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Document Figure 13 The inhibitor 2-((3,4-dihydroxy-2-nitrophenyl)vinyl)phenylketone modeled into the active site of rat (a) and pig (b) COMT. Page 356 ously this one amino acid differences in the active site of the isoenzymes can explain the significant differences in the inhibitory potency of vinylphenylketone against these enzymes. From the structural point of view it seems that the position of the side-chain substitution (for example at C5 in entacapone and C4 in vinylphenylketone) is not critical for the inhibitor binding. In both cases the substituent has sufficient space to adapt to the protein structure, and in fact, large substituents reach from the active site cavity to the solvent (Figure 13). The tenfold higher inhibitory activity of entacapone compared with vinylphenylketone against human COMT can be accounted for <strong>by</strong> the electron- withdrawing effect of the side-chain substitution. In the case of entacapone, the side chain at position C5 has a more beneficial electronic influence on the 2- hydroxyl of the inhibitor producing a better inhibition (see Section VI). VI. Mechanism of the COMT Inhibition By Nitrocatechols As described above, catechols with strong electronegative groups are potent inhibitors of COMT. These compounds seem to bind well to the active site, but in spite of that they are very poor substrates. It has been shown, with nitecapone http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_356.html (1 of 2) [4/5/2004 5:28:54 PM]
Document Figure 14 The energy profile (as calculated at the 3-21G//PM3 level [24]) for the proton transfer step A rarrow.gif B and the methyl transfer step B rarrow.gif C for 3,4-dinitrocatechol as a substrate. in a rat COMT assay, that the rate of nitecapone methylation is equivalent to about 1% of the rate of dopamine methylation [47]. Page 357 The energy profile for the hypothetical methylation of 3,5-dinitrocatechol is shown in Figure 14 [24]. The electronegative nitro groups strongly stabilize the ionized catechol–COMT complex, and the energy barrier for the methylation step is high (see Figure 9 for comparison). This can be understood as decreased nucleophilicity of the hydroxyl oxygen, due to the electron-withdrawing properties of the nitro groups. The electronic effect of the substituents of the catechol ring to the nucleophilicity of the hydroxyl group at the active site can be readily seen from the molecular electrostatic potential (MEP) surfaces of the system. The MEP surfaces were calculated at the PM3 level and plotted at –20 kcal/mol for catechol and 3,5-dinitrocatechol at the active site of COMT [24]. The results are summarized in Figure 15. In the case of catechol the effect of the proton transfer form OH to Lys144 is seen as a remarkable increase in the negative potential between AdoMet and the substrate. 3,5-Dinitro substitution of the catechol ring http://legacy.netlibrary.com/nlreader/nlReader.dll?bookid=12640&filename=Page_357.html (1 of 2) [4/5/2004 5:28:58 PM]
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Structure-based Drug Design 14 Stru
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Document 2 Structural Studies of HI
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Document Analysis of various HIV-1
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Document Table 3 HIV-1 RT Amino Aci
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Document Page 67 Biochemical data s
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Document Chris Tantillo. The work i
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Document Page 72 16. Goldman ME, Nu
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Document 45. Majumadar C, Abbotts J
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Document reverse transcriptase inhi
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Document 89. Hughes SH, Arnold E, H
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Document 106. Cirino NM, Cameron CE
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Document 122. Marshall WS, Beaton G
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Document dine) and didanosine (dide
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Document 163. Lacey SF, Larder BA.
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Document Page 108 mulate during tre
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Document when metals are bound. Fin
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Document cubation of phosphotyrosin
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Document 4 Bradykinin Receptor Anta
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Document Page 121 Nearly all cells
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Document Page 127 The des-Arg 9 for
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Document receptor, it has not yet b
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Document Figure 6 Rat and human B2
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Document Page 141 receptor with int
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Document Figure 9 Composition of te
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Document We determined the structur
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Document Figure 3 Previously known
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Document IV. Drug Design Progressio
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Document Table 1 Inhibition Data fo
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Document Page 166 As predicated, th
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Document References 1. Parks RE Jr.
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Document 17. Ealick SE, Rule SA, Ca
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Document 6 Structural Implications
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Document Page 176 0.43 Å) as the c
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Document Cyclotheonamide A (CtA), a
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Page 415 and 416: Document 17. Szelke M. Chemistry of
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Page 421 and 422: Document Page 343 14 Structural Asp
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Document 17 Structure and Functiona
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Document Table 1 Approval Indicatio
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Document Subsequent studies have sh
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Document Page 495 of the RNA and pr
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Document Figure 5 Some compounds wh
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Document Med Biol 1991; 306:9-21; (
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Document Cyclotheonamide A (CtA), 2
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Document D ddI, 152 tumour necrosis
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Document antistasin peptides, 281 c
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Document fragment-based programs, 5
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Document [Human immunodeficiency vi
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Document antagonistic activity, 416
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Document Kininogen, 119 high molecu
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Document RT inhibitor, 41, 56 Nonpe
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Document Phosphoglycerate kinase (P
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Document [Protease targets] serinyl
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