Research Article
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Synthesis and Characterization of A New Probe For The Detection of Cystein

Year 2022, Volume: 48 Issue: 2, 79 - 87, 01.10.2022

Sait Malkondu Serkan Erdemir

https://doi.org/10.35238/sufefd.1115890
Cited By: 1

Abstract

Cysteine is an amino acid containing a thiol group, which has important roles in living organisms. Therefore, the determination of the presence and amount of cysteine is one of the main topics of interest for researchers. In the present study, a new benzothiazole-based sensor has been designed to detect cysteine by fluorescence method based on ESIPT mechanism. The molecule structure of the target probe molecule has been confirmed by methods such as FT-IR, NMR and MALDI-TOF (Matrix-Assisted Laser Desorption/Ionization time-of- flight) mass spectroscopy. In addition, the interaction mechanism between the probe and cysteine has been investigated through theoretical calculations.

Keywords

Cysteine ESIPT Fluorescence Probe

References

  • Amini, M. K., Khorasani, J. H., Khaloo, S. S. ve Tangestaninejad, S., 2003, Cobalt (II) salophen-modified carbon-paste electrode for potentiometric and voltammetric determination of cysteine, Analytical biochemistry, 320 (1), 32-38.
  • Bao, D., Wang, M., Yang, C., Yang, Y. ve Ma, X., 2017, Concerted Mechanisms of Excited-State Proton Intramolecular Transfer for Bis-2, 4-(2-benzoxazolyl)-hydroquinone and Its Derivatives, The Journal of Physical Chemistry A, 121 (43), 8217-8226.
  • Berehoiu, R. M. T., Popa, C. N. ve Popescu, S., 2013, Assessment of the E 920 additive (L-cysteine) in relation to some problems of modern food industry, ASSESSMENT, 13 (1).
  • Cebi, N., Dogan, C. E., Develioglu, A., Yayla, M. E. A. ve Sagdic, O., 2017, Detection of L-Cysteine in wheat flour by Raman microspectroscopy combined chemometrics of HCA and PCA, Food chemistry, 228, 116-124.
  • Chen, K.-Y., Tsai, H.-Y., Lin, W.-C., Chu, H.-H., Weng, Y.-C. ve Chan, C.-C., 2014, ESIPT fluorescent dyes with adjustable optical properties: Substituent and conjugation effects, Journal of Luminescence, 154, 168-177.
  • Dahal, D., McDonald, L., Bi, X., Abeywickrama, C., Gombedza, F., Konopka, M., Paruchuri, S. ve Pang, Y., 2017, An NIR-emitting lysosome-targeting probe with large Stokes shift via coupling cyanine and excited-state intramolecular proton transfer, Chemical Communications, 53 (26), 3697-3700.
  • Dai, J., Ma, C., Zhang, P., Fu, Y. ve Shen, B., 2020, Recent progress in the development of fluorescent probes for detection of biothiols, Dyes and Pigments, 177, 108321.
  • Das, M., Brahma, M. ve Krishnamoorthy, G., 2021, Light-Driven Switching between Intramolecular Proton-Transfer and Charge-Transfer States, The Journal of Physical Chemistry B, 125 (9), 2339-2350.
  • Demirkol, O., Adams, C. ve Ercal, N., 2004, Biologically important thiols in various vegetables and fruits, Journal of agricultural and food chemistry, 52 (26), 8151-8154.
  • Dickinson, D. A. ve Forman, H. J., 2002, Cellular glutathione and thiols metabolism, Biochemical pharmacology, 64 (5-6), 1019-1026.
  • Dietz, K.-J., Horling, F., Konig, J. ve Baier, M., 2002, The function of the chloroplast 2‐cysteine peroxiredoxin in peroxide detoxification and its regulation, Journal of experimental botany, 53 (372), 1321-1329.
  • Gupta, A. K., Li, W., Ruseckas, A., Lian, C., Carpenter-Warren, C. L., Cordes, D. B., Slawin, A. M., Jacquemin, D., Samuel, I. D. ve Zysman-Colman, E., 2021, Thermally activated delayed fluorescence emitters with intramolecular proton transfer for high luminance solution-processed organic light-emitting diodes, ACS applied materials & interfaces, 13 (13), 15459-15474.
  • Küster, A., Tea, I., Sweeten, S., Rozé, J.-C., Robins, R. J. ve Darmaun, D., 2008, Simultaneous determination of glutathione and cysteine concentrations and 2 H enrichments in microvolumes of neonatal blood using gas chromatography–mass spectrometry, Analytical and bioanalytical chemistry, 390 (5), 1403-1412.
