Evaluation of dipeptide nitriles as inhibitors of rhodesain, a major cysteine protease of Trypanosoma brucei
A series of dipeptide nitriles known as inhibitors of mammalian cathepsins were evaluated for inhibition of rhodesain, the cathepsin L-like protease of Trypanosoma brucei. Compound 35 consisting of a Leu residue fitting into the S2 pocket and a triarylic moiety consisting of thiophene, a 1,2,4-oxadi...
Gespeichert in:
| Hauptverfasser: | , , |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
2017
|
| In: |
Bioorganic & medicinal chemistry letters
Year: 2017, Jahrgang: 27, Heft: 1, Pages: 45-50 |
| ISSN: | 1464-3405 |
| DOI: | 10.1016/j.bmcl.2016.11.036 |
| Online-Zugang: | Verlag, Volltext: http://dx.doi.org/10.1016/j.bmcl.2016.11.036 Verlag, Volltext: http://www.sciencedirect.com/science/article/pii/S0960894X16311775 
|
| Verfasserangaben: | Tanja Schirmeister, Janina Schmitz, Sascha Jung, Torsten Schmenger, R. Luise Krauth-Siegel, Michael Gütschow |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1574249657 | ||
| 003 | DE-627 | ||
| 005 | 20230427042853.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 180508s2017 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1016/j.bmcl.2016.11.036 |2 doi | |
| 035 | |a (DE-627)1574249657 | ||
| 035 | |a (DE-576)504249657 | ||
| 035 | |a (DE-599)BSZ504249657 | ||
| 035 | |a (OCoLC)1341009289 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 32 |2 sdnb | ||
| 100 | 1 | |a Schirmeister, Tanja |d 1963- |e VerfasserIn |0 (DE-588)123234891 |0 (DE-627)706220323 |0 (DE-576)214696057 |4 aut | |
| 245 | 1 | 0 | |a Evaluation of dipeptide nitriles as inhibitors of rhodesain, a major cysteine protease of Trypanosoma brucei |c Tanja Schirmeister, Janina Schmitz, Sascha Jung, Torsten Schmenger, R. Luise Krauth-Siegel, Michael Gütschow |
| 264 | 1 | |c 2017 | |
| 300 | |a 6 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Online veröffentlicht am 15. November 2016 | ||
| 500 | |a Gesehen am 08.05.2018 | ||
| 520 | |a A series of dipeptide nitriles known as inhibitors of mammalian cathepsins were evaluated for inhibition of rhodesain, the cathepsin L-like protease of Trypanosoma brucei. Compound 35 consisting of a Leu residue fitting into the S2 pocket and a triarylic moiety consisting of thiophene, a 1,2,4-oxadiazole and a phenyl ring fitting into the S3 pocket, and compound 33 with a 3-bromo-Phe residue (S2) and a biphenyl fragment (S3) were found to inhibit rhodesain in the single-digit nanomolar range. The observed steep structure-activity relationship could be explained by covalent docking simulations. With their high selectivity indices (ca. 200) and the good antitrypanosomal activity (8μM) the compounds represent promising starting points for new rhodesain inhibitors. | ||
| 650 | 4 | |a Cysteine protease | |
| 650 | 4 | |a Dipeptide nitrile | |
| 650 | 4 | |a Inhibitor | |
| 650 | 4 | |a Rhodesain | |
| 650 | 4 | |a Trypanosoma | |
| 700 | 1 | |a Schmenger, Torsten |d 1988- |e VerfasserIn |0 (DE-588)115860887X |0 (DE-627)1020602848 |0 (DE-576)504250280 |4 aut | |
| 700 | 1 | |a Krauth-Siegel, Renate |e VerfasserIn |0 (DE-588)1050022335 |0 (DE-627)783217390 |0 (DE-576)404300200 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Bioorganic & medicinal chemistry letters |d Amsterdam [u.a.] : Elsevier Science, 1991 |g 27(2017), 1, Seite 45-50 |h Online-Ressource |w (DE-627)306717522 |w (DE-600)1501505-1 |w (DE-576)110916573 |x 1464-3405 |7 nnas |a Evaluation of dipeptide nitriles as inhibitors of rhodesain, a major cysteine protease of Trypanosoma brucei |
