2.50
Hdl Handle:
http://hdl.handle.net/10033/620816
Title:
Sulfur, selenium and tellurium pseudopeptides: synthesis and biological evaluation.
Authors:
Shaaban, Saad; Sasse, Florenz; Burkholz, Torsten; Jacob, Claus
Abstract:
A new series of sulfur, selenium and tellurium peptidomimetic compounds was prepared employing the Passerini and Ugi isocyanide based multicomponent reactions (IMCRs). These reactions were clearly superior to conventional methods traditionally used for organoselenium and organotellurium synthesis, such as classical nucleophilic substitution and coupling methods. From the biological point of view, these compounds are of considerable interest because of suspected anticancer and antimicrobial activities. While the sulfur and selenium containing compounds generally did not show either anticancer or antimicrobial activities, their tellurium based counterparts frequently exhibited antimicrobial activity and were also cytotoxic. Some of the compounds synthesized even showed selective activity against certain cancer cells in cell culture. These compounds induced a cell cycle delay in the G0/G1 phase. At closer inspection, the ER and the actin cytoskeleton appeared to be the primary cellular targets of these tellurium compounds, in line with some of our previous studies. As most of these peptidomimetic compounds also comply with Lipinski's Rule of Five, they promise good bioavailability, which needs to be studied as part of future investigations.
Affiliation:
Helmholtz Centre for infection research, Inhoffenstr. 7, 38124 Braunschweig, Germany.
Citation:
Sulfur, selenium and tellurium pseudopeptides: synthesis and biological evaluation. 2014, 22 (14):3610-9 Bioorg. Med. Chem.
Journal:
Bioorganic & medicinal chemistry
Issue Date:
15-Jul-2014
URI:
http://hdl.handle.net/10033/620816
DOI:
10.1016/j.bmc.2014.05.019
PubMed ID:
24890655
Type:
Article
Language:
en
ISSN:
1464-3391
Appears in Collections:
Publications of the research group Chemical Biology (CBIO)

Full metadata record

DC FieldValue Language
dc.contributor.authorShaaban, Saaden
dc.contributor.authorSasse, Florenzen
dc.contributor.authorBurkholz, Torstenen
dc.contributor.authorJacob, Clausen
dc.date.accessioned2017-02-13T12:49:47Z-
dc.date.available2017-02-13T12:49:47Z-
dc.date.issued2014-07-15-
dc.identifier.citationSulfur, selenium and tellurium pseudopeptides: synthesis and biological evaluation. 2014, 22 (14):3610-9 Bioorg. Med. Chem.en
dc.identifier.issn1464-3391-
dc.identifier.pmid24890655-
dc.identifier.doi10.1016/j.bmc.2014.05.019-
dc.identifier.urihttp://hdl.handle.net/10033/620816-
dc.description.abstractA new series of sulfur, selenium and tellurium peptidomimetic compounds was prepared employing the Passerini and Ugi isocyanide based multicomponent reactions (IMCRs). These reactions were clearly superior to conventional methods traditionally used for organoselenium and organotellurium synthesis, such as classical nucleophilic substitution and coupling methods. From the biological point of view, these compounds are of considerable interest because of suspected anticancer and antimicrobial activities. While the sulfur and selenium containing compounds generally did not show either anticancer or antimicrobial activities, their tellurium based counterparts frequently exhibited antimicrobial activity and were also cytotoxic. Some of the compounds synthesized even showed selective activity against certain cancer cells in cell culture. These compounds induced a cell cycle delay in the G0/G1 phase. At closer inspection, the ER and the actin cytoskeleton appeared to be the primary cellular targets of these tellurium compounds, in line with some of our previous studies. As most of these peptidomimetic compounds also comply with Lipinski's Rule of Five, they promise good bioavailability, which needs to be studied as part of future investigations.en
dc.language.isoenen
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/*
dc.subject.meshAnti-Bacterial Agentsen
dc.subject.meshAntifungal Agentsen
dc.subject.meshAntineoplastic Agentsen
dc.subject.meshBacteriaen
dc.subject.meshCell Cycleen
dc.subject.meshCell Line, Tumoren
dc.subject.meshCell Proliferationen
dc.subject.meshDose-Response Relationship, Drugen
dc.subject.meshDrug Screening Assays, Antitumoren
dc.subject.meshFungien
dc.subject.meshHumansen
dc.subject.meshMCF-7 Cellsen
dc.subject.meshMicrobial Sensitivity Testsen
dc.subject.meshMolecular Structureen
dc.subject.meshPeptidesen
dc.subject.meshPeptidomimeticsen
dc.subject.meshSeleniumen
dc.subject.meshStructure-Activity Relationshipen
dc.subject.meshSulfuren
dc.subject.meshTelluriumen
dc.titleSulfur, selenium and tellurium pseudopeptides: synthesis and biological evaluation.en
dc.typeArticleen
dc.contributor.departmentHelmholtz Centre for infection research, Inhoffenstr. 7, 38124 Braunschweig, Germany.en
dc.identifier.journalBioorganic & medicinal chemistryen

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