Thermodynamic studies of DNA complexes with antitumor platinum compounds and their analogs

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姓名

張純綾(Chun-Ling Chang) 查詢紙本館藏

畢業系所

物理學系

論文名稱

(Thermodynamic studies of DNA complexes with antitumor platinum compounds and their analogs)

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摘要(中)

順鉑（cis-Pt(NH3)2Cl2）是一種常用的抗癌藥物。順鉑的生物活性作用在DNA上會有強大的共價鍵結合和在雙螺旋結構產生中間單官能基(intermediate monofunctional)和雙官能基產物（bifunctional）並讓結構扭曲。雙官能基產物大部分為intrastrand crosslinks，intrastrand crosslinks也是在DNA上形成。
然而，順鉑是高度的細胞毒性且具有一些副作用，有些副作用會限制了它的應用。故了解DNA結合機制與順鉑的抗癌特性，有利於創造新的更有效的藥物。因此，與順鉑DNA複合物的熱力學和其他研究的特定和鉑化合物等目前已在進行。在報告本研究之前，熱力學研究主要是短鍊的DNA，雖然長鍊的DNA與鉑的結合更接近真實系統：故在此研究裡，我們有針對長鍊 DNA來進行研究。利用微分掃描熱分析儀（DSC）和紫外光譜儀進行研究。利用已開發的電腦軟體來處理實驗數據，並用模型來對實驗結果進行分析解釋。
但在之前的研究裡，有一些錯誤的觀念。如：一、熔化曲線(metling curve), 熔點(metling temperature)，在DSC的實驗結果裡，熔點範圍(metling temperature range)有很強烈地區分。二、熔點和熔點範圍沒有辦法從多峰 DSC 曲線獲得和使用。對此觀點，卻沒有任何證據。針對此一問題展開了研究。重新去計算”真實”DSC 熔化曲線。利用不同於在DSC軟體中所使用的計算方法，從不同熔化曲線，證明了DSC熔化曲線內的偏差是可以忽略。且發展一套適合的方法去量測熔點和熔點範圍在多峰DSC 曲線中且證實了其合理性。
在DNA和鉑化合物中的實驗，找到新的條件。且從實驗中，提供了兩個有用的優勢：首先，鉑化合物消除了長鍊 DNA的非特異性靜電穩定性(non-specific electrostatic stabilization)。其次，在高溫的熔化實驗（metling experiment）中鉑化合物提供了中間產物(intermediate products)穩定性。由於這些結果，由中間的單官能基(intermediate monofunctional)和最後的雙官能基產物(bifunctional product)所引起的熱穩定性（thermal stability）改變，可在單獨計量(separately measured) 和對比第一次的無鉑結合的實驗。這表示鉑化合物會減少在雙螺旋線圈變化時(helix-coil transition)焓(enthalpy)和熵（entropy），增加熔點範圍和扭曲DSC熔化曲線。這與其他之前的結果相符合。然而這些破壞結構的因子 (destructive factors)永遠會降低 DNA熔點，但這只對短鍊 DNA如此。對於長鍊DNA卻不是。Transplatin和Pt[(dien)Cl]Cl 會增加DNA 熱穩定性(thermal stability)，雖然他們的雙螺旋被破壞掉。我們證明此不尋常的結果是因為帶有大量正電荷（positive charge）的鉑化合物與雙螺旋結合中而產生的。
有一些鉑化合物和其他抗癌藥物也會形成DNA interstrand crosslinks。為了要解釋我們的實驗結果，我們研究了短鍊 DNA和長鍊 DNA的DNA interstrand crosslinks 熔化結果。這也是第一次針對crosslinking來研究局部不穩定熱因子（thermal impact of local distortions）。

摘要(英)

Cisplatin (cis-Pt(NH3)2Cl2) is a commonly used anticancer drug. Biological activity of cisplatin is exerted by strong covalent binding to DNA and distortion of the double helix by formation of intermediate monofunctional and final bifunctional products. The majority of bifunctional products are intrastrand crosslinks. Additionally, interstrand crosslinks are formed in DNA.
However, cisplatin is highly cytotoxic and has a number of side effects that limit its application. Understanding the DNA binding mechanisms and anticancer properties of cisplatin facilitates creation of new more effective drugs. Therefore, a lot of thermodynamic and other investigations of DNA complexes with cisplatin and other platinum compounds have been carried out. However, before the present study, thermodynamic investigations were mainly fulfilled for short DNAs, although long platinated DNAs are much closer to real systems. In this work, studies of long DNAs were carried out using differential scanning calorimetry (DSC) and UV spectroscopy. Computer programs have been developed and used for the processing of these experimental data. Computer modeling was carried out to explain obtained experimental results.
There are widely spread mistaken opinions that 1) Melting curve, melting temperature, temperature melting range obtained in DSC experiments strongly distinguish from their real values; 2) Melting temperature and temperature melting range cannot be obtained and used for multi-peak DSC curves. However, there were no evidences or disclaimers of this viewpoint. That issue was studied in the present work. Thereto, a procedure for recalculation of DSC melting curves into "real" ones was worked out. Using different approaches, we have demonstrated that deviation of DSC melting curves from real differential melting curves is negligible. Suitable methods for determination of the melting temperature and temperature melting range in the case of multi-peak DSC curves were developed, and their reasonableness was confirmed.
New conditions for melting experiments of DNA with platinum compounds were found. They provide two useful advantages: firstly, elimination of the non-specific electrostatic stabilization of long DNA caused by platinum compounds and, secondly, stabilization of their intermediate products against high temperature of melting experiments. Thanks to those findings, a change in thermal stability caused by intermediate monofunctional and final bifunctional products was separately measured and compared for the first time.
It was shown that platinum compounds decrease the enthalpy and entropy of the helix-coil transition, increase the temperature melting range and destroy the fine structure of DSC curves. That is in agreement with the impact of other destructive factors known before. However, those destructive factors always decrease DNA melting temperature. In the case of complexes with platinum compounds, it is true only for short DNAs. For long DNAs, this general rule is not always held. Transplatin and Pt[(dien)Cl]Cl increase DNA thermal stability, although they destroy the structure of the double helix. The mechanism of such abnormal melting behavior has been found. We have demonstrated that the unusual effect is caused by large positive charge introduced by platinum compounds into the double helix.
Some platinum compounds and many other anticancer drugs form DNA interstrand crosslinks. To explain our experimental results, the influence of DNA interstrand crosslinks on melting of short and long DNAs was studied. For the first time, the thermal impact of local distortions caused by crosslinking agents was studied besides the crosslinking effect in itself.

