The Tuberculosis Drug Candidate SQ109 and Its Analogs Have Multistage Activity against Plasmodium falciparum
Toward repositioning the antitubercular clinical candidate SQ109 as an antimalarial, analogs were investigated for structure–activity relationships for activity against asexual blood stages of the human malaria parasite Plasmodium falciparum pathogenic forms, as well as transmissible, sexual stage g...
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| Veröffentlicht in: | ACS infectious diseases 2024-09, Vol.10 (9), p.3358-3367 |
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| creator | Watson, Savannah J. van der Watt, Mariëtte E. Theron, Anjo Reader, Janette Tshabalala, Sizwe Erlank, Erica Koekemoer, Lizette L. Naude, Mariska Stampolaki, Marianna Adewole, Feyisola Sadowska, Katie Pérez-Lozano, Pilar Turcu, Andreea L. Vázquez, Santiago Ko, Jihee Mazurek, Ben Singh, Davinder Malwal, Satish R. Njoroge, Mathew Chibale, Kelly Onajole, Oluseye K. Kolocouris, Antonios Oldfield, Eric Birkholtz, Lyn-Marié |
| description | Toward repositioning the antitubercular clinical candidate SQ109 as an antimalarial, analogs were investigated for structure–activity relationships for activity against asexual blood stages of the human malaria parasite Plasmodium falciparum pathogenic forms, as well as transmissible, sexual stage gametocytes. We show that equipotent activity (IC50) in the 100–300 nM range could be attained for both asexual and sexual stages, with the activity of most compounds retained against a multidrug-resistant strain. The multistage activity profile relies on high lipophilicity ascribed to the adamantane headgroup, and antiplasmodial activity is critically dependent on the diamine linker. Frontrunner compounds showed conserved activity against genetically diverse southern African clinical isolates. We additionally validated that this series could block transmission to mosquitoes, marking these compounds as novel chemotypes with multistage antiplasmodial activity. |
| doi_str_mv | 10.1021/acsinfecdis.4c00461 |
| format | Article |
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We show that equipotent activity (IC50) in the 100–300 nM range could be attained for both asexual and sexual stages, with the activity of most compounds retained against a multidrug-resistant strain. The multistage activity profile relies on high lipophilicity ascribed to the adamantane headgroup, and antiplasmodial activity is critically dependent on the diamine linker. Frontrunner compounds showed conserved activity against genetically diverse southern African clinical isolates. We additionally validated that this series could block transmission to mosquitoes, marking these compounds as novel chemotypes with multistage antiplasmodial activity.</description><identifier>ISSN: 2373-8227</identifier><identifier>EISSN: 2373-8227</identifier><identifier>DOI: 10.1021/acsinfecdis.4c00461</identifier><identifier>PMID: 39143042</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Adamantane - analogs & derivatives ; Adamantane - chemistry ; Adamantane - pharmacology ; Animals ; Antimalarials - chemistry ; Antimalarials - pharmacology ; Antitubercular Agents - chemistry ; Antitubercular Agents - pharmacology ; Ethylenediamines ; Humans ; Inhibitory Concentration 50 ; Malaria, Falciparum - drug therapy ; Malaria, Falciparum - parasitology ; Plasmodium falciparum - drug effects ; Structure-Activity Relationship</subject><ispartof>ACS infectious diseases, 2024-09, Vol.10 (9), p.3358-3367</ispartof><rights>2024 The Authors. 