{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,20]],"date-time":"2026-01-20T11:37:55Z","timestamp":1768909075170,"version":"3.49.0"},"reference-count":52,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2024,2,20]],"date-time":"2024-02-20T00:00:00Z","timestamp":1708387200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"he Coordena\u00e7\u00e3o de Aperfei\u00e7oamento de Pessoal de N\u00edvel Superior\u2014Brasil (CAPES)","award":["001"],"award-info":[{"award-number":["001"]}]},{"name":"he Coordena\u00e7\u00e3o de Aperfei\u00e7oamento de Pessoal de N\u00edvel Superior\u2014Brasil (CAPES)","award":["UIDB\/04423\/2020 and UIDP\/04423\/2020"],"award-info":[{"award-number":["UIDB\/04423\/2020 and UIDP\/04423\/2020"]}]},{"name":"FCT\u2014Foundation for Science and Technology","award":["001"],"award-info":[{"award-number":["001"]}]},{"name":"FCT\u2014Foundation for Science and Technology","award":["UIDB\/04423\/2020 and UIDP\/04423\/2020"],"award-info":[{"award-number":["UIDB\/04423\/2020 and UIDP\/04423\/2020"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>An unreported prenylated indole derivative hydroxytakakiamide (4) was isolated, together with the previously described ergosterol (1), ergosterol acetate (2), and (3R)-3-(1H-indol-3-ylmethyl)-3, 4-dihydro-1H-1,4-benzodiazepine-2,5-dione (3), from the column fractions of the crude ethyl acetate extract of the culture of a marine sponge-associated fungus, Aspergillus fischeri MMERU 23. The structure of 4 was elucidated by the interpretation of 1D and 2D NMR spectral data and high-resolution mass spectrum. The absolute configuration of the stereogenic carbon in 3 was proposed to be the same as those of the co-occurring congeners on the basis of their biogenetic consideration and was supported by the comparison of its sign of optical rotation with those of its steroisomers. The crude ethyl acetate extract and 2 were evaluated, together with acetylaszonalenin (5) and helvolic acid (6), which were previously isolated from the same extract, for the in vivo antinociceptive activity in the mice model. The crude ethyl acetate extract exhibited antinociceptive activity in the acetic acid-induced writhing and formalin tests, while 2, 5, and 6 displayed the effects in the late phase of the formalin test. On the other hand, neither the crude ethyl acetate extract nor 2, 5, and 6 affected the motor performance of mice in both open-field and rotarod tests. Additionally, docking studies of 2, 5, and 6 were performed with 5-lipoxygenase (5-LOX) and phosphodiesterase (PDE) enzymes, PDE4 and PDE7, which are directly related to pain and inflammatory processes. Molecular docking showed that 6 has low affinity energy to PDE4 and PDE7 targets while retaining high affinity to 5-LOX. On the other hand, while 2 did not display any hydrogen bond interactions in any of its complexes, it achieved overall better energy values than 6 on the three antinociceptive targets. On the other hand, 5 has the best energy profile of all the docked compounds and was able to reproduce the crystallographic interactions of the 5-LOX complex.<\/jats:p>","DOI":"10.3390\/md22030097","type":"journal-article","created":{"date-parts":[[2024,2,21]],"date-time":"2024-02-21T06:50:22Z","timestamp":1708498222000},"page":"97","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Hydroxytakakiamide and Other Constituents from a Marine Sponge-Associated Fungus Aspergillus fischeri MMERU23, and Antinociceptive Activity of Ergosterol Acetate, Acetylaszonalenin and Helvolic Acid"],"prefix":"10.3390","volume":"22","author":[{"given":"Harol Ricardo","family":"Arias Cardona","sequence":"first","affiliation":[{"name":"Departamento de Sa\u00fade, Universidade Estadual Feira de Santana, Av. Transnordestina, Feira de Santana 3400-Papagaio, Bahia, Brazil"}]},{"given":"Bruno","family":"Cerqueira da Silva","sequence":"additional","affiliation":[{"name":"Departamento de Sa\u00fade, Universidade Estadual Feira de Santana, Av. Transnordestina, Feira de Santana 3400-Papagaio, Bahia, Brazil"}]},{"given":"Fl\u00e1via Oliveira","family":"de Lima","sequence":"additional","affiliation":[{"name":"Departamento de Sa\u00fade, Universidade Estadual Feira de Santana, Av. Transnordestina, Feira de Santana 3400-Papagaio, Bahia, Brazil"}]},{"given":"Franco