Encapsulation of alpha-mangostin and hydrophilic beta-cyclodextrins revealed by all-atom molecular dynamics simulations

Mahabusarakam, 1987, Chemical constituents of Garcinia mangostana, J. Nat. Prod., 50, 474, 10.1021/np50051a021 Nakatani, 2002, Inhibition of cyclooxygenase and prostaglandin E2 synthesis by gamma-mangostin, a xanthone derivative in mangosteen, in C6 rat glioma cells, Biochem. Pharmacol., 63, 73, 10.1016/S0006-2952(01)00810-3 Suksamrarn, 2003, Antimycobacterial activity of prenylated xanthones from the fruits of Garcinia mangostana, Chem. Pharm. Bull. (Tokyo), 51, 857, 10.1248/cpb.51.857 Suksamrarn, 2002, Xanthones from the green fruit hulls of Garcinia mangostana, J. Nat. Prod., 65, 761, 10.1021/np010566g Ee, 2006, Xanthones from Garcinia mangostana (Guttiferae), Nat. Prod. Res., 20, 1067, 10.1080/14786410500463114 Shankaranarayan, 1979, Pharmacological profile of mangostin and its derivatives, Arch. Int. Pharmacodyn. Ther., 239, 257 Matsumoto, 2003, Induction of apoptosis by xanthones from mangosteen in human leukemia cell lines, J. Nat. Prod., 66, 1124, 10.1021/np020546u Xu, 2014, Cytotoxic prenylated xanthones from the pericarps of Garcinia mangostana, Molecules, 19, 1820, 10.3390/molecules19021820 Devi Sampath, 2007, Cardioprotective effect of alpha-mangostin, a xanthone derivative from mangosteen on tissue defense system against isoproterenol-induced myocardial infarction in rats, J. Biochem. Mol. Toxicol., 21, 336, 10.1002/jbt.20199 Balunas, 2008, Xanthones from the botanical dietary supplement mangosteen (Garcinia mangostana) with aromatase inhibitory activity, J. Nat. Prod., 71, 1161, 10.1021/np8000255 Iikubo, 2002, The first direct synthesis of α-mangostin, a potent inhibitor of the acidic sphingomyelinase, Tetrahedron Lett., 43, 291, 10.1016/S0040-4039(01)02137-2 Sakagami, 2005, Antibacterial activity of alpha-mangostin against vancomycin resistant Enterococci (VRE) and synergism with antibiotics, Phytomedicine, 12, 203, 10.1016/j.phymed.2003.09.012 Gopalakrishnan, 1997, Evaluation of the antifungal activity of natural xanthones from Garcinia mangostana and their synthetic derivatives, J. Nat. Prod., 60, 519, 10.1021/np970165u Chen, 2008, Anti-inflammatory activity of mangostins from Garcinia mangostana, Food Chem. Toxicol., 46, 688, 10.1016/j.fct.2007.09.096 Gutierrez-Orozco, 2013, alpha-Mangostin: anti-inflammatory activity and metabolism by human cells, J. Agric. Food Chem., 61, 3891, 10.1021/jf4004434 Chin, 2008, Xanthones with quinone reductase-inducing activity from the fruits of Garcinia mangostana (Mangosteen), Phytochemistry, 69, 754, 10.1016/j.phytochem.2007.09.023 Jung, 2006, Antioxidant xanthones from the pericarp of Garcinia mangostana (Mangosteen), J. Agric. Food Chem., 54, 2077, 10.1021/jf052649z Minami, 1994, The International Journal of Plant Biochemistry Antioxidant xanthones from Garcinia subelliptica, Phytochemistry, 36, 501, 10.1016/S0031-9422(00)97103-6 Yu, 2007, Phenolics from hull of Garcinia mangostana fruit and their antioxidant activities, Food Chem., 104, 176, 10.1016/j.foodchem.2006.11.018 Iinuma, 1996, Antibacterial activity of xanthones from guttiferaeous plants against methicillin-resistant Staphylococcus aureus, J. Pharm. Pharmacol., 48, 861, 10.1111/j.2042-7158.1996.tb03988.x Chairungsrilerd, 1996, Pharmacological properties of alpha-mangostin, a novel histamine H1 receptor antagonist, Eur. J. Pharmacol., 314, 351, 10.1016/S0014-2999(96)00562-6 Wang, 2000, Inducible nitric oxide synthase inhibitors of Chinese herbs. Part 2: naturally occurring furanocoumarins, Bioorg. Med. Chem., 8, 2701, 10.1016/S0968-0896(00)00200-5 Nilar, Harrison, L.J. Xanthones from the heartwood of Garcinia mangostana. Phytochemistry. 