Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9

Gricela Lobo; Melina Monasterios; Juan Rodrigues; Neira Gamboa; Mario V. Capparelli; Javier Martínez-Cuevas; Michael Lein; Klaus Jung; Claudia Abramjuk; Jaime Charris

doi:10.1016/j.ejmech.2015.04.023

Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9

Gricela Lobo, Melina Monasterios, Juan Rodrigues, Neira Gamboa, Mario V. Capparelli, Javier Martínez-Cuevas, Michael Lein, Klaus Jung, Claudia Abramjuk, Jaime Charris

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

27 Citations (Scopus)

Abstract

© 2015 Elsevier Masson SAS. All rights reserved. A highly regiospecific synthesis of a series of indenoindoles is reported, together with X-ray studies and their activity against human prostate cancer cells PC-3 and LNCaP in vitro. The most effective compound 7,7-dimethyl-5-[(3,4-dichlorophenyl)]-(4bRS,9bRS)-dihydroxy-4b,5,6,7,8,9bhexahydro-indeno[1,2-b]indole-9,10-dione 7q reduced the viability in both cell lines in a time and dose-dependent manner. Inhibitory effects were also observed on the adhesion, migration, and invasion of the prostate cancer cells as well as on clonogenic possibly by inhibition of MMP-9 activity. Molecular docking of 7q and 6k into MMP-9 human active site was also performed to determine the probable binding mode.

Original language	English
Pages (from-to)	281-295
Journal	European Journal of Medicinal Chemistry
Volume	96
DOIs	https://doi.org/10.1016/j.ejmech.2015.04.023
Publication status	Published - 26 May 2015

Keywords

Cancer
Crystal
Indeno
MMP-9
Prostate
Regiospecif

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Lobo, G., Monasterios, M., Rodrigues, J., Gamboa, N., Capparelli, M. V., Martínez-Cuevas, J., Lein, M., Jung, K., Abramjuk, C., & Charris, J. (2015). Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9. European Journal of Medicinal Chemistry, 96, 281-295. https://doi.org/10.1016/j.ejmech.2015.04.023

Lobo, Gricela ; Monasterios, Melina ; Rodrigues, Juan ; Gamboa, Neira ; Capparelli, Mario V. ; Martínez-Cuevas, Javier ; Lein, Michael ; Jung, Klaus ; Abramjuk, Claudia ; Charris, Jaime. / Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9. In: European Journal of Medicinal Chemistry. 2015 ; Vol. 96. pp. 281-295.

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abstract = "{\textcopyright} 2015 Elsevier Masson SAS. All rights reserved. A highly regiospecific synthesis of a series of indenoindoles is reported, together with X-ray studies and their activity against human prostate cancer cells PC-3 and LNCaP in vitro. The most effective compound 7,7-dimethyl-5-[(3,4-dichlorophenyl)]-(4bRS,9bRS)-dihydroxy-4b,5,6,7,8,9bhexahydro-indeno[1,2-b]indole-9,10-dione 7q reduced the viability in both cell lines in a time and dose-dependent manner. Inhibitory effects were also observed on the adhesion, migration, and invasion of the prostate cancer cells as well as on clonogenic possibly by inhibition of MMP-9 activity. Molecular docking of 7q and 6k into MMP-9 human active site was also performed to determine the probable binding mode.",

keywords = "Cancer, Crystal, Indeno, MMP-9, Prostate, Regiospecif",

author = "Gricela Lobo and Melina Monasterios and Juan Rodrigues and Neira Gamboa and Capparelli, {Mario V.} and Javier Mart{\'i}nez-Cuevas and Michael Lein and Klaus Jung and Claudia Abramjuk and Jaime Charris",

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Lobo, G, Monasterios, M, Rodrigues, J, Gamboa, N, Capparelli, MV, Martínez-Cuevas, J, Lein, M, Jung, K, Abramjuk, C & Charris, J 2015, 'Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9', European Journal of Medicinal Chemistry, vol. 96, pp. 281-295. https://doi.org/10.1016/j.ejmech.2015.04.023

Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9. / Lobo, Gricela; Monasterios, Melina; Rodrigues, Juan; Gamboa, Neira; Capparelli, Mario V.; Martínez-Cuevas, Javier; Lein, Michael; Jung, Klaus; Abramjuk, Claudia; Charris, Jaime.

In: European Journal of Medicinal Chemistry, Vol. 96, 26.05.2015, p. 281-295.

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

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AU - Lobo, Gricela

AU - Monasterios, Melina

AU - Rodrigues, Juan

AU - Gamboa, Neira

AU - Capparelli, Mario V.

AU - Martínez-Cuevas, Javier

AU - Lein, Michael

AU - Jung, Klaus

AU - Abramjuk, Claudia

AU - Charris, Jaime

PY - 2015/5/26

Y1 - 2015/5/26

N2 - © 2015 Elsevier Masson SAS. All rights reserved. A highly regiospecific synthesis of a series of indenoindoles is reported, together with X-ray studies and their activity against human prostate cancer cells PC-3 and LNCaP in vitro. The most effective compound 7,7-dimethyl-5-[(3,4-dichlorophenyl)]-(4bRS,9bRS)-dihydroxy-4b,5,6,7,8,9bhexahydro-indeno[1,2-b]indole-9,10-dione 7q reduced the viability in both cell lines in a time and dose-dependent manner. Inhibitory effects were also observed on the adhesion, migration, and invasion of the prostate cancer cells as well as on clonogenic possibly by inhibition of MMP-9 activity. Molecular docking of 7q and 6k into MMP-9 human active site was also performed to determine the probable binding mode.

AB - © 2015 Elsevier Masson SAS. All rights reserved. A highly regiospecific synthesis of a series of indenoindoles is reported, together with X-ray studies and their activity against human prostate cancer cells PC-3 and LNCaP in vitro. The most effective compound 7,7-dimethyl-5-[(3,4-dichlorophenyl)]-(4bRS,9bRS)-dihydroxy-4b,5,6,7,8,9bhexahydro-indeno[1,2-b]indole-9,10-dione 7q reduced the viability in both cell lines in a time and dose-dependent manner. Inhibitory effects were also observed on the adhesion, migration, and invasion of the prostate cancer cells as well as on clonogenic possibly by inhibition of MMP-9 activity. Molecular docking of 7q and 6k into MMP-9 human active site was also performed to determine the probable binding mode.

KW - Cancer

KW - Crystal

KW - Indeno

KW - MMP-9

KW - Prostate

KW - Regiospecif

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DO - 10.1016/j.ejmech.2015.04.023

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VL - 96

SP - 281

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ER -