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3-[4-(1H-indol-3-yl)-1,3-thiazol-2-yl]-1H-pyrrolo[2,3-b]pyridines, nortopsentin Analogues with antiproliferative activity
- Source :
- Marine Drugs, Vol 13, Iss 4, Pp 1901-1924 (2015), Marine Drugs, Volume 13, Issue 4, Pages 1901-1924
- Publication Year :
- 2015
- Publisher :
- MDPI AG, 2015.
-
Abstract
- A new series of nortopsentin analogues, in which the imidazole ring of the natural product was replaced by thiazole and the indole unit bound to position 2 of the thiazole ring was substituted by a 7-azaindole moiety, was efficiently synthesized. Two of the new nortopsentin analogues showed good antiproliferative effect against the totality of the NCI full panel of human tumor cell lines (~60) having GI50 values ranging from low micromolar to nanomolar level. The mechanism of the antiproliferative effect of these derivatives, investigated on human hepatoma HepG2 cells, was pro-apoptotic, being associated with externalization of plasma membrane phosphatidylserine and mitochondrial dysfunction. Moreover, the compounds induced a concentration-dependent accumulation of cells in the subG0/G1phase, while confined viable cells in G2/M phase.
- Subjects :
- Indoles
Halogenation
Pyridines
3-b]pyridines
Pharmaceutical Science
Apoptosis
Antiproliferative activity
3-[4-(1H-indol-3-yl)-1,3-thiazol-2-yl]-1H-pyrrolo[2,3-b]pyridines
chemistry.chemical_compound
Neoplasms
Drug Discovery
Imidazole
Moiety
indolyl alkaloids
Pharmacology, Toxicology and Pharmaceutics (miscellaneous)
lcsh:QH301-705.5
Membrane Potential, Mitochondrial
Molecular Structure
3-[4-(1H-indol-3-yl)-1
3-thiazol-2-yl]-1H-pyrrolo[2
Indolyl alkaloids
Marine alkaloids
Nortopsentin analogues
Drug Discovery3003 Pharmaceutical Science
Imidazoles
Phosphatidylserine
Mitochondria
nortopsentin analogues
Indolyl alkaloid
marine alkaloids
G2 Phase
Stereochemistry
Nortopsentin analogue
Antineoplastic Agents
Methylation
Resting Phase, Cell Cycle
Article
Alkaloids
Cell Line, Tumor
Humans
Pyrroles
Thiazole
Cell Proliferation
Indole test
Natural product
Cell growth
Settore CHIM/08 - Chimica Farmaceutica
Thiazoles
chemistry
lcsh:Biology (General)
Cell culture
Drug Design
Marine alkaloid
3-[4-(1H-indol-3-yl)-1,3-thiazol-2-yl]-1H-pyrrolo[2,3-b]pyridine
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Journal :
- Marine Drugs, Vol 13, Iss 4, Pp 1901-1924 (2015), Marine Drugs, Volume 13, Issue 4, Pages 1901-1924
- Accession number :
- edsair.doi.dedup.....7471c818fd2a702c95de33aa51e7eef6