Interaction of zinc cation with some acetyl-substituted-D-penicillamines
Abstract
In the present treatment, interaction of zinc cation with N-, O- or S-acetyl substituted amino-D-penicillamines are considered within the restrictions of density functional theory and the basis set employed (at the level of B3LYP/6-31++G(d,p)). N-acetyl-D-penicillamine has some medical use as a chelating agent for many metal poisoning cases such as mercury, copper (Wilson’s disease), etc. However, affinity of the aforementioned molecule depends on various factors, such as pH, and has some adverse side effects. On the other hand, zinc is very important metabolic functions in living bodies acting as cofactor in many enzyme systems. The collected data have revealed presently that the optimized structures of the composites have exothermic heats of formation and favorable Gibbs free energy of formation values. They are thermally favored and electronically stable at the standard states. Various structural and quantum chemical data have been collected and discussed, including IR and UV-VIS spectra. The data also revealed that there exists a certain complex formation between the zinc cation and the substituted amino-D-penicillamines considered.
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Delville, A., & Detellier, C. (1986). Zn(II)–D-(−)penicillamine complexes in aqueous solution: Zn-67 nuclear magnetic resonance study. Canadian Journal of Chemistry, 64(9), 1845–1849. https://doi.org/10.1139/v86-303
Bhushan, R., & Kumar, R. (2010). Enantioresolution of DL-penicillamine. Biomedical Chromatography, 24(1), 66–82. https://doi.org/10.1002/bmc.1355
Domingo, J. L., Gómez, M., & Jones, M. M. (1998). Concurrent administration of D-penicillamine and zinc has no advantages over the use of either single agent on copper excretion in the rat. Toxicology, 126(3), 195–205. https://doi.org/10.1016/s0300-483x(98)00017-1
Chong, C. R., & Auld, D. S. (2007). Catalysis of zinc transfer by D-penicillamine to secondary chelators. Journal of Medicinal Chemistry, 50(22), 5524–5527. https://doi.org/10.1021/jm070803y
Tang, S., Bai, L., Hou, W., Hu, Z., Chen, X., Zhao, J., Liang, C., Zhang, W., Duan, Z., & Zheng, S. (2022). Comparison of the effectiveness and safety of D-penicillamine and zinc salt treatment for symptomatic Wilson disease: A systematic review and meta-analysis. Frontiers in Pharmacology, 13, Article 847436. https://doi.org/10.3389/fphar.2022.847436
Ishak, R., & Abbas, O. (2013). Penicillamine revisited: Historic overview and review of the clinical uses and cutaneous adverse effects. American Journal of Clinical Dermatology, 14(3), 223–233. https://doi.org/10.1007/s40257-013-0022-z
Habib, G. S., Saliba, W., Nashashibi, M., & Armali, Z. (2006). Penicillamine and nephrotic syndrome. European Journal of Internal Medicine, 17(5), 343–348. https://doi.org/10.1016/j.ejim.2006.03.001
Phelps, D. L., Lakatos, L., & Watts, J. L. (2001). D-penicillamine for preventing retinopathy of prematurity in preterm infants. Cochrane Database of Systematic Reviews, (1), CD001073. https://doi.org/10.1002/14651858.CD001073
Tandon, M., Dutta, S., Dogra, M. R., & Gupta, A. (2010). Oral D-penicillamine for the prevention of retinopathy of prematurity in very low birth weight infants, a randomized placebo controlled trial. Acta Paediatrica, 99(9), 1324–1328. https://doi.org/10.1111/j.1651-2227.2010.01837.x
Peters, L., Steventon, G. B., Green, S., Sturman, S., Waring, R. H., & Williams, A. C. (1994). D-penicillamine metabolism in neurodegenerative diseases: An in vivo/in vitro sulphydryl methylation study. Xenobiotica, 24(10), 1013–1020. https://doi.org/10.3109/00498259409043298
Klingenberg, S. L., & Chen, W. (2006). D-penicillamine for primary sclerosing cholangitis. Cochrane Database of Systematic Reviews, (1), CD004182. https://doi.org/10.1002/14651858.CD004182.pub3
Corrigan, J. J., Jr., Damiano, M. L., Leissinger, C., & Wulff, K. (2003). Treatment of chronic haemophilic synovitis in humans with D-penicillamine. Haemophilia, 9(1), 64–68. https://doi.org/10.1046/j.1365-2516.2003.00676.x
Kaya, T. I., Kokturk, A., Tursen, U., Ikizoglu, G., & Polat, A. (2002). D-penicillamine treatment for lipoid proteinosis. Pediatric Dermatology, 19(4), 359–362. https://doi.org/10.1046/j.1525-1470.2002.00104.x
Nagler, R., Cohen, S., Savulescu, D., Leschiner, S., Otradnov, I., & Gavish, M. (2010). Penicillamine as a potent protector against injurious effects of cigarette smoke in aerodigestive tract cancer. Oncology, 78(1), 12–19. https://doi.org/10.1159/000287967
Gupte, A., & Mumper, R. J. (2009). Elevated copper and oxidative stress in cancer cells as a target for cancer treatment. Cancer Treatment Reviews, 35(1), 32–46. https://doi.org/10.1016/j.ctrv.2008.07.004
Brem, S., Grossman, S. A., Carson, K. A., New, P., Phuphanich, S., Alavi, J. B., Mikkelsen, T., & Fisher, J. D. (2005). Phase 2 trial of copper depletion and penicillamine as antiangiogenesis therapy of glioblastoma. Neuro-Oncology, 7(3), 246–253. https://doi.org/10.1215/S1152851704000869
Squitti, R., Rossini, P. M., Cassetta, E., Moffa, F., Pasqualetti, P., Cortesi, M., Colloca, A., Rossi, L., & Finazzi-Agrò, A. (2002). D-penicillamine reduces serum oxidative stress in Alzheimer’s disease patients. European Journal of Clinical Investigation, 32(1), 51–59. https://doi.org/10.1046/j.1365-2362.2002.00933.x
Sharifian, M., Sari-Aslani, F., Hemmatinejad, B., Fallahzadeh, M. K., Kasraee, B., Khoshandish, M., Miri, R., Mohammadi-Samani, S., Jowkar, F., & Namazi, M. R. (2011). D-penicillamine, a potent melanogenesis inhibitor, lacks any depigmenting effect on black guinea pig skin: The first randomized, evaluated blinded vehicle-controlled, in vivo study. Acta Dermatovenerologica Alpina, Pannonica et Adriatica, 20(2), 51–53.
