Ферменты и их формы, используемые для обнаружения фосфорорганических соединений

Ферменты способны эффективно взаимодействовать с различными фосфорорганическими соединениями (ФОС), вступая с ними в (био)химические реакции. Изменение исходной активности ферментов в результате их ингибирования ФОС, образование продуктов деструкции ФОС под действием гидролитических ферментов и пр. могут быть определены с использованием разных физико-химических методов и использованы в биоаналитических системах для определения концентраций ФОС. Цель обзора – анализ основных научных результатов, достигнутых за последние 10 лет в развитии аналитических систем на основе ферментов, статья предназначена для разработчиков детекторов ФОС. Показано, что требования к чувствительности биосенсоров исходят из норм содержания анализируемых веществ, детектируемых в/на объектах, подлежащих обязательному контролю. Основой для разработки наибольшего числа ультрачувствительных биосенсоров являются холинэстеразы, хотя и другие ферменты также могут успешно использоваться в роли биочувствительного элемента. Наиболее технологичным решением, приближенным к практическому внедрению, можно считать биоаналитические системы, использующие иммобилизованные ферменты. Улучшение пределов обнаружения ФОС может быть достигнуто за счет использования нанообъектов вкупе с современными методами регистрации сигнала, например, с наномеханическими детекторами и преобразователями сигнала. Это сочетание технических решений обеспечивает чувствительность анализа ФОС вплоть до пг/л. Существенное развитие в настоящее время получили «безреагентные» системы, ставшие основой для производства большого числа коммерчески доступных «стрипов» (тест-полосок) для экспрессного определения ФОС. Современные запросы стимулируют бурное развитие портативных и особенно «мобильных, портативных» биосенсоров, способных закрепляться, в том числе, на одежде. Прогресс, достигнутый в области создания аффинных аминокислотных последовательностей, в перспективе позволит создавать ферментные биосенсоры на любой поверхности.

1. Лягин И.В., Ефременко Е.Н., Варфоломеев С.Д. Ферментные биосенсоры для определения пестицидов // Успехи химии. 2017. Т. 86. С. 339–355. https://doi.org/10.1070/RCR4678

2. Фосфорорганические нейротоксины: монография / Под ред. Варфоломеева С.Д., Ефременко Е.Н. М.: РИОР, 2020 380 с. https://doi.org/10.29039/02026-5

3. Samsidar A., Siddiquee S., Md Shaarani S. A review of extraction, analytical and advanced methods for determination of pesticides in environment and foodstuffs // Trends Food Sci. Technol. 2018. V. 71. P. 188–201. https://doi.org/10.1016/j.tifs.2017.11.011

4. Rotariu L., Lagarde F., Jaffrezic-Renault N., Bala C. Electrochemical biosensors for fast detection of food contaminants trends and perspective // Trac-Trends Anal. Chem. 2016. V. 79. P. 80–87. https://doi.org/10.1016/j.trac.2015.12.017

5. Díaz-González M., Gutiérrez-Capitán M., Niu P., et al. Electrochemical devices for the detection of priority pollutants listed in the EU water framework directive // Trac-Trends Anal. Chem. 2016. V. 77. P. 186–202. https://doi.org/10.1016/j.trac.2015.11.023

6. Songa E.A., Okonkwo J.O. Recent approaches to improving selectivity and sensitivity of enzymebased biosensors for organophosphorus pesticides: a review // Talanta. 2016. V. 155. P. 289–304. https://doi.org/10.1016/j.talanta.2016.04.046

7. Amine A., Arduini F., Moscone D., Palleschi G. Recent advances in biosensors based on enzyme inhibition // Biosens. Bioelectron. 2016. V. 76. P. 180–194. https://doi.org/10.1016/j.bios.2015.07.010

8. Narenderan S.T., Meyyanathan S.N., Babu B. Review of pesticide residue analysis in fruits and vegetables. Pre-treatment, extraction and detection techniques // Food Res. Int. 2020. V. 133. P. e109141. https://doi.org/10.1016/j.foodres.2020.109141

9. Lyagin I., Efremenko E. Enzymes, reacting with organophosphorus compounds as detoxifiers: diversity and functions // Int. J. Mol. Sci. 2021. V. 22. P. e1761. https://doi.org/10.3390/ijms22041761

10. Hua X., Eremin S.A., Liu F., Wang M. Antibody developments and immunoassays for organophosphorus chemicals: a review // Curr. Org. Chem. 2017. V. 21. P. 2640–2652. https://doi.org/10.2174/1385272821666170428122718

