Molecular and crystal structure of gossypol tetramethyl ether with an unknown solvate

Honkeldieva, Muhabbat; Talipov, S. A.; Mardanov, R. G.; Ибрагимов, Б. Т.

doi:10.1107/s2056989015000171

Cited by 3 publications

(3 citation statements)

References 21 publications

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“…*Significantly different from Control at P < .05. Inset in (C): space‐filling model of gossypol built according to the published crystal structures 61,62 using Molecular Modeling Pro computer software (Norgwyn Montgomery Software Inc); the unhydrated radius of the molecule calculated as a geometric mean of three dimension is ~0.63 nm…”

Section: Resultsmentioning

confidence: 99%

Lytic and sublytic effects of gossypol on red blood cells and thymocytes

Chorieva

Fayziev

Tsiferova

et al. 2020

Clin Exp Pharma Physio

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Gossypol is a natural polyphenol presently considered as a promising biological phytochemical with a range of activities including anticancer. We examined volume regulation‐dependent effects of gossypol using erythrocytes and thymic lymphocytes. Gossypol effectively lysed human red blood cells (RBC) with a half‐maximal concentration of 67.4 ± 1.6 μmol/L and in a non‐colloid osmotic manner. Sublytic gossypol doses of 1–10 μmol/L significantly protected RBC from osmotic hemolysis, but potentiated their sensitivity to the colloid‐osmotic lysis induced by a pore‐former nystatin. When added to the thymocytes suspension, gossypol caused a strong depression of the ability of cells to restore their volume under hypoosmotic stress with a half‐maximal activity at 2.1 ± 0.3 μmol/L. Gossypol suppressed regulatory volume decrease under experimental conditions, when cationic permeability was controlled by gramicidin D, and volume recovery depended mainly on anionic conductance, suggesting that the polyphenol inhibits the swelling‐induced anion permeability. In direct patch‐clamp experiments, gossypol inhibited the volume‐sensitive outwardly rectifying (VSOR) chloride channel in thymocytes and in human HCT116 and HeLa cells, possibly by a mechanism when gossypol molecule with a radius close to the size of channel pore plugs into the narrowest portion of the native VSOR chloride channel. Micromolar gossypol suppressed proliferation of thymocytes, HCT116 and HeLa cells. VSOR blockage may represent new mechanism of anticancer activity of gossypol in addition to its action as a BH3‐mimetic.

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Section: Resultsmentioning

confidence: 99%

Lytic and sublytic effects of gossypol on red blood cells and thymocytes

Chorieva

Fayziev

Tsiferova

et al. 2020

Clin Exp Pharma Physio

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“…[(2,2'-binaphthalene)-8,8'-dicarboxaldehyde,1,1',6,6',7,7'hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl] is a fat-soluble polyphenolic compound isolated from the seeds of Gossypium (cotton) [98,99]. Gossypol is widely reported in the literature for its anti-fertility [100,101], antioxidant [102],…”

Section: Gossypolmentioning

confidence: 99%

Antiviral activity of natural substances against main arboviruses DENV, ZIKV and CHIKV: literature review

Silva¹,

Santiago²,

Lopes³

et al. 2023

Cuad. Ed. Desar.

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Arboviruses have caused several epidemics worldwide, resulting in significant global health problems. Dengue virus (DENV), Zika virus (ZIKV), and Chikungunya virus (CHIKV) are endemic arboviruses throughout Brazil and have a significant impact on public health. Major gaps in protection against the most significant emerging arboviruses remain, as no antivirals are currently available, and vaccines are only available in a few countries. A potential source of antiviral compounds can be found in natural products, of which several compounds have been documented to have antiviral activities and are expected to have good efficacy and low side effects. Polyphenols and plant extracts have been studied for their antiviral properties against arboviruses and have shown promising results. Natural products continue to play an essential role in drug production and development. This study evaluated the antiviral potential of natural substances and extracts against DENV, ZIKV, and CHIKV. Original articles published between 2018 and 2022 in Portuguese and English on the antiviral activity of natural substances against arboviruses were reviewed. A total of 70 natural substances were evaluated against DENV, ZIKV, and CHIKV, and the potential antiviral activity against these viruses was analyzed. Some of these substances have shown promise in developing new antiviral compounds. With abundant natural products to screen for new antiviral compounds, they play an important role in developing new antiviral drugs and reducing arbovirus cases.

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“…Gossypol and its Schiff base formed with aniline have been previously reported to form inclusion compounds with many small organic compounds (Beketov et al, 1994;Gdaniec et al, 1996;Talipov et al, 2004). Some gossypol polymorphs (referred to as the P3 polymorph; Ibragimov et al, 1994), dianhydrogossypol (Talipov et al, 2009) and gossypol tetramethyl ether (Honkeldieva et al, 2015) form open-channel structures with channels of 5-8 Å width. In this report, we demonstrate that the Schiff base of gossypol with p-anizidine also forms an open-channel structure when the compound is crystallized from solutions in dichloromethane.…”

Section: Gossypolmentioning

confidence: 99%