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Selective colorimetric detection of cysteine based on phenylvinylbisquinoline for its potential implementation in optoelectronic sensors

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Abstract

We report a sensitive colorimetric chemosensor for cysteine based on phenylvinylbisquinoline, named M1. Selectivity for l-cysteine was demonstrated, causing a colorimetric change. The interaction between M1 and l-cysteine suggests a possible click reaction that alters the optical properties, which are consistent with the predictions in the study of TD-DFT. 1 H RMN, FTIR spectroscopies, and mass spectrometry confirmed the chemical structure obtained by the click reaction. Optical characterization revealed a bathochromic shift and a weakening of the fluorescence of M1 with increasing l-cysteine concentration. The detection limit for cysteine was 0.45 mM, the quantification limit was 1.36 mM, and the molar ratio method confirmed a stoichiometry of 1:2 between M1 and l-cysteine. This molecule can be used in electronic devices for in situ sensing of l-cysteine by a colorimetric shift.

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References

  1. W. He, L. Luo, Q. Liu, Z. Chen, Anal. Chem. 90, 4770 (2018)

    Article  CAS  Google Scholar 

  2. Y. He, L. Ma, L. Zhou, G. Liu, Y. Jiang, J. Gao, Nanomaterials 10, 1 (2020)

    Google Scholar 

  3. Q. Qiu, H. Chen, Z. You, Y. Feng, X. Wang, Y. Wang, Y. Ying, ACS Appl. Mater. Interfaces 12, 5429 (2020)

    Article  CAS  Google Scholar 

  4. S. Huang, L. Zhang, L. Dai, Y. Wang, Y. Tian, Anal. Chem. 93, 5570 (2021)

    Article  CAS  Google Scholar 

  5. P. Chandra Rao, S. Mandal, Inorg. Chem. 57, 11855 (2018)

    Article  CAS  Google Scholar 

  6. Q. Zou, F. Tao, H. Wu, W.W. Yu, T. Li, Y. Cui, Dye. Pigment. 164, 165 (2019)

    Article  CAS  Google Scholar 

  7. C. Xiao, K. Ma, G. Cai, X. Zhang, E. Vessally, J. Mol. Graph. Model. 96, 107539 (2020)

    Article  CAS  Google Scholar 

  8. H.C. Ates, J.A. Roberts, J. Lipman, A.E.G. Cass, G.A. Urban, C. Dincer, Trends Biotechnol. 38, 1262 (2020)

    Article  CAS  Google Scholar 

  9. N.M. Umesh, J. Antolin Jesila, S.F. Wang, M. Govindasamy, R.A. Alshgari, M. Ouladsmane, I.V. Asharani, Microchem. J. 167, 106244 (2021)

    Article  CAS  Google Scholar 

  10. Y. Zhang, X. Liu, S. Qiu, Q. Zhang, W. Tang, H. Liu, Y. Guo, Y. Ma, X. Guo, Y. Liu, J. Am. Chem. Soc. 141, 14643 (2019)

    Article  CAS  Google Scholar 

  11. A. Şenocak, S.O. Tümay, S. Makhseed, E. Demirbas, M. Durmuş, Biosens. Bioelectron. 174, 112819 (2021)

    Article  Google Scholar 

  12. N. Gao, R. Tan, Z. Cai, H. Zhao, G. Chang, Y. He, J. Mater. Sci. 56, 19060 (2021)

    Article  CAS  Google Scholar 

  13. H. Karimi-Maleh, H. Beitollahi, P. Senthil Kumar, S. Tajik, P. Mohammadzadeh Jahani, F. Karimi, C. Karaman, Y. Vasseghian, M. Baghayeri, J. Rouhi, P.L. Show, S. Rajendran, L. Fu, N. Zare, Food Chem. Toxicol. 164, 112961 (2022)

    Article  CAS  Google Scholar 

  14. J. Tropp, M.H. Ihde, E.R. Crater, N.C. Bell, R. Bhatta, I.C. Johnson, M. Bonizzoni, J.D. Azoulay, ACS Sens. 5, 1541 (2020)

