Low-energy electron driven reactions in 2-bromo-5-nitrothiazole

Chen, Jiakuan; Chakraborty, Dipayan; Ončák, Milan; Ptasinska, Sylwia; Denifl, Stephan

doi:10.1063/5.0246241

Title: Low-energy electron driven reactions in 2-bromo-5-nitrothiazole

Journal Article · 21 January 2025 · Journal of Chemical Physics

DOI: https://doi.org/10.1063/5.0246241 · OSTI ID:2504611

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Thiazole derivatives are biologically relevant molecules, used also in pharmaceutical applications. Herein, we report results for electron attachment to 2-bromo-5-nitrothiazole (BNT) in the gas phase. Employing two crossed electron–molecule beam experiments, we determined the efficiency curves of various fragment anions as a function of the initial electron energy between about 0 and 10 eV as well as the emission angle and kinetic energy distributions of Br− and NO2− ions formed from a resonance near 4 eV. The experiments were supported by quantum chemical calculations, exploring possible dissociation pathways along with their reaction energies. We also compared the electron attachment characteristics of BNT with those of the native thiazole molecule by performing electron attachment experiments and calculations for this molecule as well. Compared to thiazole, which is primarily degraded only by electrons with kinetic energies between about 5 and 10 eV, BNT is susceptible to low-energy electrons near 0 eV with enhanced cross section for (dissociative) electron attachment. However, although BNT offers two localization sites with high electron affinity (Br and NO2 moieties), we do not find the corresponding anions as the dominant negatively charged species formed upon electron attachment. Instead, the reaction channels with an abstraction of Br and NO2 as neutral radicals prevail, accompanied by the opening of the thiazole ring due to the relatively weak C–S bond.

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Sponsoring Organization:: USDOE

OSTI ID:: 2504611

Journal Information:: Journal of Chemical Physics, Journal Name: Journal of Chemical Physics Journal Issue: 4 Vol. 162; ISSN 0021-9606

Publisher:: American Institute of PhysicsCopyright Statement

Country of Publication:: United States

Language:: English

References (75)

