反应激活型疾病诊断荧光探针及其它相关探针的设计、合成及应用
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摘要
本文设计、合成了三类基于反应激活的荧光探针,反应前后荧光团的电子云密度得到重新排列,使得反应前后可以产生两个不同波段的荧光发射峰,因此可以对检测对象实现比例检测,大大提高了检测的精度和可信度。
1.设计、合成了N-乙酰转移酶II特异性荧光探针Amonafide。临床代谢研究发现,化合物amonafide在体内主要被N-乙酰基转移酶II催化代谢生成Acetyl-Amonafide。基于此,设计了化合物Amonafide作为N-乙酰转移酶II特异性荧光探针。化合物Amonafide和Acetyl-Amonafide在350 nm有共同的最大吸收峰,而发射波长分别在460 nm和580 nm,更重要的是代谢产物Acetyl-Amonafide的荧光量子产率高达0.74。酶水平和细胞水平实验进一步证明了探针Amonafide对NAT2的高选择性和灵敏性(1 nM)。并且成功地将探针Amonafide应用于HepG2细胞株内的N-乙酰转移酶II荧光成像检测,这为芳胺类药物的个性化给药奠定了基础。同时完成了分别针对N-乙酰转移酶I和N-乙酰转移酶II的长波长荧光探针的设计和部分合成工作。
2.以4-氨基-1,8-萘酰亚胺为荧光团母体,通过异氰酸酯键与受体对硝基苄醇链接,设计了针对肿瘤乏氧的比率型荧光探针RHP。通过ICT原理,可以使反应后的最大荧光发射波长红移(475nm到550 nm)。详细研究了探针RHP对硝基还原酶(NTR)的荧光响应和动力学曲线,同时检测了内源性还原物质对探针的影响。实验结果进一步证明了探针RHP对硝基还原酶的高选择性。乏氧／有氧实验证明,当GrHy/GrAr和B1Hy/B1Ar的比值在45以上时,细胞即处于乏氧环境。探针RHP可以作为肿瘤乏氧诊断探针用于体内实体瘤的早期诊断。同时通过乏氧原理设计并合成了基于Amonafide的前药化合物。
3.以苯并噻唑类化合物(HBTBC)为荧光团母体,设计了一类基于ESIPT的荧光探针。反应前后两种化合物的斯托克斯位移高达120 nm以上,且光谱交叉的区域少,设计的探针检测结果的可信度和准确度更高。以Tsuji-Trost烯丙基的氧化反应为基础设计了针对Pd(0)的荧光探针OHBT。当OHBT与Pd(0)反应后,最大发射波长由410 nm红移到550 nm,设计的探针对Pd(0)有着高度的选择性。同时通过滤纸对Pd(0)实现了固体荧光检测,并成功对Suzuki偶联反应产物中残留的Pd(0)进行了定量检测。
In the present work, three series of reaction-activated fluorescent probes were desiged and synthesized. Because of the rearrangement of fluorophore's electron density, probe and reaction product can produce two different wavelengths of fluorescence emission peak. Therefore, probe can detect the substrate in ratiometric way, which greatly improves the accuracy and reliability of the detection results.
1. Based on the clinical metabolic study that Amonafide was mainly metabolized by N-acetyltransferase II to Acetyl-Amonafide, we designed and synthesized N-acetyltransferase II specific probe Amonafide. Both Amonafide and Acetyl-amonafide can be excited at 350 nm, but the maximum emission wavelength is at 580 nm and 460 nm respectively. The more important thing is that the metabolism product Acetyl-amonafide has a high fluorescence quantum yield (0.72). Through enzyme and cell experiments, it was also proved that the probe had high selectivity and sensitivity (1 nM) for N-acetyltransferase II. Next, the probe was successfully applied in HepG2 fluorescence imaging. These will lay the foundation of personalized medicine.
2. Based on the hypoxia prodrug moiety of p-nitrobenzyl, a selective ratiometric fluorescent sensor (RHP) for the detection of microenvironment hypoxia was designed and synthesized. RHP can be selectively activated by bioreductive enzymes (NTR) and results in an evident blue to green fluorescent emission wavelength change in both solution phases and in cell lines, which might be the first fluorescent ratiometric probe for hypoxia in solid tumors. By hypoxia/aerobic experiments, it showed that when the GrHy/GrAr and BlHy/BlAr ratio value is above 45, the cells are in a hypoxic environment. RHP can be used as a probe for the diagnosis of hypoxia in early stage of solid tumors.
Some prodrugs which based on amonafide and activated by hypoxia were also synthesized.
3. Based on benzothiazole compounds (HBTBC), fluorescent probes of Pd (0) was designed and synthesized. Because of the Stokes shift value is up to 120 nm before and after the reaction, the detection resulted had higher reliability and accuracy.
Pd (0) fluorescent probe (OHBT) was based on Tsuji-Trost allylic oxidative insertion reaction. After reaction between OHBT and Pd, the maximum emission wavelength was shifted from 410 nm to 550 nm. OHBT had a high selectivity to Pd(0). The Pd can also be detected by solid fluorescence through a given method. OHBT was successfully applied in residual Pd detection in the Suzuki reaction.
