Synthesis, chemical characterization and biological activity of newhistone acetylation/deacetylation specific inhibitors: A novel andpotential approach to cancer therapy.

Cristina Prinzivalli, Michela Giuliano, Tiziana Fiore, Michelangelo Scopelliti, Lorenzo Pellerito, Girolamo Casella, Claudia Pellerito, Ornella Pellerito, Giulia Grasso, Cristina Prinzivalli, Claudia Pellerito, Michelangelo Scopelliti, Piera Sabatino, Tiziana Fiore, Lorenzo Pellerito, Michela Giuliano, Elisabetta Foresti, Girolamo Casella, Michele Abbate, Ornella Pellerito

Risultato della ricerca: Article

6 Citazioni (Scopus)

Abstract

Three new triorganotin(IV) complexes of valproic acid (vp1, Me3Sn-valproate; vp2, Bu3Sn-valproate;vp3, Ph3Sn-valproate) have been synthesized and investigated by spectroscopic and biological methods.An anionic, monodentate valproate ligand was observed, ester-like coordinating the tin atom on a tetracoordinated,monomeric environment. The structures, though, can distort towards a penta-coordination, as aconsequence of a long range O · · · Sn interaction. Crystallographic and NMR findings confirm this situationboth in solid state and solution. Biological finding evidenced a clear cytotoxic action of the complexes in hepatocellularcarcinoma cell cultures: one of the complexes induced an 80% cell viability reduction after 24 htreatment in HepG2 cells. This effect was accompanied by the appearance of biochemical signs of apoptosis. InChang liver cells, the same compound induced only modest effects, suggesting a potential use as anti-cancerdrug. Preliminary evaluations on hyperacetylation state of histone H3 in tributyltin-valproate treated HepG2cells showed an increase in Ac-H3 (histone H3 acetylated at lys-9 and lys-14), suggesting that the compoundmaintains the deacetylation inhibition activity of its ligand valproate.
Lingua originaleEnglish
pagine (da-a)16-25
Numero di pagine10
RivistaJournal of Inorganic Biochemistry
Volume125
Stato di pubblicazionePublished - 2013

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Acetylation
Valproic Acid
Bioactivity
Neoplasms
Histones
Therapeutics
Ligands
Rubiaceae
Tin
Hep G2 Cells
Cell culture
Liver
Cell Survival
Esters
Cell Culture Techniques
Cells
Nuclear magnetic resonance
Apoptosis
Atoms

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Inorganic Chemistry

Cita questo

Synthesis, chemical characterization and biological activity of newhistone acetylation/deacetylation specific inhibitors: A novel andpotential approach to cancer therapy. / Prinzivalli, Cristina; Giuliano, Michela; Fiore, Tiziana; Scopelliti, Michelangelo; Pellerito, Lorenzo; Casella, Girolamo; Pellerito, Claudia; Pellerito, Ornella; Grasso, Giulia; Prinzivalli, Cristina; Pellerito, Claudia; Scopelliti, Michelangelo; Sabatino, Piera; Fiore, Tiziana; Pellerito, Lorenzo; Giuliano, Michela; Foresti, Elisabetta; Casella, Girolamo; Abbate, Michele; Pellerito, Ornella.

In: Journal of Inorganic Biochemistry, Vol. 125, 2013, pag. 16-25.