  • Li, H., Li, H., Yang, L., Xu, X., Zhang, S. ve Gao, F., 2011, Excited state intramolecular proton transfer fluorescence emission of o-hydroxyphenyl-triazine derivatives, Chinese Science Bulletin, 56 (14), 1457-1460.
  • Li, M., Zheng, K., Chen, H., Liu, X., Xiao, S., Yan, J., Tan, X. ve Zhang, N., 2019, A novel 2, 5-bis (benzo [d] thiazol-2-yl) phenol scaffold-based ratiometric fluorescent probe for sensing cysteine in aqueous solution and serum, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 217, 1-7.
  • Niu, L.-Y., Chen, Y.-Z., Zheng, H.-R., Wu, L.-Z., Tung, C.-H. ve Yang, Q.-Z., 2015, Design strategies of fluorescent probes for selective detection among biothiols, Chemical Society Reviews, 44 (17), 6143-6160.
  • Özyürek, M., Baki, S., Güngör, N., Çelik, S. E., Güçlü, K. ve Apak, R., 2012, Determination of biothiols by a novel on-line HPLC-DTNB assay with post-column detection, Analytica chimica acta, 750, 173-181.
  • Paulsen, C. E. ve Carroll, K. S., 2013, Cysteine-mediated redox signaling: chemistry, biology, and tools for discovery, Chemical reviews, 113 (7), 4633-4679.
  • Qin, T., Liu, B., Huang, Y., Yang, K., Zhu, K., Luo, Z., Pan, C. ve Wang, L., 2018, Ratiometric fluorescent monitoring of methanol in biodiesel by using an ESIPT-based flavonoid probe, Sensors and Actuators B: Chemical, 277, 484-491.
  • Quig, D., 1998, Cysteine metabolism and metal toxicity, Alternative Medicine Review, 3, 262-270.
  • Ralph, T., Hitchman, M., Millington, J. ve Walsh, F., 1994, The electrochemistry of l-cystine and l-cysteine: Part 1: Thermodynamic and kinetic studies, Journal of electroanalytical chemistry, 375 (1-2), 1-15.
  • Sedgwick, A. C., Wu, L., Han, H.-H., Bull, S. D., He, X.-P., James, T. D., Sessler, J. L., Tang, B. Z., Tian, H. ve Yoon, J., 2018, Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents, Chemical Society Reviews, 47 (23), 8842-8880.
  • Stipanuk, M. H., Dominy Jr, J. E., Lee, J.-I. ve Coloso, R. M., 2006, Mammalian cysteine metabolism: new insights into regulation of cysteine metabolism, The Journal of nutrition, 136 (6), 1652S-1659S.
  • Su, Y., Li, K. ve Yu, X., 2019, Theoretical studies on the fluorescence enhancement of benzaldehydes by intermolecular hydrogen bonding, The Journal of Physical Chemistry B, 123 (4), 884-890.
  • Tao, Y., Zhang, X., Wang, J., Wang, X. ve Yang, N., 2012, Simultaneous determination of cysteine, ascorbic acid and uric acid by capillary electrophoresis with electrochemiluminescence, Journal of electroanalytical chemistry, 674, 65-70.
  • Wang, Y.-T., Jin, K. J., Myers, L. R., Glover, S. A. ve Novak, M., 2009, Hydrolysis and photolysis of 4-Acetoxy-4-(benzothiazol-2-yl)-2, 5-cyclohexadien-1-one, a model anti-tumor quinol ester, The Journal of organic chemistry, 74 (12), 4463-4471.
  • Wu, G., Fang, Y.-Z., Yang, S., Lupton, J. R. ve Turner, N. D., 2004, Glutathione metabolism and its implications for health, The Journal of nutrition, 134 (3), 489-492.
  • Xu, Z., Qin, T., Zhou, X., Wang, L. ve Liu, B., 2019, Fluorescent probes with multiple channels for simultaneous detection of Cys, Hcy, GSH, and H2S, TrAC Trends in Analytical Chemistry, 121, 115672.
  • Yan, F., Sun, X., Zu, F., Bai, Z., Jiang, Y., Fan, K. ve Wang, J., 2018, Fluorescent probes for detecting cysteine, Methods and applications in fluorescence, 6 (4), 042001.
  • Yang, M., Ma, L., Li, J. ve Kang, L., 2019, Fluorescent probe for Cu 2+ and the secondary application of the resultant complex to detect cysteine, RSC Advances, 9 (29), 16812-16818.
  • Zhang, J., Wang, N., Ji, X., Tao, Y., Wang, J. ve Zhao, W., 2020, BODIPY‐based fluorescent probes for biothiols, Chemistry–A European Journal.
  • Zhao, J., Ji, S., Chen, Y., Guo, H. ve Yang, P., 2012, Excited state intramolecular proton transfer (ESIPT): from principal photophysics to the development of new chromophores and applications in fluorescent molecular probes and luminescent materials, Physical Chemistry Chemical Physics, 14 (25), 8803-8817.