11. Duan N., Wu S., Dai S. et al. Advances in aptasensors for the detection of food contaminants // Analyst. 2016. V. 141. P. 3942–3961. https://doi.org/10.1039/c6an00952b

12. Mahmoudpour M., Torbati M., Mousavi M.-M. et al. Nanomaterial-based molecularly imprinted polymers for pesticides detection: recent trends and future prospects // TrAC-Trends Anal. Chem. 2020. V. 129. P. e115943. https://doi.org/10.1016/j.trac.2020.115943

13. Mangas I., Estevez J., Vilanova E., França T.C. New insights on molecular interactions of organophosphorus pesticides with esterases // Toxicology. 2017. V. 376. P. 30–43. https://doi.org/10.1016/j.tox.2016.06.006

14. Liu D., Chen W., Wei J. et al. A highly sensitive, dual-readout assay based on gold nanoparticles for organophosphorus and carbamate pesticides // Anal. Chem. 2012. V. 84. P. 4185–4191. https://doi.org/10.1021/ac300545p

15. Wang P., Li H., Hassan M.M. et al. Fabricating an acetylcholinesterase modulated UCNPs-Cu2+ fluorescence biosensor for ultrasensitive detection of organophosphorus pesticides-diazinon in food // J. Agric. Food Chem. 2019. V. 67. P. 4071–4079. https://doi.org/10.1021/acs.jafc.8b07201

16. Long Q., Li H., Zhang Y., Yao S. Upconversion nanoparticle-based fluorescence resonance energy transfer assay for organophosphorus pesticides // Biosens. Bioelectron. 2015. V. 68. P. 168–174. https://doi.org/10.1016/j.bios.2014.12.046

17. Wu X., Wang P., Hou S. et al. Fluorescence sensor for facile and visual detection of organophosphorus pesticides using AIE fluorogens-SiO2 -MnO2 sandwich nanocomposites // Talanta. 2019. V. 198. P. 8–14. https://doi.org/10.1016/j.talanta.2019.01.082

18. Korram J., Dewangan L., Nagwanshi R. et al. A carbon quantum dot–gold nanoparticle system as a probe for the inhibition and reactivation of acetylcholinesterase // New J. Chem. 2019. V. 43. P. 6874–6882. https://doi.org/10.1039/C9NJ00555B

19. Yang M., Liu M., Wu Z. et al. Carbon dots codoped with nitrogen and chlorine for "off-on" fluorometric determination of the activity of acetylcholinesterase and for quantification of organophosphate pesticides // Microchim. Acta. 2019. V. 186. P. e585. https://doi.org/10.1007/s00604-019-3715-z

20. Cai Y., Fang J., Wang B. et al. A signal-on detection of organophosphorus pesticides by fluorescent probe based on aggregation-induced emission // Sens. Actuator. B-Chem. 2019. V. 292. P. 156–163. https://doi.org/10.1016/j.snb.2019.04.123

21. Silletti S., Rodio G., Pezzotti G. et al. An optical biosensor based on a multiarray of enzymes for monitoringa large set of chemical classes in milk // Sens. Actuator. B-Chem. 2015. V. 215. P. 607–617. https://doi.org/10.1016/j.snb.2015.03.092

22. Huang N., Qin Y., Li M. et al. A sensitive fluorescence assay of organophosphorus pesticides using acetylcholinesterase and copper-catalyzed click chemistry // Analyst. 2019. V. 144. P. 3436–3441. https://doi.org/10.1039/C9AN00260J

23. Yao T., Liu A., Liu Y. et al. Ratiometric fluorescence sensor for organophosphorus pesticide detection based on opposite responses of two fluorescence reagents to MnO2 nanosheets // Biosens. Bioelectron. 2019. V. 145. P. e111705. https://doi.org/10.1016/j.bios.2019.111705

24. Chungchai W., Amatatongchai M., Meelapsom R. et al. Development of a novel three-dimensional microfluidic paper-based analytical device (3D-μPAD) for chlorpyrifos detection using graphene quantum-dot capped gold nanocomposite for colorimetric assay // Int. J. Environ. Anal. Chem. 2020. V. 100. P. 1160–1178. https://doi.org/10.1080/03067319.2019.1650921

