Home Aggregation behavior and thermodynamic parameters of biosurfactants (NaC/NaDC) in aqueous medium of Emtricitabine and Lamivudine (anti-HIV drugs)
Article
Licensed
Unlicensed Requires Authentication

Aggregation behavior and thermodynamic parameters of biosurfactants (NaC/NaDC) in aqueous medium of Emtricitabine and Lamivudine (anti-HIV drugs)

  • Richa Sharma

    Ms. Richa Sharma is an Assistant Professor of Chemistry at Government Degree College Una (H.P.), India and she is currently working towards her doctorate at the Department of Chemistry, Career Point University in Hamirpur, Himachal Pradesh, India. With a decade of teaching expertise and two years dedicated to research, she brings a wealth of experience to her academic pursuits.

    , Suvarcha Chauhan

    Dr. Suvarcha Chauhan, a distinguished former Professor of Chemistry at the Department of Chemistry, HPU Shimla (H.P.), India has over 25 years of extensive experience in the field. Her remarkable contributions to the scientific community encompass a prolific publication record of more than 165 research articles in journals international and national repute. Dr. Chauhan’s research interests traverse nanostructured materials, photocatalysis, sensing applications, and surfactant behavior, garnering widespread recognition with an h-index exceeding 24 and an i10-index of 63. Dr. Chauhan’s impact extends to successful completion of four research projects and the supervision of more than 21 M.Phil and 12 Ph.D. students, reflecting her dedication to mentoring the next generation of scientists.

    , Naveen Thakur

    Dr. Naveen Thakur is a Professor of Physics at Career Point University, Hamirpur (H.P.), India. He has more than 16 years of teaching and research experience. His research focuses on the electromagnetic waves and nanomaterials. He has published more than 40 research papers in peer reviewed Scopus/WOS indexed journals, including Journal of Environmental Chemical Engineering, and Dalton Transactions. He is Reviewer and Associate Editor of many Journals of National and International repute.

    and Kuldeep Kumar

    Dr. Kuldeep Kumar is an Associate Professor of Chemistry at Career Point University, Hamirpur (H.P.), India. His research focuses on the biophysical chemistry and nanotechnology, and he has published more than 40 research articles in Scopus/WOS indexed journals in the fields, including Journal of Molecular Liquids, Journal of Environmental Chemical Engineering, and Dalton Transactions. He is reviewer of many National and International Journals, and Review Editor for the Frontiers’ Journal, Nanotechnology for Energy applications. Dr. Kumar’s impact extends to successful supervision of 1 M.Phil and 2 Ph.D. students, reflecting his dedication to mentoring the next generation of scientists.

    EMAIL logo
Published/Copyright: January 30, 2024
Become an author with De Gruyter Brill

Abstract

This paper investigates the interactions and aggregation behavior of biosurfactants, sodium cholate (NaC) and sodium deoxycholate (NaDC) in aqueous solutions of Emtricitabine and Lamivudine (anti-HIV drugs). The study uses conductometry and UV–visible spectroscopy techniques to evaluate the critical micelle concentration (CMC) at different temperatures ranging from 298.15 K to 313.15 K with a variation of 5 K. The temperature dependence of the CMC was examined, and the stability of micelles was analyzed in light of the hydrophobic-hydrophilic interactions involved in this system. The CMC obtained from both the methods are in agreement. Various thermodynamic parameters, such as H m 0 , S m 0 and G m 0 have been estimated using a “pseudo-phase separation model” to understand the contribution of the chemical and de-solvation part in the micellization process. Furthermore, the enthalpy-entropy compensation plots validate the micellar stability of the studied systems.


Corresponding author: Kuldeep Kumar, Department of Chemistry, Career Point University, Hamirpur, HP 176041, India, E-mail:

About the authors

Richa Sharma

Ms. Richa Sharma is an Assistant Professor of Chemistry at Government Degree College Una (H.P.), India and she is currently working towards her doctorate at the Department of Chemistry, Career Point University in Hamirpur, Himachal Pradesh, India. With a decade of teaching expertise and two years dedicated to research, she brings a wealth of experience to her academic pursuits.