2002, 60, 541-8. Aisha, 2012, Solid dispersions of alpha-mangostin improve its aqueous solubility through self-assembly of nanomicelles, J. Pharm. Sci., 101, 815, 10.1002/jps.22806 Eastburn, 1994, Applications of modified cyclodextrins, Biotechnol. Adv., 12, 325, 10.1016/0734-9750(94)90015-9 Szejtli, 1998, Introduction and general overview of cyclodextrin chemistry, Chem. Rev., 98, 1743, 10.1021/cr970022c Del Valle, 2004, Cyclodextrins and their uses: a review, Process Biochem., 39, 1033, 10.1016/S0032-9592(03)00258-9 Szejtli, 1989, Downstream processing using cyclodextrins, Trends Biotechnol., 7, 170, 10.1016/0167-7799(89)90094-2 Brewster, 2007, Cyclodextrins as pharmaceutical solubilizers, Adv. Drug Deliv. Rev., 59, 645, 10.1016/j.addr.2007.05.012 Liu, 2002, The driving forces in the inclusion complexation of cyclodextrins, J. Incl. Phenom. Macrocycl. Chem., 42, 1, 10.1023/A:1014520830813 Sangpheak, 2014, Enhanced stability of a naringenin/2,6-dimethyl beta-cyclodextrin inclusion complex: molecular dynamics and free energy calculations based on MM- and QM-PBSA/GBSA, J. Mol. Graph. Model., 50, 10, 10.1016/j.jmgm.2014.03.001 Yang, 2010, Host-guest system of nimbin and beta-cyclodextrin or its derivatives: preparation, characterization, inclusion mode, and solubilization, J. Agric. Food Chem., 58, 8545, 10.1021/jf101079e Maeda, 2014, Inclusion complexes of melatonin with modified cyclodextrins, J. Incl. Phenom. Macrocycl. Chem., 78, 217, 10.1007/s10847-013-0290-5 Yang, 2013, Host-guest inclusion system of mangiferin with beta-cyclodextrin and its derivatives, Mater. Sci. Eng. C Mater. Biol. Appl., 33, 2386, 10.1016/j.msec.2013.02.002 Sancho, 2016, Theoretical and experimental study of inclusion complexes of beta-cyclodextrins with chalcone and 2′,4′-dihydroxychalcone, J. Phys. Chem. B, 120, 3000, 10.1021/acs.jpcb.5b11317 Ma, 2012, Alpinetin/hydroxypropyl-β-cyclodextrin host–guest system: preparation, characterization, inclusion mode, solubilization and stability, J. Pharm. Biomed. Anal., 67-68, 193, 10.1016/j.jpba.2012.04.038 Loftsson, 1996, Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization, J. Pharm. Sci., 85, 1017, 10.1021/js950534b Schneiderman, 2000, Cyclodextrins: a versatile tool in separation science, J. Chromatogr. B Biomed. Sci. Appl., 745, 83, 10.1016/S0378-4347(00)00057-8 Chatjigakis, 1992, Solubility behavior of .beta.-cyclodextrin in water/cosolvent mixtures, Anal. Chem., 64, 1632, 10.1021/ac00038a022 Szejtli, 1992, The properties and potential uses of cyclodextrin derivatives, J. Incl. Phenom. Mol. Recognit. Chem., 14, 25, 10.1007/BF01041363 Szente, 1999, Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development, Adv. Drug Deliv. Rev., 36, 17, 10.1016/S0169-409X(98)00092-1 Yates, 1958, The structure of mangostin1, J. Am. Chem. Soc., 80, 1691, 10.1021/ja01540a046 Yang, 2004, Semi-empirical PM3 study upon the complexation of β-cyclodextrin with 4,4′-benzidine and o-tolidine, J. Mol. Struct. THEOCHEM, 712, 75, 10.1016/j.theochem.2004.08.045 Rungnim, 2015, Co-solvation effect on the binding mode of the alpha-mangostin/beta-cyclodextrin inclusion complex, Beilstein J. Org. Chem., 11, 2306, 10.3762/bjoc.11.251 Snor, 