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Semisynthesis of Myristic Acid Derivatives and their Biological Activities: A Critical Insight

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Pages 455-472 | Received 19 Apr 2020, Accepted 12 Dec 2020, Published online: 03 Jan 2021

References

  • World Health Organization, WHO., Geneva, Switzerland: (2000). General Guidelines for Methodologies on Research and Evaluation of Traditional Medicine. 3-4.
  • Pal, M., Srivastava, M., Soni, D.K., Kumar, A. and Tewari, S.K. (2011). Composition and anti-microbial activity of essential oil of Myristica fragrans from Andaman Nicobar Island. Int. J. Pharm. Life Sci. 2(10): 1115-1117.
  • Chirathaworn, C., Kongcharoensuntorn, W., Dechdoungchan, T., Lowanitchapat, A., Sa-nguanmoo, P. and Poovoraan, Y. (2007). Myristica fragrans Houtt. methanolic extract induces apoptosis in a human leukemia cell line through SIRT1 mRNA down regulation. J. Med. Assoc. Thai. 90(11): 2422-2428.
  • Duarte, R.C., Fanaro, G.B., Koike, A.C.R. and Villavicencio, A.L.C.H. (2011). Irradiation effect on antifungal potential Myristica fragrans (nutmeg) essential oil, a preliminary study. Int. Nucl. Atlantic Con. 6: 60-67.
  • Olaleye, M.T., Akinmoladun, A.C. and Akindahunsi, A.A. (2006). Antioxidant properties of Myristica fragrans (Houtt) and its effect on selected organs of albino rats. Afr. J. Biotechnol. 5(13): 1274-1278.
  • Liu, S., Weibin, R., Jing, L., Hua, X., Jingan, W., Yubao, G. and Jingguo, W. (2008). Biological control of phytopathogenic fungi by fatty acids. Mycopathologia. 166: 93-102. doi: 10.1007/s11046-008-9124-1
  • Hauser, H. and Poupart, G. (1991). Lipid structure. In: Yeagle P, editor. The Structure of Bio-logical Membranes. Boca Raton, FL: CRC Press. 3-71 [Chapter 1].
  • Dowhan W. (1997). Molecular basis for membrane phospholipid diversity: Why are there so many lipids? Ann Rev Biochem. 66:199-232. doi: 10.1146/annurev.biochem.66.1.199
  • Cyber lipid Center. Fatty Acids. online, non-profit scientific organization, www.cyberlipid.org/ fa/acid0001.htm. Accessed on 18/4/2020.
  • Fahy, E., Subramaniam, S., Brown, H.A., Glass, C.K., Merrill, Jr. A.H. and Murphy, R.C. et al. (2005). A comprehensive classification system for lipids. J Lipid Res. 46: 839-62. doi: 10.1194/jlr.E400004-JLR200
  • McCullough, P. and Guy, W. (1957). Melting point purity determinations: Limitations as evidenced by calorimetric studies in the melting region. Analytica Chimica Acta. 17(1): 80-96. doi: 10.1016/S0003-2670(00)87001-4
  • Weldegirma, S. (2018). Experimental Organic Chemistry, 8th ed.; University of South Florida : Tampa.
  • Folch, J., Lees, M. and Stanley, G.H.S. (1957). A simple method for the isolation and purification of total lipids from animal tissues. J. Biol. Chem. 226: 497-509.
  • Farazi, T.A., Waksman, G. and Gordon, J.I. (2001). The biology and enzymology of protein N-myristoylation. J. Biol. Chem. 276: 39501-4. doi: 10.1074/jbc.R100042200
  • Aitken, A., Cohen, P. and Santikarn, S. et al. (1982). Identification of the NH2-terminal blocking group of calcineurin B as myristic acid. FEBS Lett. 150: 314-8. doi: 10.1016/0014-5793(82)80759-X
  • Carr, S.A., Biemann, K., Shoji, S., Parmelee, D.C. and Titani, K. (1982). n-Tetradecanoyl is the NH2-terminal blocking group of the catalytic subunit of cyclic AMP-dependent protein kinase from bovine cardiac muscle. Proc. Natl. Acad. Sci. USA. 79: 6128-31. doi: 10.1073/pnas.79.20.6128
  • Molecular Cell Biology. NCBI (National Center for Biotechnology Information). Section 3.4 Membrane Proteins, www.ncbi.nlm.nih.gov. accessed on 18/4/2020.
  • Ferguson, M.A.J. and Williams, A.F. (1988) Cell-surface anchoring of proteins via glyco-sylphosphatidylinositol structures. Annu. Rev. Biochem. 57: 285-320 doi: 10.1146/annurev.bi.57.070188.001441
  • Ikezawa, H. (2002). Glycosylphosphatidylinositol (GPI)-anchored proteins. Biol. Pharm. Bull. 25: 409. doi: 10.1248/bpb.25.409
  • Rudnick, D.A., McWherter, C.A., Gokel, G.W. and Gordon, J.I. (1993). Myristoyl CoA: protein N-myristoyltransferase. Advances in Enzymology. 67: 375-430.
  • Devadas, B., Freeman, S.K., Zupec, M.E., Lu, H.F., Nagarajan, S.R., Kishore, N.S., Lodge, J.K., Kuneman, D.W., Vinjamoori, D.V., Sikorski, J.A., McWherter, C.A., Getman, D.P. and Gordon, J.I. (1997). Design and synthesis of novel imidazole-substituted dipeptide amides as potent and selective inhibitors of Candida albicans myristoyl CoA: protein N-myristoyltransferase and identification of related tripeptide inhibitors with mechanism-based antifungal activity. J. Med. Chem., 40: 2609-2625. doi: 10.1021/jm970094w