Henrique","family":"Andrade Leite","sequence":"additional","affiliation":[{"name":"Departamento de Sa\u00fade, Universidade Estadual Feira de Santana, Av. Transnordestina, Feira de Santana 3400-Papagaio, Bahia, Brazil"}]},{"given":"Bruno Cruz","family":"de Souza","sequence":"additional","affiliation":[{"name":"Departamento de Sa\u00fade, Universidade Estadual Feira de Santana, Av. Transnordestina, Feira de Santana 3400-Papagaio, Bahia, Brazil"}]},{"given":"Hugo Neves","family":"Brand\u00e3o","sequence":"additional","affiliation":[{"name":"Departamento de Sa\u00fade, Universidade Estadual Feira de Santana, Av. Transnordestina, Feira de Santana 3400-Papagaio, Bahia, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6375-9055","authenticated-orcid":false,"given":"Jorge Maur\u00edcio","family":"David","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidade Federal da Bahia, Av. Milton Santos, s\/n\u00ba-Ondina, Salvador 40170-110, Bahia, Brazil"}]},{"given":"Clayton Queiroz","family":"Alves","sequence":"additional","affiliation":[{"name":"Departamento de Ci\u00eancias Exatas, Universidade Estadual Feira de Santana, Av. Transnordestina, Feira de Santana 3400-Papagaio, Bahia, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3321-1061","authenticated-orcid":false,"given":"Anake","family":"Kijjoa","sequence":"additional","affiliation":[{"name":"ICBAS-Instituto de Ci\u00eancias Biom\u00e9dicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2024,2,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Patyshakuliyeva, A., Falkoski, D.L., Wiebenga, A., Klaas Timmermans, K., and de Vries, R.P. (2020). Macroalgae-derived fungi have high abilities to degrade algal polymers. Microorganisms, 8.","DOI":"10.3390\/microorganisms8010052"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"378","DOI":"10.2174\/1567201813666160303104641","article-title":"Bioactive secondary metabolites from a Thai collection of soil and marine-derived fungi of the genera Neosartorya and Aspergillus","volume":"13","author":"Prompanya","year":"2016","journal-title":"Curr. Drug Deliv."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"17116","DOI":"10.1039\/D1RA01359A","article-title":"Recent updates on the bioactive compounds of the marine-derived genus Aspergillus","volume":"11","author":"Orfali","year":"2021","journal-title":"RSC Adv."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"11968","DOI":"10.1080\/07391102.2021.1966510","article-title":"Thermal shift assays of marine-derived fungalmetabolites from Aspergillus fischeri MMERU 23against Leishmania major pteridine reductase 1 and molecular dynamics studies","volume":"40","author":"Cardona","year":"2022","journal-title":"J. Biomol. Struct."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"307","DOI":"10.3390\/md9030307","article-title":"Antinociceptive and anti-Inflammatory Activity from algae of the genus Caulerpa","volume":"9","author":"Matta","year":"2011","journal-title":"Mar. Drugs"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1977","DOI":"10.3390\/md10091977","article-title":"Antinociceptive and anti-inflammatory activities of crude methanolic extract of red alga Bryothamnion triquetrum","volume":"10","author":"Matta","year":"2012","journal-title":"Mar. Drugs"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"683","DOI":"10.1016\/j.bjp.2015.07.017","article-title":"Antinociceptive activity of Sargassum polyceratium and the isolation of its chemical componentes","volume":"25","author":"Santos","year":"2015","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Shih, C.C., Hwang, H.R., Chang, C.I., Su, H.M., Chen, P.C., Kuo, H.M., Li, P.J., Wang, H.M.D., Tsui, K.H., and Lin, Y.C. (2017). Anti-inflammatory and antinociceptive effects of ethyl acetate fraction of an edible red macroalgae Sarcodia ceylanica. Int. J. Mol. Sci., 18.","DOI":"10.3390\/ijms18112437"},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Hort, M.A., J\u00fanior, F.M.R.S., Garcia, E.M., Peraza, G.G., Soares, A., Lerner, C., and Muccillo-Baisch, A.L. (2018). Antinociceptive and anti-inflammatory activities of marine sponges Aplysina caissara, Haliclona sp.. and Dragmacidon Reticulatum. Braz. Arch. Biol. Technol., 61.","DOI":"10.1590\/1678-4324-2018180104"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"689","DOI":"10.3390\/md7040689","article-title":"The