Influence of Functional Groups on the Site-Selective Dissociation of Adenine upon Low-Energy Electron Attachment Denifl, Stephan; Sulzer, Philipp; Huber, Dieter Angewandte Chemie International Edition, Vol. 46, Issue 27 https://doi.org/10.1002/anie.200700032	journal	July 2007
Reactions in Nitroimidazole Triggered by Low-Energy (0 - 2 eV) Electrons: Methylation at N1-H Completely Blocks Reactivity Tanzer, Katrin; Feketeová, Linda; Puschnigg, Benjamin Angewandte Chemie International Edition, Vol. 53, Issue 45 https://doi.org/10.1002/anie.201407452	journal	September 2014
The Effect of Solvation on Electron Attachment to Pure and Hydrated Pyrimidine Clusters Neustetter, Michael; Aysina, Julia; da Silva, Filipe Ferreira Angewandte Chemie International Edition, Vol. 54, Issue 31 https://doi.org/10.1002/anie.201503733	journal	June 2015
Reactions in Tirapazamine Induced by the Attachment of Low‐Energy Electrons: Dissociation Versus Roaming of OH Arthur‐Baidoo, Eugene; Ameixa, João; Ziegler, Patrick Angewandte Chemie International Edition, Vol. 59, Issue 39 https://doi.org/10.1002/anie.202006675	journal	August 2020
Dissociative Electron Attachment Dynamics of a Promising Cancer Drug Indicates Its Radiosensitizing Potential Izadi, Farhad; Luxford, Thomas F. M.; Sedmidubská, Barbora Angewandte Chemie International Edition, Vol. 63, Issue 41 https://doi.org/10.1002/anie.202407469	journal	September 2024
Histone H2AX phosphorylation induced by selective photolysis of BrdU‐labeled DNA with UV light: Relation to cell cycle phase Huang, Xuan; A. King, Malcolm; Halicka, H. Dorota Cytometry Part A, Vol. 62A, Issue 1 https://doi.org/10.1002/cyto.a.20086	journal	September 2004
On the mechanism of radiosensitization by 5-bromouracil Hotz, G. Molecular and General Genetics MGG, Vol. 102, Issue 1 https://doi.org/10.1007/bf00341869	journal	June 1968
Design, synthesis, and antimalarial evaluation of thiazole-derived amino acids Karade, Hitendra N.; Acharya, B. N.; Sathe, Manisha Medicinal Chemistry Research, Vol. 17, Issue 1 https://doi.org/10.1007/s00044-008-9089-0	journal	February 2008
Hypoxia in cancer: significance and impact on clinical outcome Vaupel, Peter; Mayer, Arnulf Cancer and Metastasis Reviews, Vol. 26, Issue 2 https://doi.org/10.1007/s10555-007-9055-1	journal	April 2007
Molecular radiobiology of human cell lines. I. Comparative sensitivity to X-rays and ultraviolet light of cells containing halogen-substituted DNA Erikson, R. L.; Szybalski, W. Biochemical and Biophysical Research Communications, Vol. 4, Issue 4 https://doi.org/10.1016/0006-291x(61)90229-7	journal	March 1961
Synthesis and diuretic activity of imidazo[2,1-b]thiazole acetohydrazones Andreani, Aldo; Rambaldi, Mirella; Mascellani, Giuseppe European Journal of Medicinal Chemistry, Vol. 22, Issue 1 https://doi.org/10.1016/0223-5234(87)90169-3	journal	January 1987
Radiosensitization in vitro and in vivo by 3-nitrotriazoles Shibamoto, Yuta; Sakano, Koichi; Kimura, Ryoji International Journal of Radiation OncologyBiologyPhysics, Vol. 12, Issue 7 https://doi.org/10.1016/0360-3016(86)90226-9	journal	July 1986
The mechanism of radiosensitization by electron-affinic compounds Wardman, Peter International Journal of Radiation Applications and Instrumentation. Part C. Radiation Physics and Chemistry, Vol. 30, Issue 5-6 https://doi.org/10.1016/1359-0197(87)90111-1	journal	January 1987
Radical pair formation in a single crystal of bromonitrothiazole after X-irradiation at 77 K: An ESR study Geoffroy, Michel; Berclaz, Théo; Celalyan-Berthier, Alice International Journal of Radiation Applications and Instrumentation. Part C. Radiation Physics and Chemistry, Vol. 38, Issue 6 https://doi.org/10.1016/1359-0197(91)90076-e	journal	January 1991
