Keywords: Aromatic Compounds, Complex Networks, Drug Delivery, Dynamic Light Scattering, Ionic Strength, Drug Delivery System, Fluorescence Studies, Good Stability, Heterocyclic Molecules, Hydrophobic Cavities, Spectroscopic Characteristics, Supramolecular Assemblies, Supramolecular Networks, Acetone,
Affiliations: *** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 16, 80134 Napoli, Italy
Department of Science and Technology, University of Naples Parthenope, Centro Direzionale, 80143 Napoli, Italy
Department of Chemical Science, University of Naples Federico II, Via Cinthia, 80126 Napoli, Italy
Department of Pharmacy, University of Naples Federico II, Via Mezzocannone 16, 80134 Napoli, Italy
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Chamberlain, G.R., Tulumello, D.V., Kelley, S.O., Targeted delivery of doxorubicin to mitochondria (2013) ACS Chem. Biol., 8, pp. 1389-1395
Gillies, R.G., Didier, N., Denton, M., Determination of cell number in monolayer cultures (1986) Anal. Biochem., 159, pp. 109-113
Wang, J. -H., Altukhov, O., Cheng, C. -C., Chang, F. -C., Kuo, S. -W., Supramolecular structures of uracil-functionalized PEG with multi-diamidopyridine POSS through complementary hydrogen bonding interactions (2013) Soft Matter, 9, pp. 5196-5206
Solomonov, A. V., Rumyantsev, E. V., Ivanov, S. P., Kochergin, B. A., Antina, E. V., Spectroscopic studies of the supramolecular interactions between uracil and 5-hydroxy-6-methyluracil with bovine serum albumin and its bilirubin complex (2013) Protein J., 32, pp. 343-355
Schwarting, A. E., Bobbitt, J. M., Rother, A., Atal, C. K., Khanna, K. L., Laery, J. D., Walter, W. G., The alkaloids of W. Somnifera (1963) Lloydia, 26, pp. 258-273
Dakin, H. D., West, R. A., A general reaction of amino acids (1928) J. Biol. Chem., 78, pp. 91-105
Curran, T. T., Implementation of the Dakin-West reaction for the preparation of an -amino-pentafluoroethyl ketone (1995) J. Fluorine Chem., 74, pp. 107-112
Roviello, G. N., Roviello, G., Musumeci, D., Bucci, E. M., Pedone, C., Dakin-West reaction on 1-thyminyl acetic acid for the synthesis of 1, 3-bis (1-thyminyl) -2-propanone, a heteroaromatic compound with nucleopeptide-binding properties (2012) Amino Acids, 43, pp. 1615-1623
Liang, Z. D., Long, Y., Tsai, W. B., Fu, S., Kurzrock, R., Gagea-Iurascu, M., Zhang, F., Kuo, M. T., Mechanistic basis for overcoming platinum resistance using copper chelating agents (2012) Mol. Cancer Ther., 11, pp. 2483-2494
Wei, H., Zhang, W. J., McMillen, T. S., Leboeuf, R. C., Frei, B., Copper chelation by tetrathiomolybdate inhibits vascular inflammation and atherosclerotic lesion development in apolipoprotein E-deficient mice (2012) Atherosclerosis, 223, pp. 306-313
Yoo, J. Y., Pradarelli, J., Haseley, A., Wojton, J., Kaka, A., Bratasz, A., Alvarez-Breckenridge, C. A., Kaur, B., Copper chelation enhances antitumor efficacy and systemic delivery of oncolytic HSV (2012) Clin. Cancer Res., 18, pp. 4931-4941
Cooper, G. J., Selective divalent copper chelation for the treatment of diabetes mellitus (2012) Curr. Med. Chem., 19, pp. 2828-2860
Cooper, G. J., Therapeutic potential of copper chelation with triethylenetetramine in managing diabetes and Alzheimer's disease (2011) Drugs, 71, pp. 1281-1320
Lowndes, S. A., Sheldon, H. V., Cai, S., Taylor, J. M., Harris, A. L., Copper chelator ATN-224 inhibits endothelial function by multiple mechanisms (2009) Microvasc. Res., 77, pp. 314-326
Roviello, G. N., Musumeci, D., Bucci, E. M., Pedone, C., Evidences for supramolecular organization of nucleopeptides: Synthesis, spectroscopic and biological studies of a novel dithymine l-serine tetrapeptide (2011) Mol. BioSyst., 7, pp. 1073-1080
Roviello, G. N., Mottola, A., Musumeci, D., Bucci, E. M., Pedone, C., Synthesis and aggregation properties of a novel enzymatically resistant nucleoamino acid (2012) Amino Acids, 43, pp. 1465-1470
Chamberlain, G. R., Tulumello, D. V., Kelley, S. O., Targeted delivery of doxorubicin to mitochondria (2013) ACS Chem. Biol., 8, pp. 1389-1395
Gillies, R. G., Didier, N., Denton, M., Determination of cell number in monolayer cultures (1986) Anal. Biochem., 159, pp. 109-113
Synthesis and supramolecular assembly of 1, 3-bis(1 '-uracilyl)-2-propanone
In this research work, we investigated the properties of a novel heterocyclic molecule, named by us U2CO, whose structure consists of two uracil rings connected by a 2-propanone moiety. We studied by UV the spectroscopic characteristics of U2CO as a function of temperature and ionic strength of the solution. Furthermore, dynamic light scattering (DLS) studies conducted on samples containing the uracil-containing derivative indicated the formation of non-covalent supramolecular networks based on multiple U2CO units. These aggregates contained hydrophobic cavities able to encapsulate drugs such as doxorubicin, as evidenced by fluorescence studies. This property, together with the good stability in human serum of U2CO, determined by HPLC analysis, could be an interesting feature in developing new drug delivery systems. Interestingly, UV studies suggested that U2CO is able to form complexes with copper(II) cations, which is a useful characteristic in view of potential anti-oxidant approaches.
Synthesis and supramolecular assembly of 1, 3-bis(1 '-uracilyl)-2-propanone