Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties

Megumi Kawai; Nwe Y. BaMaung; Steve D. Fidanze; Scott A. Erickson; Jason S. Tedrow; William J. Sanders; Anil Vasudevan; Chang Park; Charles Hutchins; Kenneth M. Comess; Douglas Kalvin; Jieyi Wang; Qian Zhang; Pingping Lou; Lora Tucker-Garcia; Jennifer Bouska; Randy L. Bell; Richard Lesniewski; Jack Henkin; George S. Sheppard

doi:10.1016/j.bmcl.2006.03.085

Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties

Megumi Kawai^*, Nwe Y. BaMaung, Steve D. Fidanze, Scott A. Erickson, Jason S. Tedrow, William J. Sanders, Anil Vasudevan, Chang Park, Charles Hutchins, Kenneth M. Comess, Douglas Kalvin, Jieyi Wang, Qian Zhang, Pingping Lou, Lora Tucker-Garcia, Jennifer Bouska, Randy L. Bell, Richard Lesniewski, Jack Henkin, George S. Sheppard

^*Corresponding author for this work

CLP - Chemistry of Life Processes Institute

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

44 Scopus citations

Abstract

We have screened molecules for inhibition of MetAP2 as a novel approach toward antiangiogenesis and anticancer therapy using affinity selection/mass spectrometry (ASMS) employing MetAP2 loaded with Mn²⁺ as the active site metal. After a series of anthranilic acid sulfonamides with micromolar affinities was identified, chemistry efforts were initiated. The micromolar hits were quickly improved to potent nanomolar inhibitors by chemical modifications guided by insights from X-ray crystallography.

Original language	English (US)
Pages (from-to)	3574-3577
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	16
Issue number	13
DOIs	https://doi.org/10.1016/j.bmcl.2006.03.085
State	Published - Jul 1 2006

Keywords

Antiproliferative
MetAP2
Sulfonamide

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2006.03.085

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Kawai, M., BaMaung, N. Y., Fidanze, S. D., Erickson, S. A., Tedrow, J. S., Sanders, W. J., Vasudevan, A., Park, C., Hutchins, C., Comess, K. M., Kalvin, D., Wang, J., Zhang, Q., Lou, P., Tucker-Garcia, L., Bouska, J., Bell, R. L., Lesniewski, R., Henkin, J., & Sheppard, G. S. (2006). Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties. Bioorganic and Medicinal Chemistry Letters, 16(13), 3574-3577. https://doi.org/10.1016/j.bmcl.2006.03.085

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title = "Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties",

abstract = "We have screened molecules for inhibition of MetAP2 as a novel approach toward antiangiogenesis and anticancer therapy using affinity selection/mass spectrometry (ASMS) employing MetAP2 loaded with Mn2+ as the active site metal. After a series of anthranilic acid sulfonamides with micromolar affinities was identified, chemistry efforts were initiated. The micromolar hits were quickly improved to potent nanomolar inhibitors by chemical modifications guided by insights from X-ray crystallography.",

keywords = "Antiproliferative, MetAP2, Sulfonamide",

author = "Megumi Kawai and BaMaung, {Nwe Y.} and Fidanze, {Steve D.} and Erickson, {Scott A.} and Tedrow, {Jason S.} and Sanders, {William J.} and Anil Vasudevan and Chang Park and Charles Hutchins and Comess, {Kenneth M.} and Douglas Kalvin and Jieyi Wang and Qian Zhang and Pingping Lou and Lora Tucker-Garcia and Jennifer Bouska and Bell, {Randy L.} and Richard Lesniewski and Jack Henkin and Sheppard, {George S.}",

year = "2006",

month = jul,

day = "1",

doi = "10.1016/j.bmcl.2006.03.085",

language = "English (US)",

volume = "16",

pages = "3574--3577",

journal = "Bioorganic and Medicinal Chemistry Letters",

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Kawai, M, BaMaung, NY, Fidanze, SD, Erickson, SA, Tedrow, JS, Sanders, WJ, Vasudevan, A, Park, C, Hutchins, C, Comess, KM, Kalvin, D, Wang, J, Zhang, Q, Lou, P, Tucker-Garcia, L, Bouska, J, Bell, RL, Lesniewski, R, Henkin, J & Sheppard, GS 2006, 'Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties', Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 13, pp. 3574-3577. https://doi.org/10.1016/j.bmcl.2006.03.085

TY - JOUR

T1 - Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties

AU - Kawai, Megumi

AU - BaMaung, Nwe Y.

AU - Fidanze, Steve D.

AU - Erickson, Scott A.

AU - Tedrow, Jason S.

AU - Sanders, William J.

AU - Vasudevan, Anil

AU - Park, Chang

AU - Hutchins, Charles

AU - Comess, Kenneth M.

AU - Kalvin, Douglas

AU - Wang, Jieyi

AU - Zhang, Qian

AU - Lou, Pingping

AU - Tucker-Garcia, Lora

AU - Bouska, Jennifer

AU - Bell, Randy L.

AU - Lesniewski, Richard

AU - Henkin, Jack

AU - Sheppard, George S.

PY - 2006/7/1

Y1 - 2006/7/1

N2 - We have screened molecules for inhibition of MetAP2 as a novel approach toward antiangiogenesis and anticancer therapy using affinity selection/mass spectrometry (ASMS) employing MetAP2 loaded with Mn2+ as the active site metal. After a series of anthranilic acid sulfonamides with micromolar affinities was identified, chemistry efforts were initiated. The micromolar hits were quickly improved to potent nanomolar inhibitors by chemical modifications guided by insights from X-ray crystallography.

AB - We have screened molecules for inhibition of MetAP2 as a novel approach toward antiangiogenesis and anticancer therapy using affinity selection/mass spectrometry (ASMS) employing MetAP2 loaded with Mn2+ as the active site metal. After a series of anthranilic acid sulfonamides with micromolar affinities was identified, chemistry efforts were initiated. The micromolar hits were quickly improved to potent nanomolar inhibitors by chemical modifications guided by insights from X-ray crystallography.

KW - Antiproliferative

KW - MetAP2

KW - Sulfonamide

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SN - 0960-894X

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EP - 3577

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 13

ER -

Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties

Abstract

Keywords

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