashemi, F.; Entezari, M.; Hushmandi, K.; Mohammadinejad, R.; Najafi, M. Curcumin in cancer therapy: A novel adjunct for combination chemotherapy with paclitaxel and alleviation of its adverse effects. Life Sci., 2020, 256, 117984.
[http://dx.doi.org/10.1016/j.lfs.2020.117984] [PMID: 32593707]
[http://dx.doi.org/10.1016/j.lfs.2020.117984] [PMID: 32593707]
[3]
Chainoglou, E.; Hadjipavlou-Litina, D. Curcumin analogues and derivatives with anti-proliferative and anti-inflammatory activity: Structural characteristics and molecular targets. Expert Opin. Drug Discov., 2019, 14(8), 821-842.
[http://dx.doi.org/10.1080/17460441.2019.1614560] [PMID: 31094233]
[http://dx.doi.org/10.1080/17460441.2019.1614560] [PMID: 31094233]
[4]
Trujillo, J.; Chirino, Y.I.; Molina-Jijón, E.; Andérica-Romero, A.C.; Tapia, E.; Pedraza-Chaverrí, J. Renoprotective effect of the antioxidant curcumin: Recent findings. Redox Biol., 2013, 1(1), 448-456.
[http://dx.doi.org/10.1016/j.redox.2013.09.003] [PMID: 24191240]
[http://dx.doi.org/10.1016/j.redox.2013.09.003] [PMID: 24191240]
[5]
Chainoglou, E.; Hadjipavlou-Litina, D. Curcumin in health and diseases: Alzheimer’s disease and curcumin analogues, derivatives, and hybrids. Int. J. Mol. Sci., 2020, 21(6), E1975.
[http://dx.doi.org/10.3390/ijms21061975] [PMID: 32183162]
[http://dx.doi.org/10.3390/ijms21061975] [PMID: 32183162]
[6]
Jennings, M.R.; Parks, R.J. Curcumin as an antiviral agent. Viruses, 2020, 12(11), E1242.
[http://dx.doi.org/10.3390/v12111242] [PMID: 33142686]
[http://dx.doi.org/10.3390/v12111242] [PMID: 33142686]
[7]
Menezes, J.C.J.M.D.S. Arylidene indanone scaffold: Medicinal chemistry and structure-activity relationship view. RSC Advances, 2017, 7(15), 9357-9372.
[http://dx.doi.org/10.1039/C6RA28613E]
[http://dx.doi.org/10.1039/C6RA28613E]
[8]
Fuchs, J.R.; Pandit, B.; Bhasin, D.; Etter, J.P.; Regan, N.; Abdelhamid, D.; Li, C.; Lin, J.; Li, P.K. Structure-activity relationship studies of curcumin analogues. Bioorg. Med. Chem. Lett., 2009, 19(7), 2065-2069.
[http://dx.doi.org/10.1016/j.bmcl.2009.01.104] [PMID: 19249204]
[http://dx.doi.org/10.1016/j.bmcl.2009.01.104] [PMID: 19249204]
[9]
Hanahan, D.; Weinberg, R.A. Hallmarks of cancer: The next generation. Cell, 2011, 144(5), 646-674.
[http://dx.doi.org/10.1016/j.cell.2011.02.013] [PMID: 21376230]
[http://dx.doi.org/10.1016/j.cell.2011.02.013] [PMID: 21376230]
[10]
Aggarwal, B.B.; Kumar, A.; Bharti, A.C. Anticancer potential of curcumin: Preclinical and clinical studies. Anticancer Res., 2003, 23(1A), 363-398.
[PMID: 12680238]
[PMID: 12680238]
[11]
Wilken, R.; Veena, M.S.; Wang, M.B.; Srivatsan, E.S. Curcumin: A review of anti-cancer properties and therapeutic activity in head and neck squamous cell carcinoma. Mol. Cancer, 2011, 10(1), 12.