    Article  CAS  Google Scholar 

  15. O.I. Lipskikh, E.I. Korotkova, Y.P. Khristunova, J. Barek, B. Kratochvil, Electrochim. Acta 260, 974 (2018)

    Article  CAS  Google Scholar 

  16. I.R. Suhito, K.M. Koo, T.H. Kim, Biomedicines 9, 1 (2021)

    Google Scholar 

  17. J.E. Fitzgerald, S.S. Fadaee, R. Sundaram, H. Fenniri, Sens. Actuators B Chem. 288, 332 (2019)

    Article  CAS  Google Scholar 

  18. A. Abdalla, B.A. Patel, Curr. Opin. Electrochem. 20, 78 (2020)

    Article  CAS  Google Scholar 

  19. H.E. Joe, H. Yun, S.H. Jo, M.B.G. Jun, B.K. Min, Int. J. Precis. Eng. Manuf. Green. Technol. 5, 173 (2018)

    Article  Google Scholar 

  20. X. Fang, B. Zong, S. Mao, Nano-Micro Lett. 10, 1 (2018)

    Article  Google Scholar 

  21. P. Kassal, M.D. Steinberg, I.M. Steinberg, Sens. Actuators B Chem. 266, 228 (2018)

    Article  CAS  Google Scholar 

  22. C. Anichini, W. Czepa, D. Pakulski, A. Aliprandi, A. Ciesielski, P. Samorì, Chem. Soc. Rev. 47, 4860 (2018)

    Article  CAS  Google Scholar 

  23. T. Yokota, K. Fukuda, T. Someya, Adv. Mater. 33, 1 (2021)

    Article  Google Scholar 

  24. Y. Xu, X. Hu, S. Kundu, A. Nag, N. Afsarimanesh, S. Sapra, S.C. Mukhopadhyay, T. Han, Sapra, S. C. Mukhopadhyay, and T. Han, Sensors 19, 2908 (2019)

  25. B. Liu, J. Zhuang, G. Wei, Environ. Sci. Nano 7, 2195 (2020)

    Article  CAS  Google Scholar 

  26. Z. Bielecki, T. Stacewicz, J. Wojtas, J. Mikołajczyk, D. Szabra, A. Prokopiuk, Opto-Electron. Rev. 26, 122 (2018)

    Article  Google Scholar 

  27. J.R. Askim, M. Mahmoudi, K.S. Suslick, Chem. Soc. Rev. 42, 8649 (2013)

    Article  CAS  Google Scholar 

  28. Z. Li, K.S. Suslick, ACS Sens. 1, 1330 (2016)

    Article  CAS  Google Scholar 

  29. D. Popa, F. Udrea, Sens. (Switzerland) 19, 1 (2019)

    Google Scholar 

  30. Z. Li, J.R. Askim, K.S. Suslick, Chem. Rev. 119, 231 (2019)

    Article  CAS  Google Scholar 

  31. A. Azzouz, V. Kumar, K.H. Kim, E. Ballesteros, T. Rhadfi, A.K. Malik, TrAC Trends Anal. Chem. 118, 502 (2019)

    Article  CAS  Google Scholar 

  32. C.S. Pundir, S. Lata, V. Narwal, Biosens. Bioelectron. 117, 373 (2018)

    Article  CAS  Google Scholar 

  33. Y.Y. Zhu, X.D. Wu, S.X. Gu, L. Pu, J. Am. Chem. Soc. 141, 175 (2019)

    Article  CAS  Google Scholar 

  34. A.M. Pettiwala, P.K. Singh, Indian J. Chem. Sect. B Org. Med. Chem. 57B, 293 (2018)

    CAS  Google Scholar 

  35. A. Dinu, C. Apetrei, Int. J. Mol. Sci. 23, 1 (2022)

    Article  Google Scholar 

  36. C. Lin, Y.C. Jair, Y.C. Chou, P.S. Chen, Y.C. Yeh, Anal. Chim. Acta 1041, 108 (2018)

    Article  CAS  Google Scholar 

  37. R. Kumar, G.B.V.S. Lakshmi, K. Singh, P.R. Solanki, J. Environ. Chem. Eng. 7, 103202 (2019)

    Article  CAS  Google Scholar 

  38. B.P. Jagilinki, S. Ilic, C. Trncik, A.M. Tyryshkin, D.H. Pike, W. Lubitz, E. Bill, O. Einsle, J.A. Birrell, B. Akabayov, D. Noy, V. Nanda, ACS Synth. Biol. 9, 3400 (2020)

