Prospecting for cytotoxic and antiprotozoal 4-aryl-4H-chromenes and 10-aryldihydropyrano[2,3-f]chromenes

Publication type:
Journal article
Metadata:
Autoren
  • Erlon F Martin
  • Armelle T Mbaveng
  • Milene H de Moraes
  • Victor Kuete
  • Maique W Biavatti
  • Mario Steindel
  • Thomas Efferth
  • Louis P Sandjo
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000446308600002&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1002/ardp.201800100
eISSN
1521-4184
Externe Identifier
  • Clarivate Analytics Document Solution ID: GV7LW
  • PubMed Identifier: 30137687
ISSN
0365-6233
Ausgabe der Veröffentlichung
10
Zeitschrift
ARCHIV DER PHARMAZIE
Schlüsselwörter
  • 4-aryl-4H-chromenes
  • 10-aryl[2
  • 3-f]pyranocoumarins
  • antiprotozoal activity
  • cell cycle arrest
  • cytotoxicity
Artikelnummer
ARTN e1800100
Datum der Veröffentlichung
2018
Status
Published
Titel
Prospecting for cytotoxic and antiprotozoal 4-aryl-4<i>H</i>-chromenes and 10-aryldihydropyrano[2,3-<i>f</i>]chromenes
Sub types
  • Article
Ausgabe der Zeitschrift
351

Data source: Web of Science (Lite)

Other metadata sources:
Abstract
<jats:title>Abstract</jats:title><jats:sec><jats:label /><jats:p>Different studies reported that genetic predisposition or metabolic dysfunction are the risk factors for cancer. Infectious parasitic diseases were listed among factors that predispose to cancer. Because of the resemblance between the life cycle of cancer cells and some parasites, this study aimed to prepare pyran derivatives with cytotoxic and antiprotozoal potencies. Therefore, 7 chromenes, 10 pyranocoumarins, and an unexpected intermediate were obtained from a multi‐reagent one‐pot reaction. These compounds were evaluated for their cytotoxicity on sensitive and resistant leukemia cancer cells lines and against two protozoan parasites, namely <jats:italic>Trypanosoma cruzi</jats:italic> and <jats:italic>Leishmania amazonensis</jats:italic> amastigote. Promising cytotoxicity (IC<jats:sub>50</jats:sub> values of less than 1 µM) was obtained for two of the synthetic products (<jats:bold>12</jats:bold> and <jats:bold>15</jats:bold>). Compound <jats:bold>12</jats:bold> induced apoptosis and cell cycle arrest in CCRF‐CEM leukemia cells in G0/G1 while compound <jats:bold>15</jats:bold> and doxorubicin induced apoptosis and arrest in the S and G2/M phases. Ten of these products showed trypanocidal activity, while only five of them were weakly active on <jats:italic>L. amazonensis</jats:italic>. Three of the obtained pyrans showed significant cytotoxicity and antitrypanocidal activity, simultaneously. Nevertheless, all antiparasitic compounds revealed potency with low selectivity toward THP‐1 cells used as host.</jats:p></jats:sec>
Autoren
  • Erlon F Martin
  • Armelle T Mbaveng
  • Milene H de Moraes
  • Victor Kuete
  • Maique W Biavatti
  • Mario Steindel
  • Thomas Efferth
  • Louis P Sandjo
DOI
10.1002/ardp.201800100
eISSN
1521-4184
ISSN
0365-6233
Ausgabe der Veröffentlichung
10
Zeitschrift
Archiv der Pharmazie
Sprache
en
Online publication date
2018
Datum der Veröffentlichung
2018
Status
Published
Herausgeber
Wiley
Herausgeber URL
http://dx.doi.org/10.1002/ardp.201800100
Datum der Datenerfassung
2023
Titel
Prospecting for cytotoxic and antiprotozoal 4‐aryl‐4<i>H</i>‐chromenes and 10‐aryldihydropyrano[2,3‐<i>f</i>]chromenes
Ausgabe der Zeitschrift
351