[http://dx.doi.org/10.1186/1476-4598-10-12] [PMID: 21299897]
[http://dx.doi.org/10.1186/1476-4598-10-12] [PMID: 21299897]
[12]
Karthika, C.; Hari, B.; Mano, V.; Radhakrishnan, A.; Janani, S.K.; Akter, R.; Kaushik, D.; Rahman, M.H. Curcumin as a great contributor for the treatment and mitigation of colorectal cancer. Exp. Gerontol., 2021, 152, 111438.
[http://dx.doi.org/10.1016/j.exger.2021.111438] [PMID: 34098006]
[http://dx.doi.org/10.1016/j.exger.2021.111438] [PMID: 34098006]
[13]
Aggarwal, B.B.; Sethi, G.; Baladandayuthapani, V.; Krishnan, S.; Shishodia, S. Targeting cell signaling pathways for drug discovery: An old lock needs a new key. J. Cell. Biochem., 2007, 102(3), 580-592.
[http://dx.doi.org/10.1002/jcb.21500] [PMID: 17668425]
[http://dx.doi.org/10.1002/jcb.21500] [PMID: 17668425]
[14]
Qin, Z.; Yao, F.; Hao, W.W.; Tao, G.; Yong, Q.; Zhi, R.Z. Synthesis and cytotoxic activity of novel curcumin analogues. Chin. Chem. Lett., 2008, 19(3), 281-285.
[http://dx.doi.org/10.1016/j.cclet.2007.12.035]
[http://dx.doi.org/10.1016/j.cclet.2007.12.035]
[15]
Wichitnithad, W.; Nimmannit, U.; Wacharasindhu, S.; Rojsitthisak, P. Synthesis, characterization and biological evaluation of succinate prodrugs of curcuminoids for colon cancer treatment. Molecules, 2011, 16(2), 1888-1900.
[http://dx.doi.org/10.3390/molecules16021888] [PMID: 21343891]
[http://dx.doi.org/10.3390/molecules16021888] [PMID: 21343891]
[16]
Ding, L.; Ma, S.; Lou, H.; Sun, L.; Ji, M. Synthesis and biological evaluation of curcumin derivatives with water-soluble groups as potential antitumor agents: An in vitro investigation using tumor cell lines. Molecules, 2015, 20(12), 21501-21514.
[http://dx.doi.org/10.3390/molecules201219772] [PMID: 26633344]
[http://dx.doi.org/10.3390/molecules201219772] [PMID: 26633344]
[17]
Majhi, A.; Rahman, G.M.; Panchal, S.; Das, J. Binding of curcumin and its long chain derivatives to the activator binding domain of novel protein kinase C. Bioorg. Med. Chem., 2010, 18(4), 1591-1598.
[http://dx.doi.org/10.1016/j.bmc.2009.12.075] [PMID: 20100661]
[http://dx.doi.org/10.1016/j.bmc.2009.12.075] [PMID: 20100661]
[18]
Zhang, J.; Wen, H.; Shen, F.; Wang, X.; Shan, C.; Chai, C.; Liu, J.; Li, W. Synthesis and biological evaluation of a novel series of curcumin-peptide derivatives as PepT1-mediated transport drugs. Bioorg. Chem., 2019, 92, 103163.
[http://dx.doi.org/10.1016/j.bioorg.2019.103163] [PMID: 31450166]
[http://dx.doi.org/10.1016/j.bioorg.2019.103163] [PMID: 31450166]
[19]
Jordan, B.C.; Kumar, B.; Thilagavathi, R.; Yadhav, A.; Kumar, P.; Selvam, C. Synthesis, evaluation of cytotoxic properties of promising curcumin analogues and investigation of possible molecular mechanisms. Chem. Biol. Drug Des., 2018, 91(1), 332-337.
[http://dx.doi.org/10.1111/cbdd.13061] [PMID: 28649799]
[http://dx.doi.org/10.1111/cbdd.13061] [PMID: 28649799]
[20]
Bonaccorsi, P.M.; Labbozzetta, M.; Barattucci, A.; Salerno, T.M.G.; Poma, P.; Notarbartolo, M. Synthesis of curcumin derivatives and analysis of their antitumor effects in triple negative breast cancer (TNBC) cell lines. Pharmaceuticals (Basel), 2019, 12(4), E161.
