Cover Image

Phenylalanine and phenylglycine analogues as arginine mimetics in dengue protease inhibitors

Dengue virus is an increasingly global pathogen. One of the promising targets for antiviral drug discovery against dengue and related flaviviruses such as West Nile virus is the viral serine protease NS2B-NS3. We here report the synthesis and in vitro characterization of potent peptidic inhibitors o...

Full description

Saved in:
Bibliographic Details
Main Authors: Weigel, Lena (Author) , Nitsche, Christoph (Author) , Graf, Dominik Korbinian (Author) , Bartenschlager, Ralf (Author) , Klein, Christian D. (Author)
Format: Article (Journal)
Language:English
Published: September 14, 2015
In: Journal of medicinal chemistry
Year: 2015, Volume: 58, Issue: 19, Pages: 7719-7733
ISSN:1520-4804
DOI:10.1021/acs.jmedchem.5b00612
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.jmedchem.5b00612
Get full text
Author Notes:Lena F. Weigel, Christoph Nitsche, Dominik Graf, Ralf Bartenschlager, and Christian D. Klein

MARC

LEADER 00000caa a2200000 c 4500
001 1702875415
003 DE-627
005 20230428073843.0
007 cr uuu---uuuuu
008 200629s2015 xx |||||o 00| ||eng c
024 7 |a 10.1021/acs.jmedchem.5b00612  |2 doi 
035 |a (DE-627)1702875415 
035 |a (DE-599)KXP1702875415 
035 |a (OCoLC)1341341993 
040 |a DE-627  |b ger  |c DE-627  |e rda 
041 |a eng 
084 |a 33  |2 sdnb 
100 1 |a Weigel, Lena  |e VerfasserIn  |0 (DE-588)1123972230  |0 (DE-627)877618836  |0 (DE-576)482197528  |4 aut 
245 1 0 |a Phenylalanine and phenylglycine analogues as arginine mimetics in dengue protease inhibitors  |c Lena F. Weigel, Christoph Nitsche, Dominik Graf, Ralf Bartenschlager, and Christian D. Klein 
264 1 |c September 14, 2015 
300 |a 15 
336 |a Text  |b txt  |2 rdacontent 
337 |a Computermedien  |b c  |2 rdamedia 
338 |a Online-Ressource  |b cr  |2 rdacarrier 
500 |a Gesehen am 29.06.2020 
520 |a Dengue virus is an increasingly global pathogen. One of the promising targets for antiviral drug discovery against dengue and related flaviviruses such as West Nile virus is the viral serine protease NS2B-NS3. We here report the synthesis and in vitro characterization of potent peptidic inhibitors of dengue virus protease that incorporate phenylalanine and phenylglycine derivatives as arginine-mimicking groups with modulated basicity. The most promising compounds were (4-amidino)-l-phenylalanine-containing inhibitors, which reached nanomolar affinities against dengue virus protease. The type and position of the substituents on the phenylglycine and phenylalanine side chains has a significant effect on the inhibitory activity against dengue virus protease and selectivity against other proteases. In addition, the non-natural, basic amino acids described here may have relevance for the development of other peptidic and peptidomimetic drugs such as inhibitors of the blood clotting cascade. 
700 1 |a Nitsche, Christoph  |e VerfasserIn  |0 (DE-588)1058037110  |0 (DE-627)796329567  |0 (DE-576)414020502  |4 aut 
700 1 |a Graf, Dominik Korbinian  |e VerfasserIn  |0 (DE-588)112397053X  |0 (DE-627)877615748  |0 (DE-576)482194685  |4 aut 
700 1 |a Bartenschlager, Ralf  |d 1958-  |e VerfasserIn  |0 (DE-588)1058097989  |0 (DE-627)796390509  |0 (DE-576)168706067  |4 aut 
700 1 |a Klein, Christian D.  |e VerfasserIn  |0 (DE-588)1060644894  |0 (DE-627)800410157  |0 (DE-576)416768717  |4 aut 
773 0 8 |i Enthalten in  |t Journal of medicinal chemistry  |d Washington, DC : ACS, 1959  |g 58(2015), 19, Seite 7719-7733  |h Online-Ressource  |w (DE-627)302468846  |w (DE-600)1491411-6  |w (DE-576)090855132  |x 1520-4804  |7 nnas  |a Phenylalanine and phenylglycine analogues as arginine mimetics in dengue protease inhibitors 
