Protein tyrosine phosphatase 1B inhibitors from the fungus Malbranchea albolutea

Phytochemistry - Tập 184 - Trang 112664 - 2021
Miriam Díaz-Rojas1, Huzefa Raja2, Martin González-Andrade3, José Rivera-Chávez4, Manuel Rangel-Grimaldo1, Isabel Rivero-Cruz1, Rachel Mata1
1Facultad de Química, Universidad Nacional Autónoma de México, Mexico City, 04510, Mexico
2Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, 27412, NC, USA
3Facultad de Medicina, Universidad Nacional Autónoma de México, Mexico City, Mexico
4Instituto de Química, Universidad Nacional Autónoma de México, Mexico City, Mexico

Tài liệu tham khảo

Baell, 2010, New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays, J. Med. Chem., 53, 2719, 10.1021/jm901137j Beyett, 2019, Perturbation of the interactions of calmodulin with GRK5 using a natural product chemical probe, Proc. Natl. Acad. Sci. Unit. States Am., 116, 15895, 10.1073/pnas.1818547116 Brenk, 2008, Lessons learnt from assembling screening libraries for drug discovery for neglected diseases, ChemMedChem, 3, 435, 10.1002/cmdc.200700139 Bruhn, 2017 Case, 2005, The Amber biomolecular simulation programs, J. Comput. Chem., 26, 1668, 10.1002/jcc.20290 Case, 2012 Clark, 2005, Gymnoascolides A-C: aromatic butenolides from an Australian isolate of the soil ascomycete Gymnoascus reessii, J. Nat. Prod., 68, 1226, 10.1021/np050145p Copeland, 2001 Daina, 2017, SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules, Sci. Rep., 7, 1, 10.1038/srep42717 DeLano, 2004, Use of PYMOL as a communications tool for molecular science, Abstr. Pap. Am. Chem. Soc., 228, U313 Ding, 2008, Premalbrancheamide: synthesis, isotopic labeling, biosynthetic incorporation, and detection in cultures of Malbranchea aurantiaca, Org. Lett., 10, 4863, 10.1021/ol8019633 Dowarah, 2020, Anti-diabetic drugs recent approaches and advancements, Bioorg. Med. Chem., 28, 115263, 10.1016/j.bmc.2019.115263 Egan, 2000, Prediction of drug absorption using multivariate statistics, J. Med. Chem., 43, 3867, 10.1021/jm000292e Figueroa, 2008, Malbrancheamide B, a novel compound from the fungus Malbranchea aurantiaca, Nat. Prod. Res., 22, 709, 10.1080/14786410802012361 Figueroa, 2011, Fluorescence, circular dichroism, NMR, and docking studies of the interaction of the alkaloid malbrancheamide with calmodulin, J. Enzym. Inhib. Med. Chem., 26, 378, 10.3109/14756366.2010.518964 Fraley, 2017, Function and structure of MalA/MalA', iterative halogenases for late-stage C–H functionalization of indole alkaloids, J. Am. Chem. Soc., 139, 12060, 10.1021/jacs.7b06773 Frisch, 2013 Grimblat, 2015, Beyond DP4: an improved probability for the stereochemical assignment of isomeric compounds using quantum chemical calculations of NMR shifts, J. Org. Chem., 80, 12526, 10.1021/acs.joc.5b02396 Hawksworth, 2011, The Amsterdam declaration on fungal nomenclature, IMA Fungus, 2, 105, 10.5598/imafungus.2011.02.01.14 Hosoe, 2005, 4-Benzyl-3-phenyl-5H-furan-2-one, a vasodilator isolated from Malbranchea filamentosa IFM 41300, Phytochemistry, 66, 2776, 10.1016/j.phytochem.2005.08.014 Hou, 2011, Assessing the performance of the MM/PBSA and MM/GBSA methods. The accuracy of binding free energy calculations based on molecular dynamics simulations, J. Chem. Inf. Model., 51, 69, 10.1021/ci100275a Hubka, 2013, Auxarthron ostraviense sp. nov., and A. umbrinum