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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 周必泰 | |
dc.contributor.author | Shih-Hao Su | en |
dc.contributor.author | 蘇士豪 | zh_TW |
dc.date.accessioned | 2021-06-17T05:03:07Z | - |
dc.date.available | 2028-07-23 | |
dc.date.copyright | 2018-07-26 | |
dc.date.issued | 2018 | |
dc.date.submitted | 2018-07-23 | |
dc.identifier.citation | First part:
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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/71290 | - |
dc.description.abstract | 第一部分使用氯化銅試劑進行合環反應可將含蒽的有機磷化合物轉換成帶正電性的鏻離子螢光體。此鏻離子螢光體不僅具有良好的水溶性和量子效率,其優異的光穩定性以及低度的生物毒性使得這一系列化合物具備細胞顯像之應用潛力。
第二部份實驗呈現水溶性的鉑和銥錯合物的合成以及光物理性質研究,它們都具有輔助配位基(bis(diphenylphosphino)benzene (dppb), P^P*)。這些錯合物在周圍配位基的調控下,具備相當大的光物理性質差異,像是激發以及放光範圍,以及激發態生存期對氧氣分子的敏感程度。此外這些新合成的錯合物都具備有相當高的雙光子吸收截面,雖然它們整體而言,為具有負電性的錯合物,但是仍然能被海拉細胞攝入並且具有極低的細胞毒性,綜合上述這些特性,使得它們具有雙光子磷光生存期顯像的能力。特別是顯像效果最佳的錯合物[(ppy)2Ir(sulfo-dppb)] (Ir1*),當其進入海拉細胞後,在正常大氣和純氮氣的環境下,磷光生存期的差異達到兩倍,再者,我們使用被異種移植海拉細胞的無胸腺裸鼠進行活體實驗,我們發現到不論是點滴注射或局部注射Ir1*錯合物,都未產生劇烈的毒性,而且仔細分析裸鼠的磷光生存期影像後,我們發現Ir1*錯合物的生存期在正常肌肉組織和腫瘤之間有統計上的差別,證明其監測缺氧環境的能力。 | zh_TW |
dc.description.abstract | The first part is 6-memberd P-heterocycle has been fused with polyaromatic framework through intramolecular transformation of anthracene-based phosphine induced by CuCl2. The resulting hydrophilic phosphonium fluorophores exhibit extremely high quantum efficiency along with prominent stability and low toxicity that make them suitable for imaging purposes.
The second part presents synthesis and photophysical investigation of cyclometalated water-soluble Pt(II) and Ir(III) complexes containing auxiliary sulfonated diphosphine (bis(diphenylphosphino)benzene (dppb), P^P*) ligand. The complexes demonstrate considerable variations in excitation (extending up to 450 nm) and emission bands (with maxima ranging from ca. 450 to ca. 650 nm), as well as in the sensitivity of excited state lifetimes to molecular oxygen (from almost negligible to more than 4-fold increase in degassed solution). Moreover, all the complexes possess high two-photon absorption cross sections (400-500 GM for Pt complexes, and 600-700 GM for Ir complexes). Despite their negative net charge, all the complexes demonstrate good uptake by HeLa cells and low cytotoxicity within the concentration and time ranges suitable for two-photon phosphorescence lifetime (PLIM) microscopy. The most promising complex, [(ppy)2Ir(sulfo-dppb)] (Ir1*), upon incubation in HeLa cells demonstrates two-fold lifetime variations under normal and nitrogen atmosphere, correspondingly. Moreover, its in vivo evaluation in athymic nude mice bearing HeLa xenografts did not reveal acute toxicity upon both intravenous administration and topical injection. Finally, Ir1* demonstrated statistically significant difference in lifetimes between normal tissue (muscle) and tumor in macroscopic in vivo PLIM imaging. | en |
dc.description.provenance | Made available in DSpace on 2021-06-17T05:03:07Z (GMT). No. of bitstreams: 1 ntu-107-R05223156-1.pdf: 2345247 bytes, checksum: 7740563cff10d40fbc1dae8ed4118e88 (MD5) Previous issue date: 2018 | en |
dc.description.tableofcontents | 中文摘要……………………………………………………………………………... i