773 1 8 |g volume:58  |g year:2015  |g number:19  |g pages:7719-7733  |g extent:15  |a Phenylalanine and phenylglycine analogues as arginine mimetics in dengue protease inhibitors 
856 4 0 |u https://doi.org/10.1021/acs.jmedchem.5b00612  |x Verlag  |x Resolving-System  |z lizenzpflichtig  |3 Volltext 
951 |a AR 
992 |a 20200629 
993 |a Article 
994 |a 2015 
998 |g 1060644894  |a Klein, Christian D.  |m 1060644894:Klein, Christian D.  |d 160000  |d 160100  |e 160000PK1060644894  |e 160100PK1060644894  |k 0/160000/  |k 1/160000/160100/  |p 5  |y j 
998 |g 1058097989  |a Bartenschlager, Ralf  |m 1058097989:Bartenschlager, Ralf  |d 910000  |d 911700  |e 910000PB1058097989  |e 911700PB1058097989  |k 0/910000/  |k 1/910000/911700/  |p 4 
998 |g 112397053X  |a Graf, Dominik Korbinian  |m 112397053X:Graf, Dominik Korbinian  |d 160000  |d 160100  |e 160000PG112397053X  |e 160100PG112397053X  |k 0/160000/  |k 1/160000/160100/  |p 3 
998 |g 1058037110  |a Nitsche, Christoph  |m 1058037110:Nitsche, Christoph  |d 160000  |d 160100  |e 160000PN1058037110  |e 160100PN1058037110  |k 0/160000/  |k 1/160000/160100/  |p 2 
998 |g 1123972230  |a Weigel, Lena  |m 1123972230:Weigel, Lena  |d 160000  |d 160100  |e 160000PW1123972230  |e 160100PW1123972230  |k 0/160000/  |k 1/160000/160100/  |p 1  |x j 
999 |a KXP-PPN1702875415  |e 3692143761 
BIB |a Y 
SER |a journal 
JSO |a {"recId":"1702875415","title":[{"title_sort":"Phenylalanine and phenylglycine analogues as arginine mimetics in dengue protease inhibitors","title":"Phenylalanine and phenylglycine analogues as arginine mimetics in dengue protease inhibitors"}],"name":{"displayForm":["Lena F. Weigel, Christoph Nitsche, Dominik Graf, Ralf Bartenschlager, and Christian D. Klein"]},"type":{"bibl":"article-journal","media":"Online-Ressource"},"language":["eng"],"physDesc":[{"extent":"15 S."}],"note":["Gesehen am 29.06.2020"],"person":[{"display":"Weigel, Lena","role":"aut","given":"Lena","roleDisplay":"VerfasserIn","family":"Weigel"},{"given":"Christoph","display":"Nitsche, Christoph","role":"aut","roleDisplay":"VerfasserIn","family":"Nitsche"},{"display":"Graf, Dominik Korbinian","role":"aut","given":"Dominik Korbinian","roleDisplay":"VerfasserIn","family":"Graf"},{"given":"Ralf","role":"aut","display":"Bartenschlager, Ralf","roleDisplay":"VerfasserIn","family":"Bartenschlager"},{"family":"Klein","roleDisplay":"VerfasserIn","given":"Christian D.","display":"Klein, Christian D.","role":"aut"}],"origin":[{"dateIssuedDisp":"September 14, 2015","dateIssuedKey":"2015"}],"relHost":[{"physDesc":[{"extent":"Online-Ressource"}],"note":["Gesehen am 02.10.2020"],"origin":[{"publisherPlace":"Washington, DC ; Easton, Pa.","dateIssuedDisp":"1959-","dateIssuedKey":"1959","publisher":"ACS ; ACS"}],"id":{"zdb":["1491411-6"],"issn":["1520-4804"],"eki":["302468846"]},"recId":"302468846","disp":"Phenylalanine and phenylglycine analogues as arginine mimetics in dengue protease inhibitorsJournal of medicinal chemistry","title":[{"title_sort":"Journal of medicinal chemistry","title":"Journal of medicinal chemistry"}],"part":{"volume":"58","issue":"19","extent":"15","pages":"7719-7733","text":"58(2015), 19, Seite 7719-7733","year":"2015"},"name":{"displayForm":["American Chemical Society"]},"type":{"bibl":"periodical","media":"Online-Ressource"},"language":["eng"],"pubHistory":["1.1959 -"]}],"id":{"doi":["10.1021/acs.jmedchem.5b00612"],"eki":["1702875415"]}} 
SRT |a WEIGELLENAPHENYLALAN1420 

Similar Items