Chiral Drugs. An Overview
Open accessAbstract
About more than half of the drugs currently in use are chiral compounds and near 90% of the last ones are marketed as racemates consisting of an equimolar mixture of two enantiomers. Although they have the same chemical structure, most isomers of chiral drugs exhibit marked differences in biological activities such as pharmacology, toxicology, pharmacokinetics, metabolism etc. Some mechanisms of these properties are also explained. Therefore, it is important to promote the chiral separation and analysis of racemic drugs in pharmaceutical industry as well as in clinic in order to eliminate the unwanted isomer from the preparation and to find an optimal treatment and a right therapeutic control for the patient. In this article, we review the nomenclature, pharmacology, toxicology, pharmacokinetics, metabolism etc of some usual chiral drugs as well as their mechanisms. Different techniques used for the chiral separation in pharmaceutical industry as well as in clinical analyses are also examined.
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
The stereoselective engagement of protein targets is a feature of numerous chemical probes and drugs.
“The stereoselective engagement of protein targets is a feature of numerous chemical probes and drugs15–19”
From Expedited mapping of the ligandable proteome using fully functionalized enantiomeric probe pairs (2019) · cites this paper as [16]
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Cites
Role of Pharmacokinetics and Metabolism in Drug Discovery and Development
Lin, J. H., & Lu, A. Y. H. (1997) · Pharmacological Reviews · doi:10.1016/s0031-6997(24)01340-1 · Cited by 713 · see citing works
Barrett, A. M., & Cullum, V. A. (1968) · British Journal of Pharmacology · doi:10.1111/j.1476-5381.1968.tb07949.x · Cited by 583 · see citing works
Enantioselective Aspects of Drug Action and Disposition: Therapeutic Pitfalls
Jamali, F., Mehvar, R., & Pasutto, F. M. (1989) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.2600780902 · Cited by 395 · see citing works
Pharmacodynamic and pharmacokinetic differences between drug enantiomers in humans: An overview
Drayer, D. (1986) · Clinical pharmacology and therapy · doi:10.1038/clpt.1986.150 · Cited by 299 · see citing works
Stereochemistry in Drug Action
McConathy, J., & Owens, M. J. (2003) · The Primary Care Companion For CNS Disorders · doi:10.4088/pcc.v05n0202 · Cited by 297 · see citing works
The importance of stereoselective determination of drugs in the clinical laboratory
Rentsch, K. (2002) · Journal of Biochemical and Biophysical Methods · doi:10.1016/s0165-022x(02)00124-0 · Cited by 233 · see citing works
Mechanism of action of barbiturates.
Ho, I., & Harris, R. (1981) · Annual Review of Pharmacology and Toxicology · doi:10.1146/annurev.pa.21.040181.000503 · Cited by 197 · see citing works
Bioanalysis of drugs by liquid-phase microextraction coupled to separation techniques.
Pedersen-Bjergaard, S., & Rasmussen, K. (2005) · Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · doi:10.1016/j.jchromb.2004.08.034 · Cited by 193 · see citing works
The specification of asymmetric configuration in organic chemistry
Cahn, R., Ingold, C., & Prelog, V. (1956) · Experientia · doi:10.1007/bf02157171 · Cited by 190 · see citing works
Chiral Separations By Liquid Chromatography And Related Technologies
Aboul-Enein, H., & Ali, I. (2003) · doi:10.1201/9780203911112 · Cited by 140
Screening approach for chiral separation of pharmaceuticals
Perrin, C., Matthijs, N., Mangelings, D., et al. (2002) · doi:10.1016/s0021-9673(01)01573-4 · Cited by 137
Pharmacology of chiral compounds: 2-arylpropionic acid derivatives.
Landoni, M., & Soraci, A. (2001) · Current drug metabolism · doi:10.2174/1389200013338810 · Cited by 128 · see citing works
The Influence of β-Adrenoceptor Blocking Agents on Plasma Thyroxine and Triiodothyronine
Wiersinga, W. M., & TOUBER, J. L. (1977) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jcem-45-2-293 · Cited by 113 · see citing works
Chirality: a blueprint for the future
Burke, D. L., & Henderson, D. J. (2002) · British Journal of Anaesthesia · doi:10.1093/bja/88.4.563 · Cited by 112 · see citing works
Thalidomide: Tragic Past and Promising Future
Rajkumar, S. V. (2004) · Mayo Clinic Proceedings · doi:10.4065/79.7.899 · Cited by 104 · see citing works
Clinical eftects and pharmacokinetics of racemic methadone and its optical isomers
Olsen, G. D., Wendel, H. A., Livermore, J. O., et al. (1977) · Clinical Pharmacology & Therapeutics · doi:10.1002/cpt1977212147 · Cited by 104 · see citing works
Chirality in Drug Design and Development
Reddy, I. K., & Mehvar, R. (2007) · doi:10.1201/9780203021811 · Cited by 94
Enantioselective inhibition of TNF-? release by thalidomide and thalidomide-analogues
Wnendt, S., Finkam, M., Winter, W., Ossig, J., Raabe, G., & Zwingenberger, K. (1996) · Chirality · doi:10.1002/(sici)1520-636x(1996)8:5 · Cited by 94 · see citing works
Eap, C. B., Finkbeiner, T., Gastpar, M., Scherbaum, N., Powell, K., & Baumann, P. (1996) · European Journal of Clinical Pharmacology · doi:10.1007/s002280050128 · Cited by 92 · see citing works
Toyo'oka, T. (2002) · Journal of Biochemical and Biophysical Methods · doi:10.1016/s0165-022x(02)00127-6 · Cited by 92 · see citing works
Chiral separations : methods and protocols
Gübitz, G., & Schmid, M. (2004) · doi:10.1385/1592596487 · Cited by 91
Preparative chiral chromatographic resolution of enantiomers in drug discovery.