associated with non-dermatophytic onychomycosis, Med. Mycol., 51, 614, 10.3109/13693786.2013.770608 2019 Jiménez-Arreola, 2020, Dimeric phenalenones from Talaromyces sp. (IQ-313) inhibit hPTP1B1-400: insights into mechanistic kinetics from in vitro and in silico studies, Bioorg. Chem., 101, 103893, 10.1016/j.bioorg.2020.103893 Kalyaanamoorthy, 2017, ModelFinder: fast model selection for accurate phylogenetic estimates, Nat. Methods, 14, 587, 10.1038/nmeth.4285 Kerru, 2018, Current anti-diabetic agents and their molecular targets: a review, Eur. J. Med. Chem., 152, 436, 10.1016/j.ejmech.2018.04.061 Kijjoa, 2011, Sartoryglabrins, analogs of ardeemins, from Neosartorya Glabra, Nat. Prod. Commun., 6, 807 Kollman, 2000, Calculating structures and free energies of complex molecules: combining molecular mechanics and continuum models, Acc. Chem. Res., 33, 889, 10.1021/ar000033j Kumar, 2020, Protein tyrosine phosphatase (PTP1B): a promising drug target against life-threatening ailments, Curr. Mol. Pharmacol., 13, 17, 10.2174/1874467212666190724150723 Lipinski, 1996, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Deliv. Rev., 64, 4 Madariaga-Mazón, 2015, Insights on the vasorelaxant mode of action of malbrancheamide, J. Pharm. Pharmacol., 67, 551, 10.1111/jphp.12346 Marcarino, 2020, NMR calculations with quantum methods: development of new tools for structural elucidation and beyond, Acc. Chem. Res., 53, 1922, 10.1021/acs.accounts.0c00365 Martínez-Luis, 2005, Phytotoxins from the fungus Malbranchea aurantiaca, Phytochemistry, 66, 1012, 10.1016/j.phytochem.2005.03.005 Martínez-Luis, 2006, Malbrancheamide, a new calmodulin inhibitor from the fungus Malbranchea aurantiaca, Tetrahedron, 62, 1817, 10.1016/j.tet.2005.11.047 Mendes, 2016, Alkaloidal metabolites from Aspergillus felis and their activities against Paracoccidioides brasiliensis, Phytochem. Lett., 17, 28, 10.1016/j.phytol.2016.06.006 Muegge, 2001, Simple selection criteria for drug-like chemical matter, J. Med. Chem., 44, 1841, 10.1021/jm015507e Nguyen, 2015, IQ-TREE: a fast and effective stochastic algorithm for estimating maximum-likelihood phylogenies, Mol. Biol. Evol., 32, 268, 10.1093/molbev/msu300 Raja, 2017, Fungal identification using molecular tools: a primer for the natural products research community, J. Nat. Prod., 80, 756, 10.1021/acs.jnatprod.6b01085 Rangel-Grimaldo, 2020, α-Glucosidase and protein tyrosine phosphatase 1B inhibitors from Malbranchea circinata, J. Nat. Prod., 83, 675, 10.1021/acs.jnatprod.9b01108 Rebollar-Ramos, 2018, Additional α−glucosidase inhibitors from Malbranchea flavorosea (leotiomycetes, Ascomycota), J. Antibiot., 71, 862, 10.1038/s41429-018-0075-6 Roe, 2013, PTRAJ and CPPTRAJ: software for processing and analysis of molecular dynamics trajectory data, J. Chem. Theor. Comput., 9, 3084, 10.1021/ct400341p Salomon-Ferrer, 2013, Routine microsecond molecular dynamics simulations with AMBER on GPUs. 2. Explicit solvent particle mesh ewald, J. Chem. Theor. Comput., 9, 3878, 10.1021/ct400314y Sarrocco, 2015, A polyphasic contribution to the knowledge of Auxarthron (Onygenaceae), Mycol. Prog., 14, 112, 10.1007/s11557-015-1128-x Schlegel, 2003, 7-Methoxy-2,3-dimethylbenzofuran-5-ol, a new antioxidant from Malbranchea cinnamomea HKI 0286, J. Antibiot., 56, 917, 10.7164/antibiotics.56.917 Segel, 1994 Sigler, 1976, Taxonomy