[http://dx.doi.org/10.3390/ph12040161] [PMID: 31717764]
[http://dx.doi.org/10.3390/ph12040161] [PMID: 31717764]
[21]
Ohtsu, H.; Xiao, Z.; Ishida, J.; Nagai, M.; Wang, H-K.; Itokawa, H.; Su, C-Y.; Shih, C.; Chiang, T.; Chang, E.; Lee, Y.; Tsai, M.Y.; Chang, C.; Lee, K.H. Antitumor agents. 217. Curcumin analogues as novel androgen receptor antagonists with potential as anti-prostate cancer agents. J. Med. Chem., 2002, 45(23), 5037-5042.
[http://dx.doi.org/10.1021/jm020200g] [PMID: 12408714]
[http://dx.doi.org/10.1021/jm020200g] [PMID: 12408714]
[22]
Lozada-García, M.C.; Enríquez, R.G.; Ramírez-Apán, T.O.; Nieto-Camacho, A.; Palacios-Espinosa, J.F.; Custodio-Galván, Z.; Soria-Arteche, O.; Pérez-Villanueva, J. Synthesis of curcuminoids and evaluation of their cytotoxic and antioxidant properties. Molecules, 2017, 22(4), E633.
[http://dx.doi.org/10.3390/molecules22040633] [PMID: 28420097]
[http://dx.doi.org/10.3390/molecules22040633] [PMID: 28420097]
[23]
Ferrari, E.; Lazzari, S.; Marverti, G.; Pignedoli, F.; Spagnolo, F.; Saladini, M. Synthesis, cytotoxic and combined cDDP activity of new stable curcumin derivatives. Bioorg. Med. Chem., 2009, 17(8), 3043-3052.
[http://dx.doi.org/10.1016/j.bmc.2009.03.016] [PMID: 19329324]
[http://dx.doi.org/10.1016/j.bmc.2009.03.016] [PMID: 19329324]
[24]
Sribalan, R.; Kirubavathi, M.; Banuppriya, G.; Padmini, V. Synthesis and biological evaluation of new symmetric curcumin derivatives. Bioorg. Med. Chem. Lett., 2015, 25(19), 4282-4286.
[http://dx.doi.org/10.1016/j.bmcl.2015.07.088] [PMID: 26264500]
[http://dx.doi.org/10.1016/j.bmcl.2015.07.088] [PMID: 26264500]
[25]
Wang, P.; She, G.; Yang, Y.; Li, Q.; Zhang, H.; Liu, J.; Cao, Y.; Xu, X.; Lei, H. Synthesis and biological evaluation of new ligustrazine derivatives as anti-tumor agents. Molecules, 2012, 17(5), 4972-4985.
[http://dx.doi.org/10.3390/molecules17054972] [PMID: 22547319]
[http://dx.doi.org/10.3390/molecules17054972] [PMID: 22547319]
[26]
Al-Wabli, R.I.; AboulWafa, O.M.; Youssef, K.M. Synthesis of curcumin and ethylcurcumin bioconjugates as potential antitumor agents. Med. Chem. Res., 2012, 21(6), 874-890.
[http://dx.doi.org/10.1007/s00044-011-9587-3]
[http://dx.doi.org/10.1007/s00044-011-9587-3]
[27]
Srivastava, S.; Gupta, P.; Singh, R.P.; Jafri, A.; Arshad, M.; Banerjee, M. Synthesis, spectroscopic characterization, theoretical study and anti hepatic cancer activity study of 4-(1E,3Z,6E)-3-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-5-oxohepta-1,3,6-tr ien-1-yl)-2-methoxyphenyl 4-nitrobenzoate, a novel curcumin congener. J. Mol. Struct., 2017, 1141, 678-686.
[http://dx.doi.org/10.1016/j.molstruc.2017.04.008]
[http://dx.doi.org/10.1016/j.molstruc.2017.04.008]
[28]
Botta, L.; Filippi, S.; Bizzarri, B.M.; Zippilli, C.; Meschini, R.; Pogni, R.; Baratto, M.C.; Villanova, L.; Saladino, R. Synthesis and evaluation of artemisinin-based hybrid and dimer derivatives as antimelanoma agents. ACS Omega, 2019, 5(1), 243-251.