25. Cao J., Wang M., She Y. et al. Rapid colorimetric determination of the pesticides carbofuran and dichlorvos by exploiting their inhibitory effect on the aggregation of peroxidase-mimicking platinum nanoparticles // Microchim. Acta. 2019. V. 186. P. e390. https://doi.org/10.1007/s00604-019-3485-7

26. Jin L., Hao Z., Zheng Q. et al. A facile microfluidic paper-based analytical device for acetylcholinesterase inhibition assay utilizing organic solvent extraction in rapid detection of pesticide residues in food // Anal. Chim. Acta. 2020. V. 1100. P. 215–224. https://doi.org/10.1016/j.aca.2019.11.067

27. Duan R., Hao X., Li Y., Li H. Detection of acetylcholinesterase and its inhibitors by liquid crystal biosensor based on whispering gallery mode // Sens. Actuator. B-Chem. 2020. V. 308. P. e127672. https://doi.org/10.1016/j.snb.2020.127672

28. Cetrangolo G.P., Gori C., Rusko J. et al. Determination of picomolar concentrations of paraoxon in human urine by fluorescence-based enzymatic assay // Sensors. 2019. V. 19. P. e4852. https://doi.org/10.3390/s19224852

29. Yan X., Li H., Wang X., Su X. A novel fluorescence probing strategy for the determination of parathion-methyl // Talanta. 2015. V. 131. P. 88–94. https://doi.org/10.1016/j.talanta.2014.07.032

30. Yan X., Li H., Yan Y., Su X. Selective detection of parathion-methyl based on near-infrared CuInS2 quantum dots // Food Chem. 2015. V. 173. P. 179–184. https://doi.org/10.1016/j.foodchem.2014.09.152

31. Zhang F., Liu Y., Ma P. et al. A Mn-doped ZnS quantum dots-based ratiometric fluorescence probe for lead ion detection and "off-on" strategy for methyl parathion detection // Talanta. 2019. V. 204. P. 13–19. https://doi.org/10.1016/j.talanta.2019.05.071

32. Thakur S., Kumar P., Reddy M.V. et al. Enhancement in sensitivity of fluorescence based assay for organophosphates detection by silica coated silver nanoparticles using organophosphate hydrolase // Sens. Actuator. B-Chem. 2013. V. 178. P. 458–464. https://doi.org/10.1016/j.snb.2013.01.010

33. Thakur S., Reddy M.V., Siddavattam D., Paul A.K. A fluorescence based assay with pyranine labeled hexa-histidine tagged organophosphorus hydrolase (OPH) for determination of organophosphates // Sens. Actuator. B-Chem. 2012. V. 163. P. 153–158. https://doi.org/10.1016/j.snb.2012.01.024

34. Ibarra Bouzada L.M.E., Hernández S.R., Kergaravat S.V. Glyphosate detection from commercial formulations: comparison of screening analytic methods based on enzymatic inhibition // Int. J. Environ. Anal. Chem. 2021. in press. https://doi.org/10.1080/03067319.2019.1691176

35. Yan X., Li H., Han X., Su X. A ratiometric fluorescent quantum dots based biosensor for organophosphorus pesticides detection by inner-filter effect // Biosens. Bioelectron. 2015. V. 74. P. 277–283. https://doi.org/10.1016/j.bios.2015.06.020

36. Diaz A.N., Sanchez F.G., Aguilar A. et al.. Fast stopped-flow enzymatic sensing of fenitrothion in grapes and orange juice // J. Food Compos. Anal. 2015. V. 42. P. 187–192. https://doi.org/10.1016/j.jfca.2015.04.005

37. Dong J., Yang H., Li Y. et al. Fluorescence sensor for organophosphorus pesticide detection based on the alkaline phosphatase-triggered reaction // Anal. Chim. Acta. 2020. V. 1131. P. 102–108. https://doi.org/10.1016/j.aca.2020.07.048

38. Meng X., Wei J., Ren X. et al. A simple and sensitive fluorescence biosensor for detection of organophosphorus pesticides using H2 O2 -sensitive quantum dots/bi-enzyme // Biosens. Bioelectron. 2013. V. 47. P. 402–407. https://doi.org/10.1016/j.bios.2013.03.053

39. Sahub C., Tuntulani T., Nhujak T., Tomapatanaget B. Effective biosensor based on graphene quantum dots via enzymatic reaction for directly photoluminescence detection of organophosphate pesticide // Sens. Actuator. B-Chem. 2018. V. 258. P. 88–97. https://doi.org/10.1016/j.snb.2017.11.072