Suvarcha Chauhan

Dr. Suvarcha Chauhan, a distinguished former Professor of Chemistry at the Department of Chemistry, HPU Shimla (H.P.), India has over 25 years of extensive experience in the field. Her remarkable contributions to the scientific community encompass a prolific publication record of more than 165 research articles in journals international and national repute. Dr. Chauhan’s research interests traverse nanostructured materials, photocatalysis, sensing applications, and surfactant behavior, garnering widespread recognition with an h-index exceeding 24 and an i10-index of 63. Dr. Chauhan’s impact extends to successful completion of four research projects and the supervision of more than 21 M.Phil and 12 Ph.D. students, reflecting her dedication to mentoring the next generation of scientists.

Naveen Thakur

Dr. Naveen Thakur is a Professor of Physics at Career Point University, Hamirpur (H.P.), India. He has more than 16 years of teaching and research experience. His research focuses on the electromagnetic waves and nanomaterials. He has published more than 40 research papers in peer reviewed Scopus/WOS indexed journals, including Journal of Environmental Chemical Engineering, and Dalton Transactions. He is Reviewer and Associate Editor of many Journals of National and International repute.

Kuldeep Kumar

Dr. Kuldeep Kumar is an Associate Professor of Chemistry at Career Point University, Hamirpur (H.P.), India. His research focuses on the biophysical chemistry and nanotechnology, and he has published more than 40 research articles in Scopus/WOS indexed journals in the fields, including Journal of Molecular Liquids, Journal of Environmental Chemical Engineering, and Dalton Transactions. He is reviewer of many National and International Journals, and Review Editor for the Frontiers’ Journal, Nanotechnology for Energy applications. Dr. Kumar’s impact extends to successful supervision of 1 M.Phil and 2 Ph.D. students, reflecting his dedication to mentoring the next generation of scientists.

Acknowledgments

Authors would like to thank the Department of Chemistry, Career Point University, Hamirpur (H.P.), India and the Department of Chemistry, Himachal Pradesh University, Shimla (H.P.), India, for providing required research facilities to carry out this work.

  1. Research ethics: Not applicable.

  2. Author contributions: The authors have accepted responsibility for the entire content of this manuscript and approved its submission. Richa Sharma: Methodology, investigation, data curation, writing: original draft preparation. Suvarcha Chauhan: Writing: reviewing and editing. Naveen Thakur: Reviewing and editing. Kuldeep Kumar: Conceptualization, supervision, writing: reviewing and editing.

  3. Competing interests: The authors state no conflict of interest.

  4. Research funding: None declared.

  5. Data availability: Not applicable.

References

1. Azum, N., Rub, M. A., Asiri, A. M. Aggregation Behavior of Antipsychotic Drug Under the Influence of Bile Salt in Aqueous/Urea Solution. J. Oleo Sci. 2020, 69, 327–335; https://doi.org/10.5650/jos.ess19256.Search in Google Scholar PubMed

2. Holm, R., Mullertz, A., Mu, H. Bile Salts and Their Importance for Drug Absorption. Int. J. Pharm. 2013, 453, 44–55; https://doi.org/10.1016/j.ijpharm.2013.04.003.Search in Google Scholar PubMed

3. Azum, N., Rub, M. A., Asiri, A. M. Association Behavior of Bile Salts Binary Mixtures in an Aqueous System: A Tensiometric and Fluorometric Study. J. Phys. Org. Chem. 2020, 33, e4015; https://doi.org/10.1002/poc.4015.Search in Google Scholar

4. Din, K. U., Rub, M. A., Naqvi, A. Z. Aqueous Amphiphilic Drug (Amitriptyline Hydrochloride)–Bile Salt Mixtures at Different Temperatures. Colloids Surf. B Biointerfaces 2011, 84, 285–291; https://doi.org/10.1016/j.colsurfb.2011.01.008.Search in Google Scholar PubMed

5. Valderrama, J. M., Wilde, P., Macierzanka, A., Mackie, A. The Role of Bile Salts in Digestion. Adv. Colloid Interfaces Sci. 2011, 165, 36–46; https://doi.org/10.1016/j.cis.2010.12.002.Search in Google Scholar PubMed

6. Das, S., Dey, J., Mukhim, T., Ismail, K. Effect of Sodium Salicylate, Sodium Oxalate, and Sodium Chloride on the Micellization and Adsorption of Sodium Deoxycholate in Aqueous Solutions. J. Colloid Interface Sci. 2011, 357, 434–439; https://doi.org/10.1016/j.jcis.2011.02.020.Search in Google Scholar PubMed