Design and synthesis of 1,2-dithiolane derivatives and evaluation of their neuroprotective activity Koufaki, Maria; Kiziridi, Christina; Nikoloudaki, Faidra Bioorganic & Medicinal Chemistry Letters, Vol. 17, Issue 15 https://doi.org/10.1016/j.bmcl.2007.05.036	journal	August 2007
Theoretical evaluation of adiabatic and vertical electron affinity of some radiosensitizers in solution using FEP, ab initio and DFT methods Ramalho, Teodorico C.; de Alencastro, Ricardo Bicca; La-Scalea, Mauro Aquiles Biophysical Chemistry, Vol. 110, Issue 3 https://doi.org/10.1016/j.bpc.2004.03.002	journal	August 2004
Chemical Radiosensitizers for Use in Radiotherapy Wardman, P. Clinical Oncology, Vol. 19, Issue 6 https://doi.org/10.1016/j.clon.2007.03.010	journal	August 2007
Nitric oxide delivery to cancer: Why and how? Sonveaux, Pierre; Jordan, Bénédicte F.; Gallez, Bernard European Journal of Cancer, Vol. 45, Issue 8 https://doi.org/10.1016/j.ejca.2008.12.018	journal	May 2009
Application and synthesis of thiazole ring in clinically approved drugs Niu, Zhen-Xi; Wang, Ya-Tao; Zhang, Sheng-Nan European Journal of Medicinal Chemistry, Vol. 250 https://doi.org/10.1016/j.ejmech.2023.115172	journal	March 2023
Negative ion formation by low energy electron attachment to gas-phase 5-nitrouracil Ptasińska, Sylwia; Alizadeh, Elahe; Sulzer, Philipp International Journal of Mass Spectrometry, Vol. 277, Issue 1-3 https://doi.org/10.1016/j.ijms.2008.06.008	journal	November 2008
Production of low-energy electrons by ionizing radiation Pimblott, Simon M.; LaVerne, Jay A. Radiation Physics and Chemistry, Vol. 76, Issue 8-9 https://doi.org/10.1016/j.radphyschem.2007.02.012	journal	August 2007
Dissociative electron attachment to CCl4 molecules at low electron energies with meV resolution Klar, D.; Ruf, M. -W.; Hotop, H. International Journal of Mass Spectrometry, Vol. 205, Issue 1-3 https://doi.org/10.1016/s1387-3806(00)00271-2	journal	February 2001
Nitro-Group-Containing Drugs Nepali, Kunal; Lee, Hsueh-Yun; Liou, Jing-Ping Journal of Medicinal Chemistry, Vol. 62, Issue 6 https://doi.org/10.1021/acs.jmedchem.8b00147	journal	October 2018
Stability of the Parent Anion of the Potential Radiosensitizer 8-Bromoadenine Formed by Low-Energy (<3 eV) Electron Attachment Schürmann, Robin; Tanzer, Katrin; Dąbkowska, Iwona The Journal of Physical Chemistry B, Vol. 121, Issue 23 https://doi.org/10.1021/acs.jpcb.7b02130	journal	June 2017
Ultraviolet photoelectron spectrum of nitrite anion Ervin, Kent M.; Ho, Joe; Lineberger, W. C. The Journal of Physical Chemistry, Vol. 92, Issue 19 https://doi.org/10.1021/j100330a017	journal	September 1988
Theoretical and ESR/ENDOR single-crystal study of an azaallyl radical Reddy, Malledi V. V. S.; Celalyan-Berthier, Alice.; Geoffroy, Michel. Journal of the American Chemical Society, Vol. 110, Issue 9 https://doi.org/10.1021/ja00217a009	journal	April 1988
The Deprotonation of Thiazole and Related Bases¹ Olofson, R. A.; Landesberg, J. M.; Houk, K. N. Journal of the American Chemical Society, Vol. 88, Issue 18 https://doi.org/10.1021/ja00970a032	journal	September 1966
On the Mechanism of Thiamine Action. IV. ¹ Evidence from Studies on Model Systems Breslow, Ronald Journal of the American Chemical Society, Vol. 80, Issue 14 https://doi.org/10.1021/ja01547a064	journal	July 1958
Structure-activity relationships of a series of 2-amino-4-thiazole-containing renin inhibitors Patt, William C.; Hamilton, Harriet W.; Taylor, Michael D. Journal of Medicinal Chemistry, Vol. 35, Issue 14 https://doi.org/10.1021/jm00092a006	journal	July 1992
N-(4-Substituted-thiazolyl)oxamic acid derivatives, new series of potent, orally active antiallergy agents Hargrave, Karl D.; Hess, Friedrich K.; Oliver, James T. Journal of Medicinal Chemistry, Vol. 26, Issue 8 https://doi.org/10.1021/jm00362a014	journal	August 1983