Andersson, S., & Allenmark, S. (2002) · Journal of Biochemical and Biophysical Methods · doi:10.1016/s0165-022x(02)00126-4 · Cited by 90 · see citing works
Matthijs, N., Maftouh, M., & Heyden, Y. V. (2006) · Journal of Chromatography A · doi:10.1016/j.chroma.2006.01.106 · Cited by 85 · see citing works
Chen, J., Korfmacher, W. A., & Hsieh, Y. (2005) · Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · doi:10.1016/j.jchromb.2005.02.012 · Cited by 80 · see citing works
Echizen, H., Manz, M., & Eichelbaum, M. (1988) · Journal of Cardiovascular Pharmacology · doi:10.1097/00005344-198811000-00007 · Cited by 70 · see citing works
Impact of Stereoselectivity on the Pharmacokinetics and Pharmacodynamics of Antiarrhythmic Drugs
Mehvar, R., Brocks, D., & Vakily, M. (2002) · Clinical Pharmacokinetics · doi:10.2165/00003088-200241080-00001 · Cited by 68 · see citing works
Coronary Vasodilator and Cardiac Effects of Optical Isomers of Verapamil in the Dog
Satoh, K., Yanagisawa, T., & Taira, N. (1980) · Journal of Cardiovascular Pharmacology · doi:10.1097/00005344-198005000-00008 · Cited by 59 · see citing works
Radwan, M., Abdine, H., Al-Quadeb, B. T., et al. (2006) · Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · doi:10.1016/j.jchromb.2005.10.031 · Cited by 55 · see citing works
Staroverov, S. M., Kuznetsov, M., Nesterenko, P. N., et al. (2006) · Journal of Chromatography A · doi:10.1016/j.chroma.2006.01.073 · Cited by 54 · see citing works
THYROXINE AND TRIIODOTHYRONINE LEVELS IN HYPERTHYROID PATIENTS DURING TREATMENT WITH PROPRANOLOL
Harrower, A. D. B., Fyffe, J. A., Horn, D. B., & Strong, J. (1977) · Clinical Endocrinology · doi:10.1111/j.1365-2265.1977.tb02938.x · Cited by 51 · see citing works
He, H., SUN, C., WANG, X., Pham‐Huy, C., Chikhi‐Chorfi, N., Galons, H., Thévenin, M., Claude, J., & Warnet, J. (2004) · Journal of Chromatography B · doi:10.1016/j.jchromb.2004.10.048 · Cited by 51 · see citing works
Self-citationBenzodiazepine receptors in the central nervous system.
Skolnick, P., & Paul, S. (1982) · International review of neurobiology · doi:10.1016/s0074-7742(08)60623-6 · Cited by 49 · see citing works
Levalbuterol Nebulizer Solution: Is It Worth Five Times the Cost of Albuterol?
Asmus, M. J., & Hendeles, L. (2000) · Pharmacotherapy · doi:10.1592/phco.20.3.123.34776 · Cited by 48 · see citing works
Stoschitzky, K., Lindner, W., Egginger, G., et al. (1992) · Clinical pharmacology and therapy · doi:10.1038/clpt.1992.45 · Cited by 47 · see citing works
Chirality Clinical Pharmacokinetic and Pharmacodynamic Considerations
Lee, E. J. D., & Williams, K. (1990) · Clinical Pharmacokinetics · doi:10.2165/00003088-199018050-00001 · Cited by 47 · see citing works
Whats New in Chromatographic Enantioseparations
Bojarski, J., Aboul-Enein, H., & Ghanem, A. (2005) · doi:10.2174/1573411052948433 · Cited by 47
Three-dimensional pharmacology, a subject ranging from ignorance to overstatements.
Waldeck, B. (2003) · Acta Pharmacologica et Toxicologica · doi:10.1046/j.1600-0773.2003.pto930502.x · Cited by 45 · see citing works
Liu, J., & Liu, R. H. (2002) · Journal of Biochemical and Biophysical Methods · doi:10.1016/s0165-022x(02)00136-7 · Cited by 44 · see citing works
Pham-Huy, C., Chikhi-Chorfi, N., Galons, H., et al. (1997) · Journal of Chromatography B: Biomedical Sciences and Applications · doi:10.1016/s0378-4347(97)00317-4 · Cited by 42 · see citing works
Self-citationPham-Huy, C., Radenen, B., Sahui-Gnassi, A., et al. (1995) · Journal of chromatography. B, Biomedical applications · doi:10.1016/0378-4347(94)00511-3 · Cited by 42 · see citing works
Self-citationBiomedical aspects of chiral molecules
Patočka, J., & Dvořák, A. (2004) · doi:10.32725/jab.2004.011 · Cited by 37
Studies on the antihypertensive action of the optical isomers of propranolol in man
Rahn, K., Hawlina, A., Kersting, F., et al. (2004) · Naunyn-Schmiedeberg's Archives of Pharmacology · doi:10.1007/bf00498314 · Cited by 36 · see citing works
Inside the isomers: the tale of chiral switches
Somogyi, A. A., Bochner, F., & Foster, D. J. R. (2004) · Australian Prescriber · doi:10.18773/austprescr.2004.039 · Cited by 35 · see citing works
Pham-Huy, C., Villain-Pautet, G., He, H., et al. (2002) · Journal of Biochemical and Biophysical Methods · doi:10.1016/s0165-022x(02)00123-9 · Cited by 35 · see citing works
Self-citationMartins, L., Yegles, M., Chung, H., et al. (2005) · Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · doi:10.1016/j.jchromb.2004.12.037 · Cited by 34 · see citing works
Boralli, V. B., Coelho, E., Cerqueira, P. M., et al. (2005) · Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · doi:10.1016/j.jchromb.2005.06.038 · Cited by 34 · see citing works