of Malbranchea and some other Hyphomycetes with arthroconidia [Fungi, new taxa], Mycotaxon, 4, 349 Sigler, 2002, Auxarthron teleomorphs for Malbranchea filamentosa and Malbranchea albolutea and relationships within Auxarthron, Stud. Mycol., 47, 111 Teague, 1999, The design of leadlike combinatorial libraries, Angew. Chem. Int. Ed., 38, 3743, 10.1002/(SICI)1521-3773(19991216)38:24<3743::AID-ANIE3743>3.0.CO;2-U Talavera, 2007, Improvement of phylogenies after removing divergent and ambiguously aligned blocks from protein sequence alignments, Syst. Biol., 56, 564, 10.1080/10635150701472164 Taylor, 2011, One Fungus = One Name: DNA and fungal nomenclature twenty years after PCR, IMA Fungus, 2, 113, 10.5598/imafungus.2011.02.02.01 Tian, 2020, Ff19SB: amino-acid-specific protein backbone parameters trained against quantum mechanics energy surfaces in solution, J. Chem. Theor. Comput., 16, 528, 10.1021/acs.jctc.9b00591 Veber, 2002, Molecular properties that influence the oral bioavailability of drug candidates, J. Med. Chem., 45, 2615, 10.1021/jm020017n Verastegui-Omaña, 2017, α-Glucosidase inhibitors from Malbranchea flavorosea, J. Nat. Prod., 80, 190, 10.1021/acs.jnatprod.6b00977 Verma, 2017, Protein tyrosine phosphatase 1B inhibitors as antidiabetic agents–A brief review, Bioorg. Chem., 70, 267, 10.1016/j.bioorg.2016.12.004 Wakana, 2008, Structures of new triterpene glycosides, malbrancheosides A-D, from Malbranchea filamentosa, Heterocycles, 75, 1109, 10.3987/COM-07-11283 Wakana, 2009, The cytotoxic and antifungal activities of two new sesquiterpenes, malfilanol A and B, derived from Malbranchea filamentosa, J. Antibiot., 62, 217, 10.1038/ja.2009.9 Wakana, 2014, Cytotoxic anthrasteroid glycosides, malsterosides A-C, from Malbranchea filamentosa, J. Antibiot., 67, 585, 10.1038/ja.2014.43 Walker, 2008, The implementation of a fast and accurate QM/MM potential method in Amber, J. Comput. Chem., 29, 1019, 10.1002/jcc.20857 Watts, 2011, Utilizing DART mass spectrometry to pinpoint halogenated metabolites from a marine invertebrate-derived fungus, J. Org. Chem., 76, 6201, 10.1021/jo2009593 Wiesmann, 2004, Allosteric inhibition of protein tyrosine phosphatase 1B, Nat. Struct. Mol. Biol., 11, 730, 10.1038/nsmb803 Yang, 2009, Discovery of new natural products by intact-cell mass spectrometry and LC-SPE-NMR: malbranpyrroles, novel polyketides from thermophilic fungus Malbranchea sulfurea, Chem. Eur J., 15, 11573, 10.1002/chem.200901556 Yang, 2020, Trichothecrotocins D–L, antifungal agents from a potato-associated Trichothecium crotocinigenum, J. Nat. Prod., 83, 2756, 10.1021/acs.jnatprod.0c00695 Zhang, 2020, PhyloSuite: an integrated and scalable desktop platform for streamlined molecular sequence data management and evolutionary phylogenetics studies, Mol. Ecol. Resour., 20, 348, 10.1111/1755-0998.13096 Zhang, 2014, Four ardeemin analogs from endophytic Aspergillus fumigatus SPS-02 and their reversal effects on multidrug-resistant tumor cells, Chem. Biodivers., 11, 85, 10.1002/cbdv.201300220 Zhao, 2018, Protein tyrosine phosphatase 1B inhibitors from natural sources, Arch Pharm. Res. (Seoul), 41, 130, 10.1007/s12272-017-0997-8 Zhou, 2004, Relative free energy of binding and binding mode calculations of HIV-1 RT inhibitors based on dock-MM-PB/GS, Proteins Struct. Funct. Genet., 57, 493, 10.1002/prot.20223