New N-arylsulfonyl-N-alkoxyaminoacetohydroxamic acids as selective inhibitors of gelatinase a (MMP-2)

Armando Rossello; Elisa Nuti; Elisabetta Orlandini; Paolo Carelli; Simona Rapposelli; Marco Macchia; Filippo Minutolo; Laura Carbonaro; Adriana Albini; Roberto Benelli; Giovanni Cercignani; Gillian Murphy; Aldo Balsamo

doi:10.1016/j.bmc.2004.01.047

New N-arylsulfonyl-N-alkoxyaminoacetohydroxamic acids as selective inhibitors of gelatinase a (MMP-2)

Armando Rossello, Elisa Nuti, Elisabetta Orlandini, Paolo Carelli, Simona Rapposelli, Marco Macchia, Filippo Minutolo, Laura Carbonaro, Adriana Albini, Roberto Benelli, Giovanni Cercignani, Gillian Murphy, Aldo Balsamo

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

Abstract

New N-arylsulfonyl-substituted alkoxyaminoaceto hydroxamic acid derivatives of types 8 and 10 designed as oxa-analogues of known sulfonamide-based MMPi of types 2 and 7 were synthesized and tested for their inhibitory activities on some matrix metalloproteinases. The combination of a biphenylsulfonamide group with oxyamino oxygen in the pharmacophoric central skeleton of sulfonamide-based MMPi obtained in the new sulfonamides 10 seems to be able to give selectivity for MMP-2 over MMP-1. The most potent derivative of this type, 10a, shows similar anti-invasive properties to the analogue reference drug CGS27023A, 2, in an in vitro model of invasion on matrigel, carried out on cellular lines of fibrosarcoma HT1080 (tumoural cells over-expressing MMP-2 and MMP-9).

Original language	English
Pages (from-to)	2441-2450
Number of pages	10
Journal	Bioorganic and Medicinal Chemistry
Volume	12
Issue number	9
DOIs	https://doi.org/10.1016/j.bmc.2004.01.047
Publication status	Published - May 1 2004

Keywords

Gelatinase A inhibitors
MMP-2 selective
Sulfonamide-based MMP inhibitors

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Organic Chemistry
Drug Discovery
Pharmaceutical Science

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10.1016/j.bmc.2004.01.047

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Rossello, A., Nuti, E., Orlandini, E., Carelli, P., Rapposelli, S., Macchia, M., Minutolo, F., Carbonaro, L., Albini, A., Benelli, R., Cercignani, G., Murphy, G., & Balsamo, A. (2004). New N-arylsulfonyl-N-alkoxyaminoacetohydroxamic acids as selective inhibitors of gelatinase a (MMP-2). Bioorganic and Medicinal Chemistry, 12(9), 2441-2450. https://doi.org/10.1016/j.bmc.2004.01.047

New N-arylsulfonyl-N-alkoxyaminoacetohydroxamic acids as selective inhibitors of gelatinase a (MMP-2). / Rossello, Armando; Nuti, Elisa; Orlandini, Elisabetta; Carelli, Paolo; Rapposelli, Simona; Macchia, Marco; Minutolo, Filippo; Carbonaro, Laura; Albini, Adriana ; Benelli, Roberto; Cercignani, Giovanni; Murphy, Gillian; Balsamo, Aldo.

In: Bioorganic and Medicinal Chemistry, Vol. 12, No. 9, 01.05.2004, p. 2441-2450.

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

Rossello, A, Nuti, E, Orlandini, E, Carelli, P, Rapposelli, S, Macchia, M, Minutolo, F, Carbonaro, L, Albini, A , Benelli, R, Cercignani, G, Murphy, G & Balsamo, A 2004, 'New N-arylsulfonyl-N-alkoxyaminoacetohydroxamic acids as selective inhibitors of gelatinase a (MMP-2)', Bioorganic and Medicinal Chemistry, vol. 12, no. 9, pp. 2441-2450. https://doi.org/10.1016/j.bmc.2004.01.047

Rossello, Armando ; Nuti, Elisa ; Orlandini, Elisabetta ; Carelli, Paolo ; Rapposelli, Simona ; Macchia, Marco ; Minutolo, Filippo ; Carbonaro, Laura ; Albini, Adriana ; Benelli, Roberto ; Cercignani, Giovanni ; Murphy, Gillian ; Balsamo, Aldo. / New N-arylsulfonyl-N-alkoxyaminoacetohydroxamic acids as selective inhibitors of gelatinase a (MMP-2). In: Bioorganic and Medicinal Chemistry. 2004 ; Vol. 12, No. 9. pp. 2441-2450.

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abstract = "New N-arylsulfonyl-substituted alkoxyaminoaceto hydroxamic acid derivatives of types 8 and 10 designed as oxa-analogues of known sulfonamide-based MMPi of types 2 and 7 were synthesized and tested for their inhibitory activities on some matrix metalloproteinases. The combination of a biphenylsulfonamide group with oxyamino oxygen in the pharmacophoric central skeleton of sulfonamide-based MMPi obtained in the new sulfonamides 10 seems to be able to give selectivity for MMP-2 over MMP-1. The most potent derivative of this type, 10a, shows similar anti-invasive properties to the analogue reference drug CGS27023A, 2, in an in vitro model of invasion on matrigel, carried out on cellular lines of fibrosarcoma HT1080 (tumoural cells over-expressing MMP-2 and MMP-9).",

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AU - Carelli, Paolo

AU - Rapposelli, Simona

AU - Macchia, Marco

AU - Minutolo, Filippo

AU - Carbonaro, Laura

AU - Albini, Adriana

AU - Benelli, Roberto

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New N-arylsulfonyl-N-alkoxyaminoacetohydroxamic acids as selective inhibitors of gelatinase a (MMP-2)

Abstract

Keywords

ASJC Scopus subject areas

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