SÍNTESIS, ACTIVIDAD ANTIBACTERIANA E INTERACCIÓN DEL ADN CON COMPLEJOS DE INCLUSIÓN ENTRE COMPUESTOS LANTÁNIDOS Y β-CICLODEXTRINA

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Dorian Polo Cerón

Resumen

En este trabajo se han sintetizado complejos de lantánidos a partir de los derivados cloruros de La(III), Ce(III), Sm (III) e Yb(III) con ligandos cinamato, presentando coordinación bidentada entre el grupo carboxilo del ligando y el metal lantánido. Estos compuestos se utilizaron como huéspedes de la β-ciclodextrina con el fin de obtener complejos de inclusión mediante el método de co-precipitación, utilizando N,N-dimetilformamida como disolvente. Los productos de inclusión obtenidos fueron caracterizados mediante espectroscopia IR-ATR, Raman, UV-vis, RMN 1H, RMN 13C, DRX, TGA-DSC, análisis elemental y complexometría con EDTA. Se realizaron pruebas de actividad antibacteriana empleando 6 cepas ATTC (S. aureus ATCC 25923, S. aureus ATCC 29213, E. coli ATCC 25922, P. aeruginosa ATCC 27853, S. Typhimurium ATCC 14028 y K. pneumoniae ATCC BAA-2146) mediante el método de microdilución con caldo Mueller-Hinton; los resultados de actividad biológica para los complejos lantánidos permitieron evidenciar el efecto sinérgico entre el catión lantánido y el ligando cinamato. Igualmente, para los complejos de inclusión se observó una disminución de la concentración mínima inhibitoria (CMI) respecto a los complejos lantánidos iniciales. Los resultados obtenidos con el ADN de timo de ternera y el ADN plasmídico pBR322 permiten proponer una interacción electrostática entre los complejos evaluados y la estructura molecular del ADN.

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Referencias

[1] G. Wright, “Solving the antibiotics crisis”, ACS Infect. Dis., vol. 1, no. 2, pp. 80-84, Jan. 2015. http://pubs.acs.org/doi/abs/10.1021/id500052s.
[2] R. Hamidpour, M. Hamidpour, S. Hamidpour, M. Shahlari, “Cinnamon from the selection of traditional applications to its novel effects on the inhibition of angiogenesis in cancer cells and prevention of Alzheimer's disease, and a series of functions such as antioxidant, anticholesterol, antidiabetes, antibacterial, antifungal, nematicidal, acaracidal, and repellent activities”, J. Tradit. Complement. Med., vol. 5, no. 2, pp. 66-70, Apr. 2015. https://doi.org/10.1016/j.jtcme.2014.11.008.
[3] Y. Zhang, X. Liu, Y. Wang, P. Jiang, S. Y. Queck, “Antibacterial activity and mechanism of cinnamon essential oil against Escherichia coli and Staphylococcus aureus”, Food Control, vol. 59, pp. 282-289, Jan. 2016. https://doi.org/10.1016/j.foodcont.2015.05.032.
[4] C. Letizia, J. Cocchiara, A. Lapczynski, J. Lalko, A. Api, “Fragrance material review on cinnamic acid”, Food Chem. Toxicol., vol. 43, no. 6, pp. 925-943, Jun. 2005. https://doi.org/10.1016/j.fct.2004.09.015.
[5] B. Narasimhan, D. Belsare, D. Pharande, V. Mourya, A. Dhake, “Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations”, Eur. J. Med. Chem., vol. 39, no. 10, pp. 827-834. Oct. 2004. https://doi.org/10.1016/j.ejmech.2004.06.013.
[6] P. Sharma, “Cinnamic acid derivatives: A new chapter of various pharmacological activities”. J. Chem. Pharm. Res., vol. 3, no. 2, pp. 403-423. Jan. 2011. http://www.jocpr.com/abstract/cinnamic-acid-derivatives-a-new-chapter-of-various-pharmacological-activities-712.html.