2007, On the structure of anhydrous β-cyclodextrin, Chem. Phys. Lett., 441, 159, 10.1016/j.cplett.2007.05.007 Alecu, 2010, Computational thermochemistry: scale factor databases and scale factors for Vibrational frequencies obtained from electronic model chemistries, J. Chem. Theory Comput., 6, 2872, 10.1021/ct100326h Wu, 2003, Detailed analysis of grid-based molecular docking: a case study of CDOCKER-A CHARMm-based MD docking algorithm, J. Comput. Chem., 24, 1549, 10.1002/jcc.10306 Case, 2016 Kirschner, 2008, GLYCAM06: a generalizable biomolecular force field. Carbohydrates, J. Comput. Chem., 29, 622, 10.1002/jcc.20820 Harrach, 2014, Structure and dynamics of TIP3P, TIP4P, and TIP5P water near smooth and atomistic walls of different hydroaffinity, J. Chem. Phys., 140, 10.1063/1.4872239 Gotz, 2012, Routine microsecond molecular dynamics simulations with AMBER on GPUs. 1. Generalized born, J. Chem. Theory Comput., 8, 1542, 10.1021/ct200909j Le Grand, 2013, SPFP: speed without compromise—a mixed precision model for GPU accelerated molecular dynamics simulations, Comput. Phys. Commun., 184, 374, 10.1016/j.cpc.2012.09.022 Salomon-Ferrer, 2013, Routine microsecond molecular dynamics simulations with AMBER on GPUs. 2. Explicit solvent particle mesh Ewald, J. Chem. Theory Comput., 9, 3878, 10.1021/ct400314y York, 1993, The effect of long-range electrostatic interactions in simulations of macromolecular crystals: a comparison of the Ewald and truncated list methods, J. Chem. Phys., 99, 8345, 10.1063/1.465608 Ryckaert, 1977, Numerical integration of the Cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes, J. Comput. Phys., 23, 327, 10.1016/0021-9991(77)90098-5 Roe, D.R., Cheatham, T.E., 3rd. PTRAJ and CPPTRAJ: software for processing and analysis of molecular dynamics trajectory data. J. Chem. Theory Comput.. 2013, 9, 3084-95. Genheden, 2015, The MM/PBSA and MM/GBSA methods to estimate ligand-binding affinities, Expert Opin. Drug Discovery, 10, 449, 10.1517/17460441.2015.1032936 Bea, 2006, Chelate effect in cyclodextrin dimers: a computational (MD, MM/PBSA, and MM/GBSA) study, J. Org. Chem., 71, 2056, 10.1021/jo052469o Greenidge, 2013, MM/GBSA binding energy prediction on the PDBbind data set: successes, failures, and directions for further improvement, J. Chem. Inf. Model., 53, 201, 10.1021/ci300425v Rastelli, 2010, Fast and accurate predictions of binding free energies using MM-PBSA and MM-GBSA, J. Comput. Chem., 31, 797 Higuchi, 1965, K. A. Phase-solubility techniques, Adv. Anal. Chem. Instrum., 4, 117 Kerdpol, 2019 Steiner, 1998 Yong, 2008, Structural behaviour of 2-hydroxypropyl-beta-cyclodextrin in water: molecular dynamics simulation studies, Pharm. Res., 25, 1092, 10.1007/s11095-007-9506-y Sangpheak, 2015, Physical properties and biological activities of hesperetin and naringenin in complex with methylated beta-cyclodextrin, Beilstein J. Org. Chem., 11, 2763, 10.3762/bjoc.11.297 Kicuntod, 2016, Inclusion complexation of pinostrobin with various cyclodextrin derivatives, J. Mol. Graph. Model., 63, 91, 10.1016/j.jmgm.2015.11.005 Schönbeck, 2010, Hydroxypropyl-substituted β-cyclodextrins: influence of degree of substitution on the thermodynamics of complexation with tauroconjugated and glycoconjugated bile salts, Langmuir, 26, 17949, 10.1021/la103124n Ferreira, 2013, Antioxidant activity of the mangiferin inclusion complex with β-cyclodextrin, LWT Food Sci. Technol., 51, 129, 10.1016/j.lwt.2012.09.032