40. Huang S., Yao J., Chu X. et al. One-step facile synthesis of nitrogen-doped carbon dots: a ratiometric fluorescent probe for evaluation of acetylcholinesterase activity and detection of organophosphorus pesticides in tap water and food // J. Agric. Food Chem. 2019. V. 67. P. 11244–11255. https://doi.org/10.1021/acs.jafc.9b03624

41. Sahin A., Dooley K., Cropek D.M. et al. A dual enzyme electrochemical assay for the detection of organophosphorus compounds using organophosphorus hydrolase and horseradish peroxidase // Sens. Actuator. B-Chem. 2011. V. 158. P. 353–360. https://doi.org/10.1016/j.snb.2011.06.034

42. Drechsel L., Schulz M., von Stetten F. et al. Electrochemical pesticide detection with AutoDip-a portable platform for automation of crude sample analyses // Lab Chip. 2015. V. 15. P. 704–710. https://doi.org/10.1039/c4lc01214c

43. Zhao H., Ji X., Wang B. et al. An ultra-sensitive acetylcholinesterase biosensor based on reduced graphene oxide-Au nanoparticles-β-cyclodextrin/Prussian blue-chitosan nanocomposites for organophosphorus pesticides detection // Biosens. Bioelectron. 2015. V. 65. P. 23–30. https://doi.org/10.1016/j.bios.2014.10.007

44. He L., Cui B., Liu J. et al. Novel electrochemical biosensor based on core-shell nanostructured composite of hollow carbon spheres and polyaniline for sensitively detecting malathion // Sens. Actuator. B-Chem. 2018. V. 258. P. 813–821. https://doi.org/10.1016/j.snb.2017.11.161

45. Wei W., Dong S., Huang G. et al. MOF-derived Fe2 O3 nanoparticle embedded in porous carbon as electrode materials for two enzyme-based biosensors // Sens. Actuator. B-Chem. 2018. V. 260. P. 189–197. https://doi.org/10.1016/j.snb.2017.12.207

46. Lang Q., Han L., Hou C. et al. A sensitive acetylcholinesterase biosensor based on gold nanorods modified electrode for detection of organophosphate pesticide // Talanta. 2016. V. 156-157. P. 34–41. https://doi.org/10.1016/j.talanta.2016.05.002

47. Kaur N., Thakur H., Prabhakar N. Conducting polymer and multi-walled carbon nanotubes nanocomposites based amperometric biosensor for detection of organophosphate // J. Electroanal. Chem. 2016. V. 775. P. 121–128. https://doi.org/10.1016/j.jelechem.2016.05.037

48. Zou B., Chu Y., Xia J. Monocrotophos detection with a bienzyme biosensor based on ionic-liquid-modified carbon nanotubes // Anal. Bioanal. Chem. 2019. V. 411. P. 2905–2914. https://doi.org/10.1007/s00216-019-01743-z

49. Chen D., Liu Z., Fu J. et al. Electrochemical acetylcholinesterase biosensor based on multi-walled carbon nanotubes/dicyclohexyl phthalate modified screen-printed electrode for detection of chlorpyrifos // J. Electroanal. Chem. 2017. V. 801. P. 185–191. https://doi.org/10.1016/j.jelechem.2017.06.032

50. Thakkar J.B., Gupta S., Prabha C.R. Acetylcholine esterase enzyme doped multiwalled carbon nanotubes for the detection of organophosphorus pesticide using cyclic voltammetry // Int. J. Biol. Macromol. 2019. V. 137. P. 895–903. https://doi.org/10.1016/j.ijbiomac.2019.06.162

51. Mahmoudi E., Fakhri H., Hajian A. et al. High-performance electrochemical enzyme sensor for organophosphate pesticide detection using modified metal-organic framework sensing platforms // Bioelectrochemistry. 2019. V. 130. P. e107348. https://doi.org/10.1016/j.bioelechem.2019.107348

52. Song D., Wang Y., Lu X. et al. Ag nanoparticles-decorated nitrogen-fluorine co-doped monolayer MoS2 nanosheet for highly sensitive electrochemical sensing of organophosphorus pesticides // Sens. Actuator. B-Chem. 2018. V. 267. P. 5–13. https://doi.org/10.1016/j.snb.2018.04.016

53. Lu X., Tao L., Song D. et al. Bimetallic Pd@Au nanorods based ultrasensitive acetylcholinesterase biosensor for determination of organophosphate pesticides //Sens. Actuator. B-Chem. 2018. V. 255. P. 2575–2581. https://doi.org/10.1016/j.snb.2017.09.063

