Synthesis of 4-Thio-5-iodouridine and The Interaction Between It and Human Serum Albumin

WANG Jian; ZHENG Xue-fang; CAO Hong-yu; ZHANG Xiao-hui

doi:10.3788/fgxb20133403.0361

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Synthesis of 4-Thio-5-iodouridine and The Interaction Between It and Human Serum Albumin

更新时间：2020-08-12

- Synthesis of 4-Thio-5-iodouridine and The Interaction Between It and Human Serum Albumin
- Chinese Journal of Luminescence Vol. 34, Issue 3, Pages: 361-368(2013)
- 作者机构：
  
  1. 大连大学环境与化学工程学院,辽宁大连,116622
  2. 辽宁省生物有机化学重点实验室,辽宁大连,116622
- 作者简介：
- 基金信息：
- DOI：10.3788/fgxb20133403.0361
  CLC： O657.3
- Received：18 October 2012，
  
  Revised：13 December 2012，
  
  Published：10 March 2013
- 稿件说明：
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王健, 郑学仿, 曹洪玉, 张晓辉. 4-硫-5-碘尿苷的合成及其与人血清白蛋白间的相互作用[J]. 发光学报, 2013,34(3): 361-368

WANG Jian, ZHENG Xue-fang, CAO Hong-yu, ZHANG Xiao-hui. Synthesis of 4-Thio-5-iodouridine and The Interaction Between It and Human Serum Albumin[J]. Chinese Journal of Luminescence, 2013,34(3): 361-368
王健, 郑学仿, 曹洪玉, 张晓辉. 4-硫-5-碘尿苷的合成及其与人血清白蛋白间的相互作用[J]. 发光学报, 2013,34(3): 361-368 DOI： 10.3788/fgxb20133403.0361.

WANG Jian, ZHENG Xue-fang, CAO Hong-yu, ZHANG Xiao-hui. Synthesis of 4-Thio-5-iodouridine and The Interaction Between It and Human Serum Albumin[J]. Chinese Journal of Luminescence, 2013,34(3): 361-368 DOI： 10.3788/fgxb20133403.0361.

摘要

基于硫碱基(thio-base)的易烷基化、易氧化、强紫外长波(UVA)吸收等独特的性质

以及核苷类化合物的抗肿瘤活性

设计合成了一种新化合物4-硫-5-碘尿苷

通过NMR、IR、UV、MS对其结构进行了表征。在模拟生理条件下

利用荧光光谱法、紫外-可见吸收光谱法以及圆二色谱法研究了4-硫-5-碘尿苷与人血清白蛋白(HSA)的相互作用。结果表明

4-硫-5-碘尿苷对HSA荧光具有静态猝灭作用。运用Stern-Volmer方程计算了体系的猝灭常数

利用Lineweaver-Burk方程计算了二者的结合常数

并且确定了4-硫-5-碘尿苷与HSA之间的主要作用力类型为疏水作用力

根据能量转移理论求得4-硫-5-碘尿苷与HSA的结合距离及能量转移率。此外

通过圆二色谱法考察了4-硫-5-碘尿苷对HSA作用前后的构型结构的影响。

Abstract

Based on the special properties of thio-base

such as easy to oxidization

alkylation

and the strong absorption of longer ultraviolet wave-UVA

etc.

and the anti-tumor activity of nucleoside compounds

a new compound of 4-thio-5-iodouridine was designed and synthesized. The structure was characterized by Infrared spectroscopy

nuclear magnetic resonanceand mass spectrometry. At the same time

the interactions between 4-thio-5-iodouridine and human serum albumin (HSA) were investigated by the fluorescence spectroscopy

ultraviolet-visible absorption spectrum(UV-Vis) and circular dichroism spectrum(CD). The results show that 4-thio-5-iodouridine has a static fluorescence quenching on human serum albumin (HSA). The quenching constants were calculated according to Stern-Volmer equation

and Lineweaver-Burk equation was used to calculate the binding constants. The main forces of both interactions have typical hydrophobic interaction from thermodynamic data to determination. The distance and FRET(fluorescence resonance energy transfer) efficiency between HSA and 4-thio-5-iodouridine were calculated according to Frster resonance energy transfer theory. The conformation of 4-thio-5-iodouridine on human serum albumin was studied using CD.