[7] S. Venkateswarlu, M. Ramachandra, A. Krishnaraju, G. Trimurtulu, G. Subbaraju, “Antioxidant and antimicrobial activity evaluation of polyhydroxycinnamic acid ester derivatives”, Indian J. Chem., vol. 45B, pp. 252-257, Jan. 2006. http://hdl.handle.net/123456789/6188.
[8] A. Chambel, C. Viegas, I. Sá-Correia, “Effect of cinnamic acid on the growth and on plasma membrane 1H-ATPase activity Saccharomyces cerevisiae”, Inter. J. Food Microbiol., vol. 50, no. 3, pp. 173-179, Sep. 1999. https://doi.org/10.1016/S0168-1605(99)00100-2.
[9] S. Adisakwattana, K. Sookkongwaree, S. Roengsumran, A. Petsom, N. Ngamrojnavanich, W. Chavasiri, D. Deesamer, S. Yibchok, “Structure–activity relationships of trans-cinnamic acid derivatives on a-glucosidase inhibition”, Bioorg. Med. Chem. Lett., vol. 14, no. 11, pp. 2893–2896, Jun. 2004. https://doi.org/10.1016/j.bmcl.2004.03.037.
[10] S. Carvalho, E. Silva, M. Souza, M. Lourenc¸ F. Vicenteb, “Synthesis and antimycobacterial evaluation of new trans-cinnamic acid hydrazide derivatives”, Bioorg. Med. Chem. Lett., vol. 18, no. 2, pp. 538–541, Jan. 2008. https://doi.org/10.1016/j.bmcl.2007.11.091.
[11] F. Bisogno, L. Mascoti, C. Sanchez, F. Garibotto, F. Giannini, M. Kurina-Sanz, R. Enriz, “Structure-antifungal activity relationship of cinnamic acid derivatives”, J. Agr. Food Chem., vol. 55, no. 26, pp. 10635–10640, Nov. 2007. http://pubs.acs.org/doi/abs/10.1021/jf0729098.
[12] A. Aragon-Muriel, D. Polo-Cerón, “Synthesis, characterization, thermal behavior, and antifungal activity of La(III) complexes with cinnamates and 4-methoxyphenylacetate”, J. Rare Earths, vol. 31, no. 11, pp. 1106-1113, Nov. 2013. https://doi.org/10.1016/S1002-0721(12)60412-8.
[13] E. M. Martin Del Valle, “Cyclodextrins and their uses: a review”. Process Biochem., vol. 39, no. 9, pp. 1033–1046, May 2004. https://doi.org/10.1016/S0032-9592(03)00258-9.
[14] E. Santos, J. Kamimura, L. Hill, C. Gomes, “Characterization of carvacrol beta-cyclodextrin inclusion complexes as delivery systems for antibacterial and antioxidant applications”, Food Sci. Technol., vol. 60, no. 1, pp. 583-592, Jan. 2015. https://doi.org/10.1016/j.lwt.2014.08.046.
[15] K. Uekama, F. Hirayama, T. Irie, “Cyclodextrin Drug Carrier Systems”, Chem. Rev., vol. 98, no. 5, pp. 2045-2076, Jul. 1998. http://pubs.acs.org/doi/abs/10.1021/cr970025p.
[16] C. Demicheli, R. Ochoa, J. Da Silva, C. Falcao, B. Rossi-Bergmann, A. De Melo, R. Sinisterra, F. Frézard, “Oral Delivery of Meglumine Antimoniate-β-Cyclodextrin Complex for Treatment of Leishmaniasis”, Antimicrob. Agents Chemother., vol. 48, no. 1, pp. 100-103, Jan. 2004. https://dx.doi.org/10.1128%2FAAC.48.1.100-103.2004.
