UV-Visible Absorption Studies of Gossypol-Metal Cation Complexes in Acetonitrile Solution

Marciniak, Bronisław; Kozubek, Halina; Brzeziński, Bogumił

doi:10.1080/00387019108021760

Cited by 5 publications

(3 citation statements)

References 14 publications

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“…Nomeir et al [21,22] found that gossypol only accounted for 0–40% of the initial concentrations after being stored for 29 days by HPLC method. Marciniak et al [23,24] showed that the UV-vis absorption spectra of gossypol changed drastically in solution over time. However, none of those studies reported to what structures gossypol had changed.…”

Section: Introductionmentioning

confidence: 99%

“…For this reason, studies were carried out to transform gossypol into diastereoisomeric Schiff bases to separate the racemic mixture. However, it was very difficult to obtain the enantiomers of gossypol [24,25]. Further studies on gossypol Schiff base indicated that the compound existed in solution as two tautomeric forms of enamine–enamine and imine–imine [26] However, it was difficult to evaluate the stability of gossypol without systematical and sufficient data.…”

Section: Introductionmentioning

confidence: 99%

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Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study

et al. 2019

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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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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study

et al. 2019

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“…For the complexes with Be 2+ , Ni 2+ , Cu 2+ , Dy 3+ , Gd 3+ , Tb 3+ and Eu 3+ [32,[54][55][56] cations in acetonitrile the lactol-lactol tautomeric form is realized whereas for complexes with Zn 2+ , Fe 2+ and Fe 3+ cations, the ketol-ketol form of gossypol is observed [32,56,57]. The exemplary structures of complexes with metal cations coordinated by different tautomeric forms of gossypol are shown in Scheme 4 and Scheme 5 [32,57].…”

Section: Methodsmentioning

confidence: 96%

Biological Properties of Schiff Bases and Azo Derivatives of Phenols

Przybylski¹,

Huczyński²,

Pyta³

et al. 2009

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Aza-derivatives of phenols such as Schiff bases and hydrazones are an important and interesting group of chemical compounds. They exhibit a number of biological activities and play an important role in the regulation of many biochemical processes. Due to these properties, these compounds are potentialy useful for the design and production of novel anticancer, antimalaria, antivirus and antimicrobial drugs.The primary aim of the present review is to compare selected groups of phenol-derivatives containing azo-, heterocyclic, aromatic, alkyl and sugar moieties in view of their potential use and undesired effects, since some of them are widely used as dyes in the industry.Despite the vast number of azo derivatives of phenols which were synthesized and tested with respect to their biological activities, there is a continuous search for compounds of this group which might exhibit interesting, new biological effects.The main contribution to the development of Schiff base chemistry undoubtedly came from pharmaceutical research that began with the early studies of Hugo Schiff in the 19th century. Indeed, a vast number of publications on this matter underline the relevance of Schiff bases and related compounds in chemistry, pharmacy, biochemistry and industry. GOSSYPOLGossypol (Scheme 1) is a bisesquiterpene with interesting physico-chemical properties and pronounced biological activities. Despite many useful biological and physiological characteristics the main obstacle in using this compound as a drug is its relatively high toxicity and some other side effects [1][2][3][4][5]. The toxicity of gossypol is directed mainly towards the reproductive system, liver, heart and lipid membranes [6,7]. In the last thirty years biological and medical applications of gossypol and its derivatives mainly of its Schiff bases were on the focus of research. More than two thousand publications about gossypol and its derivates in medical therapy show the importance of this compound today. Scheme 1.

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Structures of Complexes of Gossypol with Ferrous Sulfate Based on High‐Performance Liquid Chromatography Separation, Spectroscopic Analysis, and PM3 calculations

et al. 2019

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The complexes of gossypol with Fe2+ were prepared by using methanol as solvent in the presence of CO2 atmosphere. The results from FT‐IR spectra analysis indicated that the aromatic aldehyde groups in gossypol molecules were entirely involved in coordination with Fe2+. UV‐Vis absorption spectrum of the complexes in methanol solution displays blue‐shift in comparison with that of gossypol. Five compounds from the complexes were isolated by high performance liquid chromatography. The structures of the complexes are consistent with PM3 calculations. Two compounds were formed by coordination of gossypol with Fe2+ at 1:2 molar ratio, other three compounds were formed by chelation of gossypol with Fe2+ at molar ratio by 1:1, 1:3, and 1:4 respectively.

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UV-Visible Absorption Studies of Gossypol-Metal Cation Complexes in Acetonitrile Solution

Cited by 5 publications

References 14 publications

Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study

Investigating Stability and Tautomerization of Gossypol—A Spectroscopy Study

Biological Properties of Schiff Bases and Azo Derivatives of Phenols

Structures of Complexes of Gossypol with Ferrous Sulfate Based on High‐Performance Liquid Chromatography Separation, Spectroscopic Analysis, and PM3 calculations

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