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Acetate gossypol

CAS# 12542-36-8

Acetate gossypol

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Chemical structure

Acetate gossypol

3D structure

Chemical Properties of Acetate gossypol

Cas No. 12542-36-8 SDF Download SDF
PubChem ID 227456 Appearance Powder
Formula C32H34O10 M.Wt 578.61
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms (±)-Gossypol-acetic acid
Solubility DMSO : 25 mg/mL (43.21 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name acetic acid;7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde
SMILES CC1=C(C(=C2C(=C1)C(=C(C(=C2C=O)O)O)C(C)C)O)C3=C(C=C4C(=C3O)C(=C(C(=C4C(C)C)O)O)C=O)C.CC(=O)O
Standard InChIKey NIOHNDKHQHVLKA-UHFFFAOYSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Acetate gossypol

The seeds of Gossypium herbaceum L.

Biological Activity of Acetate gossypol

DescriptionAcetate gossypol has antifertility action. Acetate gossypol is a potent inhibitor of Bcl-2 and Bcl-xl, it has significant antiproliferative and antiapoptotic effects on multiple myeloma cells in vitro and in vivo, it also has apoptosis-inducing activity in primary cultured leukemia cells.
TargetsBcl-2/Bax | Caspase | Bcl-xl
In vitro

Induction of apoptosis and antitumor effects of a small molecule inhibitor of Bcl-2 and Bcl-xl, gossypol acetate, in multiple myeloma in vitro and in vivo.[Pubmed: 23708869 ]

Oncol Rep. 2013 Aug;30(2):731-8.

The aim of the present study was to investigate the induction of apoptosis and antitumor effects of Acetate gossypol in multiple myeloma and the possible mechanism(s) of action.
METHODS AND RESULTS:
Our results showed that Acetate gossypol resulted in a dose- and time-dependent inhibition of multiple myeloma cell proliferation, with an IC50 value to both U266 and Wus1 cells at 2.4, 2.2 μM at 48 h after treatment. Acetate gossypol effectively induced the apoptosis of multiple myeloma cells as demonstrated by typical morphological changes, DNA ladder formation and increase in the percentage of cells in subdiploid peak. Furthermore, colorimetric assays showed activation of both caspase-3 and caspase-9. Bcl-2 and Bcl-xl expression was decreased by 86.5±1.2% and 35.9±3.6%, respectively, after treatment with Acetate gossypol at 25 μmol/l for 24 h. Preliminary studies in vivo showed that a growth inhibition (T/C) of 30.9% (gossypol acetate 40 mg/kg) was obtained in Balb/C mice bearing Wus1 cells. In addition, there was no body weight loss for the treated group in comparison with the vehicle mice.
CONCLUSIONS:
Our results demonstrated that the potent inhibitor of Bcl-2 and Bcl-xl Acetate gossypol had significant antiproliferative and antiapoptotic effects on multiple myeloma cells in vitro and in vivo. Acetate gossypol may represent a promising new anticancer agent with a novel molecular mechanism and warrants further investigation as a single agent, or in combination with other chemotherapeutics, for human multiple myeloma with Bcl-2 overexpression.

Effect of gossypol acetate on proliferation and apoptosis in Raji lymphoblastoid cell line[Pubmed: 19968063 ]

Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 2009 Oct;31(5):527-32.

To investigate the effects of gossypol acetate(Acetate gossypol ) on proliferation and apoptosis in Raji lymphoblastoid cells and explore the possible mechanism.
METHODS AND RESULTS:
Trypan blue staining and ethyl thiazolyl diphenyl-tetrazolium bromide (MTT) assay were performed to measure the effect of gossypol acetate on the growth of Raji cells. The morphologic changes were observed with Wright's staining assay. Apoptosis was identified by agarose-gel electrophoresis and annexin V-FITC marked flow cytometry (FCM) analysis. The distribution of cell cycle, apoptosis rate, and Bcl-2 protein expression were analyzed by FCM. Caspase-3 activity was detected by colorimetric assay. Gossypol acetate inhibited proliferation and induced apoptosis of Raji cells at concentration higher than 5 micromol/L. The effects were both dose- and time- dependent. Cycle analysis indicated the alteration of cell cycle and G0/G1 arrest. The activation of Caspase-3 was observed by colorimetric assay. The results of flow cytometry showed that the down-regulation of Bcl-2 protein expression and the activation of Caspase-3 seemed to occur simultaneously.
CONCLUSIONS:
Gossypol acetate can inhibit the growth of Raji cells and induce their apoptosis. The mechanism may be related to the alteration of cell cycle and the down-regulation of Bcl-2 protein expression.

