[Dock-fans] TZD Tautomers

Nancy nancy5villa at gmail.com
Thu Jan 13 17:49:14 PST 2011


Considering that others have stated that tautomeric form can be one of the
most important factors when preparing ligands docking, could you clarify
what you mean by "tautomeric form is the least of your worries"?

Thanks,
Nancy



On Thu, Jan 13, 2011 at 7:56 PM, John Irwin <jir322 at gmail.com> wrote:

> Single point IC50, no dose response, no IC50 curve, no test for
> aggregation. Tautomeric form is the least of your worries.
>
> On Thu, Jan 13, 2011 at 1:27 PM, Nancy <nancy5villa at gmail.com> wrote:
>
>> Hi All,
>>
>> I happened to find a published article where molecular docking simulations
>> of TZDs against a novel protein is detailed:
>>
>> "Structure-based design of a thiazolidinedione which targets the
>> mitochondrial protein mitoNEET" Bioorg Med Chem Lett. 2010 Feb
>> 1;20(3):819-23
>>
>> In this paper, the authors, using MarvinSketch v3.5.4, determined that the
>> TZDs would exist predominantly in the enol form at pH 7.4, as opposed to the
>> diketone form (see attached figure).  It appears that the article's tautomer
>> prediction was based only on the pH prior to docking, and had nothing to do
>> with ligand-protein interactions.
>>
>> Does anyone know if the diketone or enol, or perhaps a different tautomer,
>> would be predominant at pH 7.4?
>>
>> Thanks in advance.
>> Nancy
>>
>>
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>>
>
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