Abstract
Docking simulation between chlorogenic acid and H5N1 influenza virus neuraminidase (NA) was performed and the binding free energies of the best pose and average for the best three different poses of H5N1 NA–chlorogenic acid complex are −9.71 and −9.27 kcal/mol, respectively, which is lower than those of H5N1 NA–oseltamivir complex (−7.13 and −6.39 kcal/mol) by using ArgusLab docking method. The hydrogen bonds could be formed between chlorogenic acid and the H5N1 NA amino acid residues Arg156 and Thr439. Arg152 from the 150-cavity makes polar contact with the –COOH group in chlorogenic acid. Chlorogenic acid could be a potential H5N1 influenza A virus NA inhibitor.
Similar content being viewed by others
References
Almeida AA, Farah A, Silva DA, Nunan EA, Gloria MB (2006) Antibacterial activity of coffee extracts and selected coffee chemical compounds against enterobacteria. J Agric Food Chem 54:8738–8743
Bandyopadhyay G, Biswas T, Roy KC, Mandal S, Mandal C, Pal BC (2004) Chlorogenic acid inhibits Bcr-Abl tyrosine kinase and triggers p38 mitogen-activated protein kinase dependent apoptosis in chronicmyelogenous leukemic cells. Blood 104:2514–2522
DeLano WL (2004) The PyMOL molecular graphics system. DeLano Scientific, San Carlos, USA
do Santos MD, Almeida MC, Lopes NP, de Souza GE (2006) Evaluation of the antiinflammatory, analgesic and antipyretic activities of the natural polyphenol chlorogenic acid. Biol Pharm Bull 29:2236–2240
Du QS, Wang SQ, Chou KC (2007) Analogue inhibitors by modifying oseltamivir based on the crystal neuraminidase structure for treating drug-resistant H5N1 virus. Biochem Biophys Res Commun 362:525–531
Dunn CJ, Goa KL (1999) Zanamivir: a review of its use in influenza. Drugs 58:761–784
Feng R, Lu Y, Bowman LL, Qian Y, Castranova V, Ding M (2005) Inhibition of activator protein-1, NF-kappaB, and MAPKs and induction of phase 2 detoxifying enzyme activity by chlorogenic acid. J Biol Chem 280:27888–27895
Huang MT, Smart RC, Wong CQ, Conney AH (1988) Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Cancer Res 48:5941–5946
Katarina N, Slavica F, Danica A (2008) QSAR study of imidazoline antihypertensive drugs. Bioorganic Med Chem 16:7134–7140
Kono Y, Kashine S, Yoneyama T, Sakamoto Y, Matsui Y, Shibata H (1998) Iron chelation by chlorogenic acid as a natural antioxidant. Biosci Biotechnol Biochem 62:22–27
Le QM, Kiso M, Someya K, Sakai YT, Nguyen TH, Nguyen KH, Pham ND, Ngyen HH, Yamada S, Muramoto Y, Horimoto T, Takada A, Goto H, Suzuki T, Suzuki Y, Kawaoka Y (2005) Avian flu: isolation of drug-resistant H5N1 virus. Nature 437:1108
Lew W, Chen X, Kim CU (2000) Discovery and development of GS 4104 (oseltamivir): an orally active influenza neuraminidase inhibitor. Curr Med Chem 7:663–672
McKimm-Breschkin JL (2000) Resistance of influenza viruses to neuraminidase inhibitors—a review. Antiviral Res 47:1–17
Mishin VP, Hayden FG, Gubareva LV (2005) Susceptibilities of antiviral-resistant influenza viruses to novel neuraminidase inhibitors. Antimicrob Agents Chemother 49:4515–4520
Nardini M, Cirillo E, Natella F, Scaccini C (2002) Absorption of phenolic acids in humans after coffee consumption. J Agric Food Chem 50:5735–5741
Petar MM (2009) On the structure-based design of novel inhibitors of H5N1 influenza A virus neuraminidase (NA). Biophys Chem 140:35–38
Russell RJ, Haire LF, Stevens DJ, Collins PJ, Lin YP, Blackburn GM, Hay AJ, Gamblin SJ, Skehel JJ (2006) The structure of H5N1 avian influenza neuraminidase suggests new opportunities for drug design. Nature 443:45–49
Shan JH, Fu J, Zhao ZH, Kong XQ, Huang H, Luo L, Yin ZM (2009) Chlorogenic acid inhibits lipopolysaccharide-induced cyclooxygenase-2 expression in RAW264.7 cells through suppressing NF-κB and JNK/AP-1 activation. Int Immunopharmacol 1–7
Thompson MA (2004) ArgusLab 4.0.1. Planaria Software, LLC, Seattle, WA, http://www.ArgusLab.com
Thompson MA (2004b) Poster presentation: molecular docking using arguslab: an efficient shape-based search algorithm and the AScore scoring function. Fall ACS meeting, Philadelphia
Ward P, Small I, Smith J, Suter P, Dutkowski R (2005) Oseltamivir (Tamiflu) and its potential for use in the event of an influenza pandemic. J Antimicrob Chemother 55(Suppl. 1):i5–i21
Zang LY, Cosma G, Gardner H, Castranova V, Vallyathan V (2003) Effect of chlorogenic acid on hydroxyl radical. Mol Cell Biochem 247:205–210
Zhao Z, Shin HS, Satsu H, Totsuka M, Shimizu M (2008) 5-Caffeoylquinic acid and caffeic acid down-regulate the oxidative stress- and TNF-α-induced secretion of interleukin-8 from Caco-2 cells. J Agric Food Chem 56:3863–3868
Acknowledgments
This work was granted by National Natural Science Foundation of China (No. 30760213, 30870254, 30970296) and Hubei Province Natural Science Foundation Innovation Team Program (No. 2007ABC008).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Luo, HJ., Wang, JZ., Chen, JF. et al. Docking study on chlorogenic acid as a potential H5N1 influenza A virus neuraminidase inhibitor. Med Chem Res 20, 554–557 (2011). https://doi.org/10.1007/s00044-010-9336-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-010-9336-z