Dehalogenation of 5-Halouracils after Low Energy Electron Attachment: A Density Functional Theory Investigation Li, Xifeng; Sanche, Léon; Sevilla, Michael D. The Journal of Physical Chemistry A, Vol. 106, Issue 46 https://doi.org/10.1021/jp021669q	journal	October 2002
Theory and Application of Dissociative Electron Capture in Molecular Identification Havey, Crystal D.; Eberhart, Mark; Jones, Travis The Journal of Physical Chemistry A, Vol. 110, Issue 13 https://doi.org/10.1021/jp056166+	journal	March 2006
Electron-Induced Elimination of the Bromide Anion from Brominated Nucleobases. A Computational Study Chomicz, Lidia; Rak, Janusz; Storoniak, Piotr The Journal of Physical Chemistry B, Vol. 116, Issue 19 https://doi.org/10.1021/jp3008738	journal	May 2012
Fundamental Mechanisms of DNA Radiosensitization: Damage Induced by Low-Energy Electrons in Brominated Oligonucleotide Trimers Park, Yeunsoo; Polska, Katarzyna; Rak, Janusz The Journal of Physical Chemistry B, Vol. 116, Issue 32 https://doi.org/10.1021/jp304964r	journal	August 2012
Anion Photoelectron Spectroscopy of C₃N⁻ and C₅N⁻ Yen, Terry A.; Garand, Etienne; Shreve, Alexander T. The Journal of Physical Chemistry A, Vol. 114, Issue 9 https://doi.org/10.1021/jp9093996	journal	December 2009
Effect of Nitric Oxide on the Radio-sensitivity of Tumour Cells Gray, L. H.; Green, F. O.; Hawes, C. A. Nature, Vol. 182, Issue 4640 https://doi.org/10.1038/182952a0	journal	October 1958
Exploiting tumour hypoxia in cancer treatment Brown, J. Martin; Wilson, William R. Nature Reviews Cancer, Vol. 4, Issue 6 https://doi.org/10.1038/nrc1367	journal	June 2004
Low-energy electrons transform the nimorazole molecule into a radiosensitiser Meißner, Rebecca; Kočišek, Jaroslav; Feketeová, Linda Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-10340-8	journal	June 2019
Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections Chai, Jeng-Da; Head-Gordon, Martin Physical Chemistry Chemical Physics, Vol. 10, Issue 44 https://doi.org/10.1039/b810189b	journal	January 2008
Stripping off hydrogens in imidazole triggered by the attachment of a single electron Ribar, A.; Fink, K.; Li, Z. Physical Chemistry Chemical Physics, Vol. 19, Issue 9 https://doi.org/10.1039/c6cp08773f	journal	January 2017
Imidazoles as potential anticancer agents Ali, Imran; Lone, Mohammad Nadeem; Aboul-Enein, Haasan Y. Med. Chem. Commun., Vol. 8, Issue 9 https://doi.org/10.1039/c7md00067g	journal	January 2017
Dissociative electron attachment induced ring opening in five-membered heterocyclic compounds Li, Zhou; Carmichael, Ian; Ptasińska, Sylwia Physical Chemistry Chemical Physics, Vol. 20, Issue 27 https://doi.org/10.1039/c8cp02718h	journal	January 2018
Electron attachment to microhydrated 4-nitro- and 4-bromo-thiophenol Sala, Leo; Sedmidubská, Barbora; Vinklárek, Ivo Physical Chemistry Chemical Physics, Vol. 23, Issue 33 https://doi.org/10.1039/d1cp02019f	journal	January 2021
Decomposition of triazole and 3-nitrotriazole upon low-energy electron attachment Saqib, Muhammad; Izadi, Farhad; Isierhienrhien, Leon U. Physical Chemistry Chemical Physics, Vol. 25, Issue 20 https://doi.org/10.1039/d3cp01162c	journal	January 2023
Fragmentation of 5-fluorouridine induced by low energy (< 12 eV) electrons: insights into the radiosensitization of DNA Wierzbicka, Paulina; Abdoul-Carime, Hassan; Kopyra, Janina Physical Chemistry Chemical Physics, Vol. 26, Issue 11 https://doi.org/10.1039/d3cp04745h	journal	January 2024
Interaction of low-energy electrons with radiosensitizers Sedmidubská, Barbora; Kočišek, Jaroslav Physical Chemistry Chemical Physics, Vol. 26, Issue 12 https://doi.org/10.1039/d3cp06003a	journal	January 2024