antinociceptive and anti-inflammatory activities of caulerpin, a bisindole alkaloid isolated from seaweeds of the genus Caulerpa","volume":"7","author":"Souza","year":"2009","journal-title":"Mar. Drugs"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"966","DOI":"10.1016\/j.ijbiomac.2020.05.166","article-title":"Chemical structure, anti-inflammatory and antinociceptive activities of a sulfated polysaccharide from Gracilaria intermedia alga","volume":"159","author":"Costa","year":"2020","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Sung, C.S., Cheng, H.J., Chen, N.F., Tang, S.H., Kuo, H.M., Sung, P.J., Chen, W.F., and Wen, Z.H. (2023). Antinociceptive effects of aaptamine, a sponge component, on peripheral neuropathy in rats. Mar. Drugs, 21.","DOI":"10.3390\/md21020113"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"405","DOI":"10.1007\/s10600-014-0971-3","article-title":"Secondary metabolites of the marine fungus Penicillium chrysogenum","volume":"50","author":"Wang","year":"2014","journal-title":"Chem. Nat. Compd."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"329","DOI":"10.1055\/s-2006-958093","article-title":"Antinociceptive properties of steroids isolated from Phyllanthus corcovadensis in mice","volume":"61","author":"Santos","year":"1995","journal-title":"Planta Med."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1163","DOI":"10.1007\/s00210-017-1416-x","article-title":"Anti-nociceptive effect of stigmasterol in mouse models of acute and chronic pain","volume":"390","author":"Walker","year":"2017","journal-title":"Naunyn Schmiedebergs Arch. Pharmacol."},{"key":"ref_16","first-page":"238","article-title":"Beta-sitosterol and its antinociceptive mechanism action","volume":"46","year":"2021","journal-title":"J. Fac. Pharm. Ankara"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1002\/jssc.201000577","article-title":"Separation and purification of ergosterol and stigmasterol in Anoectochilus roxburghii (wall) Lindl by high-speed counter-current chromatography","volume":"34","author":"Huang","year":"2011","journal-title":"J. Sep. Sci."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"May Zin, W.W., Buttachon, S., Tida Dethoup, T., Fernande, C., Cravo, S., Pinto, M.M.M., Gales, L., Pereira, J.A., Silva, A.M.S., and Sekeroglu, N. (2016). New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702. Mar. Drugs, 14.","DOI":"10.3390\/md14070136"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"3776","DOI":"10.3390\/md13063776","article-title":"A new meroditerpene and a new tryptoquivaline analog from the algicolous fungus Neosartorya takakii KUFC 7898","volume":"13","author":"Buttachon","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_20","first-page":"100","article-title":"Acetylaszonalenin biosynthesis in Neosartorya fischeri: Identification of the biosynthetic gene cluster by genomic mining and functional proof of the genes bybiochemical investigation","volume":"284","author":"Yin","year":"2009","journal-title":"J. Biochem. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"11116","DOI":"10.1016\/j.tet.2013.11.009","article-title":"Indole-benzodiazepine-2,5-dione derivatives from a soil fungus Aspergillus sp. PSU-RSPG185","volume":"69","author":"Rukachaisirikul","year":"2013","journal-title":"Tetrahedron"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1016\/S0304-3959(00)00476-0","article-title":"Characterization of nociceptive responses and spinal releases of nitric oxide metabolites and glutamate evoked by different concentrations of formalin in rats","volume":"92","author":"Okuda","year":"2001","journal-title":"Pain"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1328","DOI":"10.1111\/j.1460-9568.1994.tb00323.x","article-title":"Intracellular messengers contributing to persistent nociception and hyperalgesia induced by L-glutamate and substance P in the rat formalin pain model","volume":"6","author":"Coderre","year":"1994","journal-title":"Eur. J. Neurosci."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/0304-3959(87)90088-1","article-title":"The formalin test in mice: Dissociation between inflammatory and non-inflammatory pain","volume":"30","author":"Hunskaar","year":"1987","journal-title":"Pain"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1175","DOI":"10.1038\/sj.bjp.0705724","article-title":"Involvement of bradykinin, cytokines, sympathetic amines and prostaglandins in formalin-induced orofacial nociception in rats","volume":"141","author":"Chichorro","year":"2004","journal-title":"Br. J. Pharmacol."