本文關(guān)鍵詞：新型5-meso-修飾尾式卟啉的合成及光譜性能研究　出處：《湖南科技大學(xué)》2016年碩士論文　論文類型：學(xué)位論文

  更多相關(guān)文章： 二氫嘧啶酮 尾式卟啉 硫離子 熒光探針

【摘要】：卟啉化合物卟啉是高度共軛的?電子體系,它具有大的剛性平面芳香環(huán)結(jié)構(gòu),環(huán)內(nèi)電子流動性好,且在可見光區(qū)具有極強(qiáng)的吸收和優(yōu)良的供電子特性,此外卟啉化合物還具有許多獨(dú)特的理化性質(zhì)。由于卟啉化合物環(huán)平面具有易修飾的特點(diǎn),因此通過對其進(jìn)行一系列選擇性的修飾,可以得到在光動力化學(xué)藥物治療、生物熒光探針和生物成像等方面有廣泛應(yīng)用前景的新尾式卟啉化合物。本論文主要開展了以下兩方面的研究:1.由于3,4-二氫嘧啶酮及其衍生物(DHPM)是一種重要的藥物中間體,具有特殊的治療性質(zhì)和藥理活性,根據(jù)藥物設(shè)計(jì)拼合原理,設(shè)計(jì)將DHPM及其衍生物修飾卟啉環(huán)5-meso位,將DHPM衍生物以二溴烷烴為橋連接到卟啉上,以達(dá)到提高光動力化學(xué)藥物治療中光敏劑藥物活性的目的。本文合成了10個新型DHPM修飾的尾式卟啉及其金屬鋅配合物。通過單晶衍射,證實(shí)了尾式鋅卟啉配合物中尾端的活性基團(tuán)DHPM與鋅配位,我們推測由于配位鍵的拉伸作用,使卟啉環(huán)發(fā)生了扭曲;并通過1H NMR、13C NMR、HR-MS、IR等方法對所有的新化合物結(jié)構(gòu)進(jìn)行了表征。2.由于卟啉具有良好的細(xì)胞組織穿透性,而且是一種天然熒光團(tuán);設(shè)計(jì)利用光誘導(dǎo)電子轉(zhuǎn)移機(jī)理以強(qiáng)吸電子基團(tuán)2,4-二硝基苯磺酰基修飾卟啉5-meso位,制備了一種可用于硫離子檢測的新型2,4-二硝基苯磺�；揎椀奈彩竭策鵁晒馓结槨Ｔ撎结樐軐α螂x子實(shí)行高靈敏度、高選擇性的熒光檢測且已被成功地應(yīng)用于活細(xì)胞中S2-的成像。與現(xiàn)有的有機(jī)小分子熒光探針相比,該熒光探針具有較長的熒光發(fā)射波長(λem650nm),可在近紅外區(qū)實(shí)現(xiàn)對微量硫離子的高靈敏度、高選擇性、高時效性檢測,在生物和環(huán)境檢測領(lǐng)域有著巨大的應(yīng)用前景。
[Abstract]:Porphyrins are highly conjugated? The electronic system has a large rigid planar aromatic ring structure, good electron fluidity in the ring, strong absorption and excellent electron supply characteristics in the visible region. In addition, porphyrin compounds also have many unique physicochemical properties. Because porphyrins have the characteristics of easy modification, they are modified by a series of selective modification. New tail porphyrin compounds with wide application prospect in photodynamic chemotherapeutic therapy, biofluorescence probe and biological imaging can be obtained. In this paper, the following two aspects of research are mainly carried out: 1. 4-dihydropyrimidinone and its derivative DHPMs are important drug intermediates with special therapeutic properties and pharmacological activities. DHPM and its derivatives were designed to modify the 5-meso position of porphyrin ring, and the DHPM derivatives were bridged to porphyrins with dibromoalkanes. In order to improve the drug activity of Guang Min in photodynamic chemotherapeutic therapy, ten novel DHPM modified tail porphyrin and its metal zinc complexes were synthesized by single crystal diffraction. The coordination of DHPM with zinc in the tail zinc porphyrin complex was confirmed. We speculated that the porphyrin ring was distorted due to the stretching of the coordination bond. The structures of all new compounds were characterized by 1H NMR-13C NMR-HR-MSIR. 2. Because porphyrin has good cell tissue penetration. And it is a kind of natural fluorescence group; Using photoinduced electron transfer mechanism to modify the 5-meso site of porphyrin with strong electron-absorbing group 2n 4- dinitrobenzene sulfonyl group, a new type of 2 can be prepared for sulfur ion detection. A tail porphyrin fluorescence probe modified with 4-dinitrobenzene sulfonyl group was developed, which can be highly sensitive to sulfur ions. Highly selective fluorescence detection has been successfully used in the imaging of S2- in living cells, compared with the existing organic small molecular fluorescence probes. The fluorescence probe has a long fluorescence emission wavelength (位 em650nm) and can be used to detect trace sulfur ions with high sensitivity, selectivity and timeliness in near infrared region. It has great application prospect in the field of biological and environmental detection.
【學(xué)位授予單位】：湖南科技大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2016
【分類號】：O626

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本文編號：1371599