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references

Lipsett M N. The isolation of 4-thiouridylic acid from the soluble ribonucleic acid of escherichia coli [J]. J. Biol. Chem., 1965, 240(10):3975-3978.[2] Milder S J, Kliger D S. Spectroscopy and photochemistry of thiouracils-implications for the mechanism of photocrosslinking in transfer-RNA [J]. J. Am. Chem. Soc., 1985, 107(25):7365-7373.[3] Morrison H.In Bioorganic Photochemistry:Photochemistry and The Nucleic Acids [M]. New York: Wiley, 1990:379-425.[4] Xu Y Z, Zheng Q G, Swann P F. Preparation of oligodeoxynucleotidescontaining 6-methylthiopurine residues by chemical synthesis or specific methylation [J]. Nucleosides & Nucleotides, 1995, 14(3/4/5):929-933.[5] Favre A, Saintome C, Fourrey J L, et al. Thionucleobases as intrinsic photoaffinity probes of nucleic acid structure and nucleic acid-protein interactions [J]. J. Photochem. Photobiol.B, 1998, 42(2):109-124.[6] Xu Y Z, Reactive DNA. 2. Thioguanine used as a peg site for direct and specific introduction of biologically useful functional groups [J]. Bioorg. Med. Chem. Lett., 1998, 8(14):1839-1844.[7] Xu Y Z. Thiobase DNA:The chemistry and some applications in cancer studies [J]. Prog.Nat. Sci., 2002, 10:401-413.[8] Reelfs O, Xu Y Z, Massey A, et al. Thiothymidine plus low-dose UVA kills hyperproliferative human skin cells indepen-dently of their human papilloma virus status [J]. Mol. Cancer Ther., 2007, 6(9):2487-2495.[9] Liu Z Y, Pan T. Equivalent waveband selection of VIS-NIR spectroscopic measurement for hemoglobin [J]. Opt. Precision Eng.(光学精密工程), 2012, 20(10):2170-2175 (in Chinese).[10] Gemenetzidis E, Shavorskaya O, Xu Y Z, et al. Topical 4-thiothymidine is a viable photosensitiser for the photodynamic therapy of skin malignancies [J]. J. Dermatolog. Treat., 2011, 39(22):7698-7703.[11] Reelfs O, Karran P, Young A R.4-thiothymidine sensitization of DNA to UVA offers potential for a novel photochemotherapy [J]. Photoch. Photobio. Sci., 2012, 11(1):148-154.[12] Warren M A, Murray J B, Connolly B A. Synthesis and characterisation of oligodeoxy- nucleotides containing thio analogues of (6-4) pyrimidine-pyrimidinone photo-dimers [J]. J. Mol. Biol., 1998, 279(1):89-100.[13] Massey A, Xu Y Z, Karran P. Photoactivation of DNA thiobases as a potential novel therapeutic option [J]. Current Biology, 2001, 11(14):1142-1146.[14] Loakes D. Modified Nucleosides, Synthesis and Applications [M]. India: Research Signpost, 2002:1-16.[15] O'donovan P, Perrett C M, Zhang X, et al. Azathioprine and UVA light generate mutagenic oxidative DNA damage [J]. Science, 2005, 309(5742):1871-1874.[16] Yan Y, Xu J, Chen G Z. Protein conformation in solution by three-dimensional fluorescence spectrometry [J]. Sci. China Ser. B , 1996, 39(5):527-535 (in Chinese).[17] Wu Q H, Wang D Y, Zhou X, et al. Study on the interaction between daidzein and human serum albumin [J]. Spectrosc. Spectral. Anal.(光谱学与光谱分析), 2009, 19(7):1911-1914 (in Chinese).[18] Liang J, Fen S L. Interaction between ambroxolhydrochloride and human serum albumin studied by spectroscopic and molecular modeling methods [J]. Spectrosc. Spectral. Anal.(光谱学与光谱分析), 2011, 31(4):1020-1024 (in Chinese).[19] Morris J R, Philip J B, Jerzy G. Nucleic acid related compounds. 38. smooth and high-yield iodination and chlorination at C-5 of uracil bases and p-toluyl-protected nucleosides [J]. Can. J. Chem., 1982, 60:554-557.[20] Vineet K, Sanjay V M. Ionic liquid mediated synthesis of 5-halouracil nucleosides:Key precursors for potential antiviral drugs nucleosides [J]. Nucleosides & Nucleotides, 2009, 28(9):821-834.[21] Wu D, Xu G Y. Study on protein-surfactant interaction by spectroscopic methods [J]. Acta Physico-Chimica Sinica(物理化学学报), 2006, 22(2):254 (in Chinese).[22] Stryer L. Fluorescence energy transfer as a spectroscopic ruler [J]. Annu. Rev. Biochem., 1978, 47(3):819-846.[23] Bi S Y, Ding L, Song D Q, et al. Studies on the binding mechanism of several antibiotics and human serum albumin [J]. Acta Chimica Sinica(化学学报), 2005, 63(23):2169-2173 (in Chinese).[24] Xu J G, Wang B Z.Fluorescence Analysis Method [M]. Beijing: Science Press, 2006:64 (in Chinese).[25] Hu Y J, Liu Y, Zhang L X, et al. Studies of interaction between colchicine and bovine serum albumin by fluorescence quenching method [J]. J. Mol. Struct., 2005, 750(1/2/3):174-178.[26] Xie B, Wan B J, Qin Z H. Interaction between congo red and human serum albumin by fluorescence quenching method [J]. Chin. J. Spectrosc.Lab.(光谱实验室), 2011, 28(2):764-769 (in Chinese).[27] Liu B S, Yang C, Wang J, et al. Luminescence mechanism study of the conjugation reaction between cefpirome sulfate and bovine serum albumin [J]. Chin. J. Lumin. (发光学报),2011, 32(3):293-299 (in Chinese).[28] Kandagal P B, Shaikh S M T, Manjunatha D H, et al. Spectroscopic studies on the binding of bioactive phenothiazine compounds to human serum albumin [J]. J. Photochem. Photobiol. A:Chem., 2007, 189(1):121-127.[29] Yu X, Liu R H, Ji D H, et al. Spectroscopic studies on the interactions between 3,4-dihydropyrimidin-2-(1-H)-ones and bovine serum albumin [J]. Spectrochim. Acta A, 2010, 77(1):213-218.[30] Chen D W, Xie Q J, Su Y H, et al. Fluorescent studies on the interactions between Au nanoparticles and quercetin as well as bovine hemoglobin [J]. J. Anal. Sci.(分析科学学报), 2008, 24(3):259-264 (in Chinese).[31] Mandal P, Bardhan M, Ganguly T. A detailed spectroscopic study on the interaction of rhodamine 6G with human hemoglobin [J]. J. Photochem. Photobiol.B, 2010, 99(2):78-86.[32] Pei M Y, Zheng X F, Cao H Y, et al. Spectroscopic studies on interaction between 3-bromopyruvic acid and human serum albumin [J]. Chin. J. Anal. Chem. (分析化学), 2010, 7(38):948-952 (in Chinese).

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