Chikhi-Chorfi, N., Pham-Huy, C., Galons, H., et al. (1998) · Journal of Chromatography B: Biomedical Sciences and Applications · doi:10.1016/s0378-4347(98)00375-2 · Cited by 34 · see citing works
Self-citationA CONVENIENT ASYMMETRIC SYNTHESIS OF THALIDOMIDE
Robin, S., Zhu, J.-R., Galons, H., et al. (1995) · doi:10.1016/0957-4166(95)00155-i · Cited by 32
Self-citationJohannsen, M., Peper, S., & Depta, A. (2002) · Journal of Biochemical and Biophysical Methods · doi:10.1016/s0165-022x(02)00132-x · Cited by 30 · see citing works
Single-isomer levalbuterol: A review of the acute data
Nowak, R. (2003) · Current Allergy and Asthma Reports · doi:10.1007/s11882-003-0031-8 · Cited by 29 · see citing works
Hong, Z., Fan, G., Chai, Y., Yin, X., Wen, J., & Wu, Y. (2005) · Journal of Chromatography B · doi:10.1016/j.jchromb.2005.08.012 · Cited by 28 · see citing works
Wei, S., Guo, H.-F., & Lin, J.-M. (2006) · Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · doi:10.1016/j.jchromb.2005.12.044 · Cited by 28 · see citing works
Stereoselectivity of Antibodies for the Bioanalysis of Chiral Drugs
Got, P., & Scherrmann, J. (1997) · Pharmaceutical Research · doi:10.1023/a:1012161814494 · Cited by 26 · see citing works
Chiral chromatographic separation of β-blockers
Agrawal, Y., & Patel, R. (2005) · Journal of Chromatography B · doi:10.1016/j.jchromb.2005.03.003 · Cited by 24 · see citing works
Marzo, A., & Heftmann, E. (2002) · Journal of Biochemical and Biophysical Methods · doi:10.1016/s0165-022x(02)00128-8 · Cited by 24 · see citing works
Thalidomide enantiomers: Determination in biological samples by HPLC and vancomycin-CSP
Murphy-Poulton, S. F., Boyle, F. M., Gu, X. Q., & Mather, L. E. (2005) · Journal of Chromatography B · doi:10.1016/j.jchromb.2005.11.023 · Cited by 23 · see citing works
An expeditious synthesis of cyclic imides
Flaih, N., Pham-Huy, C., & Galons, H. (1999) · doi:10.1016/s0040-4039(99)00590-0 · Cited by 23
Self-citationHe, H., Liu, Y., Sun, C., et al. (2004) · Journal of Chromatographic Science · doi:10.1093/chromsci/42.2.62 · Cited by 23 · see citing works
Self-citationPham‐Huy, C., Sahui-Gnassi, A., Saada, V., Gramond, J. P., Galons, H., Achard, S., Levresse, V., Fompeydie, D., & Claude, J. (1994) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/0731-7085(94)e0028-y · Cited by 20 · see citing works
Self-citationDavies, B. J., Herbert, M., Culbert, J., et al. (2006) · Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · doi:10.1016/j.jchromb.2005.12.046 · Cited by 19 · see citing works
Pham-Huy, C., Galons, H., Voisin, J., et al. (1997) · International Journal of Immunopharmacology · doi:10.1016/s0192-0561(97)00067-2 · Cited by 16 · see citing works
Self-citationSide effects and toxic reactions of chiral drugs: a clinical perspective.
Eichelbaum, M. (1995) · Archives of toxicology. Supplement. = Archiv fur Toxikologie. Supplement · doi:10.1007/978-3-642-79451-3_44 · Cited by 13 · see citing works
Gübitz, G., & Schmid, M. (2004) · doi:10.1385/1-59259-648-7:001 · Cited by 11
Selective antibodies to propranolol enantiomers produced from a new conjugate.
Sahui-Gnassi, A., Pham-Huy, C., Galons, H., et al. (1993) · Chirality · doi:10.1002/chir.530050610 · Cited by 11 · see citing works
Self-citationSTEREOCHEMICAL TERMS AND CONCEPTS: AN OVERVIEW*
Wainer, I., & Marcotte, A. (2001) · doi:10.1081/crp-100108173 · Cited by 10
Chikhi-Chorfi, N., Galons, H., Pham-Huy, C., et al. (2001) · Chirality · doi:10.1002/chir.1018 · Cited by 10 · see citing works
Self-citationASYMMETRIC CATALYSIS WINS: Chemistry Nobel honors Knowles, Noyori, Sharpless for chiral syntheses
Borman, S. (2001) · doi:10.1021/cen-v079n042.p005 · Cited by 9
Chikhi-Chorfi, N., Pham-Huy, C., Sandouk, P., et al. (1998) · doi:10.1016/s0378-4274(98)80410-4 · Cited by 5
Self-citationPham-Huy, C., Sahui-Gnassi, A., Massicot, F., et al. (1995) · Archives of toxicology. Supplement. = Archiv fur Toxikologie. Supplement · doi:10.1007/978-3-642-79451-3_45 · Cited by 3 · see citing works
Self-citationChapter 2 Chemical methods for the investigation of stereochemical problems in biology
Bentley, R. (1982) · New comprehensive biochemistry · doi:10.1016/s0167-7306(08)60393-2 · Cited by 2 · see citing works
Mann, A., & Wermuth, C. (2001) · doi:10.1051/medsci/200117111230 · Cited by 2
Enzymic Synthesis and Resolution of Enantiomerically Pure Compounds
Stirling, D. (1994) · doi:10.1002/chin.199409296 · Cited by 2
Flagged first, then by citations
12 of the 84 references couldn’t be matched to a known paper.
