Rhodamine B conjugates of triterpenoic acids are cytotoxic mitocans even at nanomolar concentrations

Publication type:
Journal article
Metadata:
Autoren
  • Sven Sommerwerk
  • Lucie Heller
  • Christoph Kerzig
  • Annemarie E Kramell
  • Rene Csuk
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000397172800001&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1016/j.ejmech.2016.12.040
eISSN
1768-3254
Externe Identifier
  • Clarivate Analytics Document Solution ID: EP1VQ
  • PubMed Identifier: 28033541
ISSN
0223-5234
Zeitschrift
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Schlüsselwörter
  • Triterpenes
  • Maslinic acid
  • Mitocan
  • Cytotoxicity
  • Rhodamine B
  • Betulinic acid
  • Oleanolic acid
  • Ursolic acid
  • Platanic acid
  • Glycyrrhetinic acid
Paginierung
1 - 9
Datum der Veröffentlichung
2017
Status
Published
Titel
Rhodamine B conjugates of triterpenoic acids are cytotoxic mitocans even at nanomolar concentrations
Sub types
  • Article
Ausgabe der Zeitschrift
127

Data source: Web of Science (Lite)

Other metadata sources:
Autoren
  • Sven Sommerwerk
  • Lucie Heller
  • Christoph Kerzig
  • Annemarie E Kramell
  • René Csuk
DOI
10.1016/j.ejmech.2016.12.040
ISSN
0223-5234
Zeitschrift
European Journal of Medicinal Chemistry
Sprache
en
Paginierung
1 - 9
Datum der Veröffentlichung
2017
Status
Published
Herausgeber
Elsevier BV
Herausgeber URL
http://dx.doi.org/10.1016/j.ejmech.2016.12.040
Datum der Datenerfassung
2022
Titel
Rhodamine B conjugates of triterpenoic acids are cytotoxic mitocans even at nanomolar concentrations
Ausgabe der Zeitschrift
127

Data source: Crossref

Abstract
Triterpenoic acids 1-6 exhibited very low or no cytotoxicity at all, but their corresponding 2,3-di-O-acetyl-piperazinyl amides 13-18 showed low EC<sub>50</sub> values for several human tumor cell lines. Their cytotoxicity, however, was also high for the non-malignant mouse fibroblasts NIH 3T3. A significant improvement was achieved by preparing the rhodamine B derivatives 19-24. While rhodamine B is not cytotoxic (up to a concentration of 30μM - cut-off of the assay), the triterpenoid piperazine-spacered rhodamine B derivatives were cytotoxic in nano-molar concentration. Compound 24 (a diacetylated maslinic acid derivative) was most toxic for several human tumor cell lines but less toxic for mouse fibroblasts NIH 3T3. Staining and double-staining experiments revealed 24 to act as a mitocan.
Addresses
  • Martin-Luther University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany.
Autoren
  • Sven Sommerwerk
  • Lucie Heller
  • Christoph Kerzig
  • Annemarie E Kramell
  • René Csuk
DOI
10.1016/j.ejmech.2016.12.040
eISSN
1768-3254
Externe Identifier
  • PubMed Identifier: 28033541
Funding acknowledgements
  • WissenschaftsCampus Halle WCH: W13004216
Open access
false
ISSN
0223-5234
Zeitschrift
European journal of medicinal chemistry
Schlüsselwörter
  • Cell Line, Tumor
  • NIH 3T3 Cells
  • Mitochondria
  • Animals
  • Humans
  • Mice
  • Triterpenes
  • Rhodamines
  • Apoptosis
  • Structure-Activity Relationship
  • Dose-Response Relationship, Drug
  • Hydrophobic and Hydrophilic Interactions
Sprache
eng
Medium
Print-Electronic
Online publication date
2016
Paginierung
1 - 9
Datum der Veröffentlichung
2017
Status
Published
Datum der Datenerfassung
2016
Titel
Rhodamine B conjugates of triterpenoic acids are cytotoxic mitocans even at nanomolar concentrations.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
127

Data source: Europe PubMed Central

Abstract
Triterpenoic acids 1-6 exhibited very low or no cytotoxicity at all, but their corresponding 2,3-di-O-acetyl-piperazinyl amides 13-18 showed low EC50 values for several human tumor cell lines. Their cytotoxicity, however, was also high for the non-malignant mouse fibroblasts NIH 3T3. A significant improvement was achieved by preparing the rhodamine B derivatives 19-24. While rhodamine B is not cytotoxic (up to a concentration of 30μM - cut-off of the assay), the triterpenoid piperazine-spacered rhodamine B derivatives were cytotoxic in nano-molar concentration. Compound 24 (a diacetylated maslinic acid derivative) was most toxic for several human tumor cell lines but less toxic for mouse fibroblasts NIH 3T3. Staining and double-staining experiments revealed 24 to act as a mitocan.
Date of acceptance
2016
Autoren
  • Sven Sommerwerk
  • Lucie Heller
  • Christoph Kerzig
  • Annemarie E Kramell
  • René Csuk
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/28033541
DOI
10.1016/j.ejmech.2016.12.040
eISSN
1768-3254
Zeitschrift
Eur J Med Chem
Schlüsselwörter
  • Betulinic acid
  • Cytotoxicity
  • Glycyrrhetinic acid
  • Maslinic acid
  • Mitocan
  • Oleanolic acid
  • Platanic acid
  • Rhodamine B
  • Triterpenes
  • Ursolic acid
  • Animals
  • Apoptosis
  • Cell Line, Tumor
  • Dose-Response Relationship, Drug
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Mice
  • Mitochondria
  • NIH 3T3 Cells
  • Rhodamines
  • Structure-Activity Relationship
  • Triterpenes
Sprache
eng
Country
France
Paginierung
1 - 9
PII
S0223-5234(16)31047-9
Datum der Veröffentlichung
2017
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2017
Titel
Rhodamine B conjugates of triterpenoic acids are cytotoxic mitocans even at nanomolar concentrations.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
127

Data source: PubMed

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