Sistein Tayini İçin Yeni Bir Algılayıcı Molekülün Sentezi ve Karakterizasyonu

Year 2022, Volume: 48 Issue: 2, 79 - 87, 01.10.2022

Sait Malkondu Serkan Erdemir

https://doi.org/10.35238/sufefd.1115890
Cited By: 1

Abstract

Sistein canlı organizmada önemli rolleri olan tiyol grubu içeren bir amino asittir. Dolayısıyla sistein varlığının ve miktarının tespit edilmesi araştırmacıların ilgilendiği konuların başında gelmektedir. Bu çalışmada, sisteini ESIPT mekanizmasına dayalı fluoresans metodu ile tayin etmek amacı ile benzotiyazol temelli yeni bir algılayıcı molekül tasarlanmıştır. Hedef algılayıcının molekül yapısı FT-IR, NMR ve MALDI-TOF (Matriks aracılı lazer dezorpsiyon iyonizasyon uçuş zamanı) kütle spektrokopisi gibi metotlarla aydınlatılmıştır. Ayrıca, algılayıcı ve sistein arasındaki etkileşim mekanizması teorik hesaplamalar aracılığıyla incelenmiştir.

Keywords

Sistein algılayıcı fluoresans ESIPT

References

  • Amini, M. K., Khorasani, J. H., Khaloo, S. S. ve Tangestaninejad, S., 2003, Cobalt (II) salophen-modified carbon-paste electrode for potentiometric and voltammetric determination of cysteine, Analytical biochemistry, 320 (1), 32-38.
  • Bao, D., Wang, M., Yang, C., Yang, Y. ve Ma, X., 2017, Concerted Mechanisms of Excited-State Proton Intramolecular Transfer for Bis-2, 4-(2-benzoxazolyl)-hydroquinone and Its Derivatives, The Journal of Physical Chemistry A, 121 (43), 8217-8226.
  • Berehoiu, R. M. T., Popa, C. N. ve Popescu, S., 2013, Assessment of the E 920 additive (L-cysteine) in relation to some problems of modern food industry, ASSESSMENT, 13 (1).
  • Cebi, N., Dogan, C. E., Develioglu, A., Yayla, M. E. A. ve Sagdic, O., 2017, Detection of L-Cysteine in wheat flour by Raman microspectroscopy combined chemometrics of HCA and PCA, Food chemistry, 228, 116-124.
  • Chen, K.-Y., Tsai, H.-Y., Lin, W.-C., Chu, H.-H., Weng, Y.-C. ve Chan, C.-C., 2014, ESIPT fluorescent dyes with adjustable optical properties: Substituent and conjugation effects, Journal of Luminescence, 154, 168-177.
  • Dahal, D., McDonald, L., Bi, X., Abeywickrama, C., Gombedza, F., Konopka, M., Paruchuri, S. ve Pang, Y., 2017, An NIR-emitting lysosome-targeting probe with large Stokes shift via coupling cyanine and excited-state intramolecular proton transfer, Chemical Communications, 53 (26), 3697-3700.
  • Dai, J., Ma, C., Zhang, P., Fu, Y. ve Shen, B., 2020, Recent progress in the development of fluorescent probes for detection of biothiols, Dyes and Pigments, 177, 108321.
  • Das, M., Brahma, M. ve Krishnamoorthy, G., 2021, Light-Driven Switching between Intramolecular Proton-Transfer and Charge-Transfer States, The Journal of Physical Chemistry B, 125 (9), 2339-2350.
  • Demirkol, O., Adams, C. ve Ercal, N., 2004, Biologically important thiols in various vegetables and fruits, Journal of agricultural and food chemistry, 52 (26), 8151-8154.
  • Dickinson, D. A. ve Forman, H. J., 2002, Cellular glutathione and thiols metabolism, Biochemical pharmacology, 64 (5-6), 1019-1026.
  • Dietz, K.-J., Horling, F., Konig, J. ve Baier, M., 2002, The function of the chloroplast 2‐cysteine peroxiredoxin in peroxide detoxification and its regulation, Journal of experimental botany, 53 (372), 1321-1329.
  • Gupta, A. K., Li, W., Ruseckas, A., Lian, C., Carpenter-Warren, C. L., Cordes, D. B., Slawin, A. M., Jacquemin, D., Samuel, I. D. ve Zysman-Colman, E., 2021, Thermally activated delayed fluorescence emitters with intramolecular proton transfer for high luminance solution-processed organic light-emitting diodes, ACS applied materials & interfaces, 13 (13), 15459-15474.
  • Küster, A., Tea, I., Sweeten, S., Rozé, J.-C., Robins, R. J. ve Darmaun, D., 2008, Simultaneous determination of glutathione and cysteine concentrations and 2 H enrichments in microvolumes of neonatal blood using gas chromatography–mass spectrometry, Analytical and bioanalytical chemistry, 390 (5), 1403-1412.
