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The synthesis of 2,5-bis(4-amidinophenyl)thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease
dc.creator | Opsenica, Igor | |
dc.creator | Filipović, Vuk | |
dc.creator | Nuss, Jon E. | |
dc.creator | Gomba, Laura M. | |
dc.creator | Opsenica, Dejan M. | |
dc.creator | Burnett, James C. | |
dc.creator | Gussio, Rick | |
dc.creator | Šolaja, Bogdan A. | |
dc.creator | Bavari, Sina | |
dc.date.accessioned | 2018-11-22T00:21:33Z | |
dc.date.available | 2014-03-30 | |
dc.date.issued | 2012 | |
dc.identifier.issn | 0223-5234 | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/2787 | |
dc.description.abstract | Botulinum neurotoxins (BoNTs), composed of a family of seven serotypes (categorized A-G), are the deadliest of known biological toxins. The activity of the metalloprotease, light chain (LC) component of the toxins is responsible for causing the life-threatening paralysis associated with the disease botulism. Herein we report significantly more potent analogs of novel, lead BoNT serotype A LC inhibitor 2,5-bis(4-amidinophenyl)thiophene (K-i = 10.881 mu M +/- 0.90 mu M). Specifically, synthetic modifications involved simultaneously replacing the lead inhibitor's terminal bis-amidines with secondary amines and the systematic tethering of 4-amino-7-chloroquinoline substituents to provide derivatives with K-i values ranging from 0.302 mu M (+/- 0.03 mu M) to 0.889 mu M (+/- 0.11 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved. | en |
dc.publisher | Elsevier France-Editions Scientifiques Medicales Elsevier, Paris | |
dc.relation | National Institute of Allergy and Infectious Diseases (USA) [5-U01 AI082051-02] | |
dc.relation | NATOs Public Diplomacy Division | |
dc.relation | National Cancer Institute | |
dc.relation | National Institutes of Health (USA) [HHSN261200800001E] | |
dc.rights | embargoedAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.source | European Journal of Medicinal Chemistry | |
dc.subject | Bioterrorism | en |
dc.subject | Botulinum neurotoxin | en |
dc.subject | Inhibition | en |
dc.title | The synthesis of 2,5-bis(4-amidinophenyl)thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease | en |
dc.type | article | |
dc.rights.license | BY-NC-ND | |
dcterms.abstract | Нусс, Јон Е.; Бурнетт, Јамес Ц.; Гуссио, Рицк; Бавари, Сина; Гомба, Лаура М.; Шолаја, Богдан A.; Опсеница, Игор; Опсеница, Дејан; Филиповиц, Вук; | |
dc.citation.volume | 53 | |
dc.citation.spage | 374 | |
dc.citation.epage | 379 | |
dc.identifier.wos | 000305863100040 | |
dc.identifier.doi | 10.1016/j.ejmech.2012.03.043 | |
dc.citation.other | 53: 374-379 | |
dc.citation.rank | M21 | |
dc.identifier.pmid | 22516424 | |
dc.description.other | This is the peer-reviewed version of the article: Opsenica, I., Filipovic, V., Nuss, J.E., Gomba, L.M., Opsenica, D., Burnett, J.C., Gussio, R., Solaja, B.A., Bavari, S., 2012. The synthesis of 2,5-bis(4-amidinophenyl)thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease. European Journal of Medicinal Chemistry 53, 374–379. [https://doi.org/10.1016/j.ejmech.2012.03.043] | |
dc.type.version | acceptedVersion | |
dc.identifier.scopus | 2-s2.0-84861589629 | |
dc.identifier.fulltext | https://cherry.chem.bg.ac.rs/bitstream/id/6367/nihms367708.pdf |