Dissociative electron attachment to gas-phase 5-bromouracil Abdoul-Carime, H.; Huels, M. A.; Brüning, F. The Journal of Chemical Physics, Vol. 113, Issue 7 https://doi.org/10.1063/1.1306654	journal	August 2000
Total Cross Sections for Ionization and Attachment in Gases by Electron Impact. II. Negative‐Ion Formation Rapp, Donald; Briglia, Donald D. The Journal of Chemical Physics, Vol. 43, Issue 5 https://doi.org/10.1063/1.1696958	journal	September 1965
Dissociative electron attachment to furan, tetrahydrofuran, and fructose Sulzer, Philipp; Ptasinska, Sylwia; Zappa, Fabio The Journal of Chemical Physics, Vol. 125, Issue 4 https://doi.org/10.1063/1.2222370	journal	July 2006
Photoelectron spectroscopy of CN ⁻ , NCO ⁻ , and NCS ⁻ Bradforth, Stephen E.; Kim, Eun Ha; Arnold, Don W. The Journal of Chemical Physics, Vol. 98, Issue 2 https://doi.org/10.1063/1.464244	journal	January 1993
Low-energy electron-induced dissociation in gas-phase nicotine, pyridine, and methyl-pyrrolidine Ryszka, Michal; Alizadeh, Elahe; Li, Zhou The Journal of Chemical Physics, Vol. 147, Issue 9 https://doi.org/10.1063/1.4994679	journal	September 2017
How does methylation suppress the electron-induced decomposition of 1-methyl-nitroimidazoles? Kossoski, F.; Varella, M. T. do N. The Journal of Chemical Physics, Vol. 147, Issue 16 https://doi.org/10.1063/1.5005604	journal	October 2017
Low-energy electron-induced decomposition of 5-trifluoromethanesulfonyl-uracil: A potential radiosensitizer Ameixa, J.; Arthur-Baidoo, E.; Meißner, R. The Journal of Chemical Physics, Vol. 149, Issue 16 https://doi.org/10.1063/1.5050594	journal	October 2018
4-Bromobiphenyl: Long-lived molecular anion formation and competition between electron detachment and dissociation Asfandiarov, N. L.; Pshenichnyuk, S. A.; Rakhmeyev, R. G. The Journal of Chemical Physics, Vol. 150, Issue 11 https://doi.org/10.1063/1.5082611	journal	March 2019
Electron attachment to fluorodeoxyglucose: Dissociation dynamics in a molecule of near-zero electron affinity Arthur-Baidoo, Eugene; Ončák, Milan; Denifl, Stephan The Journal of Chemical Physics, Vol. 157, Issue 7 https://doi.org/10.1063/5.0101726	journal	August 2022
Rotational Spectra of the Nitrogen‐Sulfur Carbon Chains NC _n S, n = 1–7 McCarthy, M. C.; Cooksy, A. L.; Mohamed, S. The Astrophysical Journal Supplement Series, Vol. 144, Issue 2 https://doi.org/10.1086/344727	journal	February 2003
Dissociative electron attachment to carbon dioxide via the 8.2 eV Feshbach resonance Slaughter, D. S.; Adaniya, H.; Rescigno, T. N. Journal of Physics B: Atomic, Molecular and Optical Physics, Vol. 44, Issue 20 https://doi.org/10.1088/0953-4075/44/20/205203	journal	September 2011
Dissociative electron attachment studies of gas-phase acetic acid using a velocity map imaging technique Chakraborty, Dipayan; Kharchilava, Giorgi; Carmichael, Ian Journal of Physics B: Atomic, Molecular and Optical Physics, Vol. 56, Issue 24 https://doi.org/10.1088/1361-6455/ad1745	journal	December 2023
Dissociative electron attachment to HCCCN Graupner, K.; Merrigan, T. L.; Field, T. A. New Journal of Physics, Vol. 8, Issue 7 https://doi.org/10.1088/1367-2630/8/7/117	journal	July 2006
Vanadium-mediated chemoprotection against chemical hepatocarcinogenesis in rats: haematological and histological characteristics Bishayee, A.; Karmakar, R.; Mandal, A. European Journal of Cancer Prevention, Vol. 6, Issue 1 https://doi.org/10.1097/00008469-199702000-00010	journal	February 1997
Dynamics of resonant low-energy electron attachment to ethanol-producing hydroxide anions Chakraborty, Dipayan; Slaughter, Daniel S.; Ptasinska, Sylwia Physical Review A, Vol. 108, Issue 5 https://doi.org/10.1103/physreva.108.052806	journal	November 2023