  • Li, H., Li, H., Yang, L., Xu, X., Zhang, S. ve Gao, F., 2011, Excited state intramolecular proton transfer fluorescence emission of o-hydroxyphenyl-triazine derivatives, Chinese Science Bulletin, 56 (14), 1457-1460.
  • Li, M., Zheng, K., Chen, H., Liu, X., Xiao, S., Yan, J., Tan, X. ve Zhang, N., 2019, A novel 2, 5-bis (benzo [d] thiazol-2-yl) phenol scaffold-based ratiometric fluorescent probe for sensing cysteine in aqueous solution and serum, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 217, 1-7.
  • Niu, L.-Y., Chen, Y.-Z., Zheng, H.-R., Wu, L.-Z., Tung, C.-H. ve Yang, Q.-Z., 2015, Design strategies of fluorescent probes for selective detection among biothiols, Chemical Society Reviews, 44 (17), 6143-6160.
  • Özyürek, M., Baki, S., Güngör, N., Çelik, S. E., Güçlü, K. ve Apak, R., 2012, Determination of biothiols by a novel on-line HPLC-DTNB assay with post-column detection, Analytica chimica acta, 750, 173-181.
  • Paulsen, C. E. ve Carroll, K. S., 2013, Cysteine-mediated redox signaling: chemistry, biology, and tools for discovery, Chemical reviews, 113 (7), 4633-4679.
  • Qin, T., Liu, B., Huang, Y., Yang, K., Zhu, K., Luo, Z., Pan, C. ve Wang, L., 2018, Ratiometric fluorescent monitoring of methanol in biodiesel by using an ESIPT-based flavonoid probe, Sensors and Actuators B: Chemical, 277, 484-491.
  • Quig, D., 1998, Cysteine metabolism and metal toxicity, Alternative Medicine Review, 3, 262-270.
  • Ralph, T., Hitchman, M., Millington, J. ve Walsh, F., 1994, The electrochemistry of l-cystine and l-cysteine: Part 1: Thermodynamic and kinetic studies, Journal of electroanalytical chemistry, 375 (1-2), 1-15.
  • Sedgwick, A. C., Wu, L., Han, H.-H., Bull, S. D., He, X.-P., James, T. D., Sessler, J. L., Tang, B. Z., Tian, H. ve Yoon, J., 2018, Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents, Chemical Society Reviews, 47 (23), 8842-8880.
  • Stipanuk, M. H., Dominy Jr, J. E., Lee, J.-I. ve Coloso, R. M., 2006, Mammalian cysteine metabolism: new insights into regulation of cysteine metabolism, The Journal of nutrition, 136 (6), 1652S-1659S.
  • Su, Y., Li, K. ve Yu, X., 2019, Theoretical studies on the fluorescence enhancement of benzaldehydes by intermolecular hydrogen bonding, The Journal of Physical Chemistry B, 123 (4), 884-890.
  • Tao, Y., Zhang, X., Wang, J., Wang, X. ve Yang, N., 2012, Simultaneous determination of cysteine, ascorbic acid and uric acid by capillary electrophoresis with electrochemiluminescence, Journal of electroanalytical chemistry, 674, 65-70.
  • Wang, Y.-T., Jin, K. J., Myers, L. R., Glover, S. A. ve Novak, M., 2009, Hydrolysis and photolysis of 4-Acetoxy-4-(benzothiazol-2-yl)-2, 5-cyclohexadien-1-one, a model anti-tumor quinol ester, The Journal of organic chemistry, 74 (12), 4463-4471.
  • Wu, G., Fang, Y.-Z., Yang, S., Lupton, J. R. ve Turner, N. D., 2004, Glutathione metabolism and its implications for health, The Journal of nutrition, 134 (3), 489-492.
  • Xu, Z., Qin, T., Zhou, X., Wang, L. ve Liu, B., 2019, Fluorescent probes with multiple channels for simultaneous detection of Cys, Hcy, GSH, and H2S, TrAC Trends in Analytical Chemistry, 121, 115672.
  • Yan, F., Sun, X., Zu, F., Bai, Z., Jiang, Y., Fan, K. ve Wang, J., 2018, Fluorescent probes for detecting cysteine, Methods and applications in fluorescence, 6 (4), 042001.
  • Yang, M., Ma, L., Li, J. ve Kang, L., 2019, Fluorescent probe for Cu 2+ and the secondary application of the resultant complex to detect cysteine, RSC Advances, 9 (29), 16812-16818.
  • Zhang, J., Wang, N., Ji, X., Tao, Y., Wang, J. ve Zhao, W., 2020, BODIPY‐based fluorescent probes for biothiols, Chemistry–A European Journal.
  • Zhao, J., Ji, S., Chen, Y., Guo, H. ve Yang, P., 2012, Excited state intramolecular proton transfer (ESIPT): from principal photophysics to the development of new chromophores and applications in fluorescent molecular probes and luminescent materials, Physical Chemistry Chemical Physics, 14 (25), 8803-8817.
There are 32 citations in total.