54. Jiang Y., Zhang X., Pei L. et al. Silver nanoparticles modified two-dimensional transition metal carbides as nanocarriers to fabricate acetycholinesterase-based electrochemical biosensor // Chem. Eng. J. 2018. V. 339. P. 547–556. https://doi.org/10.1016/j.cej.2018.01.111

55. Song D., Li Y., Lu X. et al. Palladiumcopper nanowires-based biosensor for the ultrasensitive detection of organophosphate pesticides // Anal. Chim. Acta. 2017. V. 982. P. 168–175. https://doi.org/10.1016/j.aca.2017.06.004

56. Lu X., Li Y., Tao L. et al. Amorphous metal boride as a novel platform for acetylcholinesterase biosensor development and detection of organophosphate pesticides // Nanotechnology. 2019. V. 30. e055501. https://doi.org/10.1088/1361-6528/aaee3f

57. Hu T., Xu J., Ye Y. et al. Visual detection of mixed organophosphorous pesticide using QDAChE aerogel based microfluidic arrays sensor // Biosens. Bioelectron. 2019. V. 136. P. 112–117. https://doi.org/10.1016/j.bios.2019.04.036

58. Sigolaeva L.V., Gladyr S.Y., Mergel O. et al. Easy-preparable butyrylcholinesterase/ microgel construct for facilitated organophosphate biosensing // Anal. Chem. 2017. V. 89. P. 6091–6098. https://doi.org/10.1021/acs.analchem.7b00732

59. Matějovský L., Pitschmann V. A strip biosensor with guinea green B and fuchsin basic color indicators on a glass nanofiber carrier for the cholinesterase detection of nerve agents // ACS Omega. 2019. V. 4. P. 20978–20986. https://doi.org/10.1021/acsomega.9b02153

60. Febbraio F., Merone L., Cetrangolo G.P. et al. Thermostable esterase 2 from Alicyclobacillus acidocaldarius as biosensor for the detection of organophosphate pesticides // Anal. Chem. 2011. V. 83. P. 1530–1536. https://doi.org/10.1021/ac102025z

61. Zhao Y., Zhang W., Lin Y., Du D. The vital function of Fe3 O4 @Au nanocomposites for hydrolase biosensor design and its application in detection of methyl parathion // Nanoscale. 2013. V. 5. P. 1121–1126. https://doi.org/10.1039/c2nr33107a

62. Anh D.H., Cheunrungsikul K., Wichitwechkarn J., Surareungchai W. A colorimetric assay for determination of methyl parathion using recombinant methyl parathion hydrolase // Biotechnol. J. 2011. V. 6. P. 565–571. https://doi.org/10.1002/biot.201000348

63. Mishra R.K., Vinu Mohan A.M., Soto F. et al. A microneedle biosensor for minimally-invasive transdermal detection of nerve agents // Analyst. 2017. V. 142. P. 918–924. https://doi.org/10.1039/c6an02625g

64. Choi B.G., Park H., Park T.J. et al. Solution chemistry of self-assembled graphene nanohybrids for high-performance flexible biosensors // ACS Nano. 2010. V. 4. P. 2910–2918. https://doi.org/10.1021/nn100145x

65. Lee J.H., Park J.Y., Min K. et al. A novel organophosphorus hydrolase-based biosensor using mesoporous carbons and carbon black for the detection of organophosphate nerve agents // Biosens. Bioelectron. 2010. V. 25. P. 1566–1570. https://doi.org/10.1016/j.bios.2009.10.013

66. Tuteja S.K., Kukkar M., Kumar P. et al. Synthesis and characterization of silica-coated silver nanoprobe for paraoxon pesticide detection // BioNanoScience. 2014. V. 4. P. 149–156. https://doi.org/10.1007/s12668-014-0129-6

67. Mishra R.K., Alonso G.A., Istamboulie G. et al. Automated flow based biosensor for quantification of binary organophosphates mixture in milk using artificial neural network // Sens. Actuator. B-Chem. 2015. V. 208. P. 228–237. https://doi.org/10.1016/j.snb.2014.11.011

68. Alonso G.A., Istamboulie G., Noguer T. et al. Rapid determination of pesticide mixtures using disposable biosensors based on genetically modified enzymes and artificial neural networks // Sens. Actuator. B-Chem. 2012. V. 164. P. 22–28. https://doi.org/10.1016/j.snb.2012.01.052

