Trials of phenanthrene opioids functionalization with hindered polycyclic carboxylic acids
Subject Areas : Phytochemistry: Isolation, Purification, CharacterizationAlessandro Venditti 1 , Ambra Pallotti 2 , Armandodoriano Bianco 3
1 - Dipartimento di Chimica, Università di Roma “La Sapienza”, Rome, Italy
2 - Dipartimento di Chimica, Università di Roma “La Sapienza”, Rome, Italy
3 - Dipartimento di Chimica, Università di Roma “La Sapienza”, Rome, Italy
Keywords:
Abstract :
Angelova, P., Kostova, K., Hinrichs, K., Tsankov, D., 2005. A convenient synthesis of long-chain 4-substituted benzyloxycarbonyl alkanethiols for the formation of self-assembled monolayers on metal substrates. Cent. Eur. J .Chem. 3(4), 658-667.
Antonilli, L., Togna, A.R., Sabatini, G., Venditti, A., Guarcini, L., Togna, G.I., Nicoletti, R., Sanasai, F., Bianco, A., Nencini, P., 2013a. Pivaloylcodeine, a new codeine derivative, for the inhibition of morphine glucoronation. An in vitro study in the rat. Bioorg. Med. Chem. 21(24), 7955-7963.
Antonilli, L., Bianco, A., Guarcini, L., Nencini, P., Nicoletti, R., Togna, A.R., Togna, G.I., Venditti, A., 2013b. Derivati della codeina come inibitori della glucoronazione della morfina. Brevetto Italiano (Italian Patent) N° IT2013RM00223 20130415.
Elovaara, E., Mikkola, J., Stockmann-Juvala, H., Luukkanen, L., Keski-Hynnilä, H., Kostiainen, R., Pasanen, M., Pelkonen, O., Vainio, H., 2007. Polycyclic aromatic hydrocarbon (PAH) metabolizing enzyme activities in human lung, and their inducibility by exposure to naphthalene, phenanthrene, pyrene, chrysene, and benzo(a)pyrene as shown in the rat lung and liver. Arch. Toxicol. 81(3), 169-182.
Franceschin, M., Nocioni, D., Biroccio, A., Micheli, E., Cacchione, S., Cingolani, C., Venditti, A., Zizza, P., Bianco, A., Altieri, A., 2014. Design and synthesis of a new dimeric xanthone derivative: enhancement of G-quadruplex selectivity and telomere damage. Org. Biomol. Chem. 12(47), 9572-9582.
Gibson, F.S., Park, M.S., Rapoport, H., 1994. Bis[[4-(2,2-dimethyl-1,3-dioxolyl)]methyl]-carbodiimmide (BDDC) and its application to residue-free esterifications, peptide couplings, and dehydrations. J. Org. Chem. 59(24), 7503-7507.
Graziottin, A., Gardner-Nix, J., Stumpf, M., Berliner, M.N., 2011. Opioids: how to improve compliance and adherence. Pain Pract. 11(6), 574-581.
Hassner, A., Vazken, A., 1978. Direct room temperature esterification of carboxylic acids. Tetrahedron Lett. 19(46), 4475-4478.
Höfle, G., Steglich, W., Vorbrüggen, H., 1978. 4-Dialkylaminopyridines as highly active acylation catalysts. Ang. Chem. Int. (English Ed) 17(8), 569-583.
Komatsu, T., Sakurada, S., Katsuyama, S., Sanai, K., Sakurada, T., 2009. Mechanism of allodynia evoked by intrathecal morphine-3-glucuronide in mice. Int. Rev. Neurobiol. 85, 207-219.
Leonelli, F., La Bella, A., Francescangeli, A., Joudioux, R., Capodilupo, A.L., Quagliariello, M., Migneco, L.M., Marini Bettolo, R., Crescenzi, V., 2005. A new and simple available class of hydrosolubles bioconjugates by coupling paclitaxel to hyaluronic acid trough a 4-hydroxybutanoic acid derived linker. Helv. Chim. Acta 88(1), 154-159.
Lewis, S.S., Hutchinson, M.R., Rezvani, N., Loram, L.C., Zhang, Y., Maier, S.F., Rice, K.C., Watkins, L.R., 2010. Evidence that intrathecal morphine-3-glucuronide may cause pain enhancement via toll-like receptor 4/MD-2 and interleukin-1beta. Neuroscience 165(2), 569-583.
Milne, R.W., Nation, R.L., Somogyi, A.A., 1996. The disposition of morphine and its 3- and 6-glucuronide metabolites in humans and animals, and the importance of the metabolites to the pharmacological effects of morphine. Drug Metab. Rev. 28(3), 345-372.
Ornano, L., Feroci, M., Guarcini, L., Venditti, A., Bianco, A., 2018. Anti-HIV agents from nature: natural compounds from Hypericum hircinum and carbocyclic nucleosides from iridoids. Stud. Nat. Prod. Chem. 56, 173-228.
Salemme, A., Togna, A. R., Mastrofrancesco, A., Cammisotto, V., Ottaviani, M., Bianco, A., Venditti, A., 2016. Anti-inflammatory effects and antioxidant activity of dihydroasparagusic acid in lipopolysaccharide-activated microglial cells. Brain Res. Bull. 120, 151-158.
Smith, H.S., 2009. Opioid Metabolism. Mayo Clin. Proc. 84(7), 613-624.
Venditti, A., Mandrone, M., Serrilli, A. M., Bianco, A., Iannello, C., Poli, F., Antognoni, F., 2013. Dihydroasparagusic acid: antioxidant and tyrosinase inhibitory activities and improved synthesis. J Agric. Food Chem. 61(28), 6848-6855.
Venditti, A., Lorenzetti, L.M., Frezza, C., Serafini, M., Ornano, L., Bianco, A., 2017. Semi-synthesis of three precursors of carbocyclic nucleoside analogues. Trends Org. Chem. 18, 101-105.
Watkins, L.R., Hutchinson, M.R., Johnston, I.N., Maier, S.F., 2005. Glia: novel counter-regulators of opioid analgesia. Trends Neurosci. 28(12), 661-669.