Rational design of some substituted phenyl azanediyl (bis) methylene phosphonic acid derivatives as potential anticancer agents and imaging probes: Computational inputs, chemical synthesis, radiolabeling, biodistribution and gamma scintigraphy

Bioorganic Chemistry - Tập 92 - Trang 103282 - 2019
Mohammed A. Khedr1, Hassan M. Rashed2,3, Hamed Farag4, Tamer M. Sakr5
1Pharmaceutical Chemistry Department, Faculty of Pharmacy, Helwan University, Postal Code: 11795, Cairo, Egypt
2Labeled Compounds Department, Hot Labs Center, Atomic Energy Authority, P.O. Box 13759, Cairo, Egypt
3Department of Pharmaceutics, Faculty of Pharmacy, Sinai University, Egypt
4Radiotherapy and Nuclear Medicine Department, National Cancer Institute, Cairo University, Cairo, Egypt
5Radioactive Isotopes and Generator Department, Hot Labs Center, Atomic Energy Authority, P.O. Box 13759, Cairo, Egypt

Tài liệu tham khảo

Tang, 2019, A radiopharmaceutical [89Zr] Zr-DFO-nimotuzumab for immunoPET with epidermal growth factor receptor expression in vivo, Nucl. Med. Biol., 70, 23, 10.1016/j.nucmedbio.2019.01.007 Sakr, 2018, In silico-based repositioning of phosphinothricin as a novel technetium-99m imaging probe with potential anti-cancer activity, Molecules, 23, 496, 10.3390/molecules23020496 Pagano, 2018, Radiopharmaceuticals for bone metastases, 345 Rotman, 2018, Drug delivery systems functionalized with bone mineral seeking agents for bone targeted therapeutics, J. Control. Release, 269, 88, 10.1016/j.jconrel.2017.11.009 Lin, 2019, Predicting binding affinities of nitrogen-containing bisphosphonates on hydroxyapatite surface by molecular dynamics, Chem. Phys. Lett., 716, 83, 10.1016/j.cplett.2018.12.008 Saha, 2018, Nuclear pharmacy, 185 Motaleb, 2011, Synthesis and preclinical pharmacological evaluation of 99mTc-TEDP as a novel bone imaging agent, J. Labelled Compd. Radiopharm., 54, 597, 10.1002/jlcr.1896 Chakraborty, 2018, Syntheses and evaluation of 68Ga-and 153Sm-labeled DOTA-conjugated bisphosphonate ligand for potential use in detection of skeletal metastases and management of pain arising from skeletal metastases, Chem. Biol. Drug Des., 92, 1618, 10.1111/cbdd.13327 Romanenko, 2018, Advances in the synthesis of functional α-organyl gem-bisphosphonates for biomedical applications, Adv. Organic Synthesis: Volume 12, 12, 200, 10.2174/9781681086804118120007 Grey, 2006, Differences between the bisphosphonates for the prevention and treatment of osteoporosis, Ther. Clin. Risk Manage., 2, 77 B.L. Furman, Bisphosphonates. xPharm: The Comprehensive Pharmacology Reference, 2007; [1–3]. Bermo, 2018, Review of extraskeletal activity on Tc-99m methylene diphosphonate bone scintigraphy and value of cross-sectional and SPECT-CT imaging correlation, Curr. Probl. Diagn. Radiol., 47, 324, 10.1067/j.cpradiol.2017.07.009 Mitterhauser, 2008, An in vitro model for the comparative evaluation of bone seeking pharmaceuticals, ALTEX-Alternat. Animal Experiment., 25, 51 Liu, 2006, Novel injectable calcium phosphate/chitosan composites for bone substitute materials, Acta Biomater., 2, 557, 10.1016/j.actbio.2006.03.007 Alves, 2010, Designing biomaterials based on biomineralization of bone, J. Mater. Chem., 20, 2911, 10.1039/b910960a Liu, 2018, 3D-QSAR, molecular docking, and ONIOM studies on the structure–activity relationships and action mechanism of nitrogen-containing bisphosphonates, Chem. Biol. Drug Des., 91, 735, 10.1111/cbdd.13134 Waller, 2019, Inhibition of farnesyl pyrophosphate (FPP) and/or geranylgeranyl pyrophosphate (GGPP) biosynthesis and its implication in the treatment of cancers, Crit. Rev. Biochem. Mol. Biol., 54, 41, 10.1080/10409238.2019.1568964 Holstein, 2011, Inhibition of farnesyl and geranylgeranyl diphosphate synthases, Enzymes, 30, 301, 10.1016/B978-0-12-415922-8.00013-6 Hellal, 2016, Synthesis, characterization and computational studies of three α-amino-phosphonic acids derivatives from Meta, Ortho and Para aminophenol, J. Mol. Struct., 1103, 110, 10.1016/j.molstruc.2015.08.070 Mosmann, 1983, Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, J. Immunol. Methods, 65, 55, 10.1016/0022-1759(83)90303-4 Gomha, 2015, Synthesis and anticancer activities of thiazoles, 1, 3-thiazines, and thiazolidine using chitosan-grafted-poly (vinylpyridine) as basic catalyst, Heterocycles, 91, 1227, 10.3987/COM-15-13210 Geskovski, 2013, Comparative biodistribution studies of technetium-99 m radiolabeled amphiphilic nanoparticles using three different reducing agents during the labeling