Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines

Jean-Yves Winum; Fabrizio Carta; Carol Ward; Peter Mullen; David Harrison; Simon P. Langdon; Alessandro Cecchi; Andrea Scozzafava; Ian Kunkler; Claudiu T. Supuran

doi:10.1016/j.bmcl.2012.05.083

Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines

Jean-Yves Winum, Fabrizio Carta, Carol Ward, Peter Mullen, David Harrison, Simon P. Langdon, Alessandro Cecchi, Andrea Scozzafava, Ian Kunkler, Claudiu T. Supuran

School of Medicine

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

Abstract

A series of 50 sulfamates were obtained by reacting 4-aminophenol with isocyanates followed by sulfamoylation. Most of the new compounds were nanomolar inhibitors of the tumor-associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms IX and XII, whereas they inhibited less cytosolic offtarget isoforms CA I and II. Some of these sulfamates showed significant antiproliferative activity in several breast cancer cell lines, such as SKBR3, MCF10A, ZR75/1, MDA-MB-361 and MCF7, constituting interesting anticancer leads. (C) 2012 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4681-4685
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	14
DOIs	https://doi.org/10.1016/j.bmcl.2012.05.083
Publication status	Published - 15 Jul 2012

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10.1016/j.bmcl.2012.05.083

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Winum, J.-Y., Carta, F., Ward, C., Mullen, P., Harrison, D., Langdon, S. P., Cecchi, A., Scozzafava, A., Kunkler, I., & Supuran, C. T. (2012). Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines. Bioorganic and Medicinal Chemistry Letters, 22(14), 4681-4685. https://doi.org/10.1016/j.bmcl.2012.05.083

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title = "Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines",

abstract = "A series of 50 sulfamates were obtained by reacting 4-aminophenol with isocyanates followed by sulfamoylation. Most of the new compounds were nanomolar inhibitors of the tumor-associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms IX and XII, whereas they inhibited less cytosolic offtarget isoforms CA I and II. Some of these sulfamates showed significant antiproliferative activity in several breast cancer cell lines, such as SKBR3, MCF10A, ZR75/1, MDA-MB-361 and MCF7, constituting interesting anticancer leads. (C) 2012 Elsevier Ltd. All rights reserved.",

author = "Jean-Yves Winum and Fabrizio Carta and Carol Ward and Peter Mullen and David Harrison and Langdon, \{Simon P.\} and Alessandro Cecchi and Andrea Scozzafava and Ian Kunkler and Supuran, \{Claudiu T.\}",

year = "2012",

month = jul,

day = "15",

doi = "10.1016/j.bmcl.2012.05.083",

language = "English",

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Winum, J-Y, Carta, F, Ward, C, Mullen, P , Harrison, D, Langdon, SP, Cecchi, A, Scozzafava, A, Kunkler, I & Supuran, CT 2012, 'Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines', Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 14, pp. 4681-4685. https://doi.org/10.1016/j.bmcl.2012.05.083

TY - JOUR

T1 - Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines

AU - Winum, Jean-Yves

AU - Carta, Fabrizio

AU - Ward, Carol

AU - Mullen, Peter

AU - Harrison, David

AU - Langdon, Simon P.

AU - Cecchi, Alessandro

AU - Scozzafava, Andrea

AU - Kunkler, Ian

AU - Supuran, Claudiu T.

PY - 2012/7/15

Y1 - 2012/7/15

N2 - A series of 50 sulfamates were obtained by reacting 4-aminophenol with isocyanates followed by sulfamoylation. Most of the new compounds were nanomolar inhibitors of the tumor-associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms IX and XII, whereas they inhibited less cytosolic offtarget isoforms CA I and II. Some of these sulfamates showed significant antiproliferative activity in several breast cancer cell lines, such as SKBR3, MCF10A, ZR75/1, MDA-MB-361 and MCF7, constituting interesting anticancer leads. (C) 2012 Elsevier Ltd. All rights reserved.

AB - A series of 50 sulfamates were obtained by reacting 4-aminophenol with isocyanates followed by sulfamoylation. Most of the new compounds were nanomolar inhibitors of the tumor-associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms IX and XII, whereas they inhibited less cytosolic offtarget isoforms CA I and II. Some of these sulfamates showed significant antiproliferative activity in several breast cancer cell lines, such as SKBR3, MCF10A, ZR75/1, MDA-MB-361 and MCF7, constituting interesting anticancer leads. (C) 2012 Elsevier Ltd. All rights reserved.

UR - https://www.scopus.com/pages/publications/84863424129

U2 - 10.1016/j.bmcl.2012.05.083

DO - 10.1016/j.bmcl.2012.05.083

M3 - Article

SN - 0960-894X

VL - 22

SP - 4681

EP - 4685

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 14

ER -

Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines

Abstract

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