[http://dx.doi.org/10.1021/acsomega.9b02600] [PMID: 31956771]
[http://dx.doi.org/10.1021/acsomega.9b02600] [PMID: 31956771]
[29]
Zhang, Q.; Zhong, Y.; Yan, L.N.; Sun, X.; Gong, T.; Zhang, Z.R. Synthesis and preliminary evaluation of curcumin analogues as cytotoxic agents. Bioorg. Med. Chem. Lett., 2011, 21(3), 1010-1014.
[http://dx.doi.org/10.1016/j.bmcl.2010.12.020] [PMID: 21215629]
[http://dx.doi.org/10.1016/j.bmcl.2010.12.020] [PMID: 21215629]
[30]
Basile, V.; Belluti, S.; Ferrari, E.; Gozzoli, C.; Ganassi, S.; Quaglino, D.; Saladini, M.; Imbriano, C. bis-dehydroxy-curcumin triggers mitochondrial-associated cell death in human colon cancer cells through er-stress induced autophagy. PLoS One, 2013, 8(1), e53664.
[http://dx.doi.org/10.1371/journal.pone.0053664] [PMID: 23326480]
[http://dx.doi.org/10.1371/journal.pone.0053664] [PMID: 23326480]
[31]
Li, J.; Wang, Y.; Yang, C.; Wang, P.; Oelschlager, D.K.; Zheng, Y.; Tian, D.A.; Grizzle, W.E.; Buchsbaum, D.J.; Wan, M. Polyethylene glycosylated curcumin conjugate inhibits pancreatic cancer cell growth through inactivation of Jab1. Mol. Pharmacol., 2009, 76(1), 81-90.
[http://dx.doi.org/10.1124/mol.109.054551] [PMID: 19395473]
[http://dx.doi.org/10.1124/mol.109.054551] [PMID: 19395473]
[32]
Manju, S.; Sreenivasan, K. Gold nanoparticles generated and stabilized by water soluble curcumin-polymer conjugate: Blood compatibility evaluation and targeted drug delivery onto cancer cells. J. Colloid Interface Sci., 2012, 368(1), 144-151.
[http://dx.doi.org/10.1016/j.jcis.2011.11.024] [PMID: 22200330]
[http://dx.doi.org/10.1016/j.jcis.2011.11.024] [PMID: 22200330]
[33]
Murphy, C.J.; Tang, H.; Van Kirk, E.A.; Shen, Y.; Murdoch, W.J. Reproductive effects of a pegylated curcumin. Reprod. Toxicol., 2012, 34(1), 120-124.
[http://dx.doi.org/10.1016/j.reprotox.2012.04.005] [PMID: 22576113]
[http://dx.doi.org/10.1016/j.reprotox.2012.04.005] [PMID: 22576113]
[34]
Amornwachirabodee, K.; Chiablaem, K.; Wacharasindhu, S.; Lirdprapamongkol, K.; Svasti, J.; Vchirawongkwin, V.; Wanichwecharungruang, S.P. Paclitaxel delivery using carrier made from curcumin derivative: Synergism between carrier and the loaded drug for effective cancer treatment. J. Pharm. Sci., 2012, 101(10), 3779-3786.
[http://dx.doi.org/10.1002/jps.23263] [PMID: 22806358]
[http://dx.doi.org/10.1002/jps.23263] [PMID: 22806358]
[35]
Dantzer, R.; O’Connor, J.C.; Freund, G.G.; Johnson, R.W.; Kelley, K.W. From inflammation to sickness and depression: When the immune system subjugates the brain. Nat. Rev. Neurosci., 2008, 9(1), 46-56.
[http://dx.doi.org/10.1038/nrn2297] [PMID: 18073775]
[http://dx.doi.org/10.1038/nrn2297] [PMID: 18073775]
[36]
Medzhitov, R. Origin and physiological roles of inflammation. Nature, 2008, 454(7203), 428-435.
