Physicochemical evaluation of new tetrahydroacridine and iodobenzoic acid hybrids as the next step in the design of potential drugs for treating Alzheimer's disease.
Alzheimer's disease
HPLC
log P determination
method validation
pKa determination
tacrine
Journal
Biomedical chromatography : BMC
ISSN: 1099-0801
Titre abrégé: Biomed Chromatogr
Pays: England
ID NLM: 8610241
Informations de publication
Date de publication:
Oct 2020
Oct 2020
Historique:
received:
01
03
2020
revised:
14
05
2020
accepted:
19
05
2020
pubmed:
26
5
2020
medline:
27
4
2021
entrez:
26
5
2020
Statut:
ppublish
Résumé
Tacrine derivatives containing iodobenzoic acid were developed as a novel multitarget-directed ligand and find potential application in the treatment of Alzheimer's disease. The aim of this study is to perform a physicochemical profile of this series. Experimental log P and pK
Substances chimiques
Cholinesterase Inhibitors
0
Iodobenzoates
0
Tacrine
4VX7YNB537
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e4906Subventions
Organisme : National Science Centre
ID : 2015/19/B/NZ7/02847
Informations de copyright
© 2020 John Wiley & Sons, Ltd.
Références
Clark, D. E. (2003). In silico prediction of blood-brain barrier permeation. Drug Discovery Today, 8(20), 927-933. https://doi.org/10.1016/s1359-6446(03)02827-7
Gleeson, M. P. (2008). Generation of a set of simple, interpretable ADMET rules of thumb. Journal of Medicinal Chemistry, 51(4), 817-834. https://doi.org/10.1021/jm701122q
Hamulakova, S., Poprac, P., Jomova, K., Brezova, V., Lauro, P., Drostinova, L., … Valko, M. (2016). Targeting copper (II)-induced oxidative stress and the acetylcholinesterase system in Alzheimer's disease using multifunctional tacrine-coumarin hybrid molecules. Journal of Inorganic Biochemistry, 161, 52-62. https://doi.org/10.1016/j.jinorgbio.2016.05.001
Hansch, C., Leo, A., & Hoekman, D. (1995). Exploring QSAR: Hydrophobic, electronic, and steric constants. Washington DC: American Chemical Society.
ICH. (2005). Q2(R1) validation of analytical procedures: Text and methodology. Paper presented at the International Conference of Harmonization, Geneve.
Liang, C., Qiao, J. Q., & Lian, H. Z. (2017). Determination of reversed-phase high performance liquid chromatography based octanol-water partition coefficients for neutral and ionizable compounds: Methodology evaluation. Journal of Chromatography a, 1528, 25-34. https://doi.org/10.1016/j.chroma.2017.10.064
Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (1997). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 23(1-3), 3-25. https://doi.org/10.1016/s0169-409x(96)00423-1
Lyday, P. A. (2000). Iodine and Iodine Compounds. In Ullmann's encyclopedia of industrial chemistry. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA. https://doi.org/10.1002/14356007.a14_381
Manallack, D. T. (2007). The pK(a) Distribution of Drugs: Application to Drug Discovery. Perspectives in Medicinal Chemistry, 1, 25-38.
Manallack, D. T., Prankerd, R. J., Yuriev, E., Oprea, T. I., & Chalmers, D. K. (2013). The significance of acid/base properties in drug discovery. Chemical Society Reviews, 42(2), 485-496. https://doi.org/10.1039/c2cs35348b
Mazak, K., & Noszal, B. (2014). Drug delivery: A process governed by species-specific lipophilicities. European Journal of Pharmaceutical Sciences, 62, 96-104. https://doi.org/10.1016/j.ejps.2014.05.017
Meanwell, N. A. (2011). Improving Drug Candidates by Design: A Focus on Physicochemical Properties As a Means of Improving Compound Disposition and Safety. Chemical Research in Toxicology, 24(9), 1420-1456. https://doi.org/10.1021/tx200211v
Musil, K., Florianova, V., Bucek, P., Dohnal, V., Kuca, K., & Musilek, K. (2016). Development and validation of a FIA/UV-vis method for pK(a) determination of oxime based acetylcholinesterase reactivators. Journal of Pharmaceutical and Biomedical Analysis, 117, 240-246. https://doi.org/10.1016/j.jpba.2015.09.010
Perrin, D. D. (1972). Dissociation constants of organic bases in aqueous solution. IUPAC chemical data series: Supplement 1972. London: Butterworths.
Sangster, J. (1997). Octanol-water partition coefficients: Fundamentals and physical chemistry. Chichester, UK: Wiley.
Scheltens, P., Blennow, K., Breteler, M. M. B., de Strooper, B., Frisoni, G. B., Salloway, S., & Van der Flier, W. M. (2016). Alzheimer's disease. Lancet, 388(10043), 505-517. https://doi.org/10.1016/s0140-6736(15)01124-1
Skibinski, R., Czarnecka, K., Girek, M., Bilichowski, I., Chufarova, N., Mikiciuk-Olasik, E., & Szymanski, P. (2018). Novel tetrahydroacridine derivatives with iodobenzoic acid moiety as multifunctional acetylcholinesterase inhibitors. Chemical Biology & Drug Design, 91(2), 505-518. https://doi.org/10.1111/cbdd.13111
Sulochana, S. P., Sharma, K., Mullangi, R., & Sukumaran, S. K. (2014). Review of the validated HPLC and LC-MS/MS methods for determination of drugs used in clinical practice for Alzheimer's disease. Biomedical Chromatography, 28(11), 1431-1490. https://doi.org/10.1002/bmc.3116
Tetko, I. V., Gasteiger, J., Todeschini, R., Mauri, A., Livingstone, D., Ertl, P., … Prokopenko, V. V. (2005). Virtual computational chemistry laboratory - design and description. Journal of Computer-Aided Molecular Design, 19(6), 453-463. https://doi.org/10.1007/s10822-005-8694-y
The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 14th ed. (2006). In M. J. O'Neil, P. E. Heckelman, C. B. Koch, & K. J. Roman (Eds.). Whitehouse Station, NJ: Merck and Co., Inc.
Wager, T. T., Hou, X. J., Verhoest, P. R., & Villalobos, A. (2010). Moving beyond Rules: The Development of a Central Nervous System Multiparameter Optimization (CNS MPO) Approach To Enable Alignment of Druglike Properties. ACS Chemical Neuroscience, 1(6), 435-449. https://doi.org/10.1021/cn100008c
Zhang, C., Du, Q. Y., Chen, L. D., Wu, W. H., Liao, S. Y., Yu, L. H., & Liang, X. T. (2016). Design, synthesis and evaluation of novel tacrine-multialkoxybenzene hybrids as multi-targeted compounds against Alzheimer's disease. European Journal of Medicinal Chemistry, 116, 200-209. https://doi.org/10.1016/j.ejmech.2016.03.077
Zhang, F. L., Xue, J. P., Shao, J. W., & Jia, L. (2012). Compilation of 222 drugs' plasma protein binding data and guidance for study designs. Drug Discovery Today, 17(9-10), 475-485. https://doi.org/10.1016/j.drudis.2011.12.018