69. El-Moghazy A.Y., Soliman E.A., Ibrahim H.Z. et al. Ultra-sensitive biosensor based on genetically engineered acetylcholinesterase immobilized in poly (vinyl alcohol)/Fe–Ni alloy nanocomposite for phosmet detection in olive oil // Food Chem. 2016. V. 203. P. 73–78. https://doi.org/10.1016/j.foodchem.2016.02.014

70. Jin R., Kong D., Zhao X. et al. Tandem catalysis driven by enzymes directed hybrid nanoflowers for on-site ultrasensitive detection of organophosphorus pesticide // Biosens. Bioelectron. 2019. V. 141. P. e111473. https://doi.org/10.1016/j.bios.2019.111473

71. Montali L., Calabretta M.M., Lopreside A. et al. Multienzyme chemiluminescent foldable biosensor for on-site detection of acetylcholinesterase inhibitors // Biosens. Bioelectron. 2020. V. 162. e112232. https://doi.org/10.1016/j.bios.2020.112232

72. Chen D., Wang J., Xu Y. Highly sensitive lateral field excited piezoelectric film acoustic enzyme biosensor // IEEE Sens. J. 2013. V. 13. P. 2217–2222. https://doi.org/10.1109/JSEN.2012.2237508

73. Chen D., Wang J., Xu Y., Zhang L. A thin film electro-acoustic enzyme biosensor allowing the detection of trace organophosphorus pesticides // Anal. Biochem. 2012. V. 429. P. 42–44. https://doi.org/10.1016/j.ab.2012.07.002

74. Chen D., Wang J., Xu Y. et al . Highly sensitive detection of organophosphorus pesticides by acetylcholinesterase-coated thin film bulk acoustic resonator mass-loading sensor // Biosens. Bioelectron. 2013. V. 41. P. 163–167. https://doi.org/10.1016/j.bios.2012.08.018

75. Zhang Y., Liu H., Yang Z. et al. An acetylcholinesterase inhibition biosensor based on a reduced graphene oxide/silver nanocluster/chitosan nanocomposite for detection of organophosphorus pesticides // Anal. Methods. 2015. V. 7. P. 6213–6219. https://doi.org/10.1039/C5AY01439E

76. Badawy M.E.I., Taktak N.E.M. Design and optimization of bioactive paper immobilized with acetylcholinesterase for rapid detection of organophosphorus and carbamate insecticides // Curr. Biotechnol. 2018. V. 7. P. 392–404. https://doi.org/10.2174/2211550108666181126121102

77. Qi F., Lan Y., Meng Z. et al . Acetylcholinesterasefunctionalized two-dimensional photonic crystals for the detection of organophosphates // RSC Adv. 2018. V. 8. P. 29385–29391. https://doi.org/10.1039/C8RA04953J

78. Qi F., Yan C., Meng Z. et al. Acetylcholinesterasefunctionalized two-dimensional photonic crystal for the sensing of G-series nerve agents // Anal. Bioanal. Chem. 2019. V. 411. P. 2577–2585. https://doi.org/10.1007/s00216-019-01700-w

79. Liu G., Guo W., Yin Z. Covalent fabrication of methyl parathion hydrolase on gold nanoparticles modified carbon substrates for designing a methyl parathion biosensor // Biosens. Bioelectron. 2014. V. 53. P. 440–446. https://doi.org/10.1016/j.bios.2013.10.025

80. Krepker M.A., Segal E. Dual-functionalized porous Si/hydrogel hybrid for label-free biosensing of organophosphorus compounds // Anal. Chem. 2013. V. 85. P. 7353–7360. https://doi.org/10.1021/ac4011815

81. Stoytcheva M., Zlatev R., Gochev V. et al. Amperometric biosensor precision improvement: application to organophosphorus pesticide determination // Anal. Methods. 2014. V. 6. P. 8232–8238. https://doi.org/10.1039/C4AY01792G

82. Mehta J., Dhaka S., Paul A.K. et al. Organophosphate hydrolase conjugated UiO-66- NH2 MOF based highly sensitive optical detection of methyl parathion // Environ. Res. 2019. V. 174. P. 46–53. https://doi.org/10.1016/j.envres.2019.04.018

83. Mehta J., Dhaka S., Bhardwaj N. et al. Application of an enzyme encapsulated metal-organic framework composite for convenient sensing and degradation of methyl parathion // Sens. Actuator. B-Chem. 2019. V. 290. P. 267–274. https://doi.org/10.1016/j.snb.2019.03.116