[http://dx.doi.org/10.1038/nature07201] [PMID: 18650913]
[http://dx.doi.org/10.1038/nature07201] [PMID: 18650913]
[37]
Zhou, Y.; Zhang, T.; Wang, X.; Wei, X.; Chen, Y.; Guo, L.; Zhang, J.; Wang, C. Curcumin modulates macrophage polarization through the inhibition of the toll-like receptor 4 expression and its signaling pathways. Cell. Physiol. Biochem., 2015, 36(2), 631-641.
[http://dx.doi.org/10.1159/000430126] [PMID: 25998190]
[http://dx.doi.org/10.1159/000430126] [PMID: 25998190]
[38]
Shehzad, A.; Rehman, G.; Lee, Y.S. Curcumin in inflammatory diseases. Biofactors, 2013, 39(1), 69-77.
[http://dx.doi.org/10.1002/biof.1066] [PMID: 23281076]
[http://dx.doi.org/10.1002/biof.1066] [PMID: 23281076]
[39]
El-Gazzar, M.G.; Zaher, N.H.; El-Hossary, E.M.; Ismail, A.F.M. Radio-protective effect of some new curcumin analogues. J. Photochem. Photobiol. B, 2016, 162, 694-702.
[http://dx.doi.org/10.1016/j.jphotobiol.2016.08.002] [PMID: 27505300]
[http://dx.doi.org/10.1016/j.jphotobiol.2016.08.002] [PMID: 27505300]
[40]
Lakey-Beitia, J.; González, Y.; Doens, D.; Stephens, D.E.; Santamaría, R.; Murillo, E.; Gutiérrez, M.; Fernández, P.L.; Rao, K.S.; Larionov, O.V.; Durant-Archibold, A.A. Assessment of novel curcumin derivatives as potent Inhibitors of inflammation and amyloid-beta aggregation in Alzheimer’s disease. J. Alzheimers Dis., 2017, 60(s1), S59-S68.
[http://dx.doi.org/10.3233/JAD-170071] [PMID: 28453488]
[http://dx.doi.org/10.3233/JAD-170071] [PMID: 28453488]
[41]
Nagappan, A.S.; Varghese, J.; Pranesh, G.T.; Jeyaseelan, V.; Jacob, M. Indomethacin inhibits activation of endothelial nitric oxide synthase in the rat kidney: Possible role of this effect in the pathogenesis of indomethacin-induced renal damage. Chem. Biol. Interact., 2014, 221, 77-87.
[http://dx.doi.org/10.1016/j.cbi.2014.07.014] [PMID: 25110317]
[http://dx.doi.org/10.1016/j.cbi.2014.07.014] [PMID: 25110317]
[42]
Liu, W.; Li, Y.; Yue, Y.; Zhang, K.; Chen, Q.; Wang, H.; Lu, Y.; Huang, M.T.; Zheng, X.; Du, Z. Synthesis and biological evaluation of curcumin derivatives containing NSAIDs for their anti-inflammatory activity. Bioorg. Med. Chem. Lett., 2015, 25(15), 3044-3051.
[http://dx.doi.org/10.1016/j.bmcl.2015.04.077] [PMID: 26048786]
[http://dx.doi.org/10.1016/j.bmcl.2015.04.077] [PMID: 26048786]
[43]
Panda, S.S.; Girgis, A.S.; Thomas, S.J.; Capito, J.E.; George, R.F.; Salman, A.; El-Manawaty, M.A.; Samir, A. Synthesis, pharmacological profile and 2D-QSAR studies of curcumin-amino acid conjugates as potential drug candidates. Eur. J. Med. Chem., 2020, 196, 112293.
[http://dx.doi.org/10.1016/j.ejmech.2020.112293] [PMID: 32311607]
[http://dx.doi.org/10.1016/j.ejmech.2020.112293] [PMID: 32311607]
[44]
Vidyarthi, N.; Mazumdar, A. Oxidative stress and antioxidant enzymes. Pharmacophore, 2014, 5(6), 889-894.
[45]
Srivastava, K.K.; Kumar, R. Stress, oxidative injury and disease. Indian J. Clin. Biochem., 2015, 30(1), 3-10.