英文摘要……………………………………………………………………………... ii First part………………………………………………………………………………. 1 Introduction………………………………………………………………………….... 1 Results and Discussion……………………………………………………………….. 4 Conclusion…………………………………………………………………............... 15 Experimental section………………………………………………………............... 16 References…………………………………………………………………………… 20 Second part …………………………………………………………………………. 24 Introduction………………………………………………………………………….. 24 Results and Discussion……………………………………………………………… 27 Conclusion…………………………………………………………………………... 42 Experimental section..………………………………………………………………. 43 References…………………………………………………………………………… 48 Figure. 1. Molecular view of the diphosphonium salt [2]I2 (thermal ellipsoids are shown at the 50% probability level). One iodide counterion is depicted. …………………… 5 Figure. 2. Absorption (dotted lines) and emission spectra (solid lines) of 1–4 (ambient conditions). ………………………………………………………………………....... 6 Figure. 3. Electron density difference plots for the lowest energy singlet excitation (S0 → S1) of the compounds 1-4 (isovalue 0.002 a.u.). During the electronic transition, the electron density increases in the blue areas and decreases in the red areas. Hydrogen atoms omitted for clarity. …………………………………………………………….. 8 Figure. 4. MTT assay for the viability of Hela cells treated with various concentrations of compounds 1–4. Error bars represent the standard deviations of three measurements. ……………………………………………………………………… 10 Figure. 5. Confocal images of living (top) Hela cells and (bottom) CCD cells incubated with 4 (1µM) for 1 hour and mitotracker (500 nM) for another 30 mins, 37 °C and under 5% CO2. Blue channel: acquisition wavelength from 460 to 620 nm, λex= 458 nm for 4; Red channel: acquisition wavelength from 640-740 nm, λex= 633 nm for MitoTracker deep red. The image of overlay area was shown in magenta. The co-localization analysis from the overlay images are quantified by Pearson's correlation coefficient (R). ………………………………………………………………………………….. 11 Figure 6. (left) Z-scan experimental data of compounds 2-4 in water (110-4 M for 2 and 210-4 M for 3 and 4) in a 1mm cell, ex=800 nm. Solid lines are the best fit. (right) One photon induced emission (black line) and two photon induced fluorescence (red line) spectra of compounds 2-4 in water. …………………………………………… 12 Figure 7. Confocal image of compound 4 in HeLa cell line (a) excitation at 458 nm Argon ion laser, (b) excited by femtosecond Ti:Sapphire laser, ex=900 nm. (c) the profile drawn from the white line appearing in (a) and (b), which shows high selectivity stained on mitochondria and independent of the one-photon or two-photon excitation. ………………………………………………………………………………………. 14 Figure. 8. Photostability test of the compounds 1–4 compared with widely used chromophores (Coumarin 480 and Fluorescein). All experiments were performed in PBS (10 mM, pH = 7.4 with 1% MeOH for 1). Samples were kept at the same absorbance (A = 0.1) at their excitation wavelength (λex = 405 nm diode laser for 1, 2 and coumarin 480; λex = 458 nm Argon ion laser for 3 ,4 and fluorescein). Fluorescence intensity at the respective emission maxima was recorded with continuous exposure to excitation light and collected by Zeiss LSM710 confocal spectral microscope equipped with 40X objective (C-APO, 1.2 water immersion). ……………………………….. 15 Figure 9. Normalized excitation (dashed) and emission (solid) spectra: (A) Pt2, Pt3 and Pt4 in 1,2-dichloroethane (λex = 420 nm for Pt2, λex = 425 nm for Pt3, λex = 440 nm for Pt4), (B) Pt2*, Pt3* and Pt4* in aqueous solution (λex = 415 nm for Pt2* and Pt3*, 425 nm for Pt4*), (C) Ir1* and Ir2* in aqueous solution, (λex = 355 and 425 nm for Ir1* and Ir2*, respectively). ………………………………………………………………….. 30 Figure 10. Open aperture Z-scan experimental measurements of Ir1*, Ir2*, Pt2*, Pt3*, and Pt4* in Water (110-4 M), obtained with 800 nm light source. Hollow circles are original experimental results, and solid line is theoretical fitting. Standard deviation estimated from three replicates. …………………………………………………….. 