Intercalation of Phenylalanine, Isocoumarin and Ochratoxin A (OTA) into LDH’s


Phenylalanine, isocoumarin and Ochratoxin A (OTA) have been intercalated within the interlayer space of layered double hydroxides. Synthesis of these nanocompounds was achieved via co-precipitation. Their physicochemical properties were studied by element chemical analysis, powder X-ray diffraction, infrared spectroscopy and thermal analyses. The presence of OTA in the interlayer is demonstrated by the study of LC-FD Analysis. On the other hand, these studies allow to check how some of the toxin is on the surface of the nanocomposite.

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Román, M. and Holgado, M. (2015) Intercalation of Phenylalanine, Isocoumarin and Ochratoxin A (OTA) into LDH’s. Open Journal of Inorganic Chemistry, 5, 52-62. doi: 10.4236/ojic.2015.53007.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] Anli, E. and Bayram, M. (2009) Ochratoxin A in Wines. Food Reviews, 25, 214-232.
[2] Alldrick, A.J. (1996) The Effects of Processing on the Occurrence of Ochratoxin A in Cereals Supplement of Volume. Food Additives and Contaminants, 13, 27-28.
[3] International Agency for Research on Cancer, IARC (1993) Monograph on the Evaluation of Carcinogenic Risks to Humans. IARC, Lyon, 489.
[4] International Agency for Research on Cancer, IARC (1983) Ochratoxin A. In Some Food Additives. In: Feed Additives and Naturally Occurring Substances, Lyon, 191-206.
[5] ChemSources (2010) Chem Sources—Chemical Search. Chemical Sources International.
[6] Monaci, L., Tantillo, G. and Palmisano, F. (2004) Determination of Ochratoxin A in Portuguese Rice Samples by High Performance Liquid Chromatography with Fluorescence Detection. Analytical and Bioanalytical Chemistry, 378, 1777-1780.
[7] Yu, J.C.C. and Lai, E.P.C. (2010) Molecularly Imprinted Polymers for Ochratoxin A Extraction and Analysis. Toxins, 2, 1536-1553.
[8] Ringot, D., Chango, A., Schneider, Y.J. and Larondelle, Y. (2006) Toxicokinetics and Toxicodynamics of Ochratoxin A, an Update. Chemico-Biological Interaction, 159, 18-46.
[9] Cole, R.J., Jarvis, B.B. and Schweikert, M.A. (2003) Ochratoxins and Related Metabolites. In: Handbook of Secondary Fungal Metabolites, Academic Press, San Diego, 615-624.
[10] Rives, V. (Ed.) (2001) Layered Double Hydroxides: Present and Future. Nova Sci. Pub, New York.
[11] Cavani, F., Trifiro, F. and Vaccari, A. (1991) Hydrotalcite-Type Anionic Clays: Preparation, Properties and Applications. Catalysis Today, 11, 173-301.
[12] Wang, B., Zhang, H., Evans, D.G. and Duan, X. (2005) Surface Modification of Layered Double Hydroxides and Incorporation of Hydrophobic Organic Compounds. Materials Chemistry and Physics, 92, 190-196.
[13] Jaubertie, C., Holgado, M.J., San Román, M.S. and Rives, V. (2006) Structural Characterization and Delamination of Lactate-Intercalated Zn, Al-Layered Double Hydroxides. Chemistry of Materials, 18, 3114-3121.
[14] San Román, M.S., Holgado, M.J., Jaubertie, C. and Rives, V. (2008) Synthesis, Characterisation and Delamination Behaviour of Lactate-Intercalated Mg, Al-Hydrotalcite-Like Compounds. Solid State Sciences, 10, 1333-1341.
[15] San Román, M.S., Holgado, M.J., Salinas, B. and Rives, V. (2012) Characterisation of Diclofenac, Ketoprofen or Chloramphenicol Succinate Encapsulated in Layered Double Hydroxides with the Hydrotalcite-Type Structure. Applied Clay Science, 55, 158-163.
[16] San Román, M.S., Holgado, M.J., Salinas, B. and Rives, V. (2013) Drug Release from Layered Double Hydroxides and from Their Polylactic Acid (PLA) Nanocomposites. Applied Clay Science, 71, 1-7.