[17] G. Deacon, M. Forsyth, P. Junk, S. Leary, W. Lee, “Synthesis and characterisation of rare earth complexes supported by para-substituted cinnamate ligands”, Z. Anorg. Allg. Chem., vol. 635, no. 6-7, pp. 833-839, May 2009. http://dx.doi.org/10.1002/zaac.200801379.
[18] Performance Standards for Antimicrobial Disk and Dilution Susceptibility Tests for Bacterial Isolated from Animals, CLSI M31-A3. 3 ed., 2008.
[19] G. Deacon, F. Huber, R. Phillips, “Diagnosis of the nature of carboxylate coordination from the direction of shifts of carbón-oxygen stretching frequencies”, Inorg. Chim. Acta., vol. 104, no. 1, pp. 41-45, Oct. 1985. https://doi.org/10.1016/S0020-1693(00)83783-4.
[20] A. Aragón-Muriel, M. Camprubi, E. Gonzalez, A. Salinas, A. Rodriguez, S. Gomez, D. Polo-Cerón, “Dual investigation of lanthanide complexes with cinnamate and phenylacetate ligands: study of the cytotoxic properties and the catalytic oxidation of styrene”, Polyhedron, vol. 80, pp. 117–128, Sep. 2014. https://doi.org/10.1016/j.poly.2014.02.040.
[21] N. Roik, L. Belyakova, “Infrared spectroscopy, x-ray diffraction and thermal analysis studies of solid b-cyclodextrin - para-aminobenzoic acid inclusion complex”, PCSS, vol. 12, no. 1, pp. 168-173, 2011. http://www.pu.if.ua/inst/phys_che/start/pcss/vol12/1201-26.pdf
[22] A. Kokkinou, S. Makedonopoulou, D. Mentzafos, “The cristal structure of the 1:1 complex of β-cyclodextrin with trans-cinnamic acid”, Carbohydr. Res., vol. 328, no. 2, pp. 135-140, Sep. 2000. https://doi.org/10.1016/S0008-6215(00)00091-4.
[23] H. Schneider, F. Hacket, V. Rüdiger, I. Ikeda, “NMR studies of cyclodextrins and cyclodextrin complexes”, Chem. Rev., vol. 98, no. 5, pp. 1755-1786, Jul. 1998. http://pubs.acs.org/doi/abs/10.1021/cr970019t.
[24] F. Giordano, C. Novak, J. Moyano, “Thermal analysis of cyclodextrins and their inclusion compounds”, Thermochim. Acta, vol. 380, no. 2, pp. 123-151, Dec. 2001. https://doi.org/10.1016/S0040-6031(01)00665-7.
[25] K. Chandrul, “Role of Macromolecules in Chromatography: Cyclodextrines”, J. Chem. Pharm. Res., vol. 3, no. 6, pp. 822-828, 2011. http://www.jocpr.com/articles/role-of-macromolecules-in-chromatography-cyclodextrines.pdf
[26] T. Pijpers, V. Mathot, B. Goderis, R. Scherrenberg, E. Van der Vegte, “High-Speed Calorimetry for the Study of the Kinetics of (De)vitrification, Crystallization, and Melting of Macromolecules”, Macromolecules, vol. 35, no. 9, pp. 3601-3613, Mar. 2002. http://pubs.acs.org/doi/abs/10.1021/ma011122u?journalCode=mamobx.
[27] R. Abu-Eittah, M. Khedr, M. Goma, W. Zordok, “The structure of cinnamic acid and cinnamoyl azides, a unique localized p system: the electronic spectra and DFT-treatment”, Int. J. Quantum. Chem., vol. 112, no. 5, pp. 1256-1272, Mar. 2012. http://dx.doi.org/10.1002/qua.23120.
