Antifungal Thiazolidines: Synthesis and Biological Evaluation of Mycosidine Congeners

Novel derivatives of Mycosidine (3,5-substituted thiazolidine-2,4-diones) are synthesized by Knoevenagel condensation and reactions of thiazolidines with chloroformates or halo-acetic acid esters. Furthermore, 5-Arylidene-2,4-thiazolidinediones and their 2-thioxo analogs containing halogen and hydro...

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Published inPharmaceuticals (Basel, Switzerland) Vol. 15; no. 5; p. 563
Main Authors Levshin, Igor B., Simonov, Alexander Y., Lavrenov, Sergey N., Panov, Alexey A., Grammatikova, Natalia E., Alexandrov, Alexander A., Ghazy, Eslam S. M. O., Savin, Nikita A., Gorelkin, Peter V., Erofeev, Alexander S., Polshakov, Vladimir I.
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 01.05.2022
MDPI
Subjects
antifungal activity
Antifungal agents
Antimicrobial agents
Cancer
Cell cycle
cell wall
Diabetic neuropathy
drug design
Drugs
Enzymes
glucose transport
Pathogens
Phosphatase
Potash
Potassium
thiazolidine-2,4-dione
Tumor necrosis factor-TNF
glucose transport
cell wall
drug design
antifungal activity
thiazolidine-2,4-dione
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Abstract Novel derivatives of Mycosidine (3,5-substituted thiazolidine-2,4-diones) are synthesized by Knoevenagel condensation and reactions of thiazolidines with chloroformates or halo-acetic acid esters. Furthermore, 5-Arylidene-2,4-thiazolidinediones and their 2-thioxo analogs containing halogen and hydroxy groups or di(benzyloxy) substituents in 5-benzylidene moiety are tested for antifungal activity in vitro. Some of the synthesized compounds exhibit high antifungal activity, both fungistatic and fungicidal, and lead to morphological changes in the Candida yeast cell wall. Based on the use of limited proteomic screening and toxicity analysis in mutants, we show that Mycosidine activity is associated with glucose transport. This suggests that this first-in-class antifungal drug has a novel mechanism of action that deserves further study.
AbstractList Novel derivatives of Mycosidine (3,5-substituted thiazolidine-2,4-diones) are synthesized by Knoevenagel condensation and reactions of thiazolidines with chloroformates or halo-acetic acid esters. Furthermore, 5-Arylidene-2,4-thiazolidinediones and their 2-thioxo analogs containing halogen and hydroxy groups or di(benzyloxy) substituents in 5-benzylidene moiety are tested for antifungal activity in vitro. Some of the synthesized compounds exhibit high antifungal activity, both fungistatic and fungicidal, and lead to morphological changes in the Candida yeast cell wall. Based on the use of limited proteomic screening and toxicity analysis in mutants, we show that Mycosidine activity is associated with glucose transport. This suggests that this first-in-class antifungal drug has a novel mechanism of action that deserves further study.
Novel derivatives of Mycosidine (3,5-substituted thiazolidine-2,4-diones) are synthesized by Knoevenagel condensation and reactions of thiazolidines with chloroformates or halo-acetic acid esters. Furthermore, 5-Arylidene-2,4-thiazolidinediones and their 2-thioxo analogs containing halogen and hydroxy groups or di(benzyloxy) substituents in 5-benzylidene moiety are tested for antifungal activity in vitro. Some of the synthesized compounds exhibit high antifungal activity, both fungistatic and fungicidal, and lead to morphological changes in the Candida yeast cell wall. Based on the use of limited proteomic screening and toxicity analysis in mutants, we show that Mycosidine activity is associated with glucose transport. This suggests that this first-in-class antifungal drug has a novel mechanism of action that deserves further study.
Novel derivatives of Mycosidine (3,5-substituted thiazolidine-2,4-diones) are synthesized by Knoevenagel condensation and reactions of thiazolidines with chloroformates or halo-acetic acid esters. Furthermore, 5-Arylidene-2,4-thiazolidinediones and their 2-thioxo analogs containing halogen and hydroxy groups or di(benzyloxy) substituents in 5-benzylidene moiety are tested for antifungal activity in vitro. Some of the synthesized compounds exhibit high antifungal activity, both fungistatic and fungicidal, and lead to morphological changes in the Candida yeast cell wall. Based on the use of limited proteomic screening and toxicity analysis in mutants, we show that Mycosidine activity is associated with glucose transport. This suggests that this first-in-class antifungal drug has a novel mechanism of action that deserves further study.Novel derivatives of Mycosidine (3,5-substituted thiazolidine-2,4-diones) are synthesized by Knoevenagel condensation and reactions of thiazolidines with chloroformates or halo-acetic acid esters. Furthermore, 5-Arylidene-2,4-thiazolidinediones and their 2-thioxo analogs containing halogen and hydroxy groups or di(benzyloxy) substituents in 5-benzylidene moiety are tested for antifungal activity in vitro. Some of the synthesized compounds exhibit high antifungal activity, both fungistatic and fungicidal, and lead to morphological changes in the Candida yeast cell wall. Based on the use of limited proteomic screening and toxicity analysis in mutants, we show that Mycosidine activity is associated with glucose transport. This suggests that this first-in-class antifungal drug has a novel mechanism of action that deserves further study.
