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Review Article Open Access Biochemistry Analytical Biochemistry Biochemistry Analytical Biochemistry ISSN: 2161-1009 Kaloo et al. Biochem Anal Biochem 2019 8:1 DOI: 10.4172/2161-1009.1000375 Volume 8 • Issue 1 • 1000375 Biochem Anal Biochem an open access journal ISSN: 2161-1009 Abstract In this work we have compiled literature wherein various attempts regarding design and development of abiotic molecular receptors amid fuorescent signaling response for selective detection of various sulphur species H 2 S HS - SO 3 2- S 2- in living cells has been presented. We have specifcally compiled the literature which presents the molecular systems deciphering the real-time potential for targeting mentioned chemical species under biological conditions or living cells. With regard to the chemical aspects of designed receptors focus has been primarily diverted towards interaction of analyte with the receptor molecule at active site. The interaction driven output as a result of electronic modulation in the molecule has been discussed besides detection limit of the analyte. In addition to all this we have also summarized the conditions for tracking of various sulphur species in bisystems. The proposed receptors from the literature have been categorized into fve classes depending on the mechanism of encounter between analyte and receptor molecule responsible for fuorescence signaling. Fluorescent Synthetic Receptors for Signaling Hydrogen Sulphide in Living Systems Kaloo MA 1 Shah WA 2 Bhat BA 12 and Gani M 1 1 Department of Chemistry Govt. Degree College Shopian Jammu and kashmir India 2 Department of Chemistry University of Kashmir Hazratbal Srinagar Jammu and kashmir India Keywords: Fluorescence Receptor Sulphite Hydrogen sulpide Cellular Imaging Introduction Sulphur S presents one of the important components that fnd a diverse and wider existence in living systems besides environment. Under the biological conditions it exists in diverse forms depending on pH. Various forms of sulphur include hydrogen sulphide H 2 S sulphide ion S 2- sulphite SO 3 2- and bisulphate HS - . Hydrogen sulfde one of the commonly found member of the reactive sulfur species traditionally considered as toxic gas with rotten egg smell. It plays crucial role in regulating the intracellular redox and other primary signaling processes involved in human health and disease 1. It may interact with downstream proteins by the post-translational cysteine sulfydration and binding to iron centers which regulate various physiological processes including ischemia reperfusion injury vasodilation apoptosis and angiogenesis 2-4. A pH-dependent equilibrium mixture with sulfte and bisulfte ions is formed when sulphur dioxide SO 2 is dissolved in water. A variety of respiratory diseases cardiovascular diseases and neurological disorders can be induced by frequently exposure of excessive levels of SO 2 and its derivatives via environmental waters or through food 56. Hence it is important to have efective monitoring of chemical species like H 2 S S 2- SO 3 2- and HS - under aqueous conditions as well as in biosystems. In this regard development of cost efective and convenient analytical tools is need of an hour. Looking at this important aspect researchers in recent past have looked at the basis of supramolecular analytical chemistry to produce abiotic molecular species in the form of “Receptors”. Among the receptors molecules deciphering fuorescent singling behavior are the ones which have to some extent shown promise for efective monitoring of mentioned sulphur based chemical species. In this review we have presented a number of fuorescent probes or reeptors for the sulphur species detection with a show a good selectivity high sensitivity and suitability for recognition in living cells besides environment. We have categorized these receptors as per the type of chemical reaction that has been induced by the present of anayte during the recognition events. Corresponding author: Kaloo MA Department of Chemistry Govt. Degree College Shopian Jammu and kashmir India Tel: 01933260204 E-mail: makandchemgmail.com Received: January 04 2019 Accepted: January 14 2019 Published January 21 2019 Citation: Kaloo MA Shah WA Bhat BA Gani M 2019 Fluorescent Synthetic Receptors for Signaling Hydrogen Sulphide in Living Systems. Biochem Anal Biochem 8: 375. doi: 10.4172/2161-1009.1000375 Copyright: © 2019 Kaloo MA et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License which permits unrestricted use distribution and reproduction in any medium provided the original author and source are credited. Receptors Based on Cleavage Reaction In this direction thiolysis of 24-dinitrophenyl ether based receptor 1 Figure 1 by HS - ion is reported by Sayed et al. Te 24-dinitrophenyl ether moiety of 1 is non-fuorescent in PBS-ethanol 9:1 v/v mixture. However presence of HS - induces hydrolysis of 24-dinitrophenyl ether moiety which yield the highly fuorescent 8-hydroxy quinoline group 7. Te fuorescent signaling response was fund suitable enough to detection minimum of 60 nM of analyte. Regarding biological applications receptor was found to be non-toxic to HeLa cells in the range concentrations of 5-50 µM. In this experiment HeLa cells were Figure 1: Molecular structure of receptor 1 with active site responsible for the detection of analyte HS - encircled.

