دورية أكاديمية
أعرض في EDS

Total Synthesis and Biological Profiling of Putative (±)-Marinoaziridine B and (±)- N -Methyl Marinoaziridine A.

التفاصيل البيبلوغرافية
العنوان: Total Synthesis and Biological Profiling of Putative (±)-Marinoaziridine B and (±)- N -Methyl Marinoaziridine A.
المؤلفون: Buljan A; Laboratory for Chiral Technologies, Scientific Center of Excellence for Marine Bioprospecting-BioProCro, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia., Stepanić V; Laboratory for Machine Learning and Knowledge Representation, Division of Electronics, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia., Čikoš A; NMR Centre, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia., Babić Brčić S; Laboratory for Aquaculture Biotechnology, Scientific Center of Excellence for Marine Bioprospecting-BioProCro, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia., Bojanić K; Laboratory for Aquaculture Biotechnology, Scientific Center of Excellence for Marine Bioprospecting-BioProCro, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia., Roje M; Laboratory for Chiral Technologies, Scientific Center of Excellence for Marine Bioprospecting-BioProCro, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia.
المصدر: Marine drugs [Mar Drugs] 2024 Jul 03; Vol. 22 (7). Date of Electronic Publication: 2024 Jul 03.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: MDPI Country of Publication: Switzerland NLM ID: 101213729 Publication Model: Electronic Cited Medium: Internet ISSN: 1660-3397 (Electronic) Linking ISSN: 16603397 NLM ISO Abbreviation: Mar Drugs Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI, [2003]-
مواضيع طبية MeSH: Aziridines*/pharmacology , Aziridines*/chemistry , Aziridines*/chemical synthesis , Staphylococcus aureus*/drug effects, Humans ; Animals ; HEK293 Cells ; Anti-Bacterial Agents/pharmacology ; Anti-Bacterial Agents/chemical synthesis ; Anti-Bacterial Agents/chemistry ; Escherichia coli/drug effects ; Zebrafish ; MCF-7 Cells ; Microbial Sensitivity Tests ; Biological Products/pharmacology ; Biological Products/chemistry ; Biological Products/chemical synthesis ; Cell Line, Tumor ; Antineoplastic Agents/pharmacology ; Antineoplastic Agents/chemical synthesis ; Antineoplastic Agents/chemistry ; Cell Proliferation/drug effects
مستخلص: The total synthesis of two new marine natural products, (±)-marinoaziridine B 7 and (±)- N -methyl marinoaziridine A 8 , was accomplished. The (±)-marinoaziridine 7 was prepared in a six-step linear sequence with a 2% overall yield. The key steps in our strategy were the preparation of the chiral epoxide (±)- 5 using the Johnson Corey Chaykovsky reaction, followed by the ring-opening reaction and the Staudinger reaction. The N , N -dimethylation of compound (±)- 7 gives (±)- N -methyl marinoaziridine A 8 . The NMR spectra of synthetized (±)-marinoaziridine B 7 and isolated natural product did not match. The compounds are biologically characterized using relevant in silico, in vitro and in vivo methods. In silico ADMET and bioactivity profiling predicted toxic and neuromodulatory effects. In vitro screening by MTT assay on three cell lines (MCF-7, H-460, HEK293T) showed that both compounds exhibited moderate to strong antiproliferative and cytotoxic effects. Antimicrobial tests on bacterial cultures of Escherichia coli and Staphylococcus aureus demonstrated the dose-dependent inhibition of the growth of both bacteria. In vivo toxicological tests were performed on zebrafish Danio rerio and showed a significant reduction of zebrafish mortality due to N -methylation in (±)- 8 .
References: Nat Prod Rep. 2016 Nov 23;33(12):1425-1446. (PMID: 27714041)
Chem Res Toxicol. 2012 Nov 19;25(11):2378-85. (PMID: 23078046)
Biochim Biophys Acta. 2013 Jun;1830(6):3670-95. (PMID: 23428572)
Mar Drugs. 2022 Aug 19;20(8):. (PMID: 36005533)
Chem Soc Rev. 2002 Sep;31(5):247-58. (PMID: 12357722)
J Nat Prod. 2012 Mar 23;75(3):311-35. (PMID: 22316239)
Int J Mol Sci. 2021 Apr 21;22(9):. (PMID: 33919163)
J Nat Prod. 2007 Mar;70(3):461-77. (PMID: 17309302)
Chem Biol. 2015 Sep 17;22(9):1270-9. (PMID: 26299672)
ACS Med Chem Lett. 2018 Sep 13;9(10):959-961. (PMID: 30344898)
Mar Drugs. 2019 Jun 06;17(6):. (PMID: 31174259)
Perspect Biol Med. 1989 Winter;32(2):244-56. (PMID: 2648321)
Sci Rep. 2021 Jan 28;11(1):2527. (PMID: 33510260)
J Nat Prod. 2016 Mar 25;79(3):629-61. (PMID: 26852623)
Austral Ecol. 2011 May 1;36(3):341-356. (PMID: 22737038)
J Nat Prod. 1997 Jan;60(1):52-60. (PMID: 9014353)
J Genet Eng Biotechnol. 2022 Jan 26;20(1):14. (PMID: 35080679)
Mar Drugs. 2022 Aug 18;20(8):. (PMID: 36005531)
Nucleic Acids Res. 2019 Jul 2;47(W1):W357-W364. (PMID: 31106366)
J Nat Prod. 2003 Jul;66(7):1022-37. (PMID: 12880330)
Mar Drugs. 2015 Jun 30;13(7):4044-136. (PMID: 26133553)
معلومات مُعتمدة: KK.01.1.1.01.0002 Croatian Government and the European Union through the European Regional Development Fund-the Competitiveness and Cohesion Operational Programme (KK.01.1.1.01) through the project Bioprospecting of the Adriatic Sea (KK.01.1.1.01.0002) granted to The Scien
فهرسة مساهمة: Keywords: ADMET; antibacterial activity; antiproliferative activity; bioactivity profiling; cytotoxicity; in silico activity; marine natural products; marinoaziridines; total synthesis
المشرفين على المادة: 0 (Aziridines)
0 (Anti-Bacterial Agents)
0 (Biological Products)
0 (Antineoplastic Agents)
تواريخ الأحداث: Date Created: 20240726 Date Completed: 20240726 Latest Revision: 20240728
رمز التحديث: 20240728
مُعرف محوري في PubMed: PMC11278217
DOI: 10.3390/md22070310
PMID: 39057419
قاعدة البيانات: MEDLINE
الوصف
تدمد:1660-3397
DOI:10.3390/md22070310