Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent∞

Vincenzo Tumiatti; Andrea Milelli; Anna Minarini; Marialuisa Micco; Anna Gasperi Campani; Laura Roncuzzi; Daniela Baiocchi; Jessica Marinello; Giovanni Capranico; Maddalena Zini; Claudio Stefanelli; Carlo Melchiorre

doi:10.1021/jm901131m

Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent∞

Vincenzo Tumiatti, Andrea Milelli, Anna Minarini, Marialuisa Micco, Anna Gasperi Campani, Laura Roncuzzi, Daniela Baiocchi, Jessica Marinello, Giovanni Capranico, Maddalena Zini, Claudio Stefanelli, Carlo Melchiorre

Istituti Ortopedici Rizzoli

Research output: Contribution to journal › Article › peer-review

Abstract

Naphthalimmide (NI) and 1,4,5,8-naphthalentetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity. NDI derivatives 1-9 were more cytotoxic than the corresponding NI derivatives 10-18. The molecular mechanisms of 1 and 2 were investigated in comparison to mitonafide. They interacted with DNA, were not topoisomerase IIR poisons, triggered caspase activation, caused p53 protein accumulation, and down-regulated AKT survival. Furthermore, 1 and 2 caused a decrease of ERK1/2 and, unlike mitonafide, inhibited ERKs phosphorylation. ∞ Dedicated to Professor Fulvio Gualtieri on the occasion of his retirement.

Original language	English
Pages (from-to)	7873-7877
Number of pages	5
Journal	Journal of Medicinal Chemistry
Volume	52
Issue number	23
DOIs	https://doi.org/10.1021/jm901131m
Publication status	Published - Dec 10 2009

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

Access to Document

10.1021/jm901131m

Fingerprint Dive into the research topics of 'Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent∞'. Together they form a unique fingerprint.

Cite this

Tumiatti, V., Milelli, A., Minarini, A., Micco, M., Campani, A. G., Roncuzzi, L., Baiocchi, D., Marinello, J., Capranico, G., Zini, M., Stefanelli, C., & Melchiorre, C. (2009). Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent∞. Journal of Medicinal Chemistry, 52(23), 7873-7877. https://doi.org/10.1021/jm901131m

Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent∞. / Tumiatti, Vincenzo; Milelli, Andrea; Minarini, Anna; Micco, Marialuisa; Campani, Anna Gasperi; Roncuzzi, Laura; Baiocchi, Daniela; Marinello, Jessica; Capranico, Giovanni; Zini, Maddalena; Stefanelli, Claudio; Melchiorre, Carlo.

In: Journal of Medicinal Chemistry, Vol. 52, No. 23, 10.12.2009, p. 7873-7877.

Research output: Contribution to journal › Article › peer-review

Tumiatti, V, Milelli, A, Minarini, A, Micco, M, Campani, AG, Roncuzzi, L, Baiocchi, D, Marinello, J, Capranico, G, Zini, M, Stefanelli, C & Melchiorre, C 2009, 'Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent∞', Journal of Medicinal Chemistry, vol. 52, no. 23, pp. 7873-7877. https://doi.org/10.1021/jm901131m

Tumiatti, Vincenzo ; Milelli, Andrea ; Minarini, Anna ; Micco, Marialuisa ; Campani, Anna Gasperi ; Roncuzzi, Laura ; Baiocchi, Daniela ; Marinello, Jessica ; Capranico, Giovanni ; Zini, Maddalena ; Stefanelli, Claudio ; Melchiorre, Carlo. / Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent∞. In: Journal of Medicinal Chemistry. 2009 ; Vol. 52, No. 23. pp. 7873-7877.

@article{9d63f66a8e3e4c20857950ca03c3370f,

title = "Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent∞",

abstract = "Naphthalimmide (NI) and 1,4,5,8-naphthalentetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity. NDI derivatives 1-9 were more cytotoxic than the corresponding NI derivatives 10-18. The molecular mechanisms of 1 and 2 were investigated in comparison to mitonafide. They interacted with DNA, were not topoisomerase IIR poisons, triggered caspase activation, caused p53 protein accumulation, and down-regulated AKT survival. Furthermore, 1 and 2 caused a decrease of ERK1/2 and, unlike mitonafide, inhibited ERKs phosphorylation. ∞ Dedicated to Professor Fulvio Gualtieri on the occasion of his retirement.",

author = "Vincenzo Tumiatti and Andrea Milelli and Anna Minarini and Marialuisa Micco and Campani, {Anna Gasperi} and Laura Roncuzzi and Daniela Baiocchi and Jessica Marinello and Giovanni Capranico and Maddalena Zini and Claudio Stefanelli and Carlo Melchiorre",

year = "2009",

month = dec,

day = "10",

doi = "10.1021/jm901131m",

language = "English",

volume = "52",

pages = "7873--7877",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent∞

AU - Tumiatti, Vincenzo

AU - Milelli, Andrea

AU - Minarini, Anna

AU - Micco, Marialuisa

AU - Campani, Anna Gasperi

AU - Roncuzzi, Laura

AU - Baiocchi, Daniela

AU - Marinello, Jessica

AU - Capranico, Giovanni

AU - Zini, Maddalena

AU - Stefanelli, Claudio

AU - Melchiorre, Carlo

PY - 2009/12/10

Y1 - 2009/12/10

N2 - Naphthalimmide (NI) and 1,4,5,8-naphthalentetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity. NDI derivatives 1-9 were more cytotoxic than the corresponding NI derivatives 10-18. The molecular mechanisms of 1 and 2 were investigated in comparison to mitonafide. They interacted with DNA, were not topoisomerase IIR poisons, triggered caspase activation, caused p53 protein accumulation, and down-regulated AKT survival. Furthermore, 1 and 2 caused a decrease of ERK1/2 and, unlike mitonafide, inhibited ERKs phosphorylation. ∞ Dedicated to Professor Fulvio Gualtieri on the occasion of his retirement.

AB - Naphthalimmide (NI) and 1,4,5,8-naphthalentetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity. NDI derivatives 1-9 were more cytotoxic than the corresponding NI derivatives 10-18. The molecular mechanisms of 1 and 2 were investigated in comparison to mitonafide. They interacted with DNA, were not topoisomerase IIR poisons, triggered caspase activation, caused p53 protein accumulation, and down-regulated AKT survival. Furthermore, 1 and 2 caused a decrease of ERK1/2 and, unlike mitonafide, inhibited ERKs phosphorylation. ∞ Dedicated to Professor Fulvio Gualtieri on the occasion of his retirement.

UR - http://www.scopus.com/inward/record.url?scp=72249110438&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=72249110438&partnerID=8YFLogxK

U2 - 10.1021/jm901131m

DO - 10.1021/jm901131m

M3 - Article

C2 - 19954251

AN - SCOPUS:72249110438

VL - 52

SP - 7873

EP - 7877

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 23

ER -