Details

Primary Language Turkish
Journal Section Research Articles
Authors

Sait Malkondu 0000-0002-6806-4188

Serkan Erdemir 0000-0003-0790-0549

Publication Date October 1, 2022
Submission Date May 13, 2022
Published in Issue Year 2022 Volume: 48 Issue: 2

Cite

APA Malkondu, S., & Erdemir, S. (2022). Sistein Tayini İçin Yeni Bir Algılayıcı Molekülün Sentezi ve Karakterizasyonu. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi, 48(2), 79-87. https://doi.org/10.35238/sufefd.1115890
AMA Malkondu S, Erdemir S. Sistein Tayini İçin Yeni Bir Algılayıcı Molekülün Sentezi ve Karakterizasyonu. sufefd. October 2022;48(2):79-87. doi:10.35238/sufefd.1115890
Chicago Malkondu, Sait, and Serkan Erdemir. “Sistein Tayini İçin Yeni Bir Algılayıcı Molekülün Sentezi Ve Karakterizasyonu”. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi 48, no. 2 (October 2022): 79-87. https://doi.org/10.35238/sufefd.1115890.
EndNote Malkondu S, Erdemir S (October 1, 2022) Sistein Tayini İçin Yeni Bir Algılayıcı Molekülün Sentezi ve Karakterizasyonu. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi 48 2 79–87.
IEEE S. Malkondu and S. Erdemir, “Sistein Tayini İçin Yeni Bir Algılayıcı Molekülün Sentezi ve Karakterizasyonu”, sufefd, vol. 48, no. 2, pp. 79–87, 2022, doi: 10.35238/sufefd.1115890.
ISNAD Malkondu, Sait - Erdemir, Serkan. “Sistein Tayini İçin Yeni Bir Algılayıcı Molekülün Sentezi Ve Karakterizasyonu”. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi 48/2 (October 2022), 79-87. https://doi.org/10.35238/sufefd.1115890.
JAMA Malkondu S, Erdemir S. Sistein Tayini İçin Yeni Bir Algılayıcı Molekülün Sentezi ve Karakterizasyonu. sufefd. 2022;48:79–87.
MLA Malkondu, Sait and Serkan Erdemir. “Sistein Tayini İçin Yeni Bir Algılayıcı Molekülün Sentezi Ve Karakterizasyonu”. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi, vol. 48, no. 2, 2022, pp. 79-87, doi:10.35238/sufefd.1115890.
Vancouver Malkondu S, Erdemir S. Sistein Tayini İçin Yeni Bir Algılayıcı Molekülün Sentezi ve Karakterizasyonu. sufefd. 2022;48(2):79-87.

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Afyon Kocatepe University Journal of Sciences and Engineering
https://doi.org/10.35414/akufemubid.1347411
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