ArticleMolecules (Basel, Switzerland)2019
Investigating Stability and Tautomerization of Gossypol-A Spectroscopy Study.
Article in Molecules (Basel, Switzerland), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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8 citing papers in PubMed, 31 citations in OpenAlex.
- Modification of Chitosan with (-)-Gossypol and (-)-Gossypol Acetic Acid Using Free-Radical Grafting Method.International journal of molecular sciences · 2025Article
- Synthesis of an amphiphilic bi-prodrug based on gossypol and cytarabine for drug self-delivery.RSC advances · 2025Article
- Article
- Blockade of CaBritish journal of pharmacology · 2024Article
- Article
- Systematic Review of Gossypol/AT-101 in Cancer Clinical Trials.Pharmaceuticals (Basel, Switzerland) · 2022Review
- Gastric floating tablet improves the bioavailability and reduces the hypokalemia effect of gossypolSaudi pharmaceutical journal : SPJ : the official publication of the Saudi Pharmaceutical Society · 2021Article
- Prediction Model with High-Performance Constitutive Androstane Receptor (CAR) Using DeepSnap-Deep Learning Approach from the Tox21 10K Compound Library.International journal of molecular sciences · 2019Article
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5 authors at 1 institution in 1 country.
Funding
Abstract
The stability of gossypol was investigated by the spectroscopic method. Gossypol was dissolved in three different solvents (CHCl₃, DMSO, and CH₃OH) under different storage conditions (dark and with nitrogen protection, natural light and with nitrogen protection, ambient air conditions) for different time intervals (0 days, 3 days, 5 days, 7 days, 15 days, 30 days, and 45 days) at room temperature. Then, the stability of gossypol was investigated by ¹H NMR, UV-vis, and HPLC-QTOF-MS spectrometry. Results showed that gossypol existed in aldehyde-aldehyde form in chloroform within five days. Then, both aldehyde-aldehyde and lactol-lactol tautomeric forms existed and maintained a stable solution for 45 days. Gossypol dissolved in methanol mainly existed in aldehyde-aldehyde form. Only a tiny amount of lactol-lactol was found in freshly prepared methanol solution. Gossypol was found to only exist in lactol-lactol form between 30-45 days. Gossypol existed in aldehyde-aldehyde, lactol-lactol, and ketol-ketol forms in dimethyl sulfoxide, and there was a competitive relationship between aldehyde-aldehyde and lactol-lactol form during the 45 days. Among all the solvents and conditions studied, gossypol was found to be highly stable in chloroform. Under the tested conditions, the natural light and atmospheric oxygen had little effect on its stability. Although the spectroscopy data seemed to be changed over time in the three different solvents, it was actually due to the tautomeric transformation rather than molecular decomposition.
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