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Research data for: Thiolated chiral naphthalene diimide derivatives as effective selectors of the β-blocker atenolol enantiomers

Version 1.0

Rode, Joanna, 2026, "Research data for: Thiolated chiral naphthalene diimide derivatives as effective selectors of the β-blocker atenolol enantiomers", https://doi.org/10.18150/LDBEPR, RepOD, V1

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Description

Atenolol 𝜷-blocker drug (ATN) to treat hypertension and cardiovascular disorders such as angina pectoris is manufactured commercially in a racemic form, while only its (S)-enantiomer shows selective 𝜷1-blocking activity. Here, a new axially chiral thiolated naphthalene diimide derivatives (HS-BIN-NDI) for the rapid, simple, and sensitive detection of ATN enantiomers is presented. The Surface Plasmon Resonance (SPR) and Atomic Force Microscopy (AFM) experiments show that interactions between a chiral selector and a chiral analyte occur only when their configurations are opposite. The extensive computational simulations support this finding. The association coefficient determined by SPR is high and indicates that the interactions are electrostatic. The analytical utility of atropisomeric HS-BIN-NDIs is proven, and the voltammetric sensors designed to determine ATN enantiomers are constructed. The developed sensors are characterized by a wide analytical operating range, nanomolar detection limit, high selectivity, and a long lifetime. Several additives like urea, creatinine, glucose, human albumin, and hemoglobin do not affect ATN sensing.

(2026-04-22)
Subject
Chemistry
Keyword

atenolol stereoisomers, atomic forcemicroscopy, chiral thiolated NDI sensor, chiral voltammetric analysis, computational analysis, surface plasmon resonance

Related Publication

A.Kowalczyk, M.Duszczyk, S.Sęk, P. F. J.Lipiński, D.Kaczorek, R.Kawęcki, I. P.Grudzinski, J. E.Rode, J. C.Dobrowolski, A. M.Nowicka, Thiolated Chiral Naphthalene Diimide Derivatives as Effective Selectors of the β-Blocker Atenolol Enantiomers. Adv. Funct. Mater.2024, 34, 2305806 https://doi.org/10.1002/adfm.202305806 doi: 10.1002/adfm.202305806

CC BY - Creative Commons Attribution 4.0 CC BY - Creative Commons Attribution 4.0

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2024_Adv_Funct_Materials_SI_Thiolated_Chiral_NDI_as_Effective_Selectors_of_the_beta-Blocker_Atenolol_Enantiomers.pdf
Adobe PDF - 3.1 MB - Apr 24, 2026 - 1 Download
MD5: e9ce158172d2790446bfde43f14c3507
License: CC BY - Creative Commons Attribution 4.0
This material includes procedures of syntheses and confirmation of the obtained substances (1H NMR, 13C NMR, ESI) as well as details of the performed calculations for interacting systems: 1. (S)-BIN-NDI with (R)-ATN and 2. (S)-BIN-NDI with (S)-ATN.
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calculated_S_BIN_NDI_receptor.zip
ZIP Archive - 1.7 MB - Apr 24, 2026 - 1 Download
MD5: 0b1fd6af38ced952703cfb69bab47e88
License: CC BY - Creative Commons Attribution 4.0
The output files for the optimization and frequency calculations of the most stable conformers of the (S)-BIN-NDI receptor. The B3LYP-D3/TZVP/PCM(ACN) computational level was used within the Gaussian 09 program. These data were used to prepare Figure 1 of the manuscript.
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calculated_S_BIN_NDI_with_S_ATN.zip
ZIP Archive - 35.8 MB - Apr 24, 2026 - 0 Downloads
MD5: 4b163e7d68ce2f47dc4c0bd784cae8f2
License: CC BY - Creative Commons Attribution 4.0
This directory contains output files for the optimization and frequency (opt+freq) as well as the counterpoise-corrected interaction energies (CP2) calculations of (S)-BIN-NDI receptor with (S)-ATN analyte. The B3LYP/def2-TZVP/PCM(water) computational level was applied and the calculations were performed with Gaussian 16 program. These data were used to prepare Table S1 and Figure S2 of the manuscript. The most stable r-1 complex is also presented at Figure 4B.
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calculated_S_BIN_NDI_with_R_ATN.zip
ZIP Archive - 34.0 MB - Apr 24, 2026 - 0 Downloads
MD5: f7c129f66e5787497124f944fe8230f4
License: CC BY - Creative Commons Attribution 4.0
This directory contains output files for the optimization and frequency (opt+freq) as well as the counterpoise-corrected interaction energies (CP2) calculations of (S)-BIN-NDI receptor with (R)-ATN analyte. The B3LYP/def2-TZVP/PCM(water) computational level was applied and the calculations were performed with Gaussian 16 program. These data were used to prepare Table S1 and Figure S2 of the manuscript. The most stable r-1 complex is also presented at Figure 4A.
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Table_S1.ods
Unknown - 48.5 KB - Apr 24, 2026 - 1 Download
MD5: 1e35c4b6e78a84587ffef21c8b4ab903
License: CC BY - Creative Commons Attribution 4.0
Table S1 from supplementary materials (PDF): Calculated (B3LYP/different basis sets/PCM with or without PCM solvent model included) total energies (E), relative to the most stable complex total energies (ΔE), and interaction energies (Eint) corrected for basis set superposition error by using the counterpoise procedure of (S)-BIN-NDI with (R)-ATN (denoted as r) or (S)-ATN (denoted as s).
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