Research works printed but not linked: 5
- [5]Katzung BG The nature of drugs In: Basic and clinical pharmacology 2004 9th New York Lange Medical Books/McGraw Hill 3 5
- [12]Ariens EJ Ariens EJ Soudijn W Timmermans PBMWM Stereoselectivity of bioactive agents: general aspects Stereochemistry and Biological activity of Drugs 1983 Oxford Blackwell Scientific 11 33
- [16]Stoschitzky K Lindner W Zernig G Racemic beta-blockers-fixed combinations of different drugs Journal of Clinical and Basic Cardiology 1998 1 1 15 19
- [24]Industry Overview organised by scientific update. Conferences An international symposium on chirality 5-7 September 1999 Cambridge University, Cambridge, UK http://www.geocities.com/jefferywinkler/bcc.doc
- [43]Scott AK Stereoisomers and drug toxicity. The value of single stereoisomer therapy Drug Safety 1993 8 2 149 159 8452656
Cited by
Sorted by citations
Free Radicals, Antioxidants in Disease and Health
Department of Pharmacy, L. S. P. C. H., Pham-Huy, L. A., He, H., Department of Analytical Chemistry, C. P. U., Pham-Huyc, C., & Laboratory of Toxicology, F. O. P. (2008) · International Journal of Biomedical Science · doi:10.59566/ijbs.2008.4089 · Cited by 3,058 · see citing works
Self-citationPatel, M., Kumar, R., Kishor, K., Mlsna, T., Pittman, C. U., & Mohan, D. (2019) · Chemical Reviews · doi:10.1021/acs.chemrev.8b00299 · Cited by 2,654 · see citing works
Adsorptive separation on metal–organic frameworks in the liquid phase
de Voorde, B. V., Bueken, B., Denayer, J. F. M., et al. (2014) · Chemical Society Reviews · doi:10.1039/c4cs00006d · Cited by 877 · see citing works
Carbon Nanotubes: Applications in Pharmacy and Medicine
He, H., Pham-Huy, L. A., Dramou, P., et al. (2013) · BioMed Research International · doi:10.1155/2013/578290 · Cited by 536 · see citing works
Self-citationPharmacologically active compounds in the environment and their chirality
Kasprzyk‐Hordern, B. (2010) · Chemical Society Reviews · doi:10.1039/c000408c · Cited by 460 · see citing works
Applications of bacterial cellulose in food, cosmetics and drug delivery
Ullah, H., Santos, H. A., & Khan, T. (2016) · Cellulose · doi:10.1007/s10570-016-0986-y · Cited by 425 · see citing works
Poynton, F. E., Bright, S. A., Blasco, S., Williams, D. C., Kelly, J. M., & Gunnlaugsson, T. (2017) · Chemical Society Reviews · doi:10.1039/c7cs00680b · Cited by 425 · see citing works
Suzuki, N., Wang, Y., Elvati, P., Qu, Z., Kim, K., Jiang, S., Baumeister, E., Lee, J., Yeom, B., Bahng, J. H., et al. (2016) · ACS Nano · doi:10.1021/acsnano.5b06369 · Cited by 398 · see citing works
Geometric deep learning on molecular representations
Atz, K., Grisoni, F., & Schneider, G. (2021) · Nature Machine Intelligence · doi:10.1038/s42256-021-00418-8 · Cited by 387 · see citing works
Nanophotonic Approaches for Chirality Sensing
Warning, L. A., Miandashti, A. R., McCarthy, L. A., Zhang, Q., Landes, C. F., & Link, S. (2021) · ACS Nano · doi:10.1021/acsnano.1c04992 · Cited by 348 · see citing works
Chiral AIEgens – Chiral recognition, CPL materials and other chiral applications
Hu, M., Feng, H., Yuan, Y., Zheng, Y., & Tang, B. Z. (2020) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2020.213329 · Cited by 322 · see citing works
Diabetes-Induced Reactive Oxygen Species: Mechanism of Their Generation and Role in Renal Injury
Fakhruddin, S., Alanazi, W. A., & Jackson, K. E. (2017) · Journal of Diabetes Research · doi:10.1155/2017/8379327 · Cited by 295 · see citing works
Chiral carbon dots: synthesis, optical properties, and emerging applications
Döring, A., Ushakova, E. V., & Rogach, A. L. (2022) · Light Science & Applications · doi:10.1038/s41377-022-00764-1 · Cited by 295 · see citing works
Global risk of pharmaceutical contamination from highly populated developing countries
Rehman, M. S. U., Rashid, N., Ashfaq, M. A., Saif, A., Ahmad, N., & Han, J. (2013) · Chemosphere · doi:10.1016/j.chemosphere.2013.02.036 · Cited by 282 · see citing works
Lateral chirality-sorting optical forces
Hayat, A., Mueller, J. P. B., & Capasso, F. (2015) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1516704112 · Cited by 281 · see citing works
Chirality of New Drug Approvals (2013–2022): Trends and Perspectives
McVicker, R. U., & O’Boyle, N. M. (2024) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.3c02239 · Cited by 261 · see citing works
Enantiospecific Optical Enhancement of Chiral Sensing and Separation with Dielectric Metasurfaces
Solomon, M. L., Hu, J., Lawrence, M., García‐Etxarri, A., & Dionne, J. A. (2018) · ACS Photonics · doi:10.1021/acsphotonics.8b01365 · Cited by 246 · see citing works