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Citation: Kaloo MA Shah WA Bhat BA Gani M 2019 Fluorescent Synthetic Receptors for Signaling Hydrogen Sulphide in Living Systems. Biochem Anal Biochem 8: 375. doi: 10.4172/2161-1009.1000375 Volume 8 • Issue 1 • 1000375 Biochem Anal Biochem an open access journal ISSN: 2161-1009 Page 2 of 4 incubated in DMEM and supplemented with 10 fetal bovine serum. Te cells were seeded in 24 mm glass cover slips in 6-well plates and allowed to settle for 24 hours. Ten the cells were treated with 1 in DMSO 1 at 30 mM. Afer 20 minutes medium was removed and solutions of diferent concentrations of NaHS in PBS were incubated for another 10-minute period. Te cells incubated with 1 showed no fuorescence whereas a marked enhancement in intracellular emission was observed in the HS - treated cells with 1 clearly indicating the possible use of 1 to detect hydrogen sulphide. In another report coumarin based receptor molecule 2 Figure 2 was reported by Xie. Author reported that the reaction mechanism for detection of SO 3 2- involves a nucleophilic addition reaction on the proposed molecule followed by intramolecular cyclization and fnally cleavage. Such an interaction between analyte and receptor fnally ends up with fuorescence signaling response. Te detection limit of 2 for SO 3 2- was found to be 0.52 µM. Concerning living cell applications receptor was found to be non-toxic to B16 cells in the range concentrations of 0- 10 µM. In this direction author studied that its capability to detect sulphite anion in living cells. He observed that once B16 cells were incubated with the receptor molecule 2 for 20 min an obvious fuorescence was found in green and blue channels. However when the probe 2 was treated with the SO 3 2- ion the fuorescence was increases in green cells dramatically. Hence the detection of SO 3 2- via green channel in living cells is doable. Receptors Based on Nucleopilic Addition Reaction In this direction a coumarin-hemicyanine receptor 3 Figures 3 and 4 was studied by Wang et al. Te molecular receptor interacts with sulphite anion via nucleophilic addition followed by rearrangement based reaction mechanism and such a molecular transformation in turn triggers fuorescence “turn on” response. Te receptor was found suitable to detect analyte around at a minimum of 0.08 µM. Importantly it had a low cytotoxicity afer a long period of 24 hours. For further living cell applications author carried out an MTT assay with diferent concentrations of SO 3 2- anion via a fuorescence imaging experiment in living cells. For bio-imaging applications freshly grown HeLa cells were incubated with SO 3 2– 100 μM for 30 min and were washed with PBS two times. Cells were subsequently treated with probe 3 5.0 μM for around 30 mins. Te probe 3 was found to be cell-permeable and showed a bright fuorescence due to the reaction with intracellular SO 3 2– anion which was later found in good agreement with the fuorescence turn-on profle of the receptor in the presence of SO 3 2– in vitro. In another study F. Chen reported a potent fuorescent receptor for sensitive and selective detection of H 2 S in diferent bufer solutions. Te key design principle is based on a coumarin moiety which acts as a fuorophore. Te receptor design is structuring three potential active sites that could react with H 2 S. A strong fuorescent in red and green channels were observed as a result of nucleophilic attack on active sites of the proposed receptor. Te detection limit of 4 for hydrogen sulphide was found to be 75 nM. It was found permeable to cells and possess low cytotoxicity. Te live cell applications of receptor were reported with bioimaging study investigated in MCF-7 cells. Receptors Based on Reduction Reaction In a study reported by Guo et al. two non-fuorescent receptors containing nitro -NO 2 group in 5 and azide -N 3 group in 6 Figure 5 were studied for anion recognition during various fuorescence experiments. Te fuorescent signaling response was attributed to the generation of amine functionality on the molecule by the reduction of nitro or azide group. Te readout response was found suitable to detect analyte at a minimum of 5-10 µM and 1-5 µM respectively for each receptor. In the bioimaging experiments human cervical carcinoma cell lines HeLa cells were incubated with 5 and 6 30 min. Te HeLa cells images were non-fuorescent at low H 2 S concentration