荧光探针的合成及表征
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摘要
以罗丹明B为原料设计合成了一系列的烷基罗丹明B酯衍生物。优化得到了适宜的工艺条件。以SOCl2为酰基化试剂,罗丹明B与醇的摩尔比为1:10,反应温度70°C,反应时间7h,罗丹明B酯衍生物的收率可达80%以上。荧光性能分析结果表明,烷基罗丹明B酯的烷基结构对其荧光强度、最大吸收和发射波长影响不大。甲基罗丹明B酯最大吸收和发射波长不受浓度的影响,荧光强度随浓度增加而增加;随着溶剂极性的增加,其最大吸收、发射波长红移,而荧光强度降低;随着激发光照射时间的增长,其最大吸收和发射波长无变化,但荧光强度明显降低,且在极性溶剂中降幅大于其在非极性溶剂中。
合成了硝基罗丹明B、氨基罗丹明B及卤代罗单明B。硝基罗丹明B与罗丹明B相比荧光强度减弱,最大吸收和发射波长红移。氨基罗丹明B与罗丹明B相比,荧光强度增强,最大吸收和发射波长红移。随着溶剂极性的增加,硝基罗丹明B和氨基罗丹明B的最大吸收和发射波长略向红移,而荧光强度降低。单卤代后罗丹明B与罗丹明B相比,荧光强度增大,最大吸收和发射波长红移,其荧光强度的顺序为I 建立了长链羧酸荧光素酯合成工艺路线,合成了一系列荧光素酯。对系列荧光素酯水解性能的研究表明,碳链越长的羧酸荧光素酯其自然水解就越难发生,稳定性能就越好。随着荧光素酯中羧基碳链的增长,脂酶检测的灵敏度有了进一步提高。筛选得到了研究脂酶的理想荧光探针二(十二酸)荧光素酯,用其可以检测0.1微克/毫升的脂酶的活性。
以氨基罗丹明B和氨基荧光素为原料,采用草酰氯单乙酯作为连接剂,合成了具有双发色基团的新化合物RH-F。该物质在紫外可见吸收光谱上出现两个吸收峰,分别接近于氨基荧光素及氨基罗丹明B。将甲基罗丹明B酯和RHB-F分别应用于测定DNA浓度,优化了分析条件,建立了共振光散射法测定痕量DNA的测定方法。
A series of alkyl rhodamine B esters were designed and synthesized from rhodamine B. The synthetic process was optimized and established. Thus, SOCl2 was used as the acylating agent, Rh B to alcohol=1:10(mole ratio), reaction temperature 70℃and reaction time 7h, the product yields are over 80%. The fluorescence analytical results indicated that the alkyl structures of Rh B esters hardly affected their fluorescence behaviors . The maximum absorption(λex) and emission wavelengths (λem) of methylrhodamine B esters are not affected by its concentration while the fluorescence intensity enhances as the concentration increases. Theλex andλem generate red shift with the enhancing of the solvent polarity while the fluorescence intensity weakens. Theλex andλem do not change with increasing of the irradiation time, but the fluorescent intensity obviously decreased. The rate of fluorescent intensity to reduce in polar solvent is larger than in apolar solvent.
Amino-Rh B, nitro-Rh B and Halogenated Rh B derivatives were synthesized. The fluorescence intensity of nitro-Rh B was lower than that of Rh B while theλex andλem were larger. The fluorescence intensity,λex andλem of amino -Rh B were stronger than those of Rh B, respectively. Theλex andλem of amino-Rh B or nitro-Rh B shifted towards the red light with increasing the solvent polarity while the fluorescence intensity decreased. The fluorescence intensity of halogenated Rh B derivatives were larger than that of RhB in a sequence of I A new route for synthesis of lipophilic fluorescein esters from acyl halide and fluorescein was established and a series of long chain fluorescein carboxylic acid esters were synthesized. The hydrolysis experiments of fluorescein esters indicated that the longer carbon chain was, the harder the natural hydrolysis was, leading to a better stability. As the carbon chain of acid is longer, the sensitivity of lipoidase detection is more improved. Using fluorescein dilaurate as the substrate, the activity of lipoidase at 0.1mg/ml was detected with an accuracy of 98.5%.
A novel dichromophoric fluorescence compound (RH-F) containing the groups of Rh B and fluorescein was synthesized from ethyl oxalyl monochloride as the conjuncter. RH-F showes two maximal absorption wavelengths corresponding to amino-fluorescein and amino-Rh B. Methyl Rh B ester and RH-F were used to determine DNA concentration, respectively. The analytical conditions were optimizedand the resonance light scattering technique of determining trace amount of ctDNA was established.
合成了硝基罗丹明B、氨基罗丹明B及卤代罗单明B。硝基罗丹明B与罗丹明B相比荧光强度减弱,最大吸收和发射波长红移。氨基罗丹明B与罗丹明B相比,荧光强度增强,最大吸收和发射波长红移。随着溶剂极性的增加,硝基罗丹明B和氨基罗丹明B的最大吸收和发射波长略向红移,而荧光强度降低。单卤代后罗丹明B与罗丹明B相比,荧光强度增大,最大吸收和发射波长红移,其荧光强度的顺序为I
以氨基罗丹明B和氨基荧光素为原料,采用草酰氯单乙酯作为连接剂,合成了具有双发色基团的新化合物RH-F。该物质在紫外可见吸收光谱上出现两个吸收峰,分别接近于氨基荧光素及氨基罗丹明B。将甲基罗丹明B酯和RHB-F分别应用于测定DNA浓度,优化了分析条件,建立了共振光散射法测定痕量DNA的测定方法。
A series of alkyl rhodamine B esters were designed and synthesized from rhodamine B. The synthetic process was optimized and established. Thus, SOCl2 was used as the acylating agent, Rh B to alcohol=1:10(mole ratio), reaction temperature 70℃and reaction time 7h, the product yields are over 80%. The fluorescence analytical results indicated that the alkyl structures of Rh B esters hardly affected their fluorescence behaviors . The maximum absorption(λex) and emission wavelengths (λem) of methylrhodamine B esters are not affected by its concentration while the fluorescence intensity enhances as the concentration increases. Theλex andλem generate red shift with the enhancing of the solvent polarity while the fluorescence intensity weakens. Theλex andλem do not change with increasing of the irradiation time, but the fluorescent intensity obviously decreased. The rate of fluorescent intensity to reduce in polar solvent is larger than in apolar solvent.
Amino-Rh B, nitro-Rh B and Halogenated Rh B derivatives were synthesized. The fluorescence intensity of nitro-Rh B was lower than that of Rh B while theλex andλem were larger. The fluorescence intensity,λex andλem of amino -Rh B were stronger than those of Rh B, respectively. Theλex andλem of amino-Rh B or nitro-Rh B shifted towards the red light with increasing the solvent polarity while the fluorescence intensity decreased. The fluorescence intensity of halogenated Rh B derivatives were larger than that of RhB in a sequence of I
A novel dichromophoric fluorescence compound (RH-F) containing the groups of Rh B and fluorescein was synthesized from ethyl oxalyl monochloride as the conjuncter. RH-F showes two maximal absorption wavelengths corresponding to amino-fluorescein and amino-Rh B. Methyl Rh B ester and RH-F were used to determine DNA concentration, respectively. The analytical conditions were optimizedand the resonance light scattering technique of determining trace amount of ctDNA was established.
引文
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