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Synthesis Of H2S Fluorescent Probe And Its Application In Biomedical Imaging

Posted on:2018-08-01Degree:MasterType:Thesis
Country:ChinaCandidate:B B DengFull Text:PDF
GTID:2334330512981902Subject:Chemistry
Abstract/Summary:PDF Full Text Request
Hydrogen sulfide(H2S)is known for its irritating odor and harmful properties,aslo it is an important endogenous gas transmitter.Hydrogen sulfide is associated with nitric oxide and carbon monoxide and is known as one of the three gaseous media in biology.The content of hydrogen sulfide in the body is related to different physiological processes.For example:hydrogen sulfide can participate in hemoglobin changes,involved in the reduction of nitroso compounds in the body,regulate the body’s function of a variety of enzymes,regulate nerve cells and neuroendocrine,diastolic vascular smooth muscle,protect the gastric mucosa,reduce the role of pressure.However,the body of hydrogen sulfide disorders will cause serious harm to the body,such as Alzheimer’s disease,Down syndrome,diabetes,cirrhosis and so on.Therefore,the detection of hydrogen sulfide in the body has a very important biological significance.In the detection technology,the fluorescent probe has the advantages of good selectivity,high sensitivity,small damage to biological samples and real-time in situ detection,and is widely used to detect hydrogen sulfide in organisms.In this paper,hydrogen sulfide fluorescent probe with different mechanism was designed and synthesized with hydrogen sulfide probe.1)BODIPY was used as the fluorescence platform to design and synthesize BH-HS probe.BH-HS probe is the first TICT mechanism to synthesize,fluorescent signal enhanced probe.With H2 S addition,the TICT mechanism was inhibited,the probe at 535 nm showed a strong fluorescence.The probe has many advantages,such as the response time is very short,low cytotoxicity,better selective resistance to other molecules and other strong interference.In addition,with the naked eye can be observed changes in the color of the solution,accompanied by UV light can also be observed under the fluorescence color change.so,it is a color sensor with a function of fluorescence probe.Based on its specificity and significant color change,the reagent can be used as a specific indicator for the presence of hydrogen sulfide molecules in aqueous solutions and in biological cells,enabling real-time qualitative and quantitative visual colorimetric methods.Fluorescence imaging of the probe showed that the probe had good cell permeability and could detect exogenous and endogenous H2 S.2)Based on the intramolecular nucleophilic substitution reaction and ESIPT mechanism,with benzothiazole as the platform,we synthesized ESIPT-HS hydrogen sulfide fluorescence probe.With H2 S addtion,the ESIPT-HS probe with enhanced fluorescence signal based on the ESIPT process.The addition of H2 S to ESIPT-HS results in a large enhancement of the fluorescence signal at 462 nm because the fluorescence of the probe is triggered by H2 S and the blue fluorescence of HBT with stronger ESIPT state emission is released.The probe shows good properties,such as large fluorescence enhancement signals,large Stokes shift,good selectivity and low cytotoxicity.Fluorescence imaging showed that ESIPT-HS was membrane permeable and was suitable for observing exogenous and endogenous H2 S in living cells.3)Hydrogen sulfide(H2S)as a signaling molecule plays a key role in many biological processes of the human body.At the organelle level,we need to study tools to explain the physiological role of H2 S in mitochondria.For this purpose,we developed a rapid response and mitochondrial targeted two-photon fluorescent H2 S probe(MT-HS)based on the ICT mechanism with naphthalimide as a fluorescent platform,which has a large fluorescence signal enhancement(40 times fluorescence enhancement).After adding H2 S to MT-HS,the fluorescence signal near 540 nm was markedly enhanced.The probe can target exogenous and endogenous H2 S in living cells,the probe has mitochondrial targeting,and has a high co-localization coefficient with Mitochondrial-Tracker.The large fluorescence signal enhancement of the two-photon probe MT-HS has a deep tissue penetration capability for H2 S imaging in the living tissue.Importantly,the probe can detect changes in fluorescence induced by H2 S in the mitochondria and due to its deep tissue permeability,it is suitable for imaging H2 S in a living tissue using a two-photon microscope.
Keywords/Search Tags:fluorescent probe, H2S, BODIPY, benzothiazole, naphthalimide
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