Antitumor Activity of New Substituted 3-(5-Imidazo[2,1-b]thiazolylmethylene)-2-indolinones and 3-(5-Imidazo[2,1-b]thiadiazolylmethylene)-2-indolinones: Selectivity against Colon Tumor Cells and Effect on Cell Cycle-Related Events

被引：69

作者：

Andreani, Aldo ^{[1
]}

Burnelli, Silvia ^{[1
]}

Granaiola, Massimiliano ^{[1
]}

Leoni, Alberto ^{[1
]}

Locatelli, Alessandra ^{[1
]}

Morigi, Rita ^{[1
]}

Rambaldi, Mirella ^{[1
]}

Varoli, Lucilla ^{[1
]}

Calonghi, Natalia ^{[2
]}

Cappadone, Concettina ^{[2
]}

Voltattomi, Manuela ^{[3
]}

Zini, Maddalena ^{[2
]}

Stefanelli, Claudio ^{[2
]}

Masotti, Lanfranco ^{[2
]}

Shoemaker, Robert H. ^{[4
]}

机构：

[1] Univ Bologna, Dipartimento Sci Farmaceut, I-40126 Bologna, Italy

[2] Univ Bologna, Dipartimento Biochim G Moruzzi, I-40126 Bologna, Italy

[3] Univ Bologna, CIRB, I-40127 Bologna, Italy

[4] NCI, Screening Technol Branch, Dev Therapeut Program, Div Canc Treatment & Diag, Frederick, MD 21702 USA

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2008年 / 51卷 / 23期

关键词：

D O I：

10.1021/jm800827q

中图分类号：

R914 [药物化学];

学科分类号：

100701 [药物化学];

摘要：

The synthesis of new 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and 3-(5-imidazo[2,1-b]thiadiazolylmethylene)-2-indolinones is reported. The antitumor activity was evaluated according to the protocols available at the National Cancer Institute (NCI), Bethesda, MD. To investigate the mechanism of action of the most potent antitumor agent of this series, its effect on growth of HT-29 colon carcinoma cells was studied. Its ability to inhibit cellular proliferation was mediated by cell cycle arrest at the G2/M phase, accompanied by inhibition of ornithine decarboxylase (ODC), the limiting enzyme of polyamine synthesis, and followed by induction of apoptosis.

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页码：7508 / 7513

页数：6

相关论文

共 23 条

[1]

SYNTHESIS AND DIURETIC ACTIVITY OF IMIDAZO[2,1-B]THIAZOLE ACETOHYDRAZONES [J].

ANDREANI, A ;

RAMBALDI, M ;

MASCELLANI, G ;

RUGARLI, P .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1987, 22 (01) :19-22

[2]

Antitumor activity of new substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and study of their effect on the cell cycle [J].

Andreani, A ;

Granaiola, M ;

Leoni, A ;

Locatelli, A ;

Morigi, R ;

Rambaldi, M ;

Garaliene, V ;

Welsh, W ;

Arora, S ;

Farruggia, G ;

Masotti, L .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (17) :5604-5607

[3]

Synthesis and potential coanthracyclinic activity of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones [J].

Andreani, A ;

Locatelli, A ;

Leoni, A ;

Rambaldi, M ;

Morigi, R ;

Bossa, R ;

Chiericozzi, M ;

Fraccari, A ;

Galatulas, I .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1997, 32 (11) :919-924

[4]

IMIDAZO[2,1-B]THIAZOLE CARBAMATES AND ACYLUREAS AS POTENTIAL INSECT CONTROL AGENTS [J].

ANDREANI, A ;

RAMBALDI, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (02) :525-529

[5]

Andreani A, 2001, ANTI-CANCER DRUG DES, V16, P167

[6]

SYNTHESIS AND CARDIOTONIC ACTIVITY OF 2,5-DIMETHOXYPHENYLIMIDAZO[2,1-B]THIAZOLES [J].

ANDREANI, A ;

RAMBALDI, M ;

LOCATELLI, A ;

BOSSA, R ;

GALATULAS, I ;

NINCI, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1992, 27 (04) :431-433

[7]

5-FORMYLIMIDAZO[2,1-B]THIAZOLES AND DERIVATIVES WITH HERBICIDAL ACTIVITY [J].

ANDREANI, A ;

RAMBALDI, M ;

LOCATELLI, A ;

ANDREANI, F .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1991, 56 (11A) :2436-2447

[8]

Andreani A, 2000, ARZNEIMITTEL-FORSCH, V50, P550

[9]

Antitumor activity of bis-indole derivatives [J].

Andreani, Aldo ;

Burnelli, Silvia ;

Granaiola, Massimiliano ;

Leoni, Alberto ;

Locatelli, Alessandra ;

Morigi, Rita ;

Rambaldi, Mirella ;

Varoli, Lucilla ;

Landi, Laura ;

Prata, Cecilia ;

Berridge, Michael V. ;

Grasso, Carole ;

Fiebig, Heinz-Herbert ;

Kelter, Gerhard ;

Burger, Angelika M. ;

Kunkel, Mark W. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4563-4570

[10]

Synthesis and antitumor activity of guanylhydrazones from 6-(2,4-dichloro-5-nitrophenyl)imidazo[2,1-b]thiazoles and 6-pyridylimidazo[2,1-b]thiazoles [J].

Andreani, Aldo ;

Burnelli, Silvia ;

Granaiola, Massimiliano ;

Leoni, Alberto ;

Locatelli, Alessandra ;

Morigi, Rita ;

Rambaldi, Mirella ;

Varoli, Lucilla ;

Farruggia, Giovanna ;

Stefanelli, Claudio ;

Masotti, Lanfranco ;

Kunkel, Mark W. .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (26) :7897-7901