| 773 | 1 | 8 | |g volume:27 |g year:2017 |g number:1 |g pages:45-50 |g extent:6 |a Evaluation of dipeptide nitriles as inhibitors of rhodesain, a major cysteine protease of Trypanosoma brucei |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1016/j.bmcl.2016.11.036 |x Verlag |x Resolving-System |3 Volltext |
| 856 | 4 | 0 | |u http://www.sciencedirect.com/science/article/pii/S0960894X16311775 |x Verlag |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20180508 | ||
| 993 | |a Article | ||
| 994 | |a 2017 | ||
| 998 | |g 1050022335 |a Krauth-Siegel, Renate |m 1050022335:Krauth-Siegel, Renate |d 700000 |d 711000 |e 700000PK1050022335 |e 711000PK1050022335 |k 0/700000/ |k 1/700000/711000/ |p 5 | ||
| 998 | |g 115860887X |a Schmenger, Torsten |m 115860887X:Schmenger, Torsten |d 140000 |e 140000PS115860887X |k 0/140000/ |p 3 | ||
| 999 | |a KXP-PPN1574249657 |e 3008500390 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"origin":[{"dateIssuedDisp":"2017","dateIssuedKey":"2017"}],"id":{"doi":["10.1016/j.bmcl.2016.11.036"],"eki":["1574249657"]},"name":{"displayForm":["Tanja Schirmeister, Janina Schmitz, Sascha Jung, Torsten Schmenger, R. Luise Krauth-Siegel, Michael Gütschow"]},"physDesc":[{"extent":"6 S."}],"relHost":[{"id":{"issn":["1464-3405"],"zdb":["1501505-1"],"eki":["306717522"]},"origin":[{"publisherPlace":"Amsterdam [u.a.]","dateIssuedDisp":"1991-","dateIssuedKey":"1991","publisher":"Elsevier Science"}],"physDesc":[{"extent":"Online-Ressource"}],"title":[{"title":"Bioorganic & medicinal chemistry letters","subtitle":"a Tetrahedron publication for rapid dissemination of preliminary communications on all aspects of bioorganic chemistry, medicinal chemistry, bioinorganic chemistry and related disciplines","title_sort":"Bioorganic & medicinal chemistry letters"}],"language":["eng"],"recId":"306717522","disp":"Evaluation of dipeptide nitriles as inhibitors of rhodesain, a major cysteine protease of Trypanosoma bruceiBioorganic & medicinal chemistry letters","note":["Gesehen am 09.11.2020"],"type":{"bibl":"periodical","media":"Online-Ressource"},"part":{"volume":"27","text":"27(2017), 1, Seite 45-50","extent":"6","year":"2017","issue":"1","pages":"45-50"},"titleAlt":[{"title":"Bioorganic and medicinal chemistry letters"}],"pubHistory":["1.1991 -"]}],"title":[{"title_sort":"Evaluation of dipeptide nitriles as inhibitors of rhodesain, a major cysteine protease of Trypanosoma brucei","title":"Evaluation of dipeptide nitriles as inhibitors of rhodesain, a major cysteine protease of Trypanosoma brucei"}],"person":[{"role":"aut","roleDisplay":"VerfasserIn","display":"Schirmeister, Tanja","given":"Tanja","family":"Schirmeister"},{"roleDisplay":"VerfasserIn","display":"Schmenger, Torsten","role":"aut","family":"Schmenger","given":"Torsten"},{"family":"Krauth-Siegel","given":"Renate","roleDisplay":"VerfasserIn","display":"Krauth-Siegel, Renate","role":"aut"}],"note":["Online veröffentlicht am 15. November 2016","Gesehen am 08.05.2018"],"type":{"bibl":"article-journal","media":"Online-Ressource"},"recId":"1574249657","language":["eng"]} | ||
| SRT | |a SCHIRMEISTEVALUATION2017 | ||