[http://dx.doi.org/10.1007/s12291-014-0441-5] [PMID: 25646036]
[http://dx.doi.org/10.1007/s12291-014-0441-5] [PMID: 25646036]
[46]
Qi, J.H.; Dong, F.X. The relevant targets of anti-oxidative stress: A review. J. Drug Target., 2021, 29(7), 677-686.
[http://dx.doi.org/10.1080/1061186X.2020.1870987] [PMID: 33401976]
[http://dx.doi.org/10.1080/1061186X.2020.1870987] [PMID: 33401976]
[47]
Jovanovic, S.V.; Boone, C.W.; Steenken, S.; Trinoga, M.; Kaskey, R.B. How curcumin works preferentially with water soluble antioxidants. J. Am. Chem. Soc., 2001, 123(13), 3064-3068.
[http://dx.doi.org/10.1021/ja003823x] [PMID: 11457017]
[http://dx.doi.org/10.1021/ja003823x] [PMID: 11457017]
[48]
Feng, J-Y.; Liu, Z-Q. Phenolic and enolic hydroxyl groups in curcumin: Which plays the major role in scavenging radicals? J. Agric. Food Chem., 2009, 57(22), 11041-11046.
[http://dx.doi.org/10.1021/jf902244g] [PMID: 19736944]
[http://dx.doi.org/10.1021/jf902244g] [PMID: 19736944]
[49]
Masuda, T.; Hidaka, K.; Shinohara, A.; Maekawa, T.; Takeda, Y.; Yamaguchi, H. Chemical studies on antioxidant mechanism of curcuminoid: Analysis of radical reaction products from curcumin. J. Agric. Food Chem., 1999, 47(1), 71-77.
[http://dx.doi.org/10.1021/jf9805348] [PMID: 10563852]
[http://dx.doi.org/10.1021/jf9805348] [PMID: 10563852]
[50]
Shimoda, K.; Hara, T.; Hamada, H.; Hamada, H. Synthesis of curcumin beta-maltooligosaccharides through biocatalytic glycosylation with Strophanthus gratus cell culture and cyclodextrin glucanotransferase. Tetrahedron Lett., 2007, 48(23), 4029-4032.
[http://dx.doi.org/10.1016/j.tetlet.2007.04.029]
[http://dx.doi.org/10.1016/j.tetlet.2007.04.029]
[51]
Parvathy, K.S.; Negi, P.S.; Srinivas, P. Antioxidant, antimutagenic and antibacterial activities of curcumin-beta-diglucoside. Food Chem., 2009, 115(1), 265-271.
[http://dx.doi.org/10.1016/j.foodchem.2008.12.036]
[http://dx.doi.org/10.1016/j.foodchem.2008.12.036]
[52]
Yanase, E.; Jang, Y. P.; Nakanishi, K. Syntheses of antioxidant flavonoid derivatives. Heterocycles, 2011, 82(2), 1151.
[http://dx.doi.org/10.3987/COM-10-S(E)102]
[http://dx.doi.org/10.3987/COM-10-S(E)102]
[53]
Bi, W.; Bi, Y.; Gao, X.; Yan, X.; Zhang, Y.; Harris, J.; Legalley, T.D.; Gibson, K.M.; Bi, L. Pharmacological protection of mitochondrial function mitigates acute limb ischemia/reperfusion injury. Bioorg. Med. Chem. Lett., 2016, 26(16), 4042-4051.
[http://dx.doi.org/10.1016/j.bmcl.2016.06.079] [PMID: 27390069]
[http://dx.doi.org/10.1016/j.bmcl.2016.06.079] [PMID: 27390069]
[54]
Parvathy, K.S.; Negi, P.S.; Srinivas, P. Curcumin-amino acid conjugates: Synthesis, antioxidant and antimutagenic attributes. Food Chem., 2010, 120(2), 523-530.
[http://dx.doi.org/10.1016/j.foodchem.2009.10.047]
[http://dx.doi.org/10.1016/j.foodchem.2009.10.047]
[55]
Harish, G.; Venkateshappa, C.; Mythri, R.B.; Dubey, S.K.; Mishra, K.; Singh, N.; Vali, S.; Bharath, M.M.S. Bioconjugates of curcumin display improved protection against glutathione depletion mediated oxidative stress in a dopaminergic neuronal cell line: Implications for Parkinson’s disease. Bioorg. Med. Chem., 2010, 18(7), 2631-2638.