The Role of Plasmon-Generated Near Fields for Enhanced Circular Dichroism Spectroscopy
Nesterov, M. L., Yin, X., Schäferling, M., et al. (2016) · ACS Photonics · doi:10.1021/acsphotonics.5b00637 · Cited by 233 · see citing works
Matveychuk, D., Thomas, R. K., Swainson, J., Khullar, A., MacKay, M.-A., Baker, G. B., & Dursun, S. M. (2020) · Therapeutic Advances in Psychopharmacology · doi:10.1177/2045125320916657 · Cited by 209 · see citing works
Enhanced Chiral Sensing with Dielectric Nanoresonators
García-Guirado, J., Svedendahl, M., Puigdollers, J., & Quidant, R. (2019) · Nano Letters · doi:10.1021/acs.nanolett.9b04334 · Cited by 213 · see citing works
Applications of OR/ECD/VCD to the structure elucidation of natural products
Mándi, A., & Kurtán, T. (2019) · Natural Product Reports · doi:10.1039/c9np00002j · Cited by 208 · see citing works
D‐Lactic Acid as a Metabolite: Toxicology, Diagnosis, and Detection
Pohanka, M. (2020) · BioMed Research International · doi:10.1155/2020/3419034 · Cited by 205 · see citing works
Chiral Supraparticles for Controllable Nanomedicine
Yeom, J., Guimarães, P. P. G., Ahn, H. M., Jung, B., Hu, Q., McHugh, K. J., Mitchell, M. J., Yun, C., Langer, R., & Jaklenec, A. (2019) · Advanced Materials · doi:10.1002/adma.201903878 · Cited by 191 · see citing works
Metallogels: Availability, Applicability, and Advanceability
Wu, H., Zheng, J., Kjøniksen, A., Wang, W., Na, Z., & Ma, J. (2019) · Advanced Materials · doi:10.1002/adma.201806204 · Cited by 183 · see citing works
Expedited mapping of the ligandable proteome using fully functionalized enantiomeric probe pairs
Wang, Y., Dix, M. M., Bianco, G., Remsberg, J. R., Lee, H.-Y., Kalocsay, M., Gygi, S. P., Forli, S., Vite, G., Lawrence, R. M., et al. (2019) · Nature Chemistry · doi:10.1038/s41557-019-0351-5 · Cited by 179 · see citing works
High Quality Factor Dielectric Metasurfaces for Ultraviolet Circular Dichroism Spectroscopy
Hu, J., Lawrence, M., & Dionne, J. A. (2019) · ACS Photonics · doi:10.1021/acsphotonics.9b01352 · Cited by 171 · see citing works
Ward, T. J., & Baker, B. A. (2008) · Analytical Chemistry · doi:10.1021/ac800662y · Cited by 171 · see citing works
Feng, H., Lam, J. W. Y., & Tang, B. Z. (2019) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2019.213142 · Cited by 168 · see citing works
Tokunaga, E., Yamamoto, T., Ito, E., & Shibata, N. (2018) · Scientific Reports · doi:10.1038/s41598-018-35457-6 · Cited by 171 · see citing works
Chirality-assisted lateral momentum transfer for bidirectional enantioselective separation
Shi, Y., Zhu, T., Zhang, T., Mazzulla, A., Tsai, D. P., Ding, W., Liu, A. Q., Cipparrone, G., Sáenz, J. J., & Qiu, C. (2020) · Light Science & Applications · doi:10.1038/s41377-020-0293-0 · Cited by 159 · see citing works
Coelho, M. M., Fernandes, C., Remião, F., & Tiritan, M. E. (2021) · Molecules · doi:10.3390/molecules26113113 · Cited by 161 · see citing works
Ni, B., Mychinko, M., Gómez‐Graña, S., Morales‐Vidal, J., Obelleiro‐Liz, M., Heyvaert, W., Vila‐Liarte, D., Zhuo, X., Albrecht, W., Zheng, G., et al. (2022) · Advanced Materials · doi:10.1002/adma.202208299 · Cited by 161 · see citing works
Mohammadi, E., Tavakoli, A., Dehkhoda, P., Jahani, Y., Tsakmakidis, K. L., Tittl, A., & Altug, H. (2019) · ACS Photonics · doi:10.1021/acsphotonics.8b01767 · Cited by 157 · see citing works
Polarization control in an X-ray free-electron laser
Lutman, A. A., MacArthur, J., Ilchen, M., et al. (2016) · Nature Photonics · doi:10.1038/nphoton.2016.79 · Cited by 154 · see citing works
Circular Dichroism Studies on Plasmonic Nanostructures
Wang, X., & Tang, Z. (2016) · Small · doi:10.1002/smll.201601115 · Cited by 154 · see citing works
All-Optical Chirality-Sensitive Sorting via Reversible Lateral Forces in Interference Fields
Zhang, T., Mahdy, M. R. C., Liu, Y., et al. (2017) · ACS Nano · doi:10.1021/acsnano.7b01428 · Cited by 150 · see citing works
Chiral assembly of organic luminogens with aggregation-induced emission
Liu, C., Yang, J., Lam, J. W. Y., Feng, H., & Tang, B. Z. (2021) · Chemical Science · doi:10.1039/d1sc02305e · Cited by 152 · see citing works
Controlled partial interpenetration in metal–organic frameworks
Ferguson, A., Liu, L., Tapperwijn, S. J., et al. (2016) · Nature Chemistry · doi:10.1038/nchem.2430 · Cited by 146 · see citing works
Cao, Z., Gao, H., Qiu, M., Jin, W., Deng, S., Wong, K., & Lei, D. (2020) · Advanced Materials · doi:10.1002/adma.201907151 · Cited by 145 · see citing works
Chiral plasmonic nanostructures: recent advances in their synthesis and applications