7. Maestre, A., Guardado, P., Moya, M. L. Thermodynamic Study of Bile Salts Micellization. J. Chem. Eng. Data 2014, 59, 433–438; https://doi.org/10.1021/je400903n.Search in Google Scholar

8. Chauhan, S., Sharma, V., Singh, K., Chauhan, M. S., Singh, K. Influence of Lactose on the Micellar Behaviour and Surface Activity of Bile Salts as Revealed Through Fluorescence and Surface Tension Studies at Varying Temperatures. J. Mol. Liq. 2016, 222, 67–76; https://doi.org/10.1016/j.molliq.2016.07.020.Search in Google Scholar

9. Chavda, S., Danino, D., Aswal, V. K., Singh, K., Marangoni, D. G., Bahadur, P. Microstructure and Transitions in Mixed Micelles of Cetyltrimethylammonium Tosylate and Bile Salts. Colloids Surf. A Physicochem. Eng. Asp. 2017, 513, 223–233; https://doi.org/10.1016/j.colsurfa.2016.10.047.Search in Google Scholar

10. Small, D. M. Size and Structure of Bile Salt Micelles: Influence of Structure, Concentration, Counterion Concentration, pH, and Temperature. Adv. Chem. 1968, 84, 31–52; https://doi.org/10.1021/ba-1968-0084.ch004.Search in Google Scholar

11. Rub, M. A., Sheikh, M. S., Asiri, A. M., Azum, N., Khan, A., Khan, A. A. P., Khan, S. B., Din, K. U. Aggregation Behaviour of Amphiphilic Drug and Bile Salt Mixtures at Different Compositions and Temperatures. J. Chem. Thermodyn. 2013, 64, 28–39; https://doi.org/10.1016/j.jct.2013.04.020.Search in Google Scholar

12. Madenci, D., Egelhaaf, S. U. Self-Assembly in Aqueous Bile Salt Solutions. Curr. Opin. Colloid Interface Sci. 2010, 15, 109–115; https://doi.org/10.1016/j.cocis.2009.11.010.Search in Google Scholar

13. Chauhan, S., Singh, K. Volumetric, Compressibility, Viscometric, and 1H NMR Analysis on Drug-Bile Salts Interactions in Aqueous Medium: Temperature and Concentration Effect. J. Chem. Eng. Data 2019, 64, 69–82; https://doi.org/10.1021/acs.jced.8b00509.Search in Google Scholar

14. Faustino, C. M. C., Serafim, C. S., Ferreira, I. N., Branco, M. A., Calado, A. R. T., Rio, L. G. Mixed Micelle Formation Between an Amino Acid-Based Anionic Gemini Surfactant and Bile Salts. Ind. Eng. Chem. Res. 2014, 53, 10112–10118; https://doi.org/10.1021/ie5003735.Search in Google Scholar

15. Vashishat, R., Sanan, R., Mahajan, R. K. Bile Salt-Surface Active Ionic Liquid Mixtures; Mixed Micellization and Solubilization of Phenothiazine. RSC Adv. 2015, 5, 72132–72141; https://doi.org/10.1039/C5RA09812B.Search in Google Scholar

16. Yadav, T., Tikariha, D., Sinha, S., Ghosh, K. K. Biophysical Studies on the Interactions Between Antidepressant Drugs and Bile Salts. J. Mol. Liq. 2017, 233, 23–28; https://doi.org/10.1016/j.molliq.2017.02.102.Search in Google Scholar

17. Diaz, A. N., Sanchez, F. G., Pareja, A. G. Cholic Acid Behavior in Water and Organic Solvent: Study of Normal and Inverted Aggregates. Colloids Surf. A Physicochem. Eng. Asp. 1998, 142, 27–34; https://doi.org/10.1016/S0927-7757(98)00370-7.Search in Google Scholar

18. Skorka, M., Asztemborska, M. Micellization of Bile Salts in a Formamide Solution: A Gas Liquid Chromatography Study. Colloids Surf. A Physicochem. Eng. Asp. 2009, 332, 1–8; https://doi.org/10.1016/j.colsurfa.2008.08.018.Search in Google Scholar