In vivo

Histopathological and biochemical effects of gossypol acetate on pituitary-gonadal axis of male albino rats.[Pubmed: 1623720]

Contraception. 1992 May;45(5):493-509.

Histopathological and biochemical effects of gossypol acetate (Acetate gossypol,GA) on pituitary-gonadal axis were investigated.
METHODS AND RESULTS:
10 and 25 mg GA/kg were administered orally to sexually mature adult male Wistar rats for 4 and 5 weeks, respectively. STH and LTH/PRL cells showed no significant changes as compared to those of controls while TSH cells showed hypertrophy, hyperplasia and degranulation in both experimental groups. Pituitary FSH, LH/ICSH cells showed progressive regression. Gonosomatic indices of sex accessory glands at 25 mg showed significant reduction in the experimental animals as compared to those of controls. The diameter of seminiferous tubules reduced and azoospermia developed. Sertoli and Leydig cells also regressed. At 10 and 25 mg GA treatment, spermatogenesis ceased at secondary spermatocytes and spermatogonia stages, respectively. Epididymis and prostate regressed. Seminal vesicle showed no significant histological variations as compared to that of control except reduction in secretion. Biochemical observations revealed increased levels of acid phosphatase, fructose and citric acid and significant reduction in glycerylphosphoryl choline in reproductive glands of both experimental groups as compared to those of controls. Possible mechanism of antifertility action of GA is discussed.

Protocol of Acetate gossypol

Cell Research

Effects of gossypol acetate on apoptosis in primary cultured cells from patients with lymphoid leukemia and its synergy with dexamethasone.[Pubmed: 22541072]

Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2012 Apr;20(2):229-34.

To investigate the effects of Acetate gossypol on apoptosis in primary cultured cells from patients with acute lymphoblastic leukemia (ALL) and chronic lymphocytic leukemia (CLL) and its synergistic effect with dexamethasone.
METHODS AND RESULTS:
The apoptosis-inducing effect of Acetate gossypol on primary cultured leukemia cells was analyzed by flow cytometry (FCM). The effect of Acetate gossypol on survival rates of Raji cells and mononuclear cells (MNC) from normal bone marrow were evaluated by MTT assay. After co-treatment with Acetate gossypol and dexamethasone, the apoptosis rate of Raji cells was detected by FCM. The results showed that Acetate gossypol was able to induce apoptosis in primary cultured ALL cells at concentrations of ≥ 5 μmol/L. The effect was concentration and time dependent. No major growth inhibitory effect was observed in MNC from normal bone marrow when they were exposed to Acetate gossypol at concentrations lower than 10 μmol/L. After exposing for 48 and 72 h, the IC(50) of Acetate gossypol for MNC from normal bone marrow was 7.1 and 9.1 times as much as the IC(50) of Raji cells. Co-treatment with 10 μmol/L Acetate gossypol and dexamethasone remarkably increased the apoptosis rate of Raji cells.
CONCLUSIONS:
It is concluded that the Acetate gossypol has apoptosis-inducing activity in primary cultured leukemia cells from patients diagnosed as ALL and CLL in vitro. The inhibitory effect of Acetate gossypol on MNC from normal bone marrow is less prominent than that on Raji cells. Co-treatment with Acetate gossypol and dexamethasone notably amplified the pro-apoptosis activity of the latter in Raji cells.

Animal Research

Effect of gossypol acetate on guinea pig epididymal spermatozoa in vivo and their susceptibility to capacitation in vitro.[Pubmed: 3972719]

J Androl. 1985 Jan-Feb;6(1):45-52.


