Design, Synthesis, and Evaluation of Curcumin Analogues As Potential Inhibitors of Bacterial Sialidase

Overview

Journal J Enzyme Inhib Med Chem

Specialty Biochemistry

Date 2018 Aug 22

PMID 30126306

Citations 13

Authors

Bo Ram Kim

Ji-Young Park

Hyung Jae Jeong

Hyung-Jun Kwon

Su-Jin Park

In-Chul Lee

Young Bae Ryu

Woo Song Lee

Affiliations

Soon will be listed here.

Abstract

Sialidases are key virulence factors that remove sialic acid from the host cell surface glycan, unmasking receptors that facilitate bacterial adherence and colonisation. In this study, we developed potential agents for treating bacterial infections caused by Streptococcus pneumoniae Nan A that inhibit bacterial sialidase using Turmeric and curcumin analogues. Design, synthesis, and structure analysis relationship (SAR) studies have been also described. Evaluation of the synthesised derivatives demonstrated that compound 5e was the most potent inhibitor of S. pneumoniae sialidase (IC = 0.2 ± 0.1 µM). This compound exhibited a 3.0-fold improvement in inhibitory activity over that of curcumin and displayed competitive inhibition. These results warrant further studies confirming the antipneumococcal activity 5e and indicated that curcumin derivatives could be potentially used to treat sepsis by bacterial infections.

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References

Du Z, Liu R, Shao W, Mao X, Ma L, Gu L . Alpha-glucosidase inhibition of natural curcuminoids and curcumin analogs. Eur J Med Chem. 2006; 41(2):213-8. DOI: 10.1016/j.ejmech.2005.10.012. View

Bogaert D, de Groot R, Hermans P . Streptococcus pneumoniae colonisation: the key to pneumococcal disease. Lancet Infect Dis. 2004; 4(3):144-54. DOI: 10.1016/S1473-3099(04)00938-7. View

Feng J, Liu Z . Phenolic and enolic hydroxyl groups in curcumin: which plays the major role in scavenging radicals?. J Agric Food Chem. 2009; 57(22):11041-6. DOI: 10.1021/jf902244g. View

Ryu Y, Jae Jeong H, Yoon S, Park J, Kim Y, Park S . Influenza virus neuraminidase inhibitory activity of phlorotannins from the edible brown alga Ecklonia cava. J Agric Food Chem. 2011; 59(12):6467-73. DOI: 10.1021/jf2007248. View

Changtam C, de Koning H, Ibrahim H, Sajid M, Gould M, Suksamrarn A . Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species. Eur J Med Chem. 2009; 45(3):941-56. DOI: 10.1016/j.ejmech.2009.11.035. View

Ispahani P, Slack R, Donald F, Weston V, Rutter N . Twenty year surveillance of invasive pneumococcal disease in Nottingham: serogroups responsible and implications for immunisation. Arch Dis Child. 2004; 89(8):757-62. PMC: 1720039. DOI: 10.1136/adc.2003.036921. View

Yang L, Connaris H, Potter J, Taylor G . Structural characterization of the carbohydrate-binding module of NanA sialidase, a pneumococcal virulence factor. BMC Struct Biol. 2015; 15:15. PMC: 4546082. DOI: 10.1186/s12900-015-0042-4. View

Lin L, Shi Q, Nyarko A, Bastow K, Wu C, Su C . Antitumor agents. 250. Design and synthesis of new curcumin analogues as potential anti-prostate cancer agents. J Med Chem. 2006; 49(13):3963-72. PMC: 2597393. DOI: 10.1021/jm051043z. View

Huh J, Quy Ha T, Kang K, Kim K, Oh W, Kim J . C-Methylated Flavonoid Glycosides from Pentarhizidium orientale Rhizomes and Their Inhibitory Effects on the H1N1 Influenza Virus. J Nat Prod. 2017; 80(10):2818-2824. DOI: 10.1021/acs.jnatprod.7b00677. View

10.

Paton J, Andrew P, Boulnois G, Mitchell T . Molecular analysis of the pathogenicity of Streptococcus pneumoniae: the role of pneumococcal proteins. Annu Rev Microbiol. 1993; 47:89-115. DOI: 10.1146/annurev.mi.47.100193.000513. View

11.

Mishra S, Palanivelu K . The effect of curcumin (turmeric) on Alzheimer's disease: An overview. Ann Indian Acad Neurol. 2009; 11(1):13-9. PMC: 2781139. DOI: 10.4103/0972-2327.40220. View

12.

Walther E, Xu Z, Richter M, Kirchmair J, Grienke U, Rollinger J . Dual Acting Neuraminidase Inhibitors Open New Opportunities to Disrupt the Lethal Synergism between Streptococcus pneumoniae and Influenza Virus. Front Microbiol. 2016; 7:357. PMC: 4800182. DOI: 10.3389/fmicb.2016.00357. View

13.

Hoffmann A, Richter M, von Grafenstein S, Walther E, Xu Z, Schumann L . Discovery and Characterization of Diazenylaryl Sulfonic Acids as Inhibitors of Viral and Bacterial Neuraminidases. Front Microbiol. 2017; 8:205. PMC: 5309245. DOI: 10.3389/fmicb.2017.00205. View

14.

Park J, Lim S, Kim B, Jae Jeong H, Kwon H, Song G . Sialidase inhibitory activity of diarylnonanoid and neolignan compounds extracted from the seeds of Myristica fragrans. Bioorg Med Chem Lett. 2017; 27(14):3060-3064. DOI: 10.1016/j.bmcl.2017.05.055. View

15.

Caruso F, Pettinari R, Rossi M, Monti E, Gariboldi M, Marchetti F . The in vitro antitumor activity of arene-ruthenium(II) curcuminoid complexes improves when decreasing curcumin polarity. J Inorg Biochem. 2016; 162:44-51. DOI: 10.1016/j.jinorgbio.2016.06.002. View

16.

Gut H, King S, Walsh M . Structural and functional studies of Streptococcus pneumoniae neuraminidase B: An intramolecular trans-sialidase. FEBS Lett. 2008; 582(23-24):3348-52. DOI: 10.1016/j.febslet.2008.08.026. View

17.

Nabavi S, Daglia M, Moghaddam A, Habtemariam S, Nabavi S . Curcumin and Liver Disease: from Chemistry to Medicine. Compr Rev Food Sci Food Saf. 2021; 13(1):62-77. DOI: 10.1111/1541-4337.12047. View

18.

Singer M, Deutschman C, Seymour C, Shankar-Hari M, Annane D, Bauer M . The Third International Consensus Definitions for Sepsis and Septic Shock (Sepsis-3). JAMA. 2016; 315(8):801-10. PMC: 4968574. DOI: 10.1001/jama.2016.0287. View

19.

OBrien K, Wolfson L, Watt J, Henkle E, Deloria-Knoll M, McCall N . Burden of disease caused by Streptococcus pneumoniae in children younger than 5 years: global estimates. Lancet. 2009; 374(9693):893-902. DOI: 10.1016/S0140-6736(09)61204-6. View

20.

Coats M, Murphy T, Paton J, Gray B, Briles D . Exposure of Thomsen-Friedenreich antigen in Streptococcus pneumoniae infection is dependent on pneumococcal neuraminidase A. Microb Pathog. 2011; 50(6):343-9. PMC: 3088309. DOI: 10.1016/j.micpath.2011.02.010. View