ArticlePloS one2017
Biological evaluation of both enantiomers of fluoro-thalidomide using human myeloma cell line H929 and others.
Article in PloS one, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 32 citations in OpenAlex.
- Copper-Catalyzed Enantioconvergent Nucleophilic Fluorination of Alkyl Electrophiles to Generate α-Fluoroamides.Journal of the American Chemical Society · 2026Article
- A Novel Nanoemulsion Formula for an Improved Delivery of a Thalidomide Analogue to Triple-Negative Breast Cancer; Synthesis, Formulation, Characterization and Molecular Studies.International journal of nanomedicine · 2023Article
- On the correlation of cereblon binding, fluorination and antiangiogenic properties of immunomodulatory drugs.Biochemical and biophysical research communications · 2021Article
- Repurposing Immunomodulatory Imide Drugs (IMiDs) in Neuropsychiatric and Neurodegenerative Disorders.Frontiers in neuroscience · 2021Review
- Contribution of Organofluorine Compounds to Pharmaceuticals.ACS omega · 2020Review
- Similar Safety Profile of the Enantiomeric N-Aminoalkyl Derivatives ofMolecules (Basel, Switzerland) · 2019Article
- Understanding the Thalidomide Chirality in Biological Processes by the Self-disproportionation of Enantiomers.Scientific reports · 2018Article
- The self-disproportionation of enantiomers (SDE): a menace or an opportunity?Chemical science · 2018Review
- Organocatalytic Asymmetric Synthesis of α-Oxetanyl and α-Azetidinyl Tertiary Alkyl Fluorides and Chlorides.Organic letters · 2018Article
- Synthesis of fluoro-functionalized diaryl-λBeilstein journal of organic chemistry · 2018Article
Corrections and comments
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Authors and funding
6 authors at 4 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Over the last few years, thalidomide has become one of the most important anti-tumour drugs for the treatment of relapsed-refractory multiple myeloma. However, besides its undesirable teratogenic side effect, its configurational instability critically limits any further therapeutic improvements of this drug. In 1999, we developed fluoro-thalidomide which is a bioisostere of thalidomide, but, in sharp contrast to the latter, it is configurationally stable and readily available in both enantiomeric forms. The biological activity of fluoro-thalidomide however, still remains virtually unstudied, with the exception that fluoro-thalidomide is not teratogenic. Herein, we report the first biological evaluation of fluoro-thalidomide in racemic and in both (R)- and (S)-enantiomerically pure forms against (in vitro) H929 cells of multiple myeloma (MM) using an annexin V assay. We demonstrate that all fluoro-thalidomides inhibited the growth of H929 MM cells without any in-vivo activation. Furthermore, we report that the enantiomeric forms of fluoro-thalidomide display different anti-tumour activities, with the (S)-enantiomer being noticeably more potent. The angiogenesis of fluoro-thalidomides is also investigated and compared to thalidomide. The data obtained in this study paves the way towards novel pharmaceutical research on fluoro-thalidomides.
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