Wu, W., & Pauly, M. (2021) · Materials Advances · doi:10.1039/d1ma00915j · Cited by 144 · see citing works
Chiral Switch: Between Therapeutical Benefit and Marketing Strategy
Hancu, G., & Modroiu, A. (2022) · Pharmaceuticals · doi:10.3390/ph15020240 · Cited by 140 · see citing works
Enhancing Enantioselective Absorption Using Dielectric Nanospheres
Ho, C.-S., García‐Etxarri, A., Zhao, Y., & Dionne, J. A. (2016) · ACS Photonics · doi:10.1021/acsphotonics.6b00701 · Cited by 133 · see citing works
Imaging in-vivo tau pathology in Alzheimer’s disease with THK5317 PET in a multimodal paradigm
Chiotis, K., Saint‐Aubert, L., Savitcheva, I., Jelić, V., Andersen, P., Jonasson, M., Eriksson, J., Lubberink, M., Almkvist, O., Wall, A. E., et al. (2016) · European Journal of Nuclear Medicine and Molecular Imaging · doi:10.1007/s00259-016-3363-z · Cited by 127 · see citing works
Solid membranes for chiral separation: A review
Liu, T., Li, Z., Wang, J., et al. (2020) · Chemical Engineering Journal · doi:10.1016/j.cej.2020.128247 · Cited by 127 · see citing works
Zhu, S., Niljianskul, N., & Buchwald, S. L. (2016) · Nature Chemistry · doi:10.1038/nchem.2418 · Cited by 126 · see citing works
Ultrasound experiments on acoustical activity in chiral mechanical metamaterials
Frenzel, T., Köpfler, J., Jung, E., Kadic, M., & Wegener, M. (2019) · Nature Communications · doi:10.1038/s41467-019-11366-8 · Cited by 119 · see citing works
Meng, L., Shi, J., Yang, C., et al. (2020) · Extreme Mechanics Letters · doi:10.1016/j.eml.2020.100869 · Cited by 125 · see citing works
Okur, S., Qin, P., Chandresh, A., Li, C., Zhang, Z., Lemmer, U., & Heinke, L. (2021) · Angewandte Chemie International Edition · doi:10.1002/anie.202013227 · Cited by 121 · see citing works
Stereodynamic Strategies to Induce and Enrich Chirality of Atropisomers at a Late Stage
Roos, C. B., Chiang, C.-H., Murray, L. A. M., et al. (2023) · Chemical Reviews · doi:10.1021/acs.chemrev.3c00327 · Cited by 122 · see citing works
Circular dichroism induced by Fano resonances in planar chiral oligomers
Hopkins, B., Poddubny, A. N., Miroshnichenko, A. E., et al. (2015) · Laser & Photonics Review · doi:10.1002/lpor.201500222 · Cited by 119 · see citing works
Advances and applications of chiral resolution in pharmaceutical field
Teng, Y., Gu, C., Chen, Z., Jiang, H., Xiong, Y., Liu, D., & Xiao, D. (2022) · Chirality · doi:10.1002/chir.23453 · Cited by 119 · see citing works
Hot Electron Generation and Cathodoluminescence Nanoscopy of Chiral Split Ring Resonators
Fang, Y., Verre, R., Shao, L., et al. (2016) · Nano Letters · doi:10.1021/acs.nanolett.6b02154 · Cited by 112 · see citing works
Zhou, Y., Wu, S., Zhou, H., Huang, H., Zhao, J. C., Deng, Y., Wang, H., Yang, Y., Yang, J., & Luo, L. (2018) · Environment International · doi:10.1016/j.envint.2018.09.041 · Cited by 111 · see citing works
Multimodal Role of Amino Acids in Microbial Control and Drug Development
Idrees, M. M., Mohammad, A. R., Karodia, N., & Rahman, A. (2020) · Antibiotics · doi:10.3390/antibiotics9060330 · Cited by 115 · see citing works
Chiral Mesostructured Inorganic Materials with Optical Chiral Response
Duan, Y., & Che, S. (2022) · Advanced Materials · doi:10.1002/adma.202205088 · Cited by 111 · see citing works
Contesini, F. J., Davanço, M. G., Borin, G., et al. (2020) · Catalysts · doi:10.3390/catal10091032 · Cited by 106 · see citing works
Enantioselective Recognition of Ammonium Carbamates in a Chiral Metal–Organic Framework
Martell, J. D., Zasada, L. B., Forse, A. C., Siegelman, R. L., Gonzalez, M. I., Oktawiec, J., Runčevski, T., Xu, J., Srebro‐Hooper, M., Milner, P. J., et al. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b09983 · Cited by 103 · see citing works
Enantiomeric Recognition and Separation by Chiral Nanoparticles
Gogoi, A., Mazumder, N., Konwer, S., et al. (2019) · Molecules · doi:10.3390/molecules24061007 · Cited by 103 · see citing works
Fan, J., & Kotov, N. A. (2020) · Advanced Materials · doi:10.1002/adma.201906738 · Cited by 109 · see citing works
The significance of chirality in contemporary drug discovery-a mini review
Senkuttuvan, N., Komarasamy, B., Krishnamoorthy, R., Sarkar, S., Dhanasekaran, S., & Anaikutti, P. (2024) · RSC Advances · doi:10.1039/d4ra05694a · Cited by 101 · see citing works
Racemic drug resolution: a comprehensive guide
Mane, S. T. (2016) · Analytical Methods · doi:10.1039/c6ay02015a · Cited by 100 · see citing works
Field detection devices for screening the quality of medicines: a systematic review
Vickers, S., Bernier, M. C., Zambrzycki, S. C., et al. (2018) · BMJ Global Health · doi:10.1136/bmjgh-2018-000725 · Cited by 98 · see citing works