[17] Costantino, V.R.L. and Pinnavaia, T.J. (1995) Basic Properties of Mg2+1-xAl3+x Layered Double Hydroxides Intercalated by Carbonate, Hydroxide, Chloride, and Sulfate Anions. Inorganic Chemistry, 34, 883-892.
[18] Holgado, M.J., Malet, P., Rives, V. and San Román, M.S. (1996) Hexacyanoferrate-Interlayered Hydrotalcite. Solid State Ionics, 92, 273-283.
[19] Choy, J.H., Choi, S.J., Oh, J.M. and Park, T. (2007) Clay Minerals and Layered Double Hydroxides for Novel Biological Applications. Applied Clay Science, 36, 122-132.
[20] Goh, K.H., Lim, T.T. and Dong, Z. (2008) Application of Layered Double Hydroxides for Removal of Oxyanions: A Review. Water Research, 42, 1343-1368.
[21] Martínez-Gallegos, S., Herrero, M. and Rives, V. (2008) Preparation of Composites by in Situ Polymerisation of PET-Hydrotalcite Using Dodecylsulphate. Materials Science Forum, 587, 568-571.
[22] Rives, V., Carriazo, D. and Martín, C. (2010) Heterogeneous Catalysis by Polyoxometalate-Intercalated Layered Double Hydroxides. In: Gil, A., Korili, S.A., Vicente, M.A. and Trujillano, R., Eds., Pillared Clays and Related Catalysts, Springer, New York, 319-397.
[23] Miyata, S. (1975) The Syntheses of Hydrotalcite-Like Compounds and Their Structure and Physico-Chemical Properties—I: The Systems Mg2+-Al3+-NO3-, Mg2+-Al3+-Cl-, Mg2+-Al3+-ClO4-, Ni2+-Al3+-Cl- and Zn2+-Al3+-Cl-. Clays and Clay Minerals, 23, 369-375.
[24] The Chemical Database (2010) The Chemical Database. The Department of Chemistry at the University of Akron. Search on CAS Number.
[25] HSDB (2010) Hazardous Substances Data Bank. National Library of Medicine. and search on CAS number
[26] JCPDS (1977) Joint Committee on Powder Diffraction Standards, International Centre for Diffraction Data, Pennsylvania, USA.
[27] Arco, M., Gutiérrez, S., Martín, C., Rives, V. and Rocha, J. (2000) Effect of the Mg:Al Ratio on Borate (or Silicate)/ Nitrate Exchange in Hydrotalcite. Journal of Solid State Chemistry, 151, 272-280.
[28] Kameda, T., Takeuchi, H. and Yoshioka, T. (2009) Hybrid Inorganic/Organic Composites of Mg-Al Layered Double Hydroxides Intercalated with Citrate, Malate, and Tartrate Prepared by Co-Precipitation. Materials Research Bulletin, 44, 840-845.
[29] Perioli, L., Ambrogi, V., Di Nauta, L., Nocchetti, M. and Rossi, C. (2011) Effects of Hydrotalcite-Like Nanostructured Compounds on Biopharmaceutical Properties and Release of BCS Class II Drugs: The Case of Flurbiprofen. Applied Clay Science, 51, 407-413.
[30] Miyoshi, T., Yoshii, K., Murayama, N. and Shibata, J. (2013) Modification of Layered Double Hydroxide with Anionic Surfactants and Its Application. Asia Science and Technology Portal, 39, 445-451.
[31] Seftel, E.M., Cool, P. and Lutic, D. (2013) Mg-Al and Zn-Fe Layered Double Hydroxides Used for Organic Species Storage and Controlled Release. Materials Science and Engineering C, 33, 5071-5078.
[32] Jiao, F.P., Fu, Z.D., Shuai, L., and Chen, X.Q. (2012) Removal of Phenylalanine from Water with Calcined CuZnAlCO3 Layered Double Hydroxides. Transactions of Nonferrous Metals Society of China, 22, 476-482.
[33] Chibwe, K. and Jones, W. (1989) Intercalation of Organic of Inorganic Anions into Layered Doluble Hydroxides. Journal of the Chemical Society, Chemical Communications, 926-927.
[34] Pinnavaia, T.J., Rameswaran, M., Dimotakis, E.D., Giannelis, E.P. and Rightor, E.G. (1989) Carbon Monoxide Hydrogenation Selectivity of Catalysts Derived from Ruthenium Clusters on Acidic Pillared Clay and Basic Layered Double-Hydroxide Supports. Faraday Discussions of the Chemical Society, 87, 227-237.