19. Guveli, D. E. The Association of Sodium Cholate and Sodium Deoxycholate in Solutions of Aromatic Alcohols. Colloids Surf. 1989, 39, 349–360; https://doi.org/10.1016/0166-6622(89)80285-9.Search in Google Scholar

20. Kumar, K., Chauhan, S. Surface Tension and UV–Visible Investigations of Aggregation and Adsorption Behavior of NaC and NaDC in Water–Amino Acid Mixtures. Fluid Phase Equilib. 2015, 394, 165–174; https://doi.org/10.1016/j.fluid.2015.03.012.Search in Google Scholar

21. Azum, N., Rub, M. A., Asiri, A. M. Bile Salt–Bile Salt Interaction in Mixed Monolayer and Mixed Micelle Formation. J. Chem. Thermodyn. 2019, 128, 406–414; https://doi.org/10.1016/j.jct.2018.08.030.Search in Google Scholar

22. Mahajan, S., Mahajan, R. K. Interactions of Phenothiazine Drugs with Bile Salts: Micellization and Binding Studies. J. Colloid Interface Sci. 2012, 387, 194–204; https://doi.org/10.1016/j.jcis.2012.07.085.Search in Google Scholar PubMed

23. Mukherjee, B., Dar, A. A., Bhat, P. A., Moulik, S. P., Das, A. R. Micellization and Adsorption Behaviour of Bile Salt Systems. RSC Adv. 2016, 6, 1769; https://doi.org/10.1039/c5ra20909a.Search in Google Scholar

24. Pigliacelli, C., Belton, P., Wilde, P., Qi, S. Probing the Molecular Interactions Between Pharmaceutical Polymeric Carriers and Bile Salts in Simulated Gastrointestinal Fluids Using NMR Spectroscopy. J. Colloid Interface Sci. 2019, 551, 147–154; https://doi.org/10.1016/j.jcis.2019.05.002.Search in Google Scholar PubMed

25. Banipal, P. K., Sohal, P., Banipal, T. S. Physicochemical and Spectral Evaluation of Theinteractional Behavior of Nicotinic Acid (vitaminB3) with Mixed [Sodium Deoxycholate (Bile Salt) + Cetyltrimethylammonium Bromide] Surfactants. J. Dispersion Sci. Technol. 2021, 42, 373–385; https://doi.org/10.1080/01932691.2019.1699426.Search in Google Scholar

26. Bechnak, L., Patra, D. Salt and Bile Salt Accelerate Self-Assembly Behavior of Poly (Ethylene Oxide)-Block-Poly (Propylene Oxide)-Block-Poly (Ethylene Oxide) Probed by Curcumin Fluorescence. Colloids Surf. A 2019, 583, 123955; https://doi.org/10.1016/j.colsurfa.2019.123955.Search in Google Scholar

27. Clulowa, A. J., Barbera, B., Salima, M., Ryanb, T., Boyda, B. J. Synergistic and Antagonistic Effects of Non-Ionic Surfactants with Bile Salt + Phospholipid Mixed Micelles on the Solubility of Poorly Water-Soluble Drugs. Int. J. Pharm. 2020, 588, 119762; https://doi.org/10.1016/j.ijpharm.2020.119762.Search in Google Scholar PubMed

28. Posa, M., Cirin, D., Krstonosic, V. Physico-Chemical Properties of Bile Salt-Tween 80 Mixed Micelles in the Viewpoint of Regular Solution Theory. Chem. Eng. Sci. 2013, 98, 195–202; https://doi.org/10.1016/j.ces.2013.05.042.Search in Google Scholar

29. Behera, S. K., Mishra, S., Mohapatra, M. Physicochemical Study of Dietary Fiber Methyl Cellulose and Human Intestinal Bile Salt Micellar Aggregates. Colloid Interface Sci. Commun. 2021, 44, 100493; https://doi.org/10.1016/j.colcom.2021.100493.Search in Google Scholar

30. Chauhan, S., Sharma, V., Pathania, L. Probing Effect of Maltodextrin on Micellar Properties of Bile Salts at Varying Temperatures: A Physico-Chemical Approach. J. Mol. Liq. 2018, 269, 304–314; https://doi.org/10.1016/j.molliq.2018.08.022.Search in Google Scholar