afer the incubation. However the cells became fuorescent turn on afer 250 μM H 2 S when the cells were incubated for another 30 min. Tis indicates that 5 and 6 are concentration dependent for the detection of H 2 S in the living cells. Receptors Based on Complexation Reaction Tis strategy is one of the oldest utilized molecular receptor approaches for detection of analyte during diverse analytical monitoring. In this direction Meng et al. reported fuorescein–aldazine based fuorescent receptor Figure 6 for S 2- ions in aqueous solution Figure 2: Molecular structure of receptor 2 with active site responsible for the detection of SO 3 2- encircled. Figure 3: Molecular structure of receptor 3 with active site responsible for the detection of SO 3 2- encircled. Figure 4: Molecular structure of receptor 4 with active site responsible for the detection of H 2 S encircled.

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Citation: Kaloo MA Shah WA Bhat BA Gani M 2019 Fluorescent Synthetic Receptors for Signaling Hydrogen Sulphide in Living Systems. Biochem Anal Biochem 8: 375. doi: 10.4172/2161-1009.1000375 Volume 8 • Issue 1 • 1000375 Biochem Anal Biochem an open access journal ISSN: 2161-1009 Page 3 of 4 8. It displays a reversible fuorescent respose with “ON-OFF-ON” mechanism in living cells. In this case Cu 2+ ion coplex of the receptor is created and then used to detection the S 2- via decomplexation mechansm. Te detection limit of this receptor 7 was found to be 0.15 µM. For studying the potential applications of this receptor in living systems cells were incubated with a 5 μM solution of receptor 7 for 30 min at 37°C. Ten the cells were washed three times with PBS. Afer incubating the cells with sodium sulfde 10 μM for another 10 min an intense green fuorescence was observed hence deciphering potential cellular applications. In another similar type of study C Li reported a reversible fuorescent probe 8 Figure 7 for sequential recognition of Cu 2+ and S 2- in aqueous and biological media. Author reported a reversible fuorescent sensing response in the form of “ON-OFF-ON” of fuorescence from the receptor molecule. Te detection limit of receptor 8 was found to be 0.11 µM. He studied that the HeLa cells displayed the strong green fuorescence afer incubated with the probe for 30 minutes at 37 o C. Afer the addition of 10 mM Cu 2+ for 10 min at 37 o C the strong fuorescence was vanished indicating complex compound of probe 8 with cation. However afer treating with 20 mM S 2- for 10 min under same temperature conditions strong fuorescence was recovered back indicating that the probe has a high sensitivity and selectivity for S 2- on the bases of forming CuS. Receptors Based on Deprotonation Reaction Tis is one of the recent studies which has taken the anion-induced deprotonation mechanism into account for the detection of S 2- . In this direction Kumar et al. reported Pyridine-26-dicarboxamide based molecular receptors for the selective detection of S 2- ions 9. However here we have mentioned best among the receptors reported in his work which possess benzothiazole rings 9 Figure 8. Tis receptor which is selective for the S 2- ion in aqueous as well as living cells contrary to the other one. Te detection limit of 9 for the analyte was calculaed to be 1.28 µM. During the biological study afer the incubation of L929 cells receptor was treated with anion and a strong fuorescence green channel was observed. Te cell imaging studies clearly illustrate that the developed receptor molecule has good cellular permeability and shows efective interaction with sulfde ion inside the cells. Conclusions In this work we present a review of literature about single molecular receptor approach for the recognition of various species of sulphur like H 2 S HS - and SO 3 2- under living cell environment. Te receptors which have been selected herein are robust under ambient conditions as well as inside living matrices. We have solely focused on molecules Figure 5: Molecular structure of receptor 6 left and 5 right with active sites for the detection of H 2 S encircled. Figure 6: Molecular structure of receptor 7 with active site responsible for the detection of S 2- encircled. Figure 7: Molecular structure of receptor 8 with active site responsible for the detection of S 2- encircled. Figure 8: Molecular structure of receptor 9 with active site responsible for the detection of S 2- encircled.