Data source: Crossref

Abstract
Different studies reported that genetic predisposition or metabolic dysfunction are the risk factors for cancer. Infectious parasitic diseases were listed among factors that predispose to cancer. Because of the resemblance between the life cycle of cancer cells and some parasites, this study aimed to prepare pyran derivatives with cytotoxic and antiprotozoal potencies. Therefore, 7 chromenes, 10 pyranocoumarins, and an unexpected intermediate were obtained from a multi-reagent one-pot reaction. These compounds were evaluated for their cytotoxicity on sensitive and resistant leukemia cancer cells lines and against two protozoan parasites, namely Trypanosoma cruzi and Leishmania amazonensis amastigote. Promising cytotoxicity (IC<sub>50</sub> values of less than 1 µM) was obtained for two of the synthetic products (12 and 15). Compound 12 induced apoptosis and cell cycle arrest in CCRF-CEM leukemia cells in G0/G1 while compound 15 and doxorubicin induced apoptosis and arrest in the S and G2/M phases. Ten of these products showed trypanocidal activity, while only five of them were weakly active on L. amazonensis. Three of the obtained pyrans showed significant cytotoxicity and antitrypanocidal activity, simultaneously. Nevertheless, all antiparasitic compounds revealed potency with low selectivity toward THP-1 cells used as host.
Addresses
  • Department of Pharmaceutical Sciences, Universidade Federal de Santa Catarina, Florianópolis, Brazil.
Autoren
  • Erlon F Martin
  • Armelle T Mbaveng
  • Milene H de Moraes
  • Victor Kuete
  • Maique W Biavatti
  • Mario Steindel
  • Thomas Efferth
  • Louis P Sandjo
DOI
10.1002/ardp.201800100
eISSN
1521-4184
Externe Identifier
  • PubMed Identifier: 30137687
Funding acknowledgements
  • Alexander von Humboldt Foundation:
  • American Friends of the Alexander von Humboldt Foundation:
  • CNPq/CAPES:
Open access
false
ISSN
0365-6233
Ausgabe der Veröffentlichung
10
Zeitschrift
Archiv der Pharmazie
Schlüsselwörter
  • Tumor Cells, Cultured
  • Humans
  • Leishmania
  • Trypanosoma cruzi
  • Benzopyrans
  • Antineoplastic Agents
  • Antiprotozoal Agents
  • Drug Screening Assays, Antitumor
  • Parasitic Sensitivity Tests
  • Apoptosis
  • Cell Proliferation
  • Molecular Structure
  • Structure-Activity Relationship
  • Dose-Response Relationship, Drug
  • Cell Cycle Checkpoints
  • THP-1 Cells
Sprache
eng
Medium
Print-Electronic
Online publication date
2018
Paginierung
e1800100
Datum der Veröffentlichung
2018
Status
Published
Datum der Datenerfassung
2018
Titel
Prospecting for cytotoxic and antiprotozoal 4-aryl-4H-chromenes and 10-aryldihydropyrano[2,3-f]chromenes.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
351

Data source: Europe PubMed Central

Abstract
Different studies reported that genetic predisposition or metabolic dysfunction are the risk factors for cancer. Infectious parasitic diseases were listed among factors that predispose to cancer. Because of the resemblance between the life cycle of cancer cells and some parasites, this study aimed to prepare pyran derivatives with cytotoxic and antiprotozoal potencies. Therefore, 7 chromenes, 10 pyranocoumarins, and an unexpected intermediate were obtained from a multi-reagent one-pot reaction. These compounds were evaluated for their cytotoxicity on sensitive and resistant leukemia cancer cells lines and against two protozoan parasites, namely Trypanosoma cruzi and Leishmania amazonensis amastigote. Promising cytotoxicity (IC50 values of less than 1 µM) was obtained for two of the synthetic products (12 and 15). Compound 12 induced apoptosis and cell cycle arrest in CCRF-CEM leukemia cells in G0/G1 while compound 15 and doxorubicin induced apoptosis and arrest in the S and G2/M phases. Ten of these products showed trypanocidal activity, while only five of them were weakly active on L. amazonensis. Three of the obtained pyrans showed significant cytotoxicity and antitrypanocidal activity, simultaneously. Nevertheless, all antiparasitic compounds revealed potency with low selectivity toward THP-1 cells used as host.
Date of acceptance
2018
Autoren
  • Erlon F Martin
  • Armelle T Mbaveng
  • Milene H de Moraes
  • Victor Kuete
  • Maique W Biavatti
  • Mario Steindel
  • Thomas Efferth
  • Louis P Sandjo
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/30137687
DOI
10.1002/ardp.201800100
eISSN
1521-4184
Funding acknowledgements
  • Alexander von Humboldt Foundation:
  • CNPq/CAPES:
Ausgabe der Veröffentlichung
10
Zeitschrift
Arch Pharm (Weinheim)
Schlüsselwörter
  • 10-aryl[2,3-f]pyranocoumarins
  • 4-aryl-4H-chromenes
  • antiprotozoal activity
  • cell cycle arrest
  • cytotoxicity
  • Antineoplastic Agents
  • Antiprotozoal Agents
  • Apoptosis
  • Benzopyrans
  • Cell Cycle Checkpoints
  • Cell Proliferation
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Leishmania
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Structure-Activity Relationship
  • THP-1 Cells
  • Trypanosoma cruzi
  • Tumor Cells, Cultured
Sprache
eng
Country
Germany
Paginierung
e1800100
Datum der Veröffentlichung
2018
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2018
Titel
Prospecting for cytotoxic and antiprotozoal 4-aryl-4H-chromenes and 10-aryldihydropyrano[2,3-f]chromenes.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
351

Data source: PubMed

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