METHODS AND RESULTS:
To determine the effects of gossypol acetate(Acetate gossypol ) on guinea pig epididymal and vas deferens sperm maturity and in vivo susceptibility to in vitro capacitation and the acrosome reaction, we examined spermatozoa removed from 37 animals fed gossypol acetate (10-15 mg/kg/day) for 5 to 9 weeks, and 15 vegetable oil-fed, age-paired control animals. In gossypol-treated, reproductively immature guinea pigs, the number of spermatozoa in the epididymis was markedly reduced (P less than 0.01) compared to controls, whereas the presence of spermatids and spermatocytes increased in the epididymis with the duration of gossypol administration. In sexually mature guinea pigs (given 15 mg/kg/day for 5 weeks), the epididymal sperm survival and forward motility were decreased significantly (P less than 0.025 and P less than 0.01, respectively), although the density of mature spermatozoa was the same as in control animals. The percentage of induced acrosome reactions (26.4 +/- 12%) was almost three-fold lower than that of control animals (72.8 +/- 4.6%). Also, in 31.5 +/- 3.8% of spermatozoa from gossypol-treated animals, as compared to only 2.4 +/- 0.7% of controls, the cytoplasmic droplet failed to migrate to its proper position in the midpiece and was retained in the neck region. With a few exceptions, spermatozoa from both experimental and control groups had comparable patterns of freeze-fractured membrane differentiations. Susceptibility to the induced acrosome reactions and the position of the retained cytoplasmic droplet reversed within 3 weeks after the end of gossypol feeding.
METHODS AND RESULTS:
This study helps establish the suitability of the guinea pig for studies on gossypol-induced infertility.

Acetate gossypol Dilution Calculator

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Preparing Stock Solutions of Acetate gossypol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7283 mL 8.6414 mL 17.2828 mL 34.5656 mL 43.207 mL
5 mM 0.3457 mL 1.7283 mL 3.4566 mL 6.9131 mL 8.6414 mL
10 mM 0.1728 mL 0.8641 mL 1.7283 mL 3.4566 mL 4.3207 mL
50 mM 0.0346 mL 0.1728 mL 0.3457 mL 0.6913 mL 0.8641 mL
100 mM 0.0173 mL 0.0864 mL 0.1728 mL 0.3457 mL 0.4321 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Acetate gossypol

Gossypol, a natural product isolated from cottonseeds and roots, binds to Bcl-xL protein and Bcl-2 protein with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively.

In Vitro:Gossypol, a natural product isolated from cottonseeds and roots that has been studied as an anticancer agent. The racemic form of Gossypol [(±)-Gossypol] is tested in several clinical trials and is well tolerated. The racemic form Gossypol ((±)-Gossypol) binds to Bcl-xL protein with a Ki of 0.5 to 0.6 μM. (±)-Gossypol also potently binds to Bcl-2 protein with a Ki value of 0.2-0.3 mM. The natural racemic Gossypol has two enantiomers, namely the (-)-Gossypol and (+)-Gossypol enantiomers. The racemic form and each of the enantiomers of Gossypol are tested against UM-SCC-6 and UM-SCC-14A in 6-day MTT assays. (-)-Gossypol exhibits greater growth inhibition relative to (±)-Gossypol than (+)-Gossypol in both cell lines tested (P<0.001). An intermediate growth inhibitory effect is observed with (±)-Gossypol but this effect is only observed at the higher dose of Gossypol (10 μM, P<0.0001)[1].

References:
[1]. Oliver CL, et al. In vitro effects of the BH3 mimetic, (-)-Gossypol, on head and neck squamous cell carcinoma cells. Clin Cancer Res. 2004 Nov 15;10(22):7757-63.

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References on Acetate gossypol

[Effect of gossypol acetate on proliferation and apoptosis in Raji lymphoblastoid cell line].[Pubmed:19968063]

Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 2009 Oct;31(5):527-32.