Risultato della ricerca: Article

Prinzivalli, C, Giuliano, M, Fiore, T, Scopelliti, M, Pellerito, L, Casella, G, Pellerito, C, Pellerito, O, Grasso, G, Prinzivalli, C, Pellerito, C, Scopelliti, M, Sabatino, P, Fiore, T, Pellerito, L, Giuliano, M, Foresti, E, Casella, G, Abbate, M & Pellerito, O 2013, 'Synthesis, chemical characterization and biological activity of newhistone acetylation/deacetylation specific inhibitors: A novel andpotential approach to cancer therapy.', Journal of Inorganic Biochemistry, vol. 125, pagg. 16-25.
Prinzivalli, Cristina ; Giuliano, Michela ; Fiore, Tiziana ; Scopelliti, Michelangelo ; Pellerito, Lorenzo ; Casella, Girolamo ; Pellerito, Claudia ; Pellerito, Ornella ; Grasso, Giulia ; Prinzivalli, Cristina ; Pellerito, Claudia ; Scopelliti, Michelangelo ; Sabatino, Piera ; Fiore, Tiziana ; Pellerito, Lorenzo ; Giuliano, Michela ; Foresti, Elisabetta ; Casella, Girolamo ; Abbate, Michele ; Pellerito, Ornella. / Synthesis, chemical characterization and biological activity of newhistone acetylation/deacetylation specific inhibitors: A novel andpotential approach to cancer therapy. In: Journal of Inorganic Biochemistry. 2013 ; Vol. 125. pagg. 16-25.
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title = "Synthesis, chemical characterization and biological activity of newhistone acetylation/deacetylation specific inhibitors: A novel andpotential approach to cancer therapy.",
abstract = "Three new triorganotin(IV) complexes of valproic acid (vp1, Me3Sn-valproate; vp2, Bu3Sn-valproate;vp3, Ph3Sn-valproate) have been synthesized and investigated by spectroscopic and biological methods.An anionic, monodentate valproate ligand was observed, ester-like coordinating the tin atom on a tetracoordinated,monomeric environment. The structures, though, can distort towards a penta-coordination, as aconsequence of a long range O · · · Sn interaction. Crystallographic and NMR findings confirm this situationboth in solid state and solution. Biological finding evidenced a clear cytotoxic action of the complexes in hepatocellularcarcinoma cell cultures: one of the complexes induced an 80{\%} cell viability reduction after 24 htreatment in HepG2 cells. This effect was accompanied by the appearance of biochemical signs of apoptosis. InChang liver cells, the same compound induced only modest effects, suggesting a potential use as anti-cancerdrug. Preliminary evaluations on hyperacetylation state of histone H3 in tributyltin-valproate treated HepG2cells showed an increase in Ac-H3 (histone H3 acetylated at lys-9 and lys-14), suggesting that the compoundmaintains the deacetylation inhibition activity of its ligand valproate.",
author = "Cristina Prinzivalli and Michela Giuliano and Tiziana Fiore and Michelangelo Scopelliti and Lorenzo Pellerito and Girolamo Casella and Claudia Pellerito and Ornella Pellerito and Giulia Grasso and Cristina Prinzivalli and Claudia Pellerito and Michelangelo Scopelliti and Piera Sabatino and Tiziana Fiore and Lorenzo Pellerito and Michela Giuliano and Elisabetta Foresti and Girolamo Casella and Michele Abbate and Ornella Pellerito",
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T1 - Synthesis, chemical characterization and biological activity of newhistone acetylation/deacetylation specific inhibitors: A novel andpotential approach to cancer therapy.

AU - Prinzivalli, Cristina

AU - Giuliano, Michela

AU - Fiore, Tiziana

AU - Scopelliti, Michelangelo

AU - Pellerito, Lorenzo

AU - Casella, Girolamo

AU - Pellerito, Claudia

AU - Pellerito, Ornella

AU - Grasso, Giulia

AU - Prinzivalli, Cristina

AU - Pellerito, Claudia

AU - Scopelliti, Michelangelo

AU - Sabatino, Piera

AU - Fiore, Tiziana

AU - Pellerito, Lorenzo

AU - Giuliano, Michela

AU - Foresti, Elisabetta

AU - Casella, Girolamo

AU - Abbate, Michele

AU - Pellerito, Ornella

PY - 2013

Y1 - 2013

N2 - Three new triorganotin(IV) complexes of valproic acid (vp1, Me3Sn-valproate; vp2, Bu3Sn-valproate;vp3, Ph3Sn-valproate) have been synthesized and investigated by spectroscopic and biological methods.An anionic, monodentate valproate ligand was observed, ester-like coordinating the tin atom on a tetracoordinated,monomeric environment. The structures, though, can distort towards a penta-coordination, as aconsequence of a long range O · · · Sn interaction. Crystallographic and NMR findings confirm this situationboth in solid state and solution. Biological finding evidenced a clear cytotoxic action of the complexes in hepatocellularcarcinoma cell cultures: one of the complexes induced an 80% cell viability reduction after 24 htreatment in HepG2 cells. This effect was accompanied by the appearance of biochemical signs of apoptosis. InChang liver cells, the same compound induced only modest effects, suggesting a potential use as anti-cancerdrug. Preliminary evaluations on hyperacetylation state of histone H3 in tributyltin-valproate treated HepG2cells showed an increase in Ac-H3 (histone H3 acetylated at lys-9 and lys-14), suggesting that the compoundmaintains the deacetylation inhibition activity of its ligand valproate.

AB - Three new triorganotin(IV) complexes of valproic acid (vp1, Me3Sn-valproate; vp2, Bu3Sn-valproate;vp3, Ph3Sn-valproate) have been synthesized and investigated by spectroscopic and biological methods.An anionic, monodentate valproate ligand was observed, ester-like coordinating the tin atom on a tetracoordinated,monomeric environment. The structures, though, can distort towards a penta-coordination, as aconsequence of a long range O · · · Sn interaction. Crystallographic and NMR findings confirm this situationboth in solid state and solution. Biological finding evidenced a clear cytotoxic action of the complexes in hepatocellularcarcinoma cell cultures: one of the complexes induced an 80% cell viability reduction after 24 htreatment in HepG2 cells. This effect was accompanied by the appearance of biochemical signs of apoptosis. InChang liver cells, the same compound induced only modest effects, suggesting a potential use as anti-cancerdrug. Preliminary evaluations on hyperacetylation state of histone H3 in tributyltin-valproate treated HepG2cells showed an increase in Ac-H3 (histone H3 acetylated at lys-9 and lys-14), suggesting that the compoundmaintains the deacetylation inhibition activity of its ligand valproate.

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