![Creative Commons License](http://i.creativecommons.org/l/by/4.0/88x31.png)
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Quinoline-Based New Chiral Derivatizing Reagents and its use in the Derivatization and Enantioseparation of Few Structurally Similar β-Blockers using Liquid Chromatography and Structural Optimization using DFT
Corresponding Author(s) : S. Sehlangia
Asian Journal of Chemistry,
Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023
Abstract
In this work, quinoline based new chiral derivatizing reagent was synthesized by introducing chiral amino acid (L-proline) in the molecule. Synthesized chiral derivatizing reagent was characterized by spectroscopic techniques (1H NMR, FT-IR, HRMS and CHNS analysis) and used in the synthesis of diastereomer of chosen β-blockers. The RP-HPLC system was used to separate synthesized diastereomers (indirect approach of enantioseparation). Acetonitrile and buffer solution was used as mobile phase for analysis. The effect of varying concentrations and pH of mobile phase was optimized for the separation of diastereomers. The density functional theory calculations were also carried out to develop the lowest energy-minimize optimized diastereomer structures and to design separation mechanisms and elution orders. The retention factor (k), selectivity factor (α), resolution factor (RS), the limit of detection (0.192 ng mL–1) and the limit of quantification (0.576 ng mL–1) were calculated in the context of the method’s validation in accordance with ICH guidelines.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- S. Jain, V. Chandra, P. Kumar Jain, K. Pathak, D. Pathak and A. Vaidya, Arab. J. Chem., 12, 4920 (2019); https://doi.org/10.1016/j.arabjc.2016.10.009
- S. Sehlangia, S. Sharma, S.K. Sharma and C.P. Pradeep, Mater. Adv., 2, 4643 (2021); https://doi.org/10.1039/D1MA00215E
- S. Sehlangia, N. Nayak, N. Garg and C.P. Pradeep, ACS Omega, 7, 24838 (2022); https://doi.org/10.1021/acsomega.2c03047
- T. Eicher, S. Hauptmann and A. Speicher, The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications, John Wiley & Sons (2013).
- N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu and S.B. Jonnalagadda, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
- D.S. Chauhan, P. Singh and M.A. Quraishi, J. Mol. Liq., 320, 114387 (2020); https://doi.org/10.1016/j.molliq.2020.114387
- S. Ghazali, J. Wang, J. Fan and X. Peng, Sens. Actuators B Chem., 239, 1237 (2017); https://doi.org/10.1016/j.snb.2016.09.126
- E.J. Song, J. Kang, G.R. You, G.J. Park, Y. Kim, S.J. Kim, C. Kim and R.G. Harrison, Dalton Trans., 42, 15514 (2013); https://doi.org/10.1039/c3dt51635k
- S. Mohandoss and T. Stalin, RSC Adv., 7, 16581 (2017); https://doi.org/10.1039/C6RA27497H
- L. Hu, L. Yin, F. Wang, D. Yu, C. Wang, M. Hui, L. Chu, X. Zhu and Z. Yan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 220, 117130 (2019); https://doi.org/10.1016/j.saa.2019.05.035
- S. Sehlangia, M. Devi, N. Nayak, N. Garg, A. Dhir and C.P. Pradeep, ChemistrySelect, 5, 5429 (2020); https://doi.org/10.1002/slct.202000674
- R. Basri, N. Ahmed, M. Khalid, M.U. Khan, M. Abdullah, A. Syed, A.M. Elgorban, S.S. Al-Rejaie, A.A.C. Braga and Z. Shafiq, Sci. Rep., 12, 4927 (2022); https://doi.org/10.1038/s41598-022-08860-3
- S. Alwera and R. Bhushan, Biomed. Chromatogr., 30, 1223 (2016); https://doi.org/10.1002/bmc.3671
