Selective inhibition of human immunodeficiency virus type 1 replication by the (-) but not the (+) enantiomer of gossypol

Lin, Tao; Schinazi, Raymond F.; Griffith, Brigitte P.; August, Elias; Eriksson, Barbro; Zheng, Duo-Kai; Huang, Liang; Prusoff, William H.

doi:10.1128/aac.33.12.2149

Cited by 106 publications

(51 citation statements)

References 29 publications

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“…It is not clear whether the inhibition of HIV-1 reverse transcriptase by gossypol is the primary mechanism of action. Lin et al (1989) have synthesized analogs of gossypol for potential antiviral activity against HIV-1.…”

Section: Antivirus Propertiesmentioning

confidence: 99%

Therapeutic potential of gossypol: An overview

Neghab

Goliaei

2013

Pharmaceutical Biology

102

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Context: Polyphenols are naturally occurring compounds found in fruits, vegetables, cereals, and beverages. Polyphenols occupy a unique place in biological science for their pharmacological properties. Gossypol is a polyphenolic compound that has attracted attention because of its biological effects. Objective: Gossypol is reported to exhibit antifertility, antioxidant, anticancer, antivirus, antiparasitic, and antimicrobial properties and lower plasma cholesterol. These are summarized with attention to the mechanisms of activity. Methods: This review summarizes the results of studies obtained in a comprehensive search of ScienceDirect, PubMed, Scirus, and Web of Science. Results and conclusion: The results of these studies provide a comprehensive understanding of the biological action of gossypol and its potential for the prevention of and therapy for resistant tumors and chronic human diseases such as HIV, malaria, and psoriasis.

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Section: Antivirus Propertiesmentioning

confidence: 99%

Therapeutic potential of gossypol: An overview

Neghab

Goliaei

2013

Pharmaceutical Biology

102

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“…16 Their high activity against viruses presents a new possibility to use derivatives of gossypol in the development of new kinds of antiviral drugs. [17][18][19][20] Moreover, an earlier investigation indicated that gossypol analogues may have therapeutic potential against human breast cancer. 21 The addition of amines to cottonseed causes lower toxicity of animal fodder.…”

Section: Introductionmentioning

confidence: 98%

Spectroscopic studies and PM3 semiempirical calculations of Schiff bases of gossypol with L‐amino acid methyl esters

Przybylski

Brzeziński

2002

Biopolymers

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Three Schiff bases of racemic gossypol with L-amino acid methyl esters are synthesized and studied by FTIR and (1)H-NMR spectroscopy, and their structures are calculated by the PM3 semiempirical method. The Schiff bases in the study exist in the solid state and in solutions as enamine forms. The existence of diastereoisomers is very visible in the (1)H-NMR spectra. The amount of the diastereoisomers depends on the amount of time the solutions are rested in diffused light. The epimerization from D,L-isomer to L,L-isomer is very slow. The structures of the Schiff bases and the hydrogen bonds within these structures are discussed.

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“…14 The presence of gossypol derivatives in the database search results posed an interesting question. The parent gossypol compound was reported in 1989 as an anti-HIV agent, 19 however, it was stated that it was unlikely to be primarily a reverse transcriptase inhibitor, although no data was presented for the effects of gossypol in a reverse transcriptase assay. In a later article (1995), 20 the effects of gossylic iminolactone (GIL) were compared to those of AZT to ascertain whether they have different targets.…”

Section: Figure 4: An Example Of An Adam (Arenediarylmethane) Structumentioning

confidence: 99%

Novel pharmacophore-based methods reveal gossypol as a reverse transcriptase inhibitor

Keller

Birch

Leach

et al. 2003

Journal of Molecular Graphics and Modelling

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In a program to identify new structural entities for the inhibition of the HIV-1 reverse transcriptase (RT) enzyme via database searching, a series of RT pharmacophores were developed. By utilising a novel filtering technique, the National Cancer Institute database of compounds was scanned producing 15 compounds to be screened for activity. A notable inclusion was a series of gossypol derivatives. The testing of a series of compounds revealed the parent compound gossypol to be an HIV-1 reverse transcriptase inhibitor. These results suggest that at least part of its anti-HIV activity is due to gossypol targeting the non-nucleoside inhibitor binding pocket of RT. AbstractIn a program to identify new structural entities for the inhibition of the HIV-1 reverse transcriptase (RT) enzyme via database searching, a series of RT pharmacophores were developed. By utilising a novel filtering technique, the National Cancer Institute database of compounds was scanned producing 15 compounds to be screened for activity. A notable inclusion was a series of gossypol derivatives. The testing of a series of compounds revealed the parent compound gossypol to be an HIV-1 reverse 2 transcriptase inhibitor. These results suggest that at least part of its anti-HIV activity is due to gossypol targeting the non-nucleoside inhibitor binding pocket of RT.

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Selective inhibition of human immunodeficiency virus type 1 replication by the (-) but not the (+) enantiomer of gossypol

Cited by 106 publications

References 29 publications

Therapeutic potential of gossypol: An overview

Therapeutic potential of gossypol: An overview

Spectroscopic studies and PM3 semiempirical calculations of Schiff bases of gossypol with L‐amino acid methyl esters

Novel pharmacophore-based methods reveal gossypol as a reverse transcriptase inhibitor

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