New lipophilic phthalimido- and 3-phenoxybenzyl sulfonates: Inhibition of antigen 85C mycolyltransferase activity and cytotoxicity

A Kovac; RA Wilson; Gurdyal Besra; M Filipic; D Kikelj; S Gobec

doi:10.1080/14756360600703214

New lipophilic phthalimido- and 3-phenoxybenzyl sulfonates: Inhibition of antigen 85C mycolyltransferase activity and cytotoxicity

A Kovac, RA Wilson, Gurdyal Besra, M Filipic, D Kikelj, S Gobec

Biosciences

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Abstract

Four new sulfonates were prepared as potential inhibitors of antigen 85C, a mycolyl transferase involved in the biosynthesis of the mycobacterial cell wall being designed on the basis of the proposed catalytic mechanism and antigen 85C crystal structure. The inhibitors contained a sulfonate moiety, 3-phenoxybenzyl alcohol or N-(hydroxyethyl)phthalimide as trehalose mimetics, and an alkyl chain of different length mimicking either the mycolate (alpha-chain or the mycolic acid (beta-branch. One compound displayed promising activity in a mycolyltransferase inhibition assay (compound 2b, IC50 = 4.3 microM). The two compounds containing a phthalimide moiety (compounds 3a and 3b) showed significant and selective cytotoxicity against the breast cancer cell line MDA-MB231.

Original language	English
Pages (from-to)	391-397
Number of pages	7
Journal	Journal of Enzyme Inhibition and Medicinal Chemistry
Volume	21
Issue number	4
DOIs	https://doi.org/10.1080/14756360600703214
Publication status	Published - 1 Aug 2006

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title = "New lipophilic phthalimido- and 3-phenoxybenzyl sulfonates: Inhibition of antigen 85C mycolyltransferase activity and cytotoxicity",

abstract = "Four new sulfonates were prepared as potential inhibitors of antigen 85C, a mycolyl transferase involved in the biosynthesis of the mycobacterial cell wall being designed on the basis of the proposed catalytic mechanism and antigen 85C crystal structure. The inhibitors contained a sulfonate moiety, 3-phenoxybenzyl alcohol or N-(hydroxyethyl)phthalimide as trehalose mimetics, and an alkyl chain of different length mimicking either the mycolate (alpha-chain or the mycolic acid (beta-branch. One compound displayed promising activity in a mycolyltransferase inhibition assay (compound 2b, IC50 = 4.3 microM). The two compounds containing a phthalimide moiety (compounds 3a and 3b) showed significant and selective cytotoxicity against the breast cancer cell line MDA-MB231.",

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T1 - New lipophilic phthalimido- and 3-phenoxybenzyl sulfonates: Inhibition of antigen 85C mycolyltransferase activity and cytotoxicity

AU - Kovac, A

AU - Wilson, RA

AU - Besra, Gurdyal

AU - Filipic, M

AU - Kikelj, D

AU - Gobec, S

PY - 2006/8/1

Y1 - 2006/8/1

N2 - Four new sulfonates were prepared as potential inhibitors of antigen 85C, a mycolyl transferase involved in the biosynthesis of the mycobacterial cell wall being designed on the basis of the proposed catalytic mechanism and antigen 85C crystal structure. The inhibitors contained a sulfonate moiety, 3-phenoxybenzyl alcohol or N-(hydroxyethyl)phthalimide as trehalose mimetics, and an alkyl chain of different length mimicking either the mycolate (alpha-chain or the mycolic acid (beta-branch. One compound displayed promising activity in a mycolyltransferase inhibition assay (compound 2b, IC50 = 4.3 microM). The two compounds containing a phthalimide moiety (compounds 3a and 3b) showed significant and selective cytotoxicity against the breast cancer cell line MDA-MB231.

AB - Four new sulfonates were prepared as potential inhibitors of antigen 85C, a mycolyl transferase involved in the biosynthesis of the mycobacterial cell wall being designed on the basis of the proposed catalytic mechanism and antigen 85C crystal structure. The inhibitors contained a sulfonate moiety, 3-phenoxybenzyl alcohol or N-(hydroxyethyl)phthalimide as trehalose mimetics, and an alkyl chain of different length mimicking either the mycolate (alpha-chain or the mycolic acid (beta-branch. One compound displayed promising activity in a mycolyltransferase inhibition assay (compound 2b, IC50 = 4.3 microM). The two compounds containing a phthalimide moiety (compounds 3a and 3b) showed significant and selective cytotoxicity against the breast cancer cell line MDA-MB231.

U2 - 10.1080/14756360600703214

DO - 10.1080/14756360600703214

M3 - Article

C2 - 17059171

SN - 1475-6374

VL - 21

SP - 391

EP - 397

JO - Journal of Enzyme Inhibition and Medicinal Chemistry

JF - Journal of Enzyme Inhibition and Medicinal Chemistry

IS - 4

ER -

New lipophilic phthalimido- and 3-phenoxybenzyl sulfonates: Inhibition of antigen 85C mycolyltransferase activity and cytotoxicity

Abstract

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