[35] Aisawa, S., Takahashi, S., Ogasawara, W., Umetsu, Y. and Narita, E. (2001) Direct Intercalation of Amino Acids into Layered Double Hydroxides by Coprecipitation. Journal of Solid State Chemistry, 162, 52-62.
[36] Fudala, A., Palinko, I. and Kiricsi, I. (1999) Amino Acids, Precursors for Cationic and Anionic Intercalation Synthesis and Characterization of Amino Acid Pillared Materials. Journal of Molecular Structure, 482, 33-37.
[37] Aisawa, S., Sasaki, S., Takahashi, S., Hirahara, H., Nakayama, H. and Narita, E. (2006) Intercalation of Amino Acids and Oligopeptides into Zn-Al Layered Double Hydroxide by Coprecipitation Reaction. Journal of Physics and Chemistry of Solids, 67, 920-925.
[38] Aisawa, S., Kudo, H., Hoshi, T., Takahashi, S., Hirahara, H., Umetsu,Y. and Narita, E. (2004) Intercalation Behavior of Amino Acids into Zn-Al-Layered Double Hydroxide by Calcination-Rehydration Reaction. Solid State Chemistry, 177, 3987-3994.
[39] Lee, T.P., Saada, B., Nga, E.P. and Sallehb, B. (2012) Zeolite Linde Type L as Micro-Solid Phase Extraction Sorbent for the High Performance Liquid Chromatography Determination of Ochratoxin A in Coffee and Cereal. Journal of Chromatography A, 1237, 46-54.
[40] Kloprogge, J.T. and Frost, R.L. (2001) Infrared and Raman Spectroscopic Studies of Layered Double Hydroxides (LDHs). In: Rives, V., Ed., Layered Double Hydroxides: Present and Future, Chapter 5, Nova Science Publishers, Inc., New York, 139-192.
[41] Kloprogge, J.T. (2005) Infrared and Raman Spectroscopy of Naturally Occurring Hydrotalcites and Their Synthetic Equivalent. In: Kloprogge, J.T., Ed., The Application of Vibrational Spectroscopy to Clay Minerals and Layered Double Hydroxides, CMS Workshop Lectures, The Clay Mineral Society, Aurora, Vol. 13, 203-238.
[42] Bellamy, L.J. (1980) The Infrared Spectra of Complex Molecules. Chapman and Hall, London.
[43] Almala, L., Rabe, V., Sánchez, B., Torrella, F., López-Pérez, J.P., Gabaldón, J.A. and Guardiola, L. (2007) Ochratoxin A in Red Paprika: Relation-Ship with the Origin of the Raw Material. Food Microbiology, 24, 319-327.
[44] Hernández, J.M., García-Vilanova, R.J., Rodríguez, P. and Toruño, I.M. (2008) Aflatoxins and Ochratoxin A in Red Paprika for Retail Sale in Spain: Occurrence and Evaluation of a Simultaneous Analytical Method. Journal of Agricultural and Food Chemistry, 56, 751-756.
[45] Juan, C., Pena, A., Lino, C., Moltó, J.C. and Mañes, J. (2008) Levels of Ochratoxin A in Wheat and Maize Bread from the Central Zone of Portugal. International Journal of Food Microbiology, 127, 284-289.
[46] Bento, J.M.V., Pena, A., Lino, C.M. and Pereira, J.A. (2009) Determination of Ochratoxin A Content in Wheat Bread Samples Collected from the Algarve and Bragança Regions, Portugal: Winter 2007. Microchemical Journal, 91, 165-169.
[47] Duarte, S., Bento, J., Pena, A., Lino, C.M., Delerue-Matos, C., Oliva-Teles, T., Morais, S., Correia, M., Oliveira, M.B.P.P., Alves, M.R. and Pereira, J.A. (2010) Monitoring of Ochratoxin A Exposure of the Portuguese Population through a Nationwide Urine Survey-Winter 2007. Science of the Total Environment, 408, 1195-1198.
[48] Pena, A., Cerejo, F., Silva, L.J.G. and Lino, C.M. (2010) Ochratoxin A Survey in Portuguese Wine by LC-FD with Direct Injection. Talanta, 82, 1556-1561.

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