84. Goud K.Y., Teymourian H., Sandhu S.S. et al. OPAA/fluoride biosensor chip towards field detection of G-type nerve agents // Sens. Actuator. B-Chem. 2020. V. 320. P. e128344. https://doi.org/10.1016/j.snb.2020.128344

85. Zehani N., Kherrat R., Dzyadevych S.V., Jaffrezic-Renault N. A microconductometric biosensor based on lipase extracted from Candida rugosa for direct and rapid detection of organophosphate pesticides // Int. J. Environ. Anal. Chem. 2015. V. 95. P. 466–479. https://doi.org/10.1080/03067319.2015.1036864

86. Chen C.-H., Yang K.-L. A liquid crystal biosensor for detecting organophosphates through the localized pH changes induced by their hydrolytic products // Sens. Actuator. B-Chem. 2013. V. 181. P. 368–374. https://doi.org/10.1016/j.snb.2013.01.036

87. El-Moghazy A.Y., Soliman E.A., Ibrahim H.Z. et al. Biosensor based on electrospun blended chitosanpoly (vinyl alcohol) nanofibrous enzymatically sensitized membranes for pirimiphos-methyl detection in olive oil // Talanta. 2016. V. 155. P. 258–264. https://doi.org/10.1016/j.talanta.2016.04.018

88. Zhang Y., Arugula M.A., Wales M. et al. A novel layer-by-layer assembled multi-enzyme/ CNT biosensor for discriminative detection between organophosphorus and non-organophosphrus pesticides // Biosens. Bioelectron. 2015. V. 67. P. 287–295. https://doi.org/10.1016/j.bios.2014.08.036

89. Dominguez R.B., Alonso G.A., Muñoz R. et al. Design of a novel magnetic particles based electrochemical biosensor for organophosphate insecticide detection in flow injection analysis // Sens. Actuator. B-Chem. 2015. V. 208. P. 491–496. https://doi.org/10.1016/j.snb.2014.11.069

90. Döring J., Rettke D., Rödel G. et al. Surface functionalization by hydrophobin-EPSPS fusion protein allows for the fast and simple detection of glyphosate // Biosensors. 2019. V. 9. P. e104. https://doi.org/10.3390/bios9030104

91. Lan W., Chen G., Cui F. et al. Development of a novel optical biosensor for detection of organophosphorus pesticides based on methyl parathion hydrolase immobilized by metal-chelate affinity // Sensors. 2012. V. 12. P. 8477–8490. https://doi.org/10.3390/s120708477

92. Kim B.S., Kim G.W., Heo N.S. et al. Development of a portable biosensor system for pesticide detection on a metal chip surface integrated with wireless communication // Food Sci. Biotechnol. 2015. V. 24. P. 743–750. https://doi.org/10.1007/s10068-015-0096-x

93. Yang M., Choi B.G., Park T.J. et al. Site-specific immobilization of gold binding polypeptide on gold nanoparticle-coated graphene sheet for biosensor application // Nanoscale. 2011. V. 3. P. 2950–2956. https://doi.org/10.1039/c1nr10197h

94. Istamboulie G., Durbiano R., Fournier D. et al. Biosensor-controlled degradation of chlorpyrifos and chlorfenvinfos using a phosphotriesterase-based detoxification column // Chemosphere. 2010. V. 78. P. 1–6. https://doi.org/10.1016/j.chemosphere.2009.10.037

95. Kergaravat S.V., Fabiano S.N., Soutullo A.R., Hernández S.R. Comparison of the performance analytical of two glyphosate electrochemical screening methods based on peroxidase enzyme inhibition // Microchem. J. 2021. V. 160, Part A. P. e105654. https://doi.org/10.1016/j.microc.2020.105654

96. Gomari M.M., Saraygord-Afshari N., Farsimadan M. et al. Opportunities and challenges of the tag-assisted protein purification techniques: Applications in the pharmaceutical industry // Biotechnol. Adv. 2020. V. 45. P. e107653. https://doi.org/10.1016/j.biotechadv.2020.107653

97. Martynko E., Kirsanov D. Application of chemometrics in biosensing: a review // Biosensors. 2020. V. 10. P. e100. https://doi.org/10.3390/bios10080100