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Citation: Kaloo MA Shah WA Bhat BA Gani M 2019 Fluorescent Synthetic Receptors for Signaling Hydrogen Sulphide in Living Systems. Biochem Anal Biochem 8: 375. doi: 10.4172/2161-1009.1000375 Volume 8 • Issue 1 • 1000375 Biochem Anal Biochem an open access journal ISSN: 2161-1009 Page 4 of 4 deciphering recognition signal as fuorescence which is strong enough to track the target sulphur species in minimal amounts in living cells. Te categorization of designed and proposed receptor strategies has been presented with respect to the mechanistic aspects involved during the course of anion interaction with proposed molecules. Te encounter between receptor molecules and sulphur species has been recognized with either reversible Chemosensing or irreversible Chemodosimetry pathway. In addition to the molecular structure of the mentioned receptors sensitivity of receptors detection limit has also been highlighted. Even though much has been talked about selectivity of proposed receptors for these anionic sulphur species but specifc recognition of any of these is still to be looked at. In this direction exclusive selectivity for HS - and SO 3 2- inside intracellular matrix will be highly desirable as these are the crucial sulphur based anions involved inside the cells. Besides these other aspects like toxicity of the new formed receptor species particular fragments produced as a result of Chemodosmetry triggered by anion needs to be taken into account while developed novel receptors. We believe the state of art target molecules discussed in this work will keep researchers biologists biochemists analytical chemists etc. interested in the arena at the top of the feld while looking to develop futuristic molecular designs which is highly efcient and convenient for complete apportionment of sulphur inside living systems. Acknowledgements We highly acknowledge Head of Institute Dr. Ali Mohammad Dar and department of chemistry Govt Degree College Shopian for their support throughout the work. M. A. Kaloo gratefully acknowledges Department of Science and Technology New Delhi for INSPIRE-FACULTY research grants DST/ INSPIRE/04/2016/000098. References 1. Lippert AR New EJ Chang CJ 2011 Reaction-based fuorescent probes for selective imaging of hydrogen sulfde in living cells. J Am Chem Soc 133: 10078-10080. 2. Blackstone E Morrison M Roth MB 2005 H 2 S induces a suspended animation-like state in mice. Sci 308: 518. 3. Yang G Wu L Jiang B Yang B Qi J et al. 2008 H 2 S as a physiologic vasorelaxant: hypertension in mice with deletion of cystathionine gamma-lyase. Sci 322: 587. 4. Yang G Wu L Wang R 2006 Pro-apoptotic effect of endogenous H 2 S on human aorta smooth muscle cells. FASEB J 20: 553-555. 5. Iwasawa S Kikuchi Y Nishiwaki Y Nakano M Michikawa T et al. 2009 Effects of SO 2 on respiratory system of adult Miyakejima resident 2 years after returning to the island. J Occup Health 51: 38-47. 6. Sang N Yun Y Li H Hou L Han M et al. 2010 SO 2 Inhalation Contributes to the Development and Progression of Ischemic Stroke in the Brain. Toxicol Sci 114: 226-236. 7. Guo Z Chen G Zeng G Li ZW 2015 Fluorescent and colorimetric sensors for environmental mercury detection. Analyst 140: 5400-5443. 8. Meng Q Zhang R Jia H Gao X Wang C et al. 2015 A reversible fuorescence chemosensor for sequentially quantitative monitoring copper and sulfde in living cells. Talanta 143: 294-301. 9. Kumar P Gupta R Kumar V Pandey S 2018 Detection of sulfde ion and gaseous H2S using a series of pyridine-26-dicarboxamide based scaffolds. Dalton Trans 47: 9536-9545.

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