31. Patel, V., Ray, D., Bahadur, A., Ma, J., Aswal, V. K., Bahadur, P. Pluronic®-Bile Salt Mixed Micelles. Colloids Surf. B Biointerfaces 2018, 166, 119–126; https://doi.org/10.1016/j.colsurfb.2018.03.001.Search in Google Scholar PubMed

32. Rub, M. A., Sheikh, M. S., Khan, F., Khan, S. B., Asiri, A. M. Bile Salts Aggregation Behavior at Various Temperatures Under the Influence of Amphiphilic Drug Imipramine Hydrochloride in Aqueous Medium. Z. Phys. Chem. 2014, 228, 747–767; https://doi.org/10.1515/zpch-2013-0495.Search in Google Scholar

33. Singh, S., Sar, S. K., Ray, T. Aggregation Behaviour of Sodium Cholate and Sodium Deoxycholate Under the Influence of Drug (Disprine) in Aqueous Solution at Various Temperatures. Sci. Res. 2016, 4, 112–119; https://doi.org/10.11648/j.sr.20160405.12.Search in Google Scholar

34. Singh, K., Chauhan, S. Study on Aggregation Properties and Interactive Nature of Bile Salts in the Presence of Drugs: A Comparative Approach. Ind. Chem. Eng. 2022, 64, 57–67; https://doi.org/10.1080/00194506.2020.1820911.Search in Google Scholar

35. Mehellou, Y., Clercq, E. D. Twenty-Six Years of Anti-HIV Drug Discovery: Where Do We Stand and Where Do We Go? J. Med. Chem. 2010, 53, 521–538; https://doi.org/10.1021/jm900492g.Search in Google Scholar PubMed

36. Zhan, P., Pannecouque, C., Clercq, E. D., Liu, X. Anti-HIV Drug Discovery and Development: Current Innovations and Future Trends. J. Med. Chem., 2016, 59, 2849−2878; https://doi.org/10.1021/acs.jmedchem.5b00497.Search in Google Scholar PubMed

37. Devunuri, N., Amminabavi, N., Chennuri, B. K., Losetty, V., Gardas, R. L. The Structural Effect on Volumetric and Acoustic Properties of Aqueous Anti-HIV Drugs (Emtricitabine and Lamivudine) at Various Temperatures. J. Mol. Liq. 2016, 214, 214–219; https://doi.org/10.1016/j.molliq.2015.12.084.Search in Google Scholar

38. Shakeel, F., Haq, N., Alsarra, I., Alshehri, S. Solubility Data, Solubility Parameters and Thermodynamic Behavior of an Antiviral Drug Emtricitabine in Different Pure Solvents: Molecular Understanding of Solubility and Dissolution. Molecules 2021, 26, 746; https://doi.org/10.3390/molecules26030746.Search in Google Scholar PubMed PubMed Central

39. Sharma, S., Kumar, K., Chauhan, S., Chauhan, M. S. Conductometric and Spectrophotometric Studies of Self-Aggregation Behavior of Streptomycin Sulphate in Aqueous Solution: Effect of Electrolytes. J. Mol. Liq. 2020, 297, 111782; https://doi.org/10.1016/j.molliq.2019.111782.Search in Google Scholar

40. Singh, K., Chauhan, S. Temperature Dependent Micellar Behaviour of Sodium Cholate and Sodium Deoxycholate in the Presence of Ceftriaxone Sodium: A Physicochemical Study. J. Mol. Liq. 2020, 316, 113833; https://doi.org/10.1016/j.molliq.2020.113833.Search in Google Scholar

41. Sharma, S., Kumar, K., Chauhan, S. Micellization Properties of Antihistaminic Drug Diphenhydramine.HCl in Aqueous Electrolytic Solution: Conductometric and Spectroscopic Studies. J. Mol. Liq. 2020, 300, 112306; https://doi.org/10.1016/j.molliq.2019.112306.Search in Google Scholar

42. Chauhan, S., Sharma, K. Effect of Temperature and Additives on the Critical Micelle Concentration and Thermodynamics of Micelle Formation of Sodium Dodecyl Benzene Sulfonate and Dodecyltrimethylammonium Bromide in Aqueous Solution: A Conductometric Study. J. Chem. Thermodyn. 2014, 71, 205–211; https://doi.org/10.1016/j.jct.2013.12.019.Search in Google Scholar