procedure, J. Labelled Compd. Radiopharm., 56, 689, 10.1002/jlcr.3097 Abd-Elal, 2016, Trans-nasal zolmitriptan novasomes: in-vitro preparation, optimization and in-vivo evaluation of brain targeting efficiency, Drug Delivery, 23, 3374, 10.1080/10717544.2016.1183721 Rashed, 2018, Preparation of 99mTc-levetiracetam intranasal microemulsion as the first radiotracer for SPECT imaging of the Synaptic Vesicle Protein SV2A, Eur. J. Pharm. Sci., 121, 29, 10.1016/j.ejps.2018.05.019 Nasr, 2018, Novel hydrazide-hydrazone and amide substituted coumarin derivatives: synthesis, cytotoxicity screening, microarray, radiolabeling and in vivo pharmacokinetic studies, Eur. J. Med. Chem., 151, 723, 10.1016/j.ejmech.2018.04.014 Rashed, 2017, Contribution of both olfactory and systemic pathways for brain targeting of nimodipine-loaded lipo-pluronics micelles: in vitro characterization and in vivo biodistribution study after intranasal and intravenous delivery, Drug Delivery, 24, 181, 10.1080/10717544.2016.1236848 Rashed, 2017, 99m Tc-hexoprenaline and 131 I-dapoxetine: preparation, in silico modeling and biological evaluation as promising lung scintigraphy radiopharmaceuticals, J. Radioanal. Nucl. Chem., 314, 1297, 10.1007/s10967-017-5500-y Sanad, 2017, In silico study and biological evaluation of 99mTc-tricabonyl oxiracetam as a selective imaging probe for AMPA receptors, J. Radioanal. Nucl. Chem., 314, 1505, 10.1007/s10967-016-5120-y Sakr, 2017, Preparation and biological profile of 99m Tc-lidocaine as a cardioselective imaging agent using 99m Tc eluted from 99 Mo/99m Tc generator based on Al–Mo gel, J. Radioanal. Nucl. Chem., 314, 2091, 10.1007/s10967-017-5560-z Bokhari, 2015, Preparation, biodistribution and scintigraphic evaluation of 99m Tc-lincomycin, Pak. J. Pharm. Sci, 28, 1965 Akbar, 2016, A review on evaluation of technetium-99m labeled radiopharmaceuticals, J. Radioanal. Nucl. Chem., 310, 477, 10.1007/s10967-016-5019-7 Essa, 2015, 99m Tc-amitrole as a novel selective imaging probe for solid tumor: In silico and preclinical pharmacological study, Eur. J. Pharm. Sci., 76, 102, 10.1016/j.ejps.2015.05.002 Al-Wabli, 2016, Platelet-12 lipoxygenase targeting via a newly synthesized curcumin derivative radiolabeled with technetium-99m, Chem. Cent. J., 10, 73, 10.1186/s13065-016-0220-x Wan, 2008, [99mTc] polyamine analogs as potential tumor imaging agent, Drug Dev. Res., 69, 520, 10.1002/ddr.20280 Sakr, 2013, Biodistribution of 99mTc-sunitinib as a potential radiotracer for tumor hypoxia imaging, J. Labelled Compd. Radiopharm., 56, 392, 10.1002/jlcr.3060 Sakr, 2014, Synthesis and biodistribution of 99m Tc-PyDA as a potential marker for tumor hypoxia imaging, Radiochemistry, 56, 76, 10.1134/S1066362214010159 Arulsudar, 2004, Preparation, characterization, and biodistribution study of technetium-99m-labeled leuprolide acetate-loaded liposomes in ehrlich ascites tumor-bearing mice, AAPS PharmSci, 6, 45, 10.1208/ps060105 Nour, 2016, Intranasal brain-targeted clonazepam polymeric micelles for immediate control of status epilepticus: in vitro optimization, ex vivo determination of cytotoxicity, in vivo biodistribution and pharmacodynamics studies, Drug Delivery, 23, 3681, 10.1080/10717544.2016.1223216 Hawary, 2011, Water-soluble derivatives of chitosan as a target delivery system of 99mTc to some organs in vivo for nuclear imaging and biodistribution, J. Radioanal. Nucl. Chem., 290, 557, 10.1007/s10967-011-1310-9 Kim, 2005, Hepatocyte-targeted nuclear imaging using 99mTc-galactosylated chitosan: conjugation, targeting, and biodistribution, J. Nucl. Med., 46, 141 Rashed, 2016, 99m Tc-zolmitriptan: radiolabeling, molecular modeling, biodistribution and gamma scintigraphy as a hopeful radiopharmaceutical for lung nuclear imaging, Radiol. Med. (Torino), 121, 935, 10.1007/s11547-016-0677-7 Harden, 1967, Isotope uptake and scanning of stomach in man with 99mTc-pertechnetate, Lancet, 289, 1305, 10.1016/S0140-6736(67)91597-8 Rashed, 2017, 99mTc-hexoprenaline and 131I-dapoxetine: preparation, in silico modeling and biological evaluation as promising lung scintigraphy radiopharmaceuticals, J. Radioanal. Nucl. Chem., 1 Kim, 2015, Synthesis and evaluation of Tc-99m-labeled RRL-containing peptide as a non-invasive tumor imaging agent in a mouse fibrosarcoma model, Ann. Nucl. Med., 29, 779, 10.1007/s12149-015-1002-6 Kim, 2015, Synthesis and evaluation of novel Tc-99 m labeled NGR-containing hexapeptides as tumor imaging agents, J. Labelled Compd. Radiopharm., 58, 30, 10.1002/jlcr.3260