Achiral, Helicity Preserving, and Resonant Structures for Enhanced Sensing of Chiral Molecules
Graf, F., Feis, J., Garcia-Santiago, X., Wegener, M., Rockstuhl, C., & Fernandez‐Corbaton, I. (2019) · ACS Photonics · doi:10.1021/acsphotonics.8b01454 · Cited by 100 · see citing works
Deep Generative Models in De Novo Drug Molecule Generation
Pang, C., Qiao, J., Zeng, X., Zou, Q., & Wei, L. (2023) · Journal of Chemical Information and Modeling · doi:10.1021/acs.jcim.3c01496 · Cited by 107 · see citing works
Recent Advances in 1,2,4‐Triazole Scaffolds as Antiviral Agents
El‐Sebaey, S. A. (2020) · ChemistrySelect · doi:10.1002/slct.202002830 · Cited by 98 · see citing works
Chiral Macrocycles for Enantioselective Recognition
Sun, G. W., Zhang, X., Zheng, Z., et al. (2024) · Journal of the American Chemical Society · doi:10.1021/jacs.4c07924 · Cited by 95 · see citing works
Substrate-Specificity of Candida rugosa Lipase and Its Industrial Application
Vanleeuw, E., Winderickx, S., Thevissen, K., Lagrain, B., Dusselier, M., Cammue, B. P. A., & Sels, B. F. (2019) · ACS Sustainable Chemistry & Engineering · doi:10.1021/acssuschemeng.9b03257 · Cited by 92 · see citing works
Experimental and Theoretical Observation of Photothermal Chirality in Gold Nanoparticle Helicoids
Miandashti, A. R., Khorashad, L. K., Kordesch, M. E., et al. (2020) · ACS Nano · doi:10.1021/acsnano.9b09062 · Cited by 92 · see citing works
Bagnall, J. P., Evans, S. E., Wort, M. T., Lubben, A., & Kasprzyk‐Hordern, B. (2012) · Journal of Chromatography A · doi:10.1016/j.chroma.2012.06.012 · Cited by 90 · see citing works
Chiral Drug Analysis in Forensic Chemistry: An Overview
Ribeiro, C. M. R., dos Santos, C. R. M., Gonçalves, V., Ramos, A., Afonso, C., & Tiritan, M. E. (2018) · Molecules · doi:10.3390/molecules23020262 · Cited by 89 · see citing works
Enantioselective activity of usnic acid: a comprehensive review and future perspectives
Galanty, A., Paśko, P., & Podolak, I. (2019) · Phytochemistry Reviews · doi:10.1007/s11101-019-09605-3 · Cited by 87 · see citing works
Vitale, P., Abbinante, V. M., Perna, F. M., Salomone, A., Cardellicchio, C., & Capriati, V. (2016) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201601064 · Cited by 87 · see citing works
Long- and short-ranged chiral interactions in DNA-assembled plasmonic chains
Martens, K., Binkowski, F., Nguyen, L., Hu, L., Govorov, A. O., Burger, S., & Liedl, T. (2021) · Nature Communications · doi:10.1038/s41467-021-22289-8 · Cited by 85 · see citing works
Self-citationAdvances of Vibrational Circular Dichroism (VCD) in bioanalytical chemistry. A review
Kurouski, D. (2017) · Analytica Chimica Acta · doi:10.1016/j.aca.2017.08.014 · Cited by 85 · see citing works
Wu, B., Xu, J., Bian, K., et al. (2022) · Journal of the American Chemical Society · doi:10.1021/jacs.2c01422 · Cited by 85 · see citing works
Chirality sorting using two-wave-interference–induced lateral optical force
Chen, H., Liang, C., Liu, S., & Lin, Z. (2016) · Physical Review A · doi:10.1103/physreva.93.053833 · Cited by 83 · see citing works
Uno, H., Punna, N., Tokunaga, E., et al. (2020) · Angewandte Chemie International Edition · doi:10.1002/anie.201915021 · Cited by 82 · see citing works
Das, T., Mohapatra, S., Mishra, N. P., et al. (2021) · ChemistrySelect · doi:10.1002/slct.202100679 · Cited by 82 · see citing works
Demystifying racemic natural products in the homochiral world
Bitchagno, G. T. M., Nchiozem‐Ngnitedem, V., Melchert, D., et al. (2022) · Nature Reviews Chemistry · doi:10.1038/s41570-022-00431-4 · Cited by 82 · see citing works
Enantioselectivity of mass spectrometry: Challenges and promises
Awad, H., & El‐Aneed, A. (2013) · Mass Spectrometry Reviews · doi:10.1002/mas.21379 · Cited by 82 · see citing works
Huang, L., Wang, S., Ma, F., Zhang, Y., Peng, Y., Xing, C., Feng, Y., Wang, X., & Peng, Y. (2018) · Pharmacological Research · doi:10.1016/j.phrs.2018.08.007 · Cited by 81 · see citing works
Das, K. K., Manna, S., & Panda, S. (2020) · Chemical Communications · doi:10.1039/d0cc06460b · Cited by 81 · see citing works
Lateral sorting of chiral nanoparticles using Fano-enhanced chiral force in visible region
Cao, T., & Qiu, Y. (2017) · Nanoscale · doi:10.1039/c7nr05464e · Cited by 78 · see citing works
Solomon, M. L., Abendroth, J. M., Poulikakos, L. V., et al. (2020) · Journal of the American Chemical Society · doi:10.1021/jacs.0c07140 · Cited by 77 · see citing works
Selective Orientation of Chiral Molecules by Laser Fields with Twisted Polarization
Tutunnikov, I., Gershnabel, E., Gold, S., et al. (2018) · The Journal of Physical Chemistry Letters · doi:10.1021/acs.jpclett.7b03416 · Cited by 76 · see citing works