關鍵字(中)

★ DNA 複合物和鉑化合物
★ 熱微差掃描分析儀
★ 光譜熔化研究
★ DNA platination 動力學
★ 高分辨熔解型材
★ 質粒DNA的熱力學

關鍵字(英)

★ DNA-complexes with platinum compounds
★ differential scanning calorimetry
★ optical melting studies
★ kinetics of DNA platination
★ high-resolution melting profiles
★ thermodynamics of plasmid DNA

論文目次

Abstract I
摘要 III
致謝 V
目錄 VI
圖目錄 VIII
表目錄 XII
List of Publications XIII
1. Introduction 1
2 The method of differential scanning calorimetry and processing of primary results 4
2.1 Preliminary remarks 4
2.2 Calculation of the sample baseline, DSC melting curve, calorimetric differential melting curve and calorimetric melting curve 5
2.3 Calculation of the excess heat capacity, enthalpy and entropy 7
2.4 Sample preparation for differential scanning calorimetry 10
3 Thermal Stability of DNA with Interstrand Crosslinks 11
3.1 Preliminary remarks 11
3.2 Model of melting for long DNA with interstrand crosslinks 12
3.3 The effect of interstrand crosslinks on melting of long DNAs 13
3.4 Comparison with experiment 16
3.5 The effect of interstrand crosslinks on melting of oligonucleotide duplexes 18
3.6 Conclusion 24
4 Temporal behavior of DNA thermal stability in the presence of platinum compounds. Role of monofunctional and bifunctional adducts 27
4.1 Preliminary remarks 27
4.2 Experimental methods 29
4.3 Thermal stability of short and long platinated DNAs in neutral medium 29
4.4 The influence of platinum compounds on thermal stability of long DNA in alkaline medium 31
4.5 The mechanism of a stronger decrease in thermal stability of platinated DNA in alkaline medium 34
4.6 The effect of interstrand crosslinks on DNA thermal stability 36
4.7 Cisplatin 36
4.8 Transplatin and its comparison with cisplatin 37
4.9 Conclusion 37
5 Theoretical modeling of the kinetics of DNA thermal stability under binding and transformation of cisplatin 39
5.1 Preliminary remarks 39
5.2 Binding to DNA and further transformation of cisplatin
39
5.3 Modeling of the time dependences of thermal stability and of the fractions of monofunctional and bifunctional adducts 40
5.4 Kinetics of cisplatin transformation and its influence on temporal behavior of DNA thermal stability under platination 42
5.5 Conclusion 45
6 Evaluation of errors in determination of DNA melting curves registered with differential scanning calorimetry 46
6.1 Preliminary remarks 46
6.2 Materials and methods 47
6.3 An exact representation of c 48
6.4 Calculation of real melting curve from calorimetric melting curve for the case of equal entropies of AT and GC base pairs (SAT=SGC) 49
6.5 Calculation of real melting curve from calorimetric melting curve without requirement of entropy equality 53
6.6 Conclusion 56
7 Processing of DSC melting curves and determination of their parameters 57
7.1 Preliminary remarks 57
7.2 Materials and methods 57
7.3 Processing of DSC curves 57
7.4 Determination of the melting temperature 61
7.5 Determination of the temperature melting range 67
7.6 The influence of ionic strength on DNA melting 70
7.7 Conclusion 72
8 Comparative thermodynamics of DNA chemically modified with antitumor drug cisplatin and its inactive analog transplatin 73
8.1 Preliminary remarks 73
8.2 Materials and methods 74
8.3 A structure of DSC thermograms and differential melting curves of DNA from Calf Thymus 74
8.4 A change in thermograms under DNA chemical modification with cisplatin and transplatin 76
8.5 The influence of antitumor drug cisplatin and its inactive analog transplatin on the parameters of DNA helix-coil transition at various ionic strengths 78
8.6 On the role of electrostatic interactions in thermodynamic properties of DNA complexes with platinum compounds 81
8.7 Compensation effects and explanation of disappearance of fine structure under platination 84
8.8 Conclusion 88
9 Conclusion and Future work 89
9.1 Conclusion 89
92 Future work 90
10 References 91

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指導教授

薛雅薇、胡進錕
(Ya-Wei Hsueh、Chin-Kun Hu)

審核日期

2013-7-9

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