- S. Alwera, ACS Sustain. Chem. Eng., 6, 11653 (2018); https://doi.org/10.1021/acssuschemeng.8b01869
- V. Alwera, S. Sehlangia and S. Alwera, Sep. Sci. Technol., 56, 2278 (2021); https://doi.org/10.1080/01496395.2020.1819826
- S. Alwera, V. Alwera and S. Sehlangia, Biomed. Chromatogr., 34, e4943 (2020); https://doi.org/10.1002/bmc.4943
- E.J.D. Lee and K.M. Williams, Clin. Pharmacokinet., 18, 339 (1990); https://doi.org/10.2165/00003088-199018050-00001
- M.Y. Ko, D.H. Shin, J.W. Oh, W.S. Asegahegn and K.H. Kim, Arch. Pharm. Res., 29, 1061 (2006); https://doi.org/10.1007/BF02969292
- L. Mohammadkhani and M.M. Heravi, ChemistrySelect, 4, 6309 (2019); https://doi.org/10.1002/slct.201900120
- A. Edwards and M. Rubin, Org. Biomol. Chem., 14, 2883 (2016); https://doi.org/10.1039/C6OB00156D
- L. Zhang, X.J. Wang, J. Wang, N. Grinberg, D.K. Krishnamurthy and C.H. Senanayake, Tetrahedron Lett., 50, 2964 (2009); https://doi.org/10.1016/j.tetlet.2009.03.220
- M. Shi, N. Ye, W. Chen, H. Wang, C. Cheung, M. Parmentier, F. Gallou and B. Wu, Org. Process Res. Dev., 24, 1543 (2020); https://doi.org/10.1021/acs.oprd.0c00303
- S. Alwera and R. Bhushan, Biomed. Chromatogr., 30, 1772 (2016); https://doi.org/10.1002/bmc.3752
- V. Alwera, S. Sehlangia and S. Alwera, J. Liq. Chromatogr. Rel. Technol., 43, 742 (2020); https://doi.org/10.1080/10826076.2020.1798250
- S. Alwera and R. Bhushan, J. Liq. Chromatogr. Rel. Technol., 40, 707 (2017); https://doi.org/10.1080/10826076.2017.1348954
- D.J. Hardee, L. Kovalchuke and T.H. Lambert, J. Am. Chem. Soc., 132, 5002 (2010); https://doi.org/10.1021/ja101292a
- S.E. McLain, A.K. Soper, A.E. Terry and A. Watts, J. Phys. Chem. B, 111, 4568 (2007); https://doi.org/10.1021/jp068340f
- B.K. Ho, E.A. Coutsias, C. Seok and K.A. Dill, Protein Sci., 14, 1011 (2005); https://doi.org/10.1110/ps.041156905
- S. Alwera and R. Bhushan, Biomed. Chromatogr., 31, e3983 (2017); https://doi.org/10.1002/bmc.3983
- J. Buchspies, D. J. Pyle, H. He and M. Szostak, Molecules, 23, 3134 (2018); https://doi.org/10.3390/molecules23123134
- W.D.G. Brittain and C.R. Coxon, Chem. Eur. J., 28, e202103305 (2022); https://doi.org/10.1002/chem.202103305
- V. Alwera, S. Sehlangia and S. Alwera, Biomed. Chromatogr., 34, e4954 (2020); https://doi.org/10.1002/bmc.4954
- H.S. Al-Shehri, V. Alwera, K.C. Nilugal and S. Alwera, Asian J. Chem., 34, 376 (2022); https://doi.org/10.14233/ajchem.2022.23550
- T.I. Ahmed, V. Alwera, V.S. Talismanov, N. Jaishetty, S. Sehlangia and S. Alwera, Asian J. Chem., 34, 1213 (2022); https://doi.org/10.14233/ajchem.2022.23706
- H.S. Al-Shehri, M.S. Patel, S. Alwera, V.S. Talismanov, V. Alwera and R.R. Macadangdang Jr., Asian J. Chem., 34, 673 (2022); https://doi.org/10.14233/ajchem.2022.23578
- ICH, Q2B Document: Validation of Analytical Procedures, International Conference of Harmonization: Geneva (1996)
References
S. Jain, V. Chandra, P. Kumar Jain, K. Pathak, D. Pathak and A. Vaidya, Arab. J. Chem., 12, 4920 (2019); https://doi.org/10.1016/j.arabjc.2016.10.009
S. Sehlangia, S. Sharma, S.K. Sharma and C.P. Pradeep, Mater. Adv., 2, 4643 (2021); https://doi.org/10.1039/D1MA00215E
S. Sehlangia, N. Nayak, N. Garg and C.P. Pradeep, ACS Omega, 7, 24838 (2022); https://doi.org/10.1021/acsomega.2c03047
T. Eicher, S. Hauptmann and A. Speicher, The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications, John Wiley & Sons (2013).