    Article  CAS  Google Scholar 

  39. B. Daher, M. Vučetić, J. Pouysségur, Front. Oncol. 10, 1 (2020)

    Article  Google Scholar 

  40. J.A. Combs, G.M. Denicola, Cancers (Basel) 11, 1 (2019)

    Article  Google Scholar 

  41. D. Rohilla, S. Chaudhary, N. Kaur, A. Shanavas, Mater. Sci. Eng. C 110, 110724 (2020)

    Article  CAS  Google Scholar 

  42. W. Zhang, J. Liu, Y. Yu, Q. Han, T. Cheng, J. Shen, B. Wang, Y. Jiang, Talanta 185, 477 (2018)

    Article  CAS  Google Scholar 

  43. F. Yan, X. Sun, F. Zu, Z. Bai, Y. Jiang, K. Fan, J. Wang, Methods Appl. Fluoresc. 6, 042001 (2018)

    Article  CAS  Google Scholar 

  44. N. Cao, H. Zhou, H. Tan, R. Qi, J. Chen, S. Zhang, J. Xu, Methods Appl. Fluoresc. 7, 1 (2019)

    Article  CAS  Google Scholar 

  45. Z. Huang, C. Wu, Y. Li, Z. Zhou, R. Xie, X. Pang, H. Xu, H. Li, Y. Zhang, Anal. Methods 11, 3280 (2019)

    Article  Google Scholar 

  46. H. Mirac Dizman, E.O. Kazancioglu, T. Shigemune, S. Takahara, N. Arsu, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 264, 120294 (2022)

    Article  CAS  Google Scholar 

  47. S. Kavitha, S.M. Jelastin Kala, A.A. Babu Christus, A. Ravikumar, RSC Adv. 11, 37162 (2021)

    Article  CAS  Google Scholar 

  48. S. Sahu, S. Sharma, T. Kant, K. Shrivas, K.K. Ghosh, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 246, 118961 (2021)

    Article  CAS  Google Scholar 

  49. Z. Huang, Y. Yang, Y. Long, H. Zheng, Anal. Methods 10, 2676 (2018)

    Article  CAS  Google Scholar 

  50. A. Senthamizhan, B. Balusamy, T. Uyar, Curr. Opin. Biomed. Eng. 13, 1 (2020)

    Article  Google Scholar 

  51. A. Dondoni, Angew. Chemie Int. Ed. 47, 8995 (2008)

    Article  CAS  Google Scholar 

  52. U. Tunca, J. Polym. Sci. Part. A Polym. Chem. 52, 3147 (2014)

    Article  CAS  Google Scholar 

  53. A.A. Aimetti, R.K. Shoemaker, C.C. Lin, K.S. Anseth, Chem. Commun. 46, 4061 (2010)

    Article  CAS  Google Scholar 

  54. C.E. Hoyle, C.N. Bowman, Angew. Chemie Int. Ed. 49, 1540 (2010)

    Article  CAS  Google Scholar 

  55. M. Pramanik, K. Choudhuri, S. Chakraborty, A. Ghosh, P. Mal, Chem. Commun. 56, 2991 (2020)

    Article  CAS  Google Scholar 

  56. F. Zou, C. Wang, W. Song, L. Shen, R. Xu, M. Wang, M. Wang, T. Sun, J. Wang, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 257, 119775 (2021)

    Article  CAS  Google Scholar 

  57. D. Chomicki, O. Kharchenko, L. Skowronski, J. Kowalonek, A. Kozanecka-Szmigiel, D. Szmigiel, V. Smokal, O. Krupka, B. Derkowska-Zielinska, Int. J. Mol. Sci. 21, 5755 (2020)

    Article  CAS  Google Scholar 

  58. A.V. Sánchez-Mendoza, V.G. Ibarra-García, J.R. Velázquez-Hernández, O.J. Hernández-Ortíz, J. Carrillo, L. Palacios-Huerta, I. Cosme, A. Alvarez-Hernandez, K. Alemán-Ayala, R.A. Vázquez-García, O.J. Hernández-Ortiz, J.E. Cerón-Castelán, F.M. Muñoz-Pérez, V. Salazar-Pereda, J.G. Ortega-Mendoza, M.A. Veloz-Rodríguez, A. Lobo-Guerrero, A. Espinosa-Roa, M.A. Rodríguez-Rivera, R.A. Vázquez-García, J. Mater. Sci. Mater. Electron. 30, 3342 (2019)

    Article  Google Scholar 

  59. J.F. Montiel Hernández, P. García Bernal, R.A. Vázquez García, A.I. Martínez Pérez, J.L. Maldonado, JCoreño Alonso, O. Coreño, Alonso, Adv. Mater. Res. 976, 80 (2014)

    Article  Google Scholar 

  60. A.H. Rojas-Calva, O.J. Hernández-Ortiz, F.M. Muñoz-Pérez, G.M. Estrada-Villegas, J.G. Ortega-Mendoza, M.A. Veloz-Rodríguez, J.L. Imbert-Palafox, R.A. Vázquez-García, J. Polym. Res. 28, 1 (2021)

