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Chromogenic substrates for cholinesterases: 1-[2-Thiazolylazo]-2-acetoxybenzene derivatives

✍ Scribed by C. van Hooidonk; C. de Borst; F.A. Mitzka; C.C. Groos


Publisher
Elsevier Science
Year
1972
Tongue
English
Weight
624 KB
Volume
48
Category
Article
ISSN
0003-2697

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✦ Synopsis


For the determination of cholinesterases it is convenient to have a direct spectrophotometric observation of the substrate hydrolysis. Acetylsalicylic acid (1) , benzoylcholine (21, a-naphthyl acetate (3)) indophenyl acetate (4)) 2,&dichloroindophenyl acetate ( 5)) and l-methylacetoxyquinolinium iodides ( 6) have been used as substrates in such procedures.

We report here on a new t.ype of chromogenic substrate (I) derived from well-known heterocyclic azo dyestuffs t'hat have found a wide application in analytical chemistry for the spcctrophotometric determination of metal ions (7,8). A difference in color exists between the ester (I) and the alcohol (II) at the pH at, which the alcohol dissociates. This difference in color can be used for the spectrophotometric assay of cholinesterases. Ye CH Ye CH /3 /3 CH o=c /3 CHOLINESTERASE +CH3CO0 e pH 7.0 5 I II S = .5-CH3, Y = CHoSOl (IA), light yellowbl ue (IIAI S = 4-N(CH,)L, Y = I (IB), blue -red (IIH) M.ATKR1AI.S .AXI:, METHODS 2-Aminothiazole (m.1~. S8.590Β°C') was obtainccl from EGA-Chemic~ KG (Germany).


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Temperature dependent IH NMR study has been performed on the substrate complex derived from zinc(II) perchlorate, (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline), and 3-acetyl-2-oxazolidinone in deuteriodichloromethane. At room temperature, two isomers of octahedral substrate complexes are ra