98. Mishra R.K., Barfidokht A., Karajic A. et al. Wearable potentiometric tattoo biosensor for onbody detection of G-type nerve agents simulants // Sens. Actuator. B-Chem. 2018. V. 273. P. 966-972. https://doi.org/10.1016/j.snb.2018.07.001

99. Fleischauer V., Heo J. An organophosphate sensor based on photo-crosslinked hydrogelentrapped E. coli // Anal. Sci. 2014. V. 30. P. 937–942. https://doi.org/10.2116/analsci.30.937

100. Tang X., Liang B., Yi T. et al. Cell surface display of organophosphorus hydrolase for sensitive spectrophotometric detection of p-nitrophenol substituted organophosphates // Enzyme Microb. Technol. 2014. V. 55. P. 107–112. https://doi.org/10.1016/j.enzmictec.2013.10.006

101. Zhang H., Li Q., Ye T., Zhang Z., Li L. Optimization of the whole-cell catalytic activity of recombinant Escherichia coli cells with surfaceimmobilized organophosphorus hydrolase // J. Environ. Biol. 2013. V. 34. P. 315–319.

102. Liu R., Yang C., Xu Y. et al. Development of a whole-cell biocatalyst/biosensor by display of multiple heterologous proteins on the Escherichia coli cell surface for the detoxification and detection of organophosphates // J. Agric. Food Chem. 2013. V. 61. P. 7810–7816. https://doi.org/10.1021/jf402999b

103. Tang X., Zhang T., Liang B. et al. Sensitive electrochemical microbial biosensor for p-nitrophenylorganophosphates based on electrode modified with cell surface-displayed organophosphorus hydrolase and ordered mesopore carbons // Biosens. Bioelectron. 2014. V. 60. P. 137–142. https://doi.org/10.1016/j.bios.2014.04.001

104. Liang B., Han L. Displaying of acetylcholinesterase mutants on surface of yeast for ultra-trace fluorescence detection of organophosphate pesticides with gold nanoclusters // Biosens. Bioelectron. 2020. V. 148. P. e111825. https://doi.org/10.1016/j.bios.2019.111825

105. Kim С., Choi B.H., Seo J.H. et al. Mussel adhesive protein-based whole cell array biosensor for detection of organophosphorus compounds // Biosens. Bioelectron. 2013. V. 41. P. 199–204. https://doi.org/10.1016/j.bios.2012.08.022

106. Efremenko E., Lyagin I., Senko O. et al. Bioluminescent nano- and micro-biosensing elements for detection of organophosphorus compounds / Eds. Rai M., Reshetilov A., Plekhanova Y., Ingle A.P. // Macro, Micro, and Nano-Biosensors. Springer, Cham, 2021. Ch. 14. P. 239–261. https://doi.org/10.1007/978-3-030-55490-3_14

107. Tamayo J., Kosaka P.M., Ruz J.J. et al. Biosensors based on nanomechanical systems // Chem. Soc. Rev. 2013. V. 42. P. 1287–1311. https://doi.org/10.1039/C2CS35293A

108. Arduini F., Moscone D. Chapter Five – Multifarious aspects of electrochemical paper-based (bio)sensors / Ed. Merkoçi A. // Comprehensive Analytical Chemistry. Elsevier, Netherlands, Amsterdam. Volume 89. 2020. Chapter 5. P. 139–161. https://doi.org/10.1016/bs.coac.2020.01.001

109. Al Mamun M.A., Yuce M.R. Recent progress in nanomaterial enabled chemical sensors for wearable environmental monitoring applications // Adv. Funct. Mater. 2020. V. 30. Pe2005703. https://doi.org/101002/adfm.202005703

110. Yucesoy D.T., Khatayevich D., Tamerler C., Sarikaya M. Rationally designed chimeric solid-binding peptides for tailoring solid interfaces // Med. Devices Sens. 2020. V. 3. e10065. https://doi.org/10.1002/mds3.10065

111. Yuan M., Yu J., Cao H., Xu F. Effective improvement in performance of a miniature FIAcalorimetric biosensing system via denoising column addition and flow rate optimization // Sens. Actuator. B-Chem. 2016. V. 229. P. 492–498. https://doi.org/10.1016/j.snb.2016.01.068

112. Li S., Zhao J., Huang R. et al. Use of high-throughput enzyme-based assay with xenobiotic metabolic capability to evaluate the inhibition of acetylcholinesterase activity by organophosphorus pesticides // Toxicol. In Vitro. 2019. V. 56. P. 93–100. https://doi.org/10.1016/j.tiv.2019.01.002