N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu and S.B. Jonnalagadda, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
D.S. Chauhan, P. Singh and M.A. Quraishi, J. Mol. Liq., 320, 114387 (2020); https://doi.org/10.1016/j.molliq.2020.114387
S. Ghazali, J. Wang, J. Fan and X. Peng, Sens. Actuators B Chem., 239, 1237 (2017); https://doi.org/10.1016/j.snb.2016.09.126
E.J. Song, J. Kang, G.R. You, G.J. Park, Y. Kim, S.J. Kim, C. Kim and R.G. Harrison, Dalton Trans., 42, 15514 (2013); https://doi.org/10.1039/c3dt51635k
S. Mohandoss and T. Stalin, RSC Adv., 7, 16581 (2017); https://doi.org/10.1039/C6RA27497H
L. Hu, L. Yin, F. Wang, D. Yu, C. Wang, M. Hui, L. Chu, X. Zhu and Z. Yan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 220, 117130 (2019); https://doi.org/10.1016/j.saa.2019.05.035
S. Sehlangia, M. Devi, N. Nayak, N. Garg, A. Dhir and C.P. Pradeep, ChemistrySelect, 5, 5429 (2020); https://doi.org/10.1002/slct.202000674
R. Basri, N. Ahmed, M. Khalid, M.U. Khan, M. Abdullah, A. Syed, A.M. Elgorban, S.S. Al-Rejaie, A.A.C. Braga and Z. Shafiq, Sci. Rep., 12, 4927 (2022); https://doi.org/10.1038/s41598-022-08860-3
S. Alwera and R. Bhushan, Biomed. Chromatogr., 30, 1223 (2016); https://doi.org/10.1002/bmc.3671
S. Alwera, ACS Sustain. Chem. Eng., 6, 11653 (2018); https://doi.org/10.1021/acssuschemeng.8b01869
V. Alwera, S. Sehlangia and S. Alwera, Sep. Sci. Technol., 56, 2278 (2021); https://doi.org/10.1080/01496395.2020.1819826
S. Alwera, V. Alwera and S. Sehlangia, Biomed. Chromatogr., 34, e4943 (2020); https://doi.org/10.1002/bmc.4943
E.J.D. Lee and K.M. Williams, Clin. Pharmacokinet., 18, 339 (1990); https://doi.org/10.2165/00003088-199018050-00001
M.Y. Ko, D.H. Shin, J.W. Oh, W.S. Asegahegn and K.H. Kim, Arch. Pharm. Res., 29, 1061 (2006); https://doi.org/10.1007/BF02969292
L. Mohammadkhani and M.M. Heravi, ChemistrySelect, 4, 6309 (2019); https://doi.org/10.1002/slct.201900120
A. Edwards and M. Rubin, Org. Biomol. Chem., 14, 2883 (2016); https://doi.org/10.1039/C6OB00156D
L. Zhang, X.J. Wang, J. Wang, N. Grinberg, D.K. Krishnamurthy and C.H. Senanayake, Tetrahedron Lett., 50, 2964 (2009); https://doi.org/10.1016/j.tetlet.2009.03.220
M. Shi, N. Ye, W. Chen, H. Wang, C. Cheung, M. Parmentier, F. Gallou and B. Wu, Org. Process Res. Dev., 24, 1543 (2020); https://doi.org/10.1021/acs.oprd.0c00303
S. Alwera and R. Bhushan, Biomed. Chromatogr., 30, 1772 (2016); https://doi.org/10.1002/bmc.3752
V. Alwera, S. Sehlangia and S. Alwera, J. Liq. Chromatogr. Rel. Technol., 43, 742 (2020); https://doi.org/10.1080/10826076.2020.1798250
S. Alwera and R. Bhushan, J. Liq. Chromatogr. Rel. Technol., 40, 707 (2017); https://doi.org/10.1080/10826076.2017.1348954
D.J. Hardee, L. Kovalchuke and T.H. Lambert, J. Am. Chem. Soc., 132, 5002 (2010); https://doi.org/10.1021/ja101292a
S.E. McLain, A.K. Soper, A.E. Terry and A. Watts, J. Phys. Chem. B, 111, 4568 (2007); https://doi.org/10.1021/jp068340f
B.K. Ho, E.A. Coutsias, C. Seok and K.A. Dill, Protein Sci., 14, 1011 (2005); https://doi.org/10.1110/ps.041156905
S. Alwera and R. Bhushan, Biomed. Chromatogr., 31, e3983 (2017); https://doi.org/10.1002/bmc.3983
J. Buchspies, D. J. Pyle, H. He and M. Szostak, Molecules, 23, 3134 (2018); https://doi.org/10.3390/molecules23123134
W.D.G. Brittain and C.R. Coxon, Chem. Eur. J., 28, e202103305 (2022); https://doi.org/10.1002/chem.202103305
V. Alwera, S. Sehlangia and S. Alwera, Biomed. Chromatogr., 34, e4954 (2020); https://doi.org/10.1002/bmc.4954
H.S. Al-Shehri, V. Alwera, K.C. Nilugal and S. Alwera, Asian J. Chem., 34, 376 (2022); https://doi.org/10.14233/ajchem.2022.23550
T.I. Ahmed, V. Alwera, V.S. Talismanov, N. Jaishetty, S. Sehlangia and S. Alwera, Asian J. Chem., 34, 1213 (2022); https://doi.org/10.14233/ajchem.2022.23706
H.S. Al-Shehri, M.S. Patel, S. Alwera, V.S. Talismanov, V. Alwera and R.R. Macadangdang Jr., Asian J. Chem., 34, 673 (2022); https://doi.org/10.14233/ajchem.2022.23578
ICH, Q2B Document: Validation of Analytical Procedures, International Conference of Harmonization: Geneva (1996)