[http://dx.doi.org/10.1016/j.bmc.2010.02.029] [PMID: 20227282]
[http://dx.doi.org/10.1016/j.bmc.2010.02.029] [PMID: 20227282]
[56]
Jha, N.; Jurma, O.; Lalli, G.; Liu, Y.; Pettus, E.H.; Greenamyre, J.T.; Liu, R.M.; Forman, H.J.; Andersen, J.K. Glutathione depletion in PC12 results in selective inhibition of mitochondrial complex I activity. Implications for Parkinson’s disease. J. Biol. Chem., 2000, 275(34), 26096-26101.
[http://dx.doi.org/10.1074/jbc.M000120200] [PMID: 10846169]
[http://dx.doi.org/10.1074/jbc.M000120200] [PMID: 10846169]
[57]
Dolai, S.; Shi, W.; Corbo, C.; Sun, C.; Averick, S.; Obeysekera, D.; Farid, M.; Alonso, A.; Banerjee, P.; Raja, K. “Clicked” sugarcurcumin conjugate: Modulator of amyloid-β and tau peptide aggregation at ultralow concentrations. ACS Chem. Neurosci., 2011, 2(12), 694-699.
[http://dx.doi.org/10.1021/cn200088r] [PMID: 22860163]
[http://dx.doi.org/10.1021/cn200088r] [PMID: 22860163]
[58]
Orlando, R.A.; Gonzales, A.M.; Royer, R.E.; Deck, L.M.; Vander Jagt, D.L. A chemical analog of curcumin as an improved inhibitor of amyloid Abeta oligomerization. PLoS One, 2012, 7(3), e31869.
[http://dx.doi.org/10.1371/journal.pone.0031869] [PMID: 22442659]
[http://dx.doi.org/10.1371/journal.pone.0031869] [PMID: 22442659]
[59]
Di Martino, R.M.C.; De Simone, A.; Andrisano, V.; Bisignano, P.; Bisi, A.; Gobbi, S.; Rampa, A.; Fato, R.; Bergamini, C.; Perez, D.I.; Martinez, A.; Bottegoni, G.; Cavalli, A.; Belluti, F. Versatility of the curcumin scaffold: Discovery of potent and balanced dual BACE-1 and GSK-3 beta Inhibitors. J. Med. Chem., 2016, 59(2), 531-544.
[http://dx.doi.org/10.1021/acs.jmedchem.5b00894] [PMID: 26696252]
[http://dx.doi.org/10.1021/acs.jmedchem.5b00894] [PMID: 26696252]
[60]
Bisceglia, F.; Seghetti, F.; Serra, M.; Zusso, M.; Gervasoni, S.; Verga, L.; Vistoli, G.; Lanni, C.; Catanzaro, M.; De Lorenzi, E.; Belluti, F. Prenylated curcumin analogues as multipotent tools to tackle Alzheimer’s disease. ACS Chem. Neurosci., 2019, 10(3), 1420-1433.
[http://dx.doi.org/10.1021/acschemneuro.8b00463] [PMID: 30556996]
[http://dx.doi.org/10.1021/acschemneuro.8b00463] [PMID: 30556996]
[61]
Kochi, A.; Lee, H.J.; Vithanarachchi, S.M.; Padmini, V.; Allen, M.J.; Lim, M.H. Inhibitory activity of curcumin derivatives towards metal-free and metal-induced amyloid-beta aggregation. Curr. Alzheimer Res., 2015, 12(5), 415-423.
[http://dx.doi.org/10.2174/1567205012666150504150125] [PMID: 25938870]
[http://dx.doi.org/10.2174/1567205012666150504150125] [PMID: 25938870]
[62]
Elmegeed, G.A.; Ahmed, H.H.; Hashash, M.A.; Abd-Elhalim, M.M.; El-kady, D.S. Synthesis of novel steroidal curcumin derivatives as anti-Alzheimer’s disease candidates: Evidences-based on in vivo study. Steroids, 2015, 101, 78-89.