43. Hoque, M. A., Mahbub, S., Hossain, M. D., Khan, M. A., Khan, J. M., Malik, A., Ahmed, A., Ahmede, M. Z. Influence of NaCl and Temperature on the Interaction Between Cephradine Monohydrate and Surfactants: Conductivity and UV–Visible Measurements. J. Mol. Liq. 2021, 328, 115418; https://doi.org/10.1016/j.molliq.2021.115418.Search in Google Scholar

44. Chauhan, S., Singh, K., Sundaresan, C. N. Physico-Chemical Characterization of Drug-Bio-Surfactant Micellar System: A Road for Developing Better Pharmaceutical Formulations. J. Mol. Liq. 2018, 266, 692–702; https://doi.org/10.1016/j.molliq.2018.07.008.Search in Google Scholar

45. Kumar, K., Patial, B. S., Chauhan, S. Conductivity and Fluorescence Studies on the Micellization Properties of Sodium Cholate and Sodium Deoxycholate in Aqueous Medium at Different Temperatures: Effect of Selected Amino Acids. J. Chem. Thermodyn. 2015, 82, 25–33; https://doi.org/10.1016/j.jct.2014.10.014.Search in Google Scholar

46. Subuddhi, U., Mishra, A. K. Micellization of Bile Salts in Aqueous Medium: A Fluorescence Study. Colloids Surf. B Biointerfaces 2007, 57, 102–107; https://doi.org/10.1016/j.colsurfb.2007.01.009.Search in Google Scholar PubMed

47. Chauhan, S., Chaudhary, P., Sharma, V. Aggregation and Adsorption Behavior of Cationic Surfactants (Cetyltrimethylammonium Bromide and Dodecyltrimethylammonium Bromide) in Aqueous Solutions of Antibiotic Drug (Amikacin Sulphate) at Different Temperatures. J. Surfactants Deterg. 2021, 24, 159–171; https://doi.org/10.1002/jsde.12462.Search in Google Scholar

48. Tanhaei, B., Saghatoleslami, N., Chenar, M. P., Ayati, A., Hesampour, M., Manttari, M. Experimental Study of CMC Evaluation in Single and Mixed Surfactant Systems, Using the UV–Vis Spectroscopic Method. J. Surfactants Deterg. 2013, 16, 357–362; https://doi.org/10.1007/s11743-012-1403-7.Search in Google Scholar

49. Chauhan, S., Negi, K. Insight of Molecular Interactions Between Short-Chain Tetraalkylammonium Bromides and Cetyltrimethylammonium Bromide: A Spectroscopic and Thermodynamic Approach. J. Surfactants Deterg. 2023, 26, 505–515; https://doi.org/10.1002/jsde.12682.Search in Google Scholar

50. Aguiar, J., Carpena, P., Molina-Bolívar, J. A., Carnero Ruiz, C. On the Determination of the Critical Micelle Concentration by the Pyrene 1:3 Ratio Method. J. Colloid Interface Sci. 2003, 258, 116–122; https://doi.org/10.1016/S0021-9797(02)00082-6.Search in Google Scholar

51. Chauhan, S., Kumari, S., Singh, K. Conductometric and Fluorescence Probe Analysis on Molecular Interactions Between Cationic Surfactants in Aqueous Medium of Glycyl Dipeptide: Concentration and Temperature Effect. J. Chem. Thermodyn. 2017, 105, 337–344; https://doi.org/10.1016/j.jct.2016.10.045.Search in Google Scholar

52. Chauhan, S., Kumar, A., Kaur, M., Chauhan, M. S. Physico-Chemical and Spectroscopic Approach to Analyse the Behaviour of Surface-Active Ionic Liquid and Conventional Surfactant in Aqueous Glycine. J. Surfactants Deterg. 2017, 20, 1129–1139; https://doi.org/10.1007/s11743-017-1993-1.Search in Google Scholar

53. Lumry, R., Rajender, S. Enthalpy-Entropy Compensation Phenomena in Water Solutions of Proteins and Small Molecules: A Ubiquitous Property of Water. Biopolymers 1970, 9, 1125–1227; https://doi.org/10.1002/bip.1970.360091002.Search in Google Scholar PubMed


Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/tsd-2023-2564).


Received: 2023-10-22
Accepted: 2024-01-09
Published Online: 2024-01-30
Published in Print: 2024-03-25

© 2024 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 29.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/tsd-2023-2564/html
Scroll to top button