Bottom-Up Engineering of Responsive Hydrogel Materials for Molecular Detection and Biosensing
Lim, J. Y. C., Goh, S. S., & Loh, X. J. (2020) · ACS Materials Letters · doi:10.1021/acsmaterialslett.0c00204 · Cited by 76 · see citing works
Tuwahatu, C. A., Yeung, C. C., Lam, Y. W., & Roy, V. A. L. (2018) · Journal of Controlled Release · doi:10.1016/j.jconrel.2018.08.023 · Cited by 76 · see citing works
Chip-Based High-Performance Liquid Chromatography for High-Speed Enantioseparations
Thürmann, S., Lotter, C., Heiland, J. J., et al. (2015) · Analytical Chemistry · doi:10.1021/acs.analchem.5b00210 · Cited by 75 · see citing works
Cofactor F420: an expanded view of its distribution, biosynthesis and roles in bacteria and archaea
Grinter, R., & Greening, C. (2021) · FEMS Microbiology Reviews · doi:10.1093/femsre/fuab021 · Cited by 73 · see citing works
Catalytic Enantioselective Flow Processes with Solid‐Supported Chiral Catalysts
Rodríguez‐Escrich, C., & Pericàs, M. À. (2018) · The Chemical Record · doi:10.1002/tcr.201800097 · Cited by 72 · see citing works
Fu, R., Zhao, Q., Han, H., et al. (2023) · Angewandte Chemie International Edition · doi:10.1002/anie.202315990 · Cited by 73 · see citing works
Optical sorting of small chiral particles by tightly focused vector beams
Li, M., Yan, S., Zhang, Y., Liang, Y., Zhang, P., & Yao, B. (2019) · Physical Review A · doi:10.1103/physreva.99.033825 · Cited by 72 · see citing works
Catalytic Asymmetric Synthesis of Chiral Caged Hydrocarbons as Arenes Bioisosteres
Yang, X.-C., Wang, J., Xiao, Y., & Feng, J. (2025) · Angewandte Chemie International Edition · doi:10.1002/anie.202505803 · Cited by 73 · see citing works
Biomimetic photonic materials derived from chitin and chitosan
Lizundia, E., Nguyen, T., Winnick, R. J., et al. (2021) · Journal of Materials Chemistry C · doi:10.1039/d0tc05381c · Cited by 71 · see citing works
Sheng, J., Pooler, D. R. S., & Feringa, B. L. (2023) · Chemical Society Reviews · doi:10.1039/d3cs00247k · Cited by 77 · see citing works
Dual Nanoresonators for Ultrasensitive Chiral Detection
Mohammadi, E., Tittl, A., Tsakmakidis, K. L., et al. (2021) · ACS Photonics · doi:10.1021/acsphotonics.1c00311 · Cited by 70 · see citing works
Nanoparticle stereochemistry-dependent endocytic processing improves in vivo mRNA delivery
Hatit, M. Z. C., Dobrowolski, C. N., Lokugamage, M. P., Loughrey, D., Ni, H., Zurla, C., Sanchez, A. J. D. S., Radmand, A., Huayamares, S. G., Zenhausern, R., et al. (2023) · Nature Chemistry · doi:10.1038/s41557-023-01138-9 · Cited by 71 · see citing works
Tandem Reactions Combining Biocatalysts and Chemical Catalysts for Asymmetric Synthesis
Wang, Y., & Zhao, H. (2016) · Catalysts · doi:10.3390/catal6120194 · Cited by 70 · see citing works
Turning chiral peptides into a racemic supraparticle to induce the self-degradation of MDM2
Yang, W., Liu, W., Li, X., Yan, J., & He, W. (2022) · Journal of Advanced Research · doi:10.1016/j.jare.2022.05.009 · Cited by 70 · see citing works
Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained Trisubstituted Alkenes
Feng, S., Hao, H., Liu, P., et al. (2019) · ACS Catalysis · doi:10.1021/acscatal.9b04871 · Cited by 68 · see citing works
- Authors
- Laboratory of Toxicology, F. O. P., Chuong, P.-H., Nguyen, L. A., Department of Pharmacy, L. S. P. C. H., He, H., & Department of Analytical Chemistry, C. P. U.
- ORCID
- He, Hua
- Venue
- International Journal of Biomedical Science
- Published
- 2006-09-15
- Volume
- 2
- Issue
- 2
- Pages
- 85-100
- ISSN
- 1550-9702 (ISSN-L)
- 1555-2810
- PMC
- PMC3614593
- OpenAlex
- W4390049991
- Cited by
- 1,224
- References
- 84
- Citations by year
- 2026: 81 · 2025: 105 · 2024: 106 · 2023: 110 · 2022: 132 · 2021: 113 · 2020: 136 · 2019: 120 · 2018: 87 · 2017: 69 · 2016: 81 · 2015: 26 · 2014: 17 · 2013: 11 · 2012: 7
- FWCI
- 1.11
- Type
- journal article
- Language
- en
- Open access
- green
- europepmc.org
- Licence
- cc-by
- Locations
- International Journal of Biomedical Science (publishedVersion)
- Europe PMC (PubMed Central) (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- PubMed
- Topics
- Physical Sciences › Chemistry › Spectroscopy › Analytical Chemistry and Chromatography
- Physical Sciences › Chemistry › Organic Chemistry › Chemistry and Stereochemistry Studies
- Physical Sciences › Chemistry › Spectroscopy › Molecular spectroscopy and chirality
- Keywords
- chiral drugs, enantiomers, racemic mixtures, enantiomer separation, pharmaceutical industry
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review