  • Gordon, J.I., Duronio, R.J., Rudnick, D.A., Adams, S.P. and Gokel, G.W. (1991). Synthesis of myristic acid analogs with anti-HIV activity that may be resistant to metabolic processing by β-oxidation. J. Biol. Chem., 266: 8647-8650.
  • Bryant, M.L., McWherter, C.A., Kishore, N.S., Gokel, G.W. and Gordon J.I. (1993). Myristoyl CoA: protein N-myristoyltransferase as a therapeutic target for inhibiting replication of human immunodeficiency virus-1.Perspect. Drug Discovery Design. 1. 193-209. doi: 10.1007/BF02171662
  • Lodge, J.K., Johnson, R.L., Weinberg, R.A. and Gordon, J.I. (1994). Comparison of myristoyl-CoA:protein N-myristoyltransferases from three pathogenic fungi: Cryptococcus neoformans, Histoplasma capsulatum, and Candida albicans. J. Biol. Chem. 269(4): 2996-3009.
  • Paige, L.A., Zheng, G., DeFrees, S.A., Cassady, J.M. and Geahlen, R.L. (1990). Metabolic activation of 2-substituted derivatives of Myristic acidto form potent inhibitors of Myristoyl CoA: Protein N-myristoyltransferase, Biochemistry. 29(46): 10566-10573. doi: 10.1021/bi00498a021
  • Nadler, M.J.S., Harrison, M.L., Ashendel, C.L., Cassady, J.M. and Geahlen, R.L. (1993). Treatment of T Cells with 2-hydroxyMyristic acid inhibits the myristoylation and alters the stability of p56lck. Biochemistry. 32(35): 9250-9255. doi: 10.1021/bi00086a034
  • Kishore, N.S., Lu, T., Knoll, L.J., Katoh, A., Rudnick, D.A., Mehta, P.P., Devadas, B., Huhn, M., Atwood, J.L., Adams, S.P., Gokel, G.W. and Gordon, J.I. (1991). The substrate specificity of saccharomyces cerevisiae Myristoyl-CoA: Protein N-myristoyltransferase. The Journal of Biological Chemistry. 266(14): 8835-8855.
  • Doering, T.L., Lu, T., Werbovetz, K.A, Gokel, G.W., Hart, G.W., Gordon, J.I. and Englund, P.L. (1994). Toxicity of Myristic acid analogs toward African trypanosomes. Proc. Natl. Acad. Sci. USA. 91: 9735-9739. doi: 10.1073/pnas.91.21.9735
  • Devadas, B., Kishore, N.S., Adams, S.P. and Gordon, J.I. (1993). Synthesis of Myristic acidanalogs with anti-HIV activity that may be resistant to metabolic processing by B-oxidation. Bioorganic and Medicinal Chemistry Letters. 3(4): 779-7784. doi: 10.1016/S0960-894X(01)81274-9
  • Zheng, G., Hu, X., Cassady, J.M., Paige, L.A. and Geahlen, R.L. (1994). Synthesis of Myristoyl CoA analogues and Myristoyl peptides as inhibitors of Myristoyl CoA:Protein N-myristoyltransferase, Journal of Pharmaceutical Sciences. 83(2): 233-238. doi: 10.1002/jps.2600830224
  • Parang, K., Knaus, E.E., Wiebe, L.I., Sardari, S., Daneshtalab, M. and Csizmadia, F. (1996). Synthesis and antifungal activities of Myristic acid analogs. Arch. Pharm. Pharm. Med. Chem. 329: 475-482. doi: 10.1002/ardp.19963291102
  • Parang, K., Wiebe, L.I., Knaus, E.E., Huang, J., Tyrrell, D.L. and Csizmadia, F. (1997). In vitro antiviral activities of Myristic acid analogs against human immunodeficiency and hepatitis B viruses. Antiviral Research. 34: 75-90. doi: 10.1016/S0166-3542(96)01022-4
  • Gordon, J.I., Gokel, G.W. and Englund, P.T. (1998). Method of inhibiting parasitic activity. United States Patent. 6,025,511:19-37.
  • Carballeira, N.M., Ortiz, D., Parang, K. and Sardari, S. (2004). Total synthesis and in vitro-antifungal activity of (±)-2-methoxytetradecanoic acid. Arch. Pharm. Pharm. Med. Chem. 337: 152-155. doi: 10.1002/ardp.200300824
  • Narashima, B., Mourya, V. and Dhake, A. (2006). Design, synthesis, antibacterial and QSAR studies of Myristic acid derivatives. Bioorganic and Medicinal Chemistry Letters. 16: 3023-3029. doi: 10.1016/j.bmcl.2006.02.056
  • Carballeira, N.M., Neill, O.R. and Parang, K. (2007). Synthesis and antifungal properties of α-methoxy and α-hydroxy substituted 4-thiatetradecanoic acids. Chemistry and Physics of lipids. 150: 82-88. doi: 10.1016/j.chemphyslip.2007.06.218
  • Deep, A., Phogat, P., Kumar, M., Kakkar, S., Mittal, S.K. and Malhotra, M. (2012). New tetradecanoic acid hydrazones in the search for antifungal agents: Synthesis and in vitro evaluations. Acta Poloniae Pharmaceutica-Drug Research. 69(1): 129-133.
  • Tan, Y., Wang, W., Wu, C., Pan, Z., Yao, G., Fang, L. and Su, W. (2017). Myristic acid-modified thymopentin for enhanced plasma stability and immune-modulating activity. International Immunopharmacology. 47: 88-94. doi: 10.1016/j.intimp.2017.03.025

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