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The New Type Of Porphyrin - Anthraquinone Compounds Synthesis And Fluorescence Properties

Posted on:2004-07-24Degree:MasterType:Thesis
Country:ChinaCandidate:X X PengFull Text:PDF
GTID:2191360095457745Subject:Organic Chemistry
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Porphyrin has special biological activity, and it is a kind of pholoconductive substance. It can be taken up and retained by tumor tissue selectively and has special affinity to tumor tissue. Porphyrin as a site-sequence specific cleavage agent of nucleic acid becomes a novel research field in recent years. It has remarkable inhibition to tumor tissue through the function of photoconductive substances. ?Porphyrin as a site-sequence specific cleavage agent of nucleic acid seems to be an expansion in molecular biology about its function in anticancer activity.Anthraquinone is a very important photoconductive substance either. It can oxidize many organic compounds through the function of photoconductive substances. Site-specific cleavages could be obtained by synthesizing some derivatives of Anthraquinone. The derivatives of Anthraquinone (Anthraquinone-2-sulfonic acid ) have already been the model of useful photoconductive substance. Its optical property has been noticed for many years. Now many derivatives of Anthraquinone have been synthesized as a photoconductive site-sequence specific cleavage agent of nucleic acid. We named them photonucleases.An ideal photoconductive agent has many characteristic properties, such as 1) highly chemical purity and definitely chemical structure; 2) lower toxicity in darkness; 3) intense absorption to the light above 650nm; 4) selective uptake and retention by tumor tissue; 5) removed from normal issue swiftly; 6) stabilization to heat and light; 7) higher fluorescence quantum yield; 8) soluble in physical pH aqueous solution.In order to cleave DNA through photo inductipn, porphyrin need beproperly equipped with recognition agent. People utilize its ability that it has the affinity to tumor tissue and synthesize a series of site-sequence specific cleavage agents of nucleic acids with high affinity and highly efficient selectivity, which is not only an expansion in the research fields of porphyrins, but also extremely useful in many aspects, such as the gene therapy of cancer, the range sequence recognition capabilities, gene immunity footprint analysis. At present, photosensitive anticancer agents have many shortcomings, such as narrow range of absorption spectrum, ill selectivity. It only can be used in the therapy of superficial tumor tissue, and is lack of good therapy to deep tumor tissue.And now people design and synthesize many site-sequence specific cleavage agents of nucleic acids. Because they can be selective excitation at specific wavelength, this property has been a keystone in the research fields of anticancer agents. As porphyrin and anthraquinone also have been widely used as cleavage agents of nucleic acids and they are all have definite ability of orientation and recognition, we synthesized several novel cleavage agents of nucleic acids and anticancer agents, and studied them by fluorescence methods.In this paper, we synthesized and characterized several novel porphyrin-anthraquinone compounds, studied them by fluorescence method. The results are as follows:1) In our paper, we synthesized and characterized three novel porphyrin-anthraquinone-2-sulfonic esters(c), two porphyrin amides (g), two porphyrin-anthraquinone-2-sulfonic amides (i), and one anthraquinone-2-sulfonic amide (h). We also synthesized and characterized three novel zincous porphyrin-anthraquinone-2-sulfonic esters (d) and onenovel zincous porphyrin-anthraquinone-2-sulfonic amide (2j).2) The fluorescence spectra of porphyrin-anthraquinone, porphyrin -anthraquinone Zn, and parent porphyrin (Ic, 2c, 3c, Id, 2d, 3d, 2i, 2j) was studied by means of fluorescence methods. The energy of singlet excited states (Es). fluorescence quantum yield and quench percentage was estimated. It is demonstrated by the data of fluorescence quench that the innermolecular electron transfer, which leads to the formation of innermolecular electric charge separating-state, occurred under excitation of light indeed. In the meantime, the effects of axial coordination on fluorescence prop...
Keywords/Search Tags:porphyrin-anthraquinone, synthesis, fluorescence property
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