Qiao, S., Cabello, C. M., Lamore, S. D., Lesson, J. L., & Wondrak, G. T. (2012). D-penicillamine targets metastatic melanoma cells with induction of the unfolded protein response (UPR) and Noxa (PMAIP1)-dependent mitochondrial apoptosis. Apoptosis, 17(10), 1079–1094. https://doi.org/10.1007/s10495-012-0746-x
Manzini, C. U., Sebastiani, M., Giuggioli, D., Manfredi, A., Colaci, M., Cesinaro, A. M., & Ferri, C. (2012). D-penicillamine in the treatment of eosinophilic fasciitis: Case reports and review of the literature. Clinical Rheumatology, 31(1), 183–187. https://doi.org/10.1007/s10067-011-1866-3
Bienaimé, F., Clerbaux, G., Plaisier, E., Mougenot, B., Ronco, P., & Rougier, J. P. (2007). D-penicillamine-induced ANCA-associated crescentic glomerulonephritis in Wilson disease. American Journal of Kidney Diseases, 50(5), 821–825. https://doi.org/10.1053/j.ajkd.2007.05.026
Sharma, R., Jain, S., & Kher, V. (2012). ANCA-associated Goodpasture’s syndrome in a patient with rheumatoid arthritis on penicillamine. Indian Journal of Nephrology, 22(1), 45–47. https://doi.org/10.4103/0971-4065.83743
Poulas, K., Koutsouraki, E., Kordas, G., Kokla, A., & Tzartos, S. J. (2012). Anti-MuSK- and anti-AChR-positive myasthenia gravis induced by D-penicillamine. Journal of Neuroimmunology, 250(1–2), 94–98. https://doi.org/10.1016/j.jneuroim.2012.05.011
Stewart, J. J. P. (1989). Optimization of parameters for semi-empirical methods I. Journal of Computational Chemistry, 10(2), 209–220. https://doi.org/10.1002/jcc.540100208
Stewart, J. J. P. (1989). Optimization of parameters for semi-empirical methods II. Journal of Computational Chemistry, 10(2), 221–264. https://doi.org/10.1002/jcc.540100209
Leach, A. R. (1997). Molecular modeling. Longman.
Kohn, W., & Sham, L. J. (1965). Self-consistent equations including exchange and correlation effects. Physical Review, 140(4A), 1133–1138. https://doi.org/10.1103/PhysRev.140.A1133
Parr, R. G., & Yang, W. (1989). Density functional theory of atoms and molecules. Oxford University Press.
Becke, A. D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38(6), 3098–3100. https://doi.org/10.1103/PhysRevA.38.3098
Vosko, S. H., Wilk, L., & Nusair, M. (1980). Accurate spin-dependent electron liquid correlation energies for local spin density calculations: A critical analysis. Canadian Journal of Physics, 58(8), 1200–1211. https://doi.org/10.1139/p80-159
Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation energy formula into a functional of the electron density. Physical Review B, 37(2), 785–789. https://doi.org/10.1103/PhysRevB.37.785
Wavefunction Inc. (2006). SPARTAN 06. Wavefunction Inc.
Fleming, I. (1976). Frontier orbitals and organic reactions. Wiley.
Bard, A. J. (1966). Chemical equilibrium. Harper & Row.
Turro, N. J. (1991). Modern molecular photochemistry. University Science Books.
Barrow, G. M. (1962). Introduction to molecular spectroscopy. McGraw-Hill/Kogakusha.
Harris, D. C., & Bertolucci, M. D. (1978). Symmetry and spectroscopy. Oxford University Press.
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