Synthesis and antiproliferative activity of a natural like glycoconjugate polycyclic compound

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Abstract

A natural like O-glycoconjugate polycyclic compound 4 was obtained by a multistep procedure starting from N-(3-methyl-1-(4-nitrophenyl)-1H-pyrazol-5-yl)acetamide. The glycosyl derivative 4 showed antiproliferative activity against all the tumoral cell lines of the NCI panel in the range 0.47–5.43 μM. Cytofluorimetric analysis performed on MDA-MB231, a very aggressive breast cancer cell line, which does not express estrogen, progesterone and HER-2/neu receptors, showed that 4 is able to induce prolonged cell cycle arrest at G2/M phase and morphological signs of differentiation. These events are correlated with down-regulation of both cyclin B1 and cdc2, the cyclins involved in G2/M transition, as well as up-regulation of cyclin-dependent kinase (CDK) inhibitor p21 Cip1/Waf1.
Lingua originaleEnglish
pagine (da-a)247-256
Numero di pagine10
RivistaEuropean Journal of Medicinal Chemistry
Volume122
Stato di pubblicazionePublished - 2016

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Polycyclic Compounds
Glycoconjugates
Cells
ErbB-2 Receptor
Cyclin-Dependent Kinase Inhibitor p21
Cyclin B1
Cell Line
Cyclins
G2 Phase
Cell Cycle Checkpoints
Cell Division
Progesterone
Estrogens
Up-Regulation
Down-Regulation
Breast Neoplasms
Derivatives
acetamide
4-nitrophenyl

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cita questo

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title = "Synthesis and antiproliferative activity of a natural like glycoconjugate polycyclic compound",
abstract = "A natural like O-glycoconjugate polycyclic compound 4 was obtained by a multistep procedure starting from N-(3-methyl-1-(4-nitrophenyl)-1H-pyrazol-5-yl)acetamide. The glycosyl derivative 4 showed antiproliferative activity against all the tumoral cell lines of the NCI panel in the range 0.47–5.43 μM. Cytofluorimetric analysis performed on MDA-MB231, a very aggressive breast cancer cell line, which does not express estrogen, progesterone and HER-2/neu receptors, showed that 4 is able to induce prolonged cell cycle arrest at G2/M phase and morphological signs of differentiation. These events are correlated with down-regulation of both cyclin B1 and cdc2, the cyclins involved in G2/M transition, as well as up-regulation of cyclin-dependent kinase (CDK) inhibitor p21 Cip1/Waf1.",
author = "Fabiana Plescia and Raimondi, {Maria Valeria} and Giuseppe Daidone and Demetrio Raffa and Marianna Lauricella and Benedetta Maggio and Antonella D'Anneo and Nicol{\`o} Prosa and Marie-Christine Scherrmann",
year = "2016",
language = "English",
volume = "122",
pages = "247--256",
journal = "European Journal of Medicinal Chemistry",
issn = "0223-5234",
publisher = "Elsevier Masson SAS",

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TY - JOUR

T1 - Synthesis and antiproliferative activity of a natural like glycoconjugate polycyclic compound

AU - Plescia, Fabiana

AU - Raimondi, Maria Valeria

AU - Daidone, Giuseppe

AU - Raffa, Demetrio

AU - Lauricella, Marianna

AU - Maggio, Benedetta

AU - D'Anneo, Antonella

AU - Prosa, Nicolò

AU - Scherrmann, Marie-Christine

PY - 2016

Y1 - 2016

N2 - A natural like O-glycoconjugate polycyclic compound 4 was obtained by a multistep procedure starting from N-(3-methyl-1-(4-nitrophenyl)-1H-pyrazol-5-yl)acetamide. The glycosyl derivative 4 showed antiproliferative activity against all the tumoral cell lines of the NCI panel in the range 0.47–5.43 μM. Cytofluorimetric analysis performed on MDA-MB231, a very aggressive breast cancer cell line, which does not express estrogen, progesterone and HER-2/neu receptors, showed that 4 is able to induce prolonged cell cycle arrest at G2/M phase and morphological signs of differentiation. These events are correlated with down-regulation of both cyclin B1 and cdc2, the cyclins involved in G2/M transition, as well as up-regulation of cyclin-dependent kinase (CDK) inhibitor p21 Cip1/Waf1.

AB - A natural like O-glycoconjugate polycyclic compound 4 was obtained by a multistep procedure starting from N-(3-methyl-1-(4-nitrophenyl)-1H-pyrazol-5-yl)acetamide. The glycosyl derivative 4 showed antiproliferative activity against all the tumoral cell lines of the NCI panel in the range 0.47–5.43 μM. Cytofluorimetric analysis performed on MDA-MB231, a very aggressive breast cancer cell line, which does not express estrogen, progesterone and HER-2/neu receptors, showed that 4 is able to induce prolonged cell cycle arrest at G2/M phase and morphological signs of differentiation. These events are correlated with down-regulation of both cyclin B1 and cdc2, the cyclins involved in G2/M transition, as well as up-regulation of cyclin-dependent kinase (CDK) inhibitor p21 Cip1/Waf1.

UR - http://hdl.handle.net/10447/180516

UR - http://www.journals.elsevier.com/european-journal-of-medicinal-chemistry/

M3 - Article

VL - 122

SP - 247

EP - 256

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

SN - 0223-5234

ER -