OBJECTIVE: To investigate the effects of gossypol acetate on proliferation and apoptosis in Raji lymphoblastoid cells and explore the possible mechanism. METHODS: Trypan blue staining and ethyl thiazolyl diphenyl-tetrazolium bromide (MTT) assay were performed to measure the effect of gossypol acetate on the growth of Raji cells. The morphologic changes were observed with Wright's staining assay. Apoptosis was identified by agarose-gel electrophoresis and annexin V-FITC marked flow cytometry (FCM) analysis. The distribution of cell cycle, apoptosis rate, and Bcl-2 protein expression were analyzed by FCM. Caspase-3 activity was detected by colorimetric assay. RESULTS: Gossypol acetate inhibited proliferation and induced apoptosis of Raji cells at concentration higher than 5 micromol/L. The effects were both dose- and time- dependent. Cycle analysis indicated the alteration of cell cycle and G0/G1 arrest. The activation of Caspase-3 was observed by colorimetric assay. The results of flow cytometry showed that the down-regulation of Bcl-2 protein expression and the activation of Caspase-3 seemed to occur simultaneously. CONCLUSION: Gossypol acetate can inhibit the growth of Raji cells and induce their apoptosis. The mechanism may be related to the alteration of cell cycle and the down-regulation of Bcl-2 protein expression.

[Effects of gossypol acetate on apoptosis in primary cultured cells from patients with lymphoid leukemia and its synergy with dexamethasone].[Pubmed:22541072]

Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2012 Apr;20(2):229-34.

To investigate the effects of gossypol acetate on apoptosis in primary cultured cells from patients with acute lymphoblastic leukemia (ALL) and chronic lymphocytic leukemia (CLL) and its synergistic effect with dexamethasone. The apoptosis-inducing effect of gossypol acetate on primary cultured leukemia cells was analyzed by flow cytometry (FCM). The effect of gossypol acetate on survival rates of Raji cells and mononuclear cells (MNC) from normal bone marrow were evaluated by MTT assay. After co-treatment with gossypol acetate and dexamethasone, the apoptosis rate of Raji cells was detected by FCM. The results showed that gossypol acetate was able to induce apoptosis in primary cultured ALL cells at concentrations of >/= 5 micromol/L. The effect was concentration and time dependent. Apoptosis-inducing concentration in CLL cells was higher than that in ALL cells. After exposing to 50 micromol/L gossypol acetate for 48 h, the apoptosis rate of ALL and CLL cells were (90.4 +/- 6.2)% and (51.7 +/- 10.3)% separately. No major growth inhibitory effect was observed in MNC from normal bone marrow when they were exposed to gossypol acetate at concentrations lower than 10 micromol/L. After exposing for 48 and 72 h, the IC(50) of gossypol acetate for MNC from normal bone marrow was 7.1 and 9.1 times as much as the IC(50) of Raji cells. Co-treatment with 10 micromol/L gossypol acetate and dexamethasone remarkably increased the apoptosis rate of Raji cells. It is concluded that the gossypol acetate has apoptosis-inducing activity in primary cultured leukemia cells from patients diagnosed as ALL and CLL in vitro. The inhibitory effect of gossypol acetate on MNC from normal bone marrow is less prominent than that on Raji cells. Co-treatment with gossypol acetate and dexamethasone notably amplified the pro-apoptosis activity of the latter in Raji cells.

Histopathological and biochemical effects of gossypol acetate on pituitary-gonadal axis of male albino rats.[Pubmed:1623720]

Contraception. 1992 May;45(5):493-509.

Histopathological and biochemical effects of gossypol acetate (GA) on pituitary-gonadal axis were investigated. 10 and 25 mg GA/kg were administered orally to sexually mature adult male Wistar rats for 4 and 5 weeks, respectively. STH and LTH/PRL cells showed no significant changes as compared to those of controls while TSH cells showed hypertrophy, hyperplasia and degranulation in both experimental groups. Pituitary FSH, LH/ICSH cells showed progressive regression. Gonosomatic indices of sex accessory glands at 25 mg showed significant reduction in the experimental animals as compared to those of controls. The diameter of seminiferous tubules reduced and azoospermia developed. Sertoli and Leydig cells also regressed. At 10 and 25 mg GA treatment, spermatogenesis ceased at secondary spermatocytes and spermatogonia stages, respectively. Epididymis and prostate regressed. Seminal vesicle showed no significant histological variations as compared to that of control except reduction in secretion. Biochemical observations revealed increased levels of acid phosphatase, fructose and citric acid and significant reduction in glycerylphosphoryl choline in reproductive glands of both experimental groups as compared to those of controls. Possible mechanism of antifertility action of GA is discussed.