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1007\/978-1-4939-8994-2_9","article-title":"The open field test for measuring locomotor activity and anxiety-like behavior","volume":"1916","author":"Kraeuter","year":"2019","journal-title":"Methods Mol. Biol."},{"key":"ref_27","first-page":"2609","article-title":"Measuring motor coordination in mice","volume":"75","author":"Deacon","year":"2013","journal-title":"J. Vis. Exp."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Yam, M.F., Loh, Y.C., Tan, C.S., Adam, S.K., Manan, N.A., and Basir, R. (2018). General pathways of pain sensation and the major neurotransmitters involved in pain regulation. Int. J. Mol. Sci., 19.","DOI":"10.3390\/ijms19082164"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"6060","DOI":"10.1039\/D0RA10657G","article-title":"Research developments in the syntheses, antiinflammatory activities and structure\u2013activity relationships of pyrimidines","volume":"11","author":"Rashid","year":"2021","journal-title":"RSC Adv."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"253","DOI":"10.2147\/JIR.S278514","article-title":"Overview on the discovery and development of anti-Inflammatory drugs: Should the focus be on synthesis or degradation of PGE2?","volume":"14","author":"Mahesh","year":"2021","journal-title":"J. Inflamm. Res."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1007\/s12325-011-0100-7","article-title":"5-Lipoxygenase metabolic contributions to NSAID-induced organ toxicity","volume":"29","author":"Burnett","year":"2012","journal-title":"Adv. Ther."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"259","DOI":"10.3389\/fphar.2020.00259","article-title":"Inhaled phosphodiesterase 4 (PDE4) inhibitors for inflammatory respiratory diseases","volume":"11","author":"Phillips","year":"2020","journal-title":"Front. Pharmacol."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"291","DOI":"10.2147\/JEP.S242961","article-title":"New avenues for phosphodiesterase inhibitors in asthma","volume":"13","author":"Matera","year":"2021","journal-title":"J. Exp. Pharmacol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"6724","DOI":"10.2174\/0929867325666180622151438","article-title":"Phytosterols and inflammation","volume":"26","author":"Vilahur","year":"2019","journal-title":"Curr. Med. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Le\u00f3n-\u00c1lvarez, E., Pacheco, C.M., Gesto-Borroto, R., Acosta-Urdapilleta, M.L., Maura T\u00e9llez-T\u00e9llez, M., Gonz\u00e1lez, R.B., N\u00fa\u00f1ez-Arag\u00f3n, P.N., Villarreal, M.L., and Taketa, A.T.C. (2024). Anti-inflammatory, radical-scavenging, and chelating activities of nor-triterpenes from Galphimia species. Rev. Bras. Farmacogn., 1\u201311.","DOI":"10.1007\/s43450-023-00506-3"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3745","DOI":"10.1016\/j.bmc.2019.06.040","article-title":"5-Lipoxygenase as a drug target: A review on trends in inhibitors structural design, SAR and mechanism based approach","volume":"27","author":"Sinha","year":"2019","journal-title":"Bioorg. Med. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Szczypka, M. (2020). Role of phosphodiesterase 7 (PDE7) in T cell activity. Effects of selective PDE7 inhibitors and dual PDE4\/7 inhibitors on T cell functions. Int. J. Mol. Sci., 21.","DOI":"10.3390\/ijms21176118"},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Paterniti, I., Mazzon, E., Gil, C., Impellizzeri, D., Palomo, V., Redondo, M., Perez, D.I., Esposito, E., Martinez, A., and Cuzzocrea, S. (2011). PDE 7 inhibitors: New potential drugs for the therapy of spinal cord injury. PLoS ONE, 6.","DOI":"10.1371\/journal.pone.0015937"},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Shinada, N.K., Schmidtke, P., and Brevern, A.G. (2020). Accurate representation of protein-ligand structural diversity in the protein data bank (PDB). Int. J. Mol. Sci., 21.","DOI":"10.3390\/ijms21062243"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Ponsaerts, L., Alders, L., Schepers, M., Oliveira, R.M.W.O., Prickaerts, J., Vanmierlo, T., and