    Article  Google Scholar 

  61. L. Hu, K. Xie, A. Gao, Y. Hu, A. Hou, Dye. Pigment 199, 110048 (2022)

    Article  CAS  Google Scholar 

  62. G. Chai, Q. Liu, Q. Fei, J. Zhang, X. Sun, H. Shan, G. Feng, Y. Huan, Luminescence 33, 153 (2018)

    Article  CAS  Google Scholar 

  63. B. Czaplinska, E. Spaczynska, R. Musiol, Med. Chem. (Los Angeles) 14, 19 (2018)

    CAS  Google Scholar 

  64. S.J. Ranee, G. Sivaraman, A.M. Pushpalatha, S. Muthusubramanian, Sens. Actuators B Chem. 255, 630 (2018)

    Article  CAS  Google Scholar 

  65. M. Amado-Briseño, O.J. Hernández-Ortíz, M.A.V. Rodríguez, K.A. Ayala, G.P. del Melero, B.R. Herrero, A.G.H. Zanabria, A.E. Roa, R.A. Vázquez-García, J. Mater. Sci. Mater. Electron. 33, 126 (2022)

    Article  Google Scholar 

  66. Y. Mikata, A. Yamashita, A. Kawamura, H. Konno, Y. Miyamoto, S. Tamotsu, Dalt. Trans. 19, 3800 (2009)

    Article  Google Scholar 

  67. S. Kaide, H. Watanabe, Y. Shimizu, S. Iikuni, Y. Nakamoto, M. Hasegawa, K. Itoh, M. Ono, ACS Chem. Neurosci. 11, 4254 (2020)

    Article  CAS  Google Scholar 

  68. A.R. Vazquez-Velazquez, R. Vazquez-Garcia, G. Hernandez-Bucio, V.A. Gonzalez-Gonzalez, I. Moggio, S. Vazquez-Rodriguez, Polym. Bull. 77, 1781 (2019)

    Article  Google Scholar 

  69. W. Gao, Y. Li, S. Wang, Res. Chem. Intermed 40, 669 (2014)

    Article  CAS  Google Scholar 

  70. M. Saga, T. Anamushi, W. Miyahara, S. Yamazaki, K. Saito, Anal. Sci. 31, 185 (2015)

    Article  CAS  Google Scholar 

  71. S. Muthusamy, L. Zhao, K. Rajalakshmi, D. Zhu, R. Soy, J. Mack, T. Nyokong, S. Wang, K.B. Lee, W. Zhu, Dye. Pigment 193, 109556 (2021)

    Article  CAS  Google Scholar 

  72. A.A. Shcherbatykh, M.S. Chernovyants, N.A. Voloshin, A.V. Chernyshev, Chem. Pap. 76, 5541 (2022)

    Article  CAS  Google Scholar 

  73. D. Liu, L.-E. Guo, X. Chen, Y. Xia, X. Hu, S. Weng, J. Iran. Chem. Soc. 19, 2377 (2022)

    Article  CAS  Google Scholar 

  74. G.A. Medeiros, J.R. Correa, L.P. de Andrade, T.O. Lopes, H.C.B. de Oliveira, A.B. Diniz, G.B. Menezes, M.O. Rodrigues, B.A.D. Neto, Sens. Actuators B Chem. 328, 128998 (2021)

    Article  CAS  Google Scholar 

  75. F. Liang, J. Chen, Y. Cheng, L. Wang, D. Ma, X. Jing, F. Wang, J. Mater. Chem. 13, 1392 (2003)

    Article  CAS  Google Scholar 

  76. D.J. Frisch, M.J. Trucks, G.W. Schlegel, H.B. Scuseria, G.E. Robb, M.A. Cheeseman, J.R. Scalmani, G. Barone, V. Petersson, G.A. Nakatsuji, H. Li, X. Caricato, M. Marenich, A. Bloino, J. Janesko, B.G. Gomperts, R. Mennucci, B. Hratchian, J. Am. Chem. Soc. 137, 3811 (2009)

    Google Scholar 

  77. S.O. Afolabi, B. Semire, M.A. Idowu, Heliyon 7, e06827 (2021)

    Article  CAS  Google Scholar 

  78. J. Chen, Q. Liu, H. Li, Z. Zhao, Z. Lu, Y. Huang, D. Xu, Front. Chem. 6, 1 (2018)

    Article  Google Scholar 

  79. M.A. Amado-Briseño, L. Zárate-Hernández, K. Alemán-Ayala, O.C. Alonso, J. Cruz-Borbolla, J.M. Vásquez-Pérez, V.E. Reyes-Cruz, M.A. Veloz-Rodríguez, E. Rueda-Soriano, T. Pandiyan, R.A. Vázquez-García, Molecules 1, 1 (2019)

