دورية أكاديمية

Synthesis of Indomorphan Pseudo-Natural Product Inhibitors of Glucose Transporters GLUT-1 and -3.

التفاصيل البيبلوغرافية
العنوان: Synthesis of Indomorphan Pseudo-Natural Product Inhibitors of Glucose Transporters GLUT-1 and -3.
المؤلفون: Ceballos J; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany.; Current address: Laboratory of Catalysis and Organic Synthesis, EPFL SB ISIC LCSO, BCH 4221, 1015, Lausanne, Switzerland., Schwalfenberg M; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany., Karageorgis G; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany.; Current address: School of Chemistry, University of Leeds, Leeds, LS2 9JT, UK., Reckzeh ES; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany.; Faculty of Chemistry and Chemical Biology, Technical University Dortmund, Otto-Hahn-Strasse 6, 44227, Dortmund, Germany., Sievers S; Compound Management and Screening Center, Dortmund, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany., Ostermann C; Compound Management and Screening Center, Dortmund, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany., Pahl A; Compound Management and Screening Center, Dortmund, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany., Sellstedt M; Department of Chemistry, Umeå University, 901 87, Umeå, Sweden.; Current address: Clinical Chemistry, Laboratory Medicine, University Hospital of Umeå, 901 85, Umeå, Sweden., Nowacki J; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany., Carnero Corrales MA; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany., Wilke J; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany.; Faculty of Chemistry and Chemical Biology, Technical University Dortmund, Otto-Hahn-Strasse 6, 44227, Dortmund, Germany., Laraia L; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany.; Current address: Department of Chemistry, Technical University of Denmark, Kemitorvet, Bygning 207, 2800, Kgs Lyngby, Denmark., Tschapalda K; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany., Metz M; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany., Sehr DA; Department of Molecular Cell Biology, Institute of Biochemistry and Pathobiochemistry, Ruhr University Bochum, 44801, Bochum, Germany., Brand S; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany., Winklhofer K; Department of Molecular Cell Biology, Institute of Biochemistry and Pathobiochemistry, Ruhr University Bochum, 44801, Bochum, Germany., Janning P; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany., Ziegler S; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany., Waldmann H; Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227, Dortmund, Germany.; Faculty of Chemistry and Chemical Biology, Technical University Dortmund, Otto-Hahn-Strasse 6, 44227, Dortmund, Germany.
المصدر: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Nov 18; Vol. 58 (47), pp. 17016-17025. Date of Electronic Publication: 2019 Oct 07.
نوع المنشور: Journal Article; Research Support, Non-U.S. Gov't
اللغة: English
بيانات الدورية: Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: MEDLINE
أسماء مطبوعة: Publication: <2004-> : Weinheim : Wiley-VCH
Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-
مواضيع طبية MeSH: Cell Proliferation*, Biological Products/*pharmacology , Glucose/*metabolism , Glucose Transporter Type 1/*antagonists & inhibitors , Glucose Transporter Type 3/*antagonists & inhibitors , Morphinans/*chemical synthesis , Neoplasms/*drug therapy, Biological Transport ; Cell Cycle ; Glycolysis ; Humans ; Tumor Cells, Cultured
مستخلص: Bioactive compound design based on natural product (NP) structure may be limited because of partial coverage of NP-like chemical space and biological target space. These limitations can be overcome by combining NP-centered strategies with fragment-based compound design through combination of NP-derived fragments to afford structurally unprecedented "pseudo-natural products" (pseudo-NPs). The design, synthesis, and biological evaluation of a collection of indomorphan pseudo-NPs that combine biosynthetically unrelated indole- and morphan-alkaloid fragments are described. Indomorphane derivative Glupin was identified as a potent inhibitor of glucose uptake by selectively targeting and upregulating glucose transporters GLUT-1 and GLUT-3. Glupin suppresses glycolysis, reduces the levels of glucose-derived metabolites, and attenuates the growth of various cancer cell lines. Our findings underscore the importance of dual GLUT-1 and GLUT-3 inhibition to efficiently suppress tumor cell growth and the cellular rescue mechanism, which counteracts glucose scarcity.
(© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)
References: Nat Chem. 2013 Jan;5(1):21-8. (PMID: 23247173)
Biochem Biophys Res Commun. 1990 Jul 16;170(1):223-30. (PMID: 2372287)
Nat Chem. 2015 Sep;7(9):737-43. (PMID: 26291946)
Medchemcomm. 2016 Sep 1;7(9):1716-1729. (PMID: 28042452)
Neoplasia. 2005 Apr;7(4):324-30. (PMID: 15967109)
J Cell Sci. 1994 Mar;107 ( Pt 3):487-96. (PMID: 8006068)
Oncogenesis. 2016 Jan 25;5:e189. (PMID: 26807644)
Nucleic Acids Res. 2014 Jan;42(Database issue):D1083-90. (PMID: 24214965)
Angew Chem Int Ed Engl. 2003 Sep 5;42(34):3996-4028. (PMID: 12973759)
Int J Cancer. 1994 Mar 1;56(5):622-9. (PMID: 8314336)
Proc Natl Acad Sci U S A. 2015 Aug 11;112(32):E4410-7. (PMID: 26216984)
Angew Chem Int Ed Engl. 2012 Apr 23;51(17):4012-22. (PMID: 22441812)
Nat Commun. 2017 Feb 06;8:14207. (PMID: 28165449)
Cell Chem Biol. 2016 Jan 21;23(1):3-9. (PMID: 26933731)
Nat Protoc. 2015 Oct;10(10):1567-93. (PMID: 26379230)
J Chem Inf Comput Sci. 2003 May-Jun;43(3):987-1003. (PMID: 12767158)
J Biol Chem. 2002 Aug 23;277(34):30409-12. (PMID: 12087111)
Anal Biochem. 2010 Sep 15;404(2):238-40. (PMID: 20494642)
J Am Chem Soc. 2014 Aug 27;136(34):11853-9. (PMID: 25074019)
Bioorg Med Chem Lett. 2015 Aug 15;25(16):3079-86. (PMID: 26115575)
Nucleic Acids Res. 2014 Jan;42(Database issue):D1091-7. (PMID: 24203711)
Biochem J. 1994 May 15;300 ( Pt 1):125-31. (PMID: 8198523)
Pathol Oncol Res. 2012 Jul;18(3):721-8. (PMID: 22270867)
Histol Histopathol. 2009 Aug;24(8):971-7. (PMID: 19554504)
Science. 2009 May 22;324(5930):1029-33. (PMID: 19460998)
Chem Commun (Camb). 2016 Jun 7;52(45):7209-12. (PMID: 27145833)
Angew Chem Int Ed Engl. 2019 Nov 18;58(47):17016-17025. (PMID: 31469221)
Nat Chem. 2009 Jun;1(3):187-92. (PMID: 21378847)
Angew Chem Int Ed Engl. 2014 Jan 3;53(1):220-4. (PMID: 24273016)
Chemotherapy. 2007;53(4):233-56. (PMID: 17595539)
Cell Chem Biol. 2019 Sep 19;26(9):1214-1228.e25. (PMID: 31303578)
FEBS J. 2014 Aug;281(15):3325-45. (PMID: 24912776)
Nat Chem. 2018 Nov;10(11):1103-1111. (PMID: 30202104)
Am J Physiol Endocrinol Metab. 2008 Aug;295(2):E242-53. (PMID: 18577699)
Chem Biol. 2014 Jun 19;21(6):766-74. (PMID: 24856821)
J Cancer. 2018 Apr 12;9(9):1582-1591. (PMID: 29760796)
ChemMedChem. 2016 Oct 19;11(20):2261-2271. (PMID: 27552707)
Org Lett. 2016 Nov 18;18(22):5948-5951. (PMID: 27934494)
Molecules. 2013 Jun 06;18(6):6620-62. (PMID: 23743888)
Nat Rev Cancer. 2011 May;11(5):325-37. (PMID: 21508971)
J Chem Inf Model. 2008 Jan;48(1):68-74. (PMID: 18034468)
Org Lett. 2013 May 17;15(10):2458-61. (PMID: 23627688)
Anticancer Res. 2015 Nov;35(11):5889-99. (PMID: 26504012)
Nat Chem. 2013 Mar;5(3):195-202. (PMID: 23422561)
Acc Chem Res. 2008 Jan;41(1):21-31. (PMID: 18159935)
Bioorg Med Chem Lett. 2016 Apr 1;26(7):1732-7. (PMID: 26949183)
Mol Med Rep. 2012 Sep;6(3):601-6. (PMID: 22752218)
Anal Biochem. 2006 Apr 1;351(1):139-45. (PMID: 16442489)
Nat Prod Rep. 2012 Aug;29(8):870-89. (PMID: 22744619)
Angew Chem Int Ed Engl. 2011 Nov 11;50(46):10800-26. (PMID: 22038946)
Chem Rev. 2006 Jul;106(7):2875-911. (PMID: 16836303)
J Med Chem. 1998 Oct 8;41(21):4143-9. (PMID: 9767649)
Cancer. 1997 Sep 15;80(6):1046-51. (PMID: 9305704)
Org Biomol Chem. 2009 Jun 21;7(12):2517-9. (PMID: 19503923)
Cell Chem Biol. 2019 Apr 18;26(4):512-523.e5. (PMID: 30686759)
Arch Pharm (Weinheim). 2001 Sep;334(8-9):284-90. (PMID: 11688139)
J Org Chem. 1967 Nov;32(11):3691-3. (PMID: 5622462)
معلومات مُعتمدة: 268309 International FP7 Ideas: European Research Council; International Alexander von Humboldt-Stiftung; International Fonds der Chemischen Industrie; Switzerland SNSF_ Swiss National Science Foundation; 350-2012-6611 International Swedish Research Council
فهرسة مساهمة: Keywords: antitumor agents; glucose transporters; inhibitors; natural products; pseudo-natural products
المشرفين على المادة: 0 (Biological Products)
0 (Glucose Transporter Type 1)
0 (Glucose Transporter Type 3)
0 (Morphinans)
0 (SLC2A1 protein, human)
0 (SLC2A3 protein, human)
IY9XDZ35W2 (Glucose)
تواريخ الأحداث: Date Created: 20190831 Date Completed: 20200921 Latest Revision: 20240723
رمز التحديث: 20240723
مُعرف محوري في PubMed: PMC6900016
DOI: 10.1002/anie.201909518
PMID: 31469221
قاعدة البيانات: MEDLINE