Synthesis and Evaluation of the Tetracyclic Ring-System of Isocryptolepine and Regioisomers for Antimalarial, Antiproliferative and Antimicrobial Activities

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Haheim, Katja S
Lindback, Emil
Tan, Kah Ni
Albrigtsen, Marte
Urdal Helgeland, Ida T
Lauga, Clemence
Matringe, Theodora
Kennedy, Emily K
Andersen, Jeanette H
Avery, Vicky M
Sydnes, Magne O
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2021
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Abstract

A series of novel quinoline-based tetracyclic ring-systems were synthesized and evaluated in vitro for their antiplasmodial, antiproliferative and antimicrobial activities. The novel hydroiodide salts 10 and 21 showed the most promising antiplasmodial inhibition, with compound 10 displaying higher selectivity than the employed standards. The antiproliferative assay revealed novel pyridophenanthridine 4b to be significantly more active against human prostate cancer (IC50 = 24 nM) than Puromycin (IC50 = 270 nM) and Doxorubicin (IC50 = 830 nM), which are used for clinical treatment. Pyridocarbazoles 9 was also moderately effective against all the employed cancer cell lines and moreover showed excellent biofilm inhibition (9a: MBIC = 100 µM; 9b: MBIC = 100 µM).

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Molecules

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26

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11

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© 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).

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Medicinal and biomolecular chemistry

Organic chemistry

Theoretical and computational chemistry

Science & Technology

Life Sciences & Biomedicine

Physical Sciences

Biochemistry & Molecular Biology

Chemistry, Multidisciplinary

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Haheim, KS; Lindback, E; Tan, KN; Albrigtsen, M; Urdal Helgeland, IT; Lauga, C; Matringe, T; Kennedy, EK; Andersen, JH; Avery, VM; Sydnes, MO, Synthesis and Evaluation of the Tetracyclic Ring-System of Isocryptolepine and Regioisomers for Antimalarial, Antiproliferative and Antimicrobial Activities, Molecules, 2021, 26 (11), pp. 3268

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