[http://dx.doi.org/10.1016/j.steroids.2015.06.003] [PMID: 26079653]
[http://dx.doi.org/10.1016/j.steroids.2015.06.003] [PMID: 26079653]
[63]
Qi, Z.; Wu, M.; Fu, Y.; Huang, T.; Wang, T.; Sun, Y.; Feng, Z.; Li, C. Palmitic acid curcumin ester facilitates protection of neuroblastoma against oligomeric a beta(40) Insult. Cell. Physiol. Biochem., 2017, 44(2), 618-633.
[http://dx.doi.org/10.1159/000485117] [PMID: 29161719]
[http://dx.doi.org/10.1159/000485117] [PMID: 29161719]
[64]
Mohammadi, F.; Moeeni, M.; Mahmudian, A.; Hassani, L. Inhibition of amyloid fibrillation of lysozyme by bisdemethoxycurcumin and diacetylbisdemethoxycurcumin. Biophys. Chem., 2018, 235, 56-65.
[http://dx.doi.org/10.1016/j.bpc.2018.02.005] [PMID: 29477768]
[http://dx.doi.org/10.1016/j.bpc.2018.02.005] [PMID: 29477768]
[65]
Wang, S.; Peng, X.; Cui, L.; Li, T.; Yu, B.; Ma, G.; Ba, X. Synthesis of water-soluble curcumin derivatives and their inhibition on lysozyme amyloid fibrillation. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2018, 190, 89-95.
[http://dx.doi.org/10.1016/j.saa.2017.09.010] [PMID: 28915469]
[http://dx.doi.org/10.1016/j.saa.2017.09.010] [PMID: 28915469]
[66]
Cui, L.; Wang, S.; Zhang, J.; Wang, M.; Gao, Y.; Bai, L.; Zhang, H.; Ma, G.; Ba, X. Effect of curcumin derivatives on hen egg white lysozyme amyloid fibrillation and their interaction study by spectroscopic methods. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2019, 223, 117365.
[http://dx.doi.org/10.1016/j.saa.2019.117365] [PMID: 31323497]
[http://dx.doi.org/10.1016/j.saa.2019.117365] [PMID: 31323497]
[67]
Narasingappa, R.B.; Javagal, M.R.; Pullabhatla, S.; Htoo, H.H.; Rao, J.K.S.; Hernandez, J.F.; Govitrapong, P.; Vincent, B. Activation of α-secretase by curcumin-aminoacid conjugates. Biochem. Biophys. Res. Commun., 2012, 424(4), 691-696.
[http://dx.doi.org/10.1016/j.bbrc.2012.07.010] [PMID: 22796219]
[http://dx.doi.org/10.1016/j.bbrc.2012.07.010] [PMID: 22796219]
[68]
Mohammadi, F.; Mahmudian, A.; Moeeni, M.; Hassani, L. Inhibition of amyloid fibrillation of hen egg-white lysozyme by the natural and synthetic curcuminoids. RSC Advances, 2016, 6(28), 23148-23160.
[http://dx.doi.org/10.1039/C5RA18992F]
[http://dx.doi.org/10.1039/C5RA18992F]
[69]
Mishra, S.; Narain, U.; Mishra, R.; Misra, K. Design, development and synthesis of mixed bioconjugates of piperic acid-glycine, curcumin-glycine/alanine and curcumin-glycine-piperic acid and their antibacterial and antifungal properties. Bioorg. Med. Chem., 2005, 13(5), 1477-1486.
[http://dx.doi.org/10.1016/j.bmc.2004.12.057] [PMID: 15698763]
[http://dx.doi.org/10.1016/j.bmc.2004.12.057] [PMID: 15698763]
[70]
Wang, H.S.; Jiang, B.L.; Huai, Q.Y. Synthesis and antimicrobial activities on staphylicoccus aureus of miscellaneous atomic curcumin derivatives. Asian J. Chem., 2013, 25(9), 4836-4838.
[http://dx.doi.org/10.14233/ajchem.2013.14118]
[http://dx.doi.org/10.14233/ajchem.2013.14118]
Article Metrics
1