Bronckaers, A. (2021). Neuroinflammation in ischemic stroke: Inhibition of cAMP-specific phosphodiesterases (PDEs) to the rescue. Biomedicines, 9.","DOI":"10.3390\/biomedicines9070703"},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Maione, F., Minosi, P., Di Giannuario, A., Raucci, F., Chini, M.G., De Vita, S., Bifulco, G., Mascolo, N., and Pieretti, S. (2019). Long-lasting anti-inflammatory and antinociceptive effects of acute ammonium glycyrrhizinate administration: Pharmacological, biochemical, and docking studies. Molecules, 24.","DOI":"10.3390\/molecules24132453"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1016\/0304-3959(83)90201-4","article-title":"Ethical guidelines for investigations of experimental pain in conscious animals","volume":"16","author":"Zimmermann","year":"1983","journal-title":"Pain"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"293","DOI":"10.1016\/j.carbpol.2014.01.064","article-title":"Extraction optimization and antinociceptive activity of (1\u21923)-\u03b2-D-glucan from Rhodotorula mucilaginosa","volume":"105","author":"Lima","year":"2014","journal-title":"Carbohydr. Polym."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1111\/j.1476-5381.1968.tb00973.x","article-title":"The abdominal constriction response and its suppression by analgesic drugs in the mouse","volume":"32","author":"Collier","year":"1968","journal-title":"Br. J. Pharmacol. Chemother."},{"key":"ref_45","first-page":"61","article-title":"The formalin test: A quantitative study of the analgesic effects of morphine, meperidine, and brain stem stimulation in rats and cats","volume":"4","author":"Dubuisson","year":"1997","journal-title":"Pain"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1347","DOI":"10.1016\/S0024-3205(01)01498-9","article-title":"Involvement of monoaminergic system in the antidepressant-like effect of the hydroalcoholic extract of Siphocampylus verticillatus","volume":"70","author":"Rodrigues","year":"2002","journal-title":"Life Sci."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"4308","DOI":"10.1016\/j.bmcl.2013.05.099","article-title":"Discovery of triazines as potent, selective and orally active PDE4 inhibitors","volume":"23","author":"Gewald","year":"2013","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"783","DOI":"10.1038\/s41589-020-0544-7","article-title":"Structural and mechanistic insights into 5-lipoxygenase inhibition by natural products","volume":"16","author":"Gilbert","year":"2020","journal-title":"Nat. Chem. Biol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"30949","DOI":"10.1074\/jbc.M504398200","article-title":"Multiple elements jointly determine inhibitor selectivity of cyclic nucleotide phosphodiesterases 4 and 7","volume":"280","author":"Wang","year":"2005","journal-title":"J. Biol. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"D437","DOI":"10.1093\/nar\/gkaa1038","article-title":"RCSB Protein data bank: Powerful new tools for exploring 3D structures of biological macromolecules for basic and applied research and education in fundamental biology, biomedicine, biotechnology, bioengineering and energy sciences","volume":"49","author":"Burley","year":"2021","journal-title":"Nucleic Acids Res."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"3891","DOI":"10.1021\/acs.jcim.1c00203","article-title":"AutoDock Vina 1.2.0: New docking methods, expanded force field, and Python bindings","volume":"61","author":"Eberhardt","year":"2021","journal-title":"J. Chem. Inf. Model."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"W443","DOI":"10.1093\/nar\/gkv315","article-title":"PLIP: Fully automated protein-ligand interaction profiler","volume":"43","author":"Salentin","year":"2015","journal-title":"Nucleic Acids Res."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/22\/3\/97\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T14:01:58Z","timestamp":1760104918000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/22\/3\/97"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,2,20]]},"references-count":52,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2024,3]]}},"alternative-id":["md22030097"],"URL":"https:\/\/doi.org\/10.3390\/md22030097","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,2,20]]}}}