Induction of apoptosis and antitumor effects of a small molecule inhibitor of Bcl-2 and Bcl-xl, gossypol acetate, in multiple myeloma in vitro and in vivo.[Pubmed:23708869]

Oncol Rep. 2013 Aug;30(2):731-8.

Gossypol is a naturally occurring polyphenolic compound extracted from cotton plants. Recent studies revealed that gossypol is a non-peptidic small molecule inhibitor of Bcl-2/Bcl-xl. The aim of the present study was to investigate the induction of apoptosis and antitumor effects of gossypol acetate in multiple myeloma and the possible mechanism(s) of action. Our results showed that gossypol acetate resulted in a dose- and time-dependent inhibition of multiple myeloma cell proliferation, with an IC50 value to both U266 and Wus1 cells at 2.4, 2.2 microM at 48 h after treatment. Gossypol acetate effectively induced the apoptosis of multiple myeloma cells as demonstrated by typical morphological changes, DNA ladder formation and increase in the percentage of cells in subdiploid peak. Furthermore, colorimetric assays showed activation of both caspase-3 and caspase-9. Bcl-2 and Bcl-xl expression was decreased by 86.5+/-1.2% and 35.9+/-3.6%, respectively, after treatment with gossypol acetate at 25 micromol/l for 24 h. Preliminary studies in vivo showed that a growth inhibition (T/C) of 30.9% (gossypol acetate 40 mg/kg) was obtained in Balb/C mice bearing Wus1 cells. In addition, there was no body weight loss for the treated group in comparison with the vehicle mice. Our results demonstrated that the potent inhibitor of Bcl-2 and Bcl-xl gossypol acetate had significant antiproliferative and antiapoptotic effects on multiple myeloma cells in vitro and in vivo. Gossypol acetate may represent a promising new anticancer agent with a novel molecular mechanism and warrants further investigation as a single agent, or in combination with other chemotherapeutics, for human multiple myeloma with Bcl-2 overexpression.

Effect of gossypol acetate on guinea pig epididymal spermatozoa in vivo and their susceptibility to capacitation in vitro.[Pubmed:3972719]

J Androl. 1985 Jan-Feb;6(1):45-52.

To determine the effects of gossypol acetate on guinea pig epididymal and vas deferens sperm maturity and in vivo susceptibility to in vitro capacitation and the acrosome reaction, we examined spermatozoa removed from 37 animals fed gossypol acetate (10-15 mg/kg/day) for 5 to 9 weeks, and 15 vegetable oil-fed, age-paired control animals. In gossypol-treated, reproductively immature guinea pigs, the number of spermatozoa in the epididymis was markedly reduced (P less than 0.01) compared to controls, whereas the presence of spermatids and spermatocytes increased in the epididymis with the duration of gossypol administration. In sexually mature guinea pigs (given 15 mg/kg/day for 5 weeks), the epididymal sperm survival and forward motility were decreased significantly (P less than 0.025 and P less than 0.01, respectively), although the density of mature spermatozoa was the same as in control animals. The percentage of induced acrosome reactions (26.4 +/- 12%) was almost three-fold lower than that of control animals (72.8 +/- 4.6%). Also, in 31.5 +/- 3.8% of spermatozoa from gossypol-treated animals, as compared to only 2.4 +/- 0.7% of controls, the cytoplasmic droplet failed to migrate to its proper position in the midpiece and was retained in the neck region. With a few exceptions, spermatozoa from both experimental and control groups had comparable patterns of freeze-fractured membrane differentiations. Susceptibility to the induced acrosome reactions and the position of the retained cytoplasmic droplet reversed within 3 weeks after the end of gossypol feeding. This study helps establish the suitability of the guinea pig for studies on gossypol-induced infertility.

Description

Gossypol acetic acid ((±)-Gossypol-acetic acid), a natural product isolated from cottonseeds and roots, binds to Bcl-xL protein and Bcl-2 protein with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively.

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