Abstract
Bis, tris and tetra(dihydrocaffeoyl)polyamine conjugates were synthesized using solid phase synthesis technique. These compounds were screened for antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) (11 strains) and vancomycin-resistant S. aureus (VRSA) (4 strains). Bis, tris and tetra(dihydrocaffeoyl)polyamine analogues showed antibacterial activity against VRSA which were better than the reference drugs, vancomycin. Tetra(dihydrocaffeoyl) polyamine conjugate exhibited the highest activity. These compounds showed no cytotoxicity against vero cells.
Similar content being viewed by others
References
Bauer, A. W., Kirby, M. D. K., Sherris, J. C., and Turck, M., Antibiotic susceptibility testing by a standardized single disk method. Am. J. Clin. Pathol., 45, 493–496 (1966).
Berger, M. L., Bitar, A.Y., Waitner, M. J., Rebernika, P., and O’sullivan, M. C., Polyamines and the NMDA receptor: Modifying intrinsic activities with aromatic substituents. Bioorg. Med. Chem. Lett., 16, 2837–2841 (2006).
Bycroft, B. W., Chan, W. C., Chhabra, S. R., and Hone, N. D., A novel lysine-protecting procedure for continuous flow solid phase synthesis of branched peptides. J. Chem. Soc., Chem Commun., 778–779 (1993).
Chitkul, B. and Bradley. M., Optimising inhibitors of trypanothione reductase using solid-phase chemistry. Bioorg. Med. Chem. Lett., 10, 2367–2369 (2000).
Fujiwara, T., Hasegawa, S., Hirashima, N., and Nakanishi, M., Gene transfection activities of amphiphilic steroid-polyamine conjugates. Biochim. Biophys. Acta, 1468, 396–402 (2000).
Funayama, S., Yoshida, K., Konno, C., and Hikino, H., Structure of kukoamine A, a hypotensive principle of Lycium chinense root barks. Tetrahedron Lett., 21, 1355–1356 (1980).
Garcia, G., Sol, V., Lamarche, F., Granet, R., Guilloton, M., Champavier, Y., and Krausz, P., Synthesis and photocytotoxic activity of new chlorin-polyamine conjugates. Bioorg. Med. Chem. Lett., 16, 3188–3192 (2006).
Karagiannis, G. and Papaioannou, D., Structure, biological activity and synthesis of polyamine analogues and conjugates. Eur. J. Org. Chem., 1841–1863 (2000).
Kuksa, V., Buchan, R., and Lin, P. K. T., Synthesis of polyamines, their derivatives, analogues and conjugates. Synthesis, 9, 1189–1207 (2000).
Mahasneh, A. M. A., Adel, M. A., and El-Oqlah, A. A. B., Antimicrobial activity of extracts of herbal plants used in the traditional medicine of Jordan. J. Ethnopharmacol., 64, 271–276 (1999).
Nash, I. A., Bycroft, B. W., and Chan, W.C., Dde-a selective primary amine protecting group: A facile solid phase synthetic approach to polyamine conjugates. Tetrahedron Lett., 37, 2625–2628 (1996).
Orain, D., Ellard, J., and Bradley, M., Protecting groups in solid-phase organic synthesis. J. Comb. Chem., 4, 1–16 (2002).
Page, P., Burrage, S., Baldock, L., and Bradley, M., The synthesis of symmetrical spermine conjugates using solid-phase chemistry. Bioorg. Med. Chem. Lett., 8, 1751–1756 (1998).
Ponasik, J. A., Strikland, C., Faerman, C., Savvides, S., Karplus, P. A., and Ganem, B., Kukoamine A and other hydrophobic acylpolyamines: potent and selective inhibitors of Crithidia fasciculata trypanothione reductase. Biochem. J., 311, 371–375 (1995).
Sarin, V. K., Kent, S. B., and Tam, J. P., Merrifield, R. B., Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction. Anal. Biochem., 117, 147–157 (1981).
Seiler, N., Douauda, F., Renault, J., Delcros, J.-G., Havouisa, R., Uriac, P., and Moulinoux, J.-P., Polyamine sulfonamides with NMDA antagonist properties are potent calmodulin antagonists and cytotoxic agents. Int. J. Biochem. Cell Biol., 30, 393–406 (1998).
Shu, Y., Jonesa, S. R., Kinney, W. A., and Selinsky, B. S., The synthesis of spermine analogs of the shark aminosterol squalamine. Steroids, 67, 291–304 (2002).
Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenny, S., and Boyd, M. R., New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening. J. Natl. Cancer Inst., 82, 1107–1112 (1990).
Sol, V., Lamarche, F., Enache, M., Garcia, G., Granet, R., Guilloton, M., Blaisb, J. C., and Krausz, P., Polyamine conjugates of meso-tritolylporphyrin and protoporphyrin IX: Potential agents for photodynamic therapy of cancers. Bioorg. Med. Chem., 14, 1364–1377 (2006).
Suzuki, I., Shigenaga, A., Nemoto, H., and Shibuya, M., Synthesis and DNA damaging ability of enediyne-polyamine conjugates. Tetrahedron Lett., 45, 1955–1959 (2004).
Yingyongnarongkul, B., Apiratikul, N., Aroonrerk, N., and Suksamrarn, A., Solid-phase synthesis and antibacterial activity of hydroxycinnamic acid amides and analogues against methicillin-resistant Staphylococcus aureus and vancomycin-resistant S. aureus. Bioorg. Med. Chem. Lett., 16, 5870–5873 (2006).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yingyongnarongkul, Be., Apiratikul, N., Aroonrerk, N. et al. Synthesis of bis, tris and tetra(dihydrocaffeoyl)polyamine conjugates as antibacterial agents against VRSA. Arch. Pharm. Res. 31, 698–704 (2008). https://doi.org/10.1007/s12272-001-1215-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-001-1215-4