High-resolution determination of the electron affinity of fluorine and bromine using crossed ion and laser beams Blondel, C.; Cacciani, P.; Delsart, C. Physical Review A, Vol. 40, Issue 7 https://doi.org/10.1103/physreva.40.3698	journal	October 1989
Threshold photodetachment of H − Lykke, K. R.; Murray, K. K.; Lineberger, W. C. Physical Review A, Vol. 43, Issue 11 https://doi.org/10.1103/physreva.43.6104	journal	June 1991
Photosensitivity and heat resistance conferred by brdu incorporation upon a thymidine kinase-deficient mouse cell line with persistent mitochondrial enzyme activity Attardi, G.; Keeley, Benneta; Tu, Catherina Journal of Cell Science, Vol. 19, Issue 1 https://doi.org/10.1242/jcs.19.1.55	journal	October 1975
Thiazoles and Thiazolidinones as Antioxidants Geronikaki, A. A.; Pitta, E. P.; Liaras, K. S. Current Medicinal Chemistry, Vol. 20, Issue 36 https://doi.org/10.2174/09298673113209990143	journal	November 2013
Synthesis, Antibacterial Activity, Interaction with Nucleobase and Molecular Docking Studies of 4-Formylbenzoic Acid Based Thiazoles Z. Laczkowski, Krzysztof; Biernasiuk, Anna; Baranowska-Laczkowska, Angelika Medicinal Chemistry, Vol. 12, Issue 6 https://doi.org/10.2174/1573406412666160201121310	journal	July 2016
Anti-inflammatory, Analgesic and Anti-ulcerogenic Activities of Novel bis-thiadiazoles, bis-thiazoles and bis-formazanes A. Muhammad, Zeinab; S. Masaret, Ghada; M. Amin, Mohamed Medicinal Chemistry, Vol. 13, Issue 3 https://doi.org/10.2174/1573406412666160920091146	journal	April 2017
Evaluation of 2-Amino-5-Nitrothiazole as a Hypoxic Cell Radiosensitizer Rockwell, Sara; Mroczkowski, Zofia; Rupp, W. Dean Radiation Research, Vol. 90, Issue 3 https://doi.org/10.2307/3575735	journal	June 1982
Reaction of Electrons with DNA: Radiation Damage to Radiosensitization Kumar, Anil; Becker, David; Adhikary, Amitava International Journal of Molecular Sciences, Vol. 20, Issue 16 https://doi.org/10.3390/ijms20163998	journal	August 2019
Evaluating the Genotoxic and Cytotoxic Effects of Thymidine Analogs, 5-Ethynyl-2′-Deoxyuridine and 5-Bromo-2′-Deoxyurdine to Mammalian Cells Haskins, Jeremy S.; Su, Cathy; Maeda, Junko International Journal of Molecular Sciences, Vol. 21, Issue 18 https://doi.org/10.3390/ijms21186631	journal	September 2020
Electron Attachment Studies with the Potential Radiosensitizer 2-Nitrofuran Saqib, Muhammad; Arthur-Baidoo, Eugene; Ončák, Milan International Journal of Molecular Sciences, Vol. 21, Issue 23 https://doi.org/10.3390/ijms21238906	journal	November 2020
Electron Attachment to 5-Fluorouracil: The Role of Hydrogen Fluoride in Dissociation Chemistry Arthur-Baidoo, Eugene; Schöpfer, Gabriel; Ončák, Milan International Journal of Molecular Sciences, Vol. 23, Issue 15 https://doi.org/10.3390/ijms23158325	journal	July 2022
2021 Census of Interstellar, Circumstellar, Extragalactic, Protoplanetary Disk, and Exoplanetary Molecules McGuire, Brett A. The Astrophysical Journal Supplement Series, Vol. 259, Issue 2 https://doi.org/10.3847/1538-4365/ac2a48	journal	March 2022
Comparison of the bromodeoxyuridine-mediated sensitization effects between low-LET and high-LET ionizing radiation on DNA double-strand breaks Fujii, Yoshihiro; Genet, Matthew D.; Roybal, Erica J. Oncology Reports, Vol. 29, Issue 6 https://doi.org/10.3892/or.2013.2354	journal	March 2013
Synthesis and pharmacological evaluation of azetidin-2-ones and thiazolidin-4-ones encompassing benzothiazole Gopal, M.; Padmashali, B.; Manohara, Yn Indian Journal of Pharmaceutical Sciences, Vol. 70, Issue 5 https://doi.org/10.4103/0250-474x.45393	journal	January 2008

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