1.设计、合成了N-乙酰转移酶II特异性荧光探针Amonafide。临床代谢研究发现,化合物amonafide在体内主要被N-乙酰基转移酶II催化代谢生成Acetyl-Amonafide。基于此,设计了化合物Amonafide作为N-乙酰转移酶II特异性荧光探针。化合物Amonafide和Acetyl-Amonafide在350 nm有共同的最大吸收峰,而发射波长分别在460 nm和580 nm,更重要的是代谢产物Acetyl-Amonafide的荧光量子产率高达0.74。酶水平和细胞水平实验进一步证明了探针Amonafide对NAT2的高选择性和灵敏性(1 nM)。并且成功地将探针Amonafide应用于HepG2细胞株内的N-乙酰转移酶II荧光成像检测,这为芳胺类药物的个性化给药奠定了基础。同时完成了分别针对N-乙酰转移酶I和N-乙酰转移酶II的长波长荧光探针的设计和部分合成工作。
2.以4-氨基-1,8-萘酰亚胺为荧光团母体,通过异氰酸酯键与受体对硝基苄醇链接,设计了针对肿瘤乏氧的比率型荧光探针RHP。通过ICT原理,可以使反应后的最大荧光发射波长红移(475nm到550 nm)。详细研究了探针RHP对硝基还原酶(NTR)的荧光响应和动力学曲线,同时检测了内源性还原物质对探针的影响。实验结果进一步证明了探针RHP对硝基还原酶的高选择性。乏氧／有氧实验证明,当GrHy/GrAr和B1Hy/B1Ar的比值在45以上时,细胞即处于乏氧环境。探针RHP可以作为肿瘤乏氧诊断探针用于体内实体瘤的早期诊断。同时通过乏氧原理设计并合成了基于Amonafide的前药化合物。
3.以苯并噻唑类化合物(HBTBC)为荧光团母体,设计了一类基于ESIPT的荧光探针。反应前后两种化合物的斯托克斯位移高达120 nm以上,且光谱交叉的区域少,设计的探针检测结果的可信度和准确度更高。以Tsuji-Trost烯丙基的氧化反应为基础设计了针对Pd(0)的荧光探针OHBT。当OHBT与Pd(0)反应后,最大发射波长由410 nm红移到550 nm,设计的探针对Pd(0)有着高度的选择性。同时通过滤纸对Pd(0)实现了固体荧光检测,并成功对Suzuki偶联反应产物中残留的Pd(0)进行了定量检测。
In the present work, three series of reaction-activated fluorescent probes were desiged and synthesized. Because of the rearrangement of fluorophore's electron density, probe and reaction product can produce two different wavelengths of fluorescence emission peak. Therefore, probe can detect the substrate in ratiometric way, which greatly improves the accuracy and reliability of the detection results.
1. Based on the clinical metabolic study that Amonafide was mainly metabolized by N-acetyltransferase II to Acetyl-Amonafide, we designed and synthesized N-acetyltransferase II specific probe Amonafide. Both Amonafide and Acetyl-amonafide can be excited at 350 nm, but the maximum emission wavelength is at 580 nm and 460 nm respectively. The more important thing is that the metabolism product Acetyl-amonafide has a high fluorescence quantum yield (0.72). Through enzyme and cell experiments, it was also proved that the probe had high selectivity and sensitivity (1 nM) for N-acetyltransferase II. Next, the probe was successfully applied in HepG2 fluorescence imaging. These will lay the foundation of personalized medicine.
2. Based on the hypoxia prodrug moiety of p-nitrobenzyl, a selective ratiometric fluorescent sensor (RHP) for the detection of microenvironment hypoxia was designed and synthesized. RHP can be selectively activated by bioreductive enzymes (NTR) and results in an evident blue to green fluorescent emission wavelength change in both solution phases and in cell lines, which might be the first fluorescent ratiometric probe for hypoxia in solid tumors. By hypoxia/aerobic experiments, it showed that when the GrHy/GrAr and BlHy/BlAr ratio value is above 45, the cells are in a hypoxic environment. RHP can be used as a probe for the diagnosis of hypoxia in early stage of solid tumors.
Some prodrugs which based on amonafide and activated by hypoxia were also synthesized.
3. Based on benzothiazole compounds (HBTBC), fluorescent probes of Pd (0) was designed and synthesized. Because of the Stokes shift value is up to 120 nm before and after the reaction, the detection resulted had higher reliability and accuracy.
Pd (0) fluorescent probe (OHBT) was based on Tsuji-Trost allylic oxidative insertion reaction. After reaction between OHBT and Pd, the maximum emission wavelength was shifted from 410 nm to 550 nm. OHBT had a high selectivity to Pd(0). The Pd can also be detected by solid fluorescence through a given method. OHBT was successfully applied in residual Pd detection in the Suzuki reaction.
引文
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