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We additionally validated that this series could block transmission to mosquitoes, marking these compounds as novel chemotypes with multistage antiplasmodial activity.</description><subject>Adamantane - analogs & derivatives</subject><subject>Adamantane - chemistry</subject><subject>Adamantane - pharmacology</subject><subject>Animals</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - pharmacology</subject><subject>Antitubercular Agents - chemistry</subject><subject>Antitubercular Agents - pharmacology</subject><subject>Ethylenediamines</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Malaria, Falciparum - drug therapy</subject><subject>Malaria, Falciparum - parasitology</subject><subject>Plasmodium falciparum - drug effects</subject><subject>Structure-Activity Relationship</subject><issn>2373-8227</issn><issn>2373-8227</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UU1rFEEQbUQxIeYXCNJHL5tUf8zXSZY1mkBExfXc1PT0TDr0zKxd3Qv5947sGtaLp6pHvfeqqMfYWwFXAqS4Rkt-6p3tPF1pC6BL8YKdS1WpVS1l9fKkP2OXRI8AIFRdaF28ZmeqEVqBlucsbB8c3-bWRZvDTJ74x5gHvsGp8x0mx398F9DwBfK7RHw9YZgH4re4d_xLDslTwsHxtU1-79MTxwH9RIl_C0jj3Pk88h6D9TuMeXzDXi2A3OWxXrCfn262m9vV_dfPd5v1_QqVLNNKQu2wapS0Stuq76ERqNuysNA6h6rudVlKrGqQfdG2WBRtg1JI0YmiAdtZdcE-HHx3uR1dZ92UIgazi37E-GRm9ObfyeQfzDDvjRAaykKUi8P7o0Ocf2VHyYyerAsBJzdnMgoaJSpZAixUdaDaOBNF1z_vEWD-ZGVOsjLHrBbVu9MTnzV_k1kI1wfCojaPc47L5-m_lr8Bh0ykVw</recordid><startdate>20240913</startdate><enddate>20240913</enddate><creator>Watson, Savannah J.</creator><creator>van der Watt, Mariëtte E.</creator><creator>Theron, Anjo</creator><creator>Reader, Janette</creator><creator>Tshabalala, Sizwe</creator><creator>Erlank, Erica</creator><creator>Koekemoer, Lizette L.</creator><creator>Naude, Mariska</creator><creator>Stampolaki, Marianna</creator><creator>Adewole, Feyisola</creator><creator>Sadowska, Katie</creator><creator>Pérez-Lozano, Pilar</creator><creator>Turcu, Andreea L.</creator><creator>Vázquez, Santiago</creator><creator>Ko, Jihee</creator><creator>Mazurek, Ben</creator><creator>Singh, Davinder</creator><creator>Malwal, Satish R.</creator><creator>Njoroge, Mathew</creator><creator>Chibale, Kelly</creator><creator>Onajole, Oluseye K.</creator><creator>Kolocouris, Antonios</creator><creator>Oldfield, Eric</creator><creator>Birkholtz, Lyn-Marié</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-5888-2905</orcidid><orcidid>https://orcid.org/0000-0002-0996-7352</orcidid><orcidid>https://orcid.org/0000-0002-1327-4727</orcidid><orcidid>https://orcid.org/0000-0002-9296-6026</orcidid><orcidid>https://orcid.org/0000-0002-8555-4963</orcidid><orcidid>https://orcid.org/0000-0001-6110-1903</orcidid><orcidid>https://orcid.org/0000-0002-7970-1509</orcidid><orcidid>https://orcid.org/0000-0001-6899-066X</orcidid><orcidid>https://orcid.org/0000-0001-7606-1932</orcidid></search><sort><creationdate>20240913</creationdate><title>The Tuberculosis Drug Candidate SQ109 and Its Analogs Have Multistage Activity against Plasmodium falciparum</title><author>Watson, Savannah J. ; 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| subjects | Adamantane - analogs & derivatives Adamantane - chemistry Adamantane - pharmacology Animals Antimalarials - chemistry Antimalarials - pharmacology Antitubercular Agents - chemistry Antitubercular Agents - pharmacology Ethylenediamines Humans Inhibitory Concentration 50 Malaria, Falciparum - drug therapy Malaria, Falciparum - parasitology Plasmodium falciparum - drug effects Structure-Activity Relationship |
| title | The Tuberculosis Drug Candidate SQ109 and Its Analogs Have Multistage Activity against Plasmodium falciparum |
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