Tometsko A M, Turula J, Comstock J
Int J Pept Protein Res. 1978 Sep;12(3):143-54. doi: 10.1111/j.1399-3011.1978.tb02878.x.
In the course of preparing aryl azide derivatives for use as photoprobes, we have observed significant light sensitivity in the precursor aryl diazonium compounds. The photosensitive properties of this class of compounds are of interest since they will seek out cationic binding sites in biological targets, and can be employed to inhibit complementary targets at acid pH. The relationship between photolytic change in the structure of diazonium compounds and the corresponding change in function of a biological target are presented. Experiments are described in which the dark and light sensitive properties of a model diazonium compound, diazobenzene sulfonate (DBS), were determined. The ultraviolet spectra were used to evaluate the dark stability and light sensitivity of DBS. Chymotrypsin and trypsin served as functioning targets for further evaluation of the photochemical properties. Both enzymes are stable to the probe in the dark at acid pH. A rapid loss of enzyme activity was observed following flash photolysis of DBS-enzyme solutions. Photolytic incorporation of radioactive DBS into chymotrypsin was observed. Aryl diazonium salts can be employed to probe the availability of complementary sites in biological targets at different acid pH values.
在制备用作光探针的芳基叠氮衍生物的过程中，我们观察到前体芳基重氮化合物具有显著的光敏感性。这类化合物的光敏性质令人感兴趣，因为它们会寻找生物靶点中的阳离子结合位点，并可用于在酸性pH值下抑制互补靶点。本文介绍了重氮化合物结构的光解变化与生物靶点功能相应变化之间的关系。描述了测定模型重氮化合物重氮苯磺酸盐（DBS）的暗敏和光敏性质的实验。紫外光谱用于评估DBS的暗稳定性和光敏感性。胰凝乳蛋白酶和胰蛋白酶作为功能靶点用于进一步评估光化学性质。在酸性pH值下，两种酶在黑暗中对探针都稳定。在DBS-酶溶液的闪光光解后，观察到酶活性迅速丧失。观察到放射性DBS光解掺入胰凝乳蛋白酶中。芳基重氮盐可用于探测在不同酸性pH值下生物靶点中互补位点的可用性。
