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 journalArticle

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 languageEnglish
Pages (from-to)2441-2450
Number of pages10
JournalBioorganic and Medicinal Chemistry
Volume12
Issue number9
DOIs
Publication statusPublished - May 1 2004

Fingerprint

Matrix Metalloproteinase Inhibitors
Matrix Metalloproteinases
Sulfonamides
Acids
Hydroxamic Acids
Derivatives
Fibrosarcoma
Skeleton
Oxygen
Pharmaceutical Preparations

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Rossello, A., Nuti, E., Orlandini, E., Carelli, P., Rapposelli, S., Macchia, M., ... 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 journalArticle

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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