32 Figure 11. (a) Phosphorescence decay curves (corresponding lifetimes are listed in the legend) of Ir1* in water under different oxygen pressures at 37 ºC. (b) The resulting Stern-Volmer plot of Ir1* quenching by oxygen. …………………………………… 34 Figure 12. Two-photon image of HeLa cell labelled with Ir1* (50μM for 18hours). Excitation: 720 nm; Detection: 480~520nm. Scale bar: 20μm. ……………………. 35 Figure 13. HeLa cell viability by MTT assay as a function of incubation concentrations of iridium and platinum complexes. Error bar represents the standard deviation calculated from three replicates. ……………………………………………………. 36 Figure 14. PLIM of HeLa cell incubated in 50μM of Ir1* in the condition of Standard O2 atmosphere (a-c) and N2 atmosphere (d-f). Bright field images (a, d); PLIM mapping (b, e); the corresponding phosphorescence lifetime distribution (c, f). Excitation wavelength: 720 nm. The scale bar: 20 μm. ………………………………………... 38 Figure 15. Photostability plot of iridium and platinum complexes compared with common luminophores, Coumarin 480 (C480) and Rhodamine B. Experimental Conditions: 10mM PBS buffer (pH 7.4); all the absorbances are fixed to 0.05 at 360 nm (Ir1* and C480, λexc = 720 nm) or at 430 nm (Ir2*, Pt2*, Pt3*, Pt4* and Rhodamine B, λexc = 860 nm). Excitation power was 32 mW. I is the emission intensity of each particular scan, and I0 is the emission intensity of the first scan. …………………... 38 Figure 16. In vivo imaging of Ir1* phosphorescence in HeLa tumor xenograft. (a) Photograph of HeLa tumor in nu/nu mouse with surgically opened skin flap; (b) PLIM of tumor in vivo after local injection of Ir1*; (c) phosphorescence decay of Ir1* in tumor (red) and signal from control tumor without injection Ir1* in the selected spot in the tumor (black); (d) in vivo confocal laser-scanning microscopy of tumor with Ir1* (ex. 750 nm, reg. 430-600 nm); (e) in vivo microscopic image of the control tumor without injection of Ir1*; (f) Emission spectra (ex. 750 nm, reg. 400-662 nm) of tumor with local injection Ir1* (1) and of control tumor without injection Ir1* (2), mean ± SD. Two tumor nodules that were injected with Ir1* are shown by the red dashed circles. Scale bars are indicated in each image. Blue curve on figure (c) is single exponential fit, green curve is instrument response function. …………………………………………....... 41 Table 1. Photophysical properties of 1–4 in solution at 298 K. ……………………... 6 Table 2. Photophysical properties of complexes. …………………………………... 29 Table 3. Excited state lifetimes of Ir1* in water and 10% fetal bovine serum (FBS). 42 | |
dc.language.iso | en | |
dc.title | 新穎微環境敏感發光體的光物理特性和應用 | zh_TW |
dc.title | Photophysical properties and applications of novel
microenvironment-sensitive luminophores | en |
dc.type | Thesis | |
dc.date.schoolyear | 106-2 | |
dc.description.degree | 碩士 | |
dc.contributor.oralexamcommittee | 何美霖,趙啟民 | |
dc.subject.keyword | 鏻離子螢光團,氯化銅,粒線體標定,皮爾森相關係數,雷射掃描式共軛焦顯微技術,水溶性鉑和銥的金屬錯合物,磺酸化雙膦配位基,雙光子吸收截面,磷光生存期影像技術,腫瘤缺氧性, | zh_TW |
dc.subject.keyword | phosphonium fluorophores,copper(II) chloride,mitochondria tracking,Pearson’s correlation coefficient,laser scanning confocal microscopy,water-soluble Pt(II) and Ir(III) complexes,sulfonated diphosphine ligand,two-photon absorption cross section,phosphorescence lifetime imaging,tumor hypoxia, | en |
dc.relation.page | 53 | |
dc.identifier.doi | 10.6342/NTU201801854 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2018-07-24 | |
dc.contributor.author-college | 理學院 | zh_TW |
dc.contributor.author-dept | 化學研究所 | zh_TW |
顯示於系所單位: | 化學系 |
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