[28] A. Essawy, M. Afifi, H. Moustafa, S. El-Medani, “DFT calculations, spectroscopic, thermal analysis and biological activity of Sm(III) and Tb(III) complexes with 2-aminobenzoic and 2-amino-5-chloro-benzoic acids”, Spectrochim. Acta A., vol. 131, pp. 388-397, Oct. 2014. https://doi.org/10.1016/j.saa.2014.04.134.
[29] T. Abbs, A. Pearl, B. Rosy, “Synthesis, characterization, cytotoxicity, DNA cleavage and antimicrobial activity of homodinuclear lanthanide complexes of phenylthioacetic acid”, J. Rare Earths, vol. 31, no. 10, pp. 1009-1016. Oct. 2013. https://doi.org/10.1016/S1002-0721(13)60022-8.
[30] J. Calvo, L. Martínez-Martínez, “Mecanismo de acción de los antimicrobianos”, Enferm. Infecc. Microbiol. Clin., vol. 27, no. 1, pp. 44–52, Jan. 2009. http://dx.doi.org/10.1016/j.eimc.2008.11.001.
[31] A. Deredjian, C. Colinon, S. Brothier, S. Favre-Bonte, B. Cournoyer, S. Nazaret, “Antibiotic and metal resistance among hospital and outdoor strains of Pseudomonas aeruginosa”, Res. Microbiol., vol. 162, no. 7, pp. 689-700, Sep. 2011. https://doi.org/10.1016/j.resmic.2011.06.007.
[32] K. Suntharalingam, O. Mendoza, A. Duarte, D. Mann, R. Vilar, “A platinum complex that binds non-covalently to DNA and induces cell death via a different mechanism than cisplatin”, Metallomics., vol. 5, pp. 514-523, Feb. 2013. https://doi.org/10.1039/C3MT20252F.
[33] Y. Sun, F. Dong, D. Wang, Y. Lib, “Crystal Structure, Supramolecular Self-Assembly and Interaction with DNA of a Mixed Ligand Manganese(II) Complex”, J. Braz. Chem. Soc., vol. 22, no. 6, pp. 1089-1095, Jun. 2011. http://dx.doi.org/10.1590/S0103-50532011000600013.
[34] N. Sohrabi, “Binding and uv/vis spectral investigation of interaction of ni(ii) piroxicam complex with calf thymus deoxyribonucleic acid (Ct-DNA): a thermodynamic approach”, J. Pharm. Sci. & Res., vol. 7, no. 8, pp. 533-537, Aug. 2015. http://www.jpsr.pharmainfo.in/Documents/Volumes/vol7Issue08/jpsr07081507.pdf
[35] A. Jamali, A. Tavakoli, J. Nazhad, “Analytical overview of DNA interaction with Morin and its metal complexes”, Eur. Food Res. Technol., vol. 235, no. 3, pp. 367–373, Sep. 2012. https://doi.org/10.1007/s00217-012-1778-8.
[36] A. Sigel, H. Sigel, R. Sigel, Interplay between metal ions and nucleic acids. New York: Springer, 2012.
[37] A. Kresel, J. Lisowski, “Enantioselective cleavage of supercoiled plasmid DNA catalyzed by chiral macrocyclic lanthanide(III) complexes”, J. Inorg. Biochem., vol. 107, no. 1, pp. 1–5, Feb. 2012. https://doi.org/10.1016/j.jinorgbio.2011.10.011.
[38] M. Komiyama, N. Takeda, H. Shigekawa, “Hydrolysis of DNA and RNA by lanthanide ions: mechanistic studies leading to new applications”, Chem. Commun., vol. 16, pp. 1443–1451, 1999. https://doi.org/10.1039/A901621J.
[39] S. Tabassum, G. Sharma, F. Arjmand, “New modulated design and synthesis of chiral CuII/SnIV bimetallic potential anticancer drug entity: In vitro DNA binding and pBR322 DNA cleavage activity”, Spectrochim. Acta Part A., vol. 90, pp. 208-217, May 2012. https://doi.org/10.1016/j.saa.2012.01.020.

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