    Google Scholar 

  80. G. Mazzone, N. Russo, E. Sicilia, Can. J. Chem. 91, 902 (2013)

    Article  CAS  Google Scholar 

  81. V.E. Matulis, E.G. Ragoyja, O.A. Ivashkevich, Int. J. Quantum Chem. 120, 1 (2020)

    Article  Google Scholar 

  82. A. Bourouina, M. Rekhis, J. Mol. Model. 23, 1 (2017)

    Article  CAS  Google Scholar 

  83. C. Sun, Y. Li, P. Song, F. Ma, Mater. (Basel) 9, 1 (2016)

    CAS  Google Scholar 

  84. K.J. Hamam, M.I. Alomari, Appl. Nanosci. 7, 261 (2017)

    Article  CAS  Google Scholar 

  85. O.J. Hernández-Ortiz, J.E. Cerón-Castelán, F.M. Muñoz-Pérez, V. Salazar-Pereda, J.G. Ortega-Mendoza, M.A. Veloz-Rodríguez, A. Lobo-Guerrero, A. Espinosa-Roa, M.A. Rodríguez-Rivera, R.A. Vázquez-García, J. Mater. Sci. Mater. Electron. 31, 3342 (2020)

    Article  Google Scholar 

  86. M. Yang, X. Chen, Y. Zou, C. Pan, B. Liu, H. Zhong, J. Mater. Sci. 48, 1014 (2013)

    Article  CAS  Google Scholar 

  87. N. Shahzad, S.M. Shah, S. Munir, A. Hana, U. Jabeen, E. Nosheen, B. Habib, A.U. Khan, Z. Hassan, M. Siddiq, H. Hussain, J. Electron. Mater. 44, 1167 (2015)

    Article  CAS  Google Scholar 

  88. A. Saboor, S.M. Shah, H. Hussain, Mater. Sci. Semicond. Process. 93, 215 (2019)

    Article  CAS  Google Scholar 

  89. Y. Li, D. Qi, P. Song, F. Ma, Material (Basel) 8, 42 (2015)

    Article  CAS  Google Scholar 

  90. P.L. Yap, Y.L. Auyoong, K. Hassan, F. Farivar, D.N.H. Tran, J. Ma, D. Losic, Chem. Eng. J. 395, 124965 (2020)

    Article  CAS  Google Scholar 

  91. K.E. Klymus, C.M. Merkes, M.J. Allison, C.S. Goldberg, C.C. Helbing, M.E. Hunter, C.A. Jackson, R.F. Lance, A.M. Mangan, E.M. Monroe, A.J. Piaggio, J.P. Stokdyk, C.C. Wilson, C.A. Richter, Environ. DNA 2, 271 (2020)

    Article  Google Scholar 

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Funding

Nery Islas Rodríguez give thanks to the CONACYT support for Grant Number 593645. Oscar Javier Hernández-Ortiz thanks CONACYT for postdoctoral fellowship.

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Authors and Affiliations

  1. Área Académica de Ciencias de la Tierra y Materiales, Área Académica de Química, Universidad Autónoma del Estado de Hidalgo (UAEH), Carretera Pachuca-Tulancingo Km. 4.5, Ciudad del Conocimiento, Mineral de la Reforma, C.P. 42184, Pachuca, Hgo., México

    N. Islas-Rodríguez, R. Muñoz, R. A. Vázquez-García, Jose A. Rodríguez & M. Reyes-Pérez

  2. Laboratorio de Química Supramolecular y Nanociencias de la Unidad Profesional Interdisciplinaria de Biotecnología del Instituto Politécnico Nacional, Av. Acueducto s/n Barrio la laguna Ticomán, Ciudad de México, 07340, México

    O. J. Hernández-Ortiz

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  1. N. Islas-Rodríguez
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Contributions

Synthesis and chemical characterization of the M1 were conducted by RAVG and NIR; OJH was responsible for the theoretical studies and optical characterization; JARÁ, NIR, and RM were accountable for the limit of detection and quantification determination. All authors contributed equally to the analysis and interpretation of the results presented here, along with the writing of the article. All authors agree with the final version.

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Correspondence to O. J. Hernández-Ortiz.

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Islas-Rodríguez, N., Muñoz, R., Vázquez-García, R.A. et al. Selective colorimetric detection of cysteine based on phenylvinylbisquinoline for its potential implementation in optoelectronic sensors. J Mater Sci: Mater Electron 34, 1116 (2023). https://doi.org/10.1007/s10854-023-10538-z

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