Pyrrolo[3,4-h]quinolinones a new class of photochemotherapeutic agents

Paola Barraja; Alessandra Montalbano; Patrizia Diana; Girolamo Cirrincione; Anna Carbone; Alessia Salvador; Daniela Vedaldi; Francesco Dall'Acqua; Giampietro Viola; Giuseppe Basso

Pyrrolo[3,4-h]quinolinones a new class of photochemotherapeutic agents

Paola Barraja, Alessandra Montalbano, Patrizia Diana, Girolamo Cirrincione, Anna Carbone, Alessia Salvador, Daniela Vedaldi, Francesco Dall'Acqua, Giampietro Viola, Giuseppe Basso

Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche

Risultato della ricerca: Article › peer review

37 Citazioni (Scopus)

Abstract

Pyrrolo[3,4-h]quinolin-2-ones were synthesized as nitrogen isosters of the angular furocoumarin angelicin, with the aim of obtaining new photochemotherapeutic agents with increased antiproliferative activity and lower undesired toxic effects. A versatile synthetic pathway was approached to allow the isolation of derivatives of the new ring system with a good substitution pattern on the pyrrole moiety. Photobiological screenings of the new compounds revealed a potent phototoxic effect and a great UVA dosedependence, reaching IC50 values at submicromolar level. The induced cellular photocytotoxicity was related to apoptosis with the involvement of mitochondria and lysosomes, alteration of cell cycle profile and membrane lipid peroxidation.

Lingua originale	English
pagine (da-a)	2326-2341
Numero di pagine	16
Rivista	BIOORGANIC & MEDICINAL CHEMISTRY
Volume	19
Stato di pubblicazione	Published - 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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Pyrrolo[3,4-h]quinolinones a new class of photochemotherapeutic agents. / Barraja, Paola ; Montalbano, Alessandra ; Diana, Patrizia ; Cirrincione, Girolamo ; Carbone, Anna; Salvador, Alessia; Vedaldi, Daniela; Dall'Acqua, Francesco; Viola, Giampietro; Basso, Giuseppe.

In: BIOORGANIC & MEDICINAL CHEMISTRY, Vol. 19, 2011, pag. 2326-2341.

Risultato della ricerca: Article › peer review

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abstract = "Pyrrolo[3,4-h]quinolin-2-ones were synthesized as nitrogen isosters of the angular furocoumarin angelicin, with the aim of obtaining new photochemotherapeutic agents with increased antiproliferative activity and lower undesired toxic effects. A versatile synthetic pathway was approached to allow the isolation of derivatives of the new ring system with a good substitution pattern on the pyrrole moiety. Photobiological screenings of the new compounds revealed a potent phototoxic effect and a great UVA dosedependence, reaching IC50 values at submicromolar level. The induced cellular photocytotoxicity was related to apoptosis with the involvement of mitochondria and lysosomes, alteration of cell cycle profile and membrane lipid peroxidation.",

keywords = "4-h]quinolinones; Angelicin heteroanalogues; Photochemotherapeutic agents; Phototoxicity, Pyrrolo[3, 4-h]quinolinones; Angelicin heteroanalogues; Photochemotherapeutic agents; Phototoxicity, Pyrrolo[3",

author = "Paola Barraja and Alessandra Montalbano and Patrizia Diana and Girolamo Cirrincione and Anna Carbone and Alessia Salvador and Daniela Vedaldi and Francesco Dall'Acqua and Giampietro Viola and Giuseppe Basso",

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AU - Barraja, Paola

AU - Montalbano, Alessandra

AU - Diana, Patrizia

AU - Cirrincione, Girolamo

AU - Carbone, Anna

AU - Salvador, Alessia

AU - Vedaldi, Daniela

AU - Dall'Acqua, Francesco

AU - Viola, Giampietro

AU - Basso, Giuseppe

PY - 2011

Y1 - 2011

N2 - Pyrrolo[3,4-h]quinolin-2-ones were synthesized as nitrogen isosters of the angular furocoumarin angelicin, with the aim of obtaining new photochemotherapeutic agents with increased antiproliferative activity and lower undesired toxic effects. A versatile synthetic pathway was approached to allow the isolation of derivatives of the new ring system with a good substitution pattern on the pyrrole moiety. Photobiological screenings of the new compounds revealed a potent phototoxic effect and a great UVA dosedependence, reaching IC50 values at submicromolar level. The induced cellular photocytotoxicity was related to apoptosis with the involvement of mitochondria and lysosomes, alteration of cell cycle profile and membrane lipid peroxidation.

AB - Pyrrolo[3,4-h]quinolin-2-ones were synthesized as nitrogen isosters of the angular furocoumarin angelicin, with the aim of obtaining new photochemotherapeutic agents with increased antiproliferative activity and lower undesired toxic effects. A versatile synthetic pathway was approached to allow the isolation of derivatives of the new ring system with a good substitution pattern on the pyrrole moiety. Photobiological screenings of the new compounds revealed a potent phototoxic effect and a great UVA dosedependence, reaching IC50 values at submicromolar level. The induced cellular photocytotoxicity was related to apoptosis with the involvement of mitochondria and lysosomes, alteration of cell cycle profile and membrane lipid peroxidation.

KW - 4-h]quinolinones; Angelicin heteroanalogues; Photochemotherapeutic agents; Phototoxicity

KW - Pyrrolo[3

KW - 4-h]quinolinones; Angelicin heteroanalogues; Photochemotherapeutic agents; Phototoxicity

KW - Pyrrolo[3

UR - http://hdl.handle.net/10447/55070

M3 - Article

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JO - BIOORGANIC & MEDICINAL CHEMISTRY

JF - BIOORGANIC & MEDICINAL CHEMISTRY

SN - 0968-0896

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