Novel derivatives of Mycosidine (3,5-substituted thiazolidine-2,4-diones) are synthesized by Knoevenagel condensation and reactions of thiazolidines with chloroformates or halo-acetic acid esters. Furthermore, 5-Arylidene-2,4-thiazolidinediones and their 2-thioxo analogs containing halogen and hydroxy groups or di(benzyloxy) substituents in 5-benzylidene moiety are tested for antifungal activity in vitro. Some of the synthesized compounds exhibit high antifungal activity, both fungistatic and fungicidal, and lead to morphological changes in the yeast cell wall. Based on the use of limited proteomic screening and toxicity analysis in mutants, we show that Mycosidine activity is associated with glucose transport. This suggests that this first-in-class antifungal drug has a novel mechanism of action that deserves further study.
Author Levshin, Igor B.
Lavrenov, Sergey N.
Gorelkin, Peter V.
Erofeev, Alexander S.
Savin, Nikita A.
Grammatikova, Natalia E.
Polshakov, Vladimir I.
Ghazy, Eslam S. M. O.
Alexandrov, Alexander A.
Panov, Alexey A.
Simonov, Alexander Y.
AuthorAffiliation 4 Department of Microbiology, Faculty of Pharmacy, Tanta University, Tanta 31111, Egypt
1 Gause Institute of New Antibiotics, 11 B. Pirogovskaya Street, 119021 Moscow, Russia; levshin@panavir.ru (I.B.L.); simonov-live@inbox.ru (A.Y.S.); satory@mail.ru (S.N.L.); ngrammatikova@yandex.ru (N.E.G.)
3 Institute of Biochemical Technology and Nanotechnology, Peoples’ Friendship University of Russia (RUDN), 6 Miklukho-Maklaya Street, 117198 Moscow, Russia
5 Research Laboratory of Biophysics, National University of Science and Technology “MISiS”, 4 Leninsky Ave., 119049 Moscow, Russia; nsavin99@mail.ru (N.A.S.); peter.gorelkin@gmail.com (P.V.G.); erofeev@polly.phys.msu.ru (A.S.E.)
2 Bach Institute of Biochemistry, Federal Research Center of Biotechnology of the RAS, 119071 Moscow, Russia; alexvir@inbi.ras.ru (A.A.A.); 1072195050@rudn.ru (E.S.M.O.G.)
6 Faculty of Fundamental Medicine, Lomonosov Moscow State University, 27/1 Lomonosovsky Ave., 119991 Moscow, Russia; vpolsha@fbm.msu.ru
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– name: 3 Institute of Biochemical Technology and Nanotechnology, Peoples’ Friendship University of Russia (RUDN), 6 Miklukho-Maklaya Street, 117198 Moscow, Russia
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– name: 5 Research Laboratory of Biophysics, National University of Science and Technology “MISiS”, 4 Leninsky Ave., 119049 Moscow, Russia; nsavin99@mail.ru (N.A.S.); peter.gorelkin@gmail.com (P.V.G.); erofeev@polly.phys.msu.ru (A.S.E.)
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/35631390$$D View this record in MEDLINE/PubMed
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Keywords glucose transport
cell wall
drug design
antifungal activity
thiazolidine-2,4-dione
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Snippet Novel derivatives of Mycosidine (3,5-substituted thiazolidine-2,4-diones) are synthesized by Knoevenagel condensation and reactions of thiazolidines with...
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SubjectTerms antifungal activity
Antifungal agents
Antimicrobial agents
Cancer
Cell cycle
cell wall
Diabetic neuropathy
drug design
Drugs
Enzymes
glucose transport
Pathogens
Phosphatase
Potash
Potassium
thiazolidine-2,4-dione
Tumor necrosis factor-TNF
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Title Antifungal Thiazolidines: Synthesis and Biological Evaluation of Mycosidine Congeners
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