Synthesis and antiproliferative activity of a natural like glycoconjugate polycyclic compound

Fabiana Plescia; Benedetta Maggio; Maria Valeria Raimondi; Marianna Lauricella; Giuseppe Daidone; Antonella D'Anneo; Demetrio Raffa; Nicolò Prosa; Marie-Christine Scherrmann

Synthesis and antiproliferative activity of a natural like glycoconjugate polycyclic compound

Fabiana Plescia, Benedetta Maggio, Maria Valeria Raimondi, Marianna Lauricella, Giuseppe Daidone, Antonella D'Anneo, Demetrio Raffa, Nicolò Prosa, Marie-Christine Scherrmann

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5 Citations (Scopus)

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.

Original language	English
Pages (from-to)	247-256
Number of pages	10
Journal	European Journal of Medicinal Chemistry
Volume	122
Publication status	Published - 2016

All Science Journal Classification (ASJC) codes

Pharmacology
Drug Discovery
Organic Chemistry

Cite this

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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 Benedetta Maggio and Raimondi, {Maria Valeria} and Marianna Lauricella and Giuseppe Daidone and Antonella D'Anneo and Demetrio Raffa 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",

}

TY - JOUR

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

AU - Plescia, Fabiana

AU - Maggio, Benedetta

AU - Raimondi, Maria Valeria

AU - Lauricella, Marianna

AU - Daidone, Giuseppe

AU - D'Anneo, Antonella

AU - Raffa, Demetrio

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

SN - 0223-5234

VL - 122

SP - 247

EP - 256

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

Synthesis and antiproliferative activity of a natural like glycoconjugate polycyclic compound

Abstract

All Science Journal Classification (ASJC) codes

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