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Gossypol Acetic Acid - CAS 12542-36-8 Catalog number: BADC-00267
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Gossypol Acetic Acid is a phenol compound from plants of the Gossypium genus, Malvaceae. It binds to Bcl-xL protein and Bcl-2 protein with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively. It exhibits antiviral activity at low concentration.
Category
ADCs Cytotoxin
Product Name
Gossypol Acetic Acid
CAS
12542-36-8
Catalog Number
BADC-00267
Molecular Formula
C32H34O10
Molecular Weight
578.61
Ordering Information
| Catalog Number | Size | Price | Quantity |
|---|---|---|---|
| BADC-00267 | 5 g | $439 |
Description
Gossypol Acetic Acid is a phenol compound from plants of the Gossypium genus, Malvaceae. It binds to Bcl-xL protein and Bcl-2 protein with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively. It exhibits antiviral activity at low concentration.
Synonyms
Gossypol acetate; Acetate gossypol
IUPAC 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
Canonical 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
InChI
InChI=1S/C30H30O8.C2H4O2/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36;1-2(3)4/h7-12,33-38H,1-6H3;1H3,(H,3,4)
InChIKey
NIOHNDKHQHVLKA-UHFFFAOYSA-N
Solubility
Acetone, not well in ether, chloroform, ethanol, not in water
Melting Point
177-182 ℃ (dec.)
LogP
6.47310
In Vitro
Gossypol acetic acid depressed significantly the metabolic rate of the cells. Glucose utilization was abolished by a starting dose of 100 micrograms/ml. Oxygen consumption of I-cells was reduced even at a smaller dose of gossypol (50 micrograms/ml). At these doses, the vitality of the cells remained (proven by trypan blue exclusion test). 3 beta-Hydroxysteroid dehydrogenase (3 beta-HSD) histochemical stain was slightly decreased. Increasing doses of gossypol caused a marked decrease in the vitality of I-cells and a dramatic drop in histochemical stain for 3 beta-HSD. The pH of the medium was not changed at any dose of treatment. In cultures of I-cells not stimulated by hCG, gossypol did not affect the tonic slow release of testosterone. Thus, gossypol acetic acid has a direct inhibitory effect on isolated rat I-cells, depressing cell metabolism.
In Vivo
The concentrations of total and free gossypol acetic acid (gossypol) in the cottonseed cake were 3.28 mg/g and 0.11 mg/g, respectively. Throughout the trial period, no animal showed clinical signs of toxicity and no effects on body weight were observed. However, there was a significantly lower number of viable ovarian follicles (20.6%) and higher number of atretic follicles (79.4%) in the gossypol-fed sheep compared to the control (85.1 and 34.9%, respectively). These findings were observed at all stages of follicular development. In the second experiment, eight ovaries from slaughterhouse were cultured with different concentrations of gossypol acetic acid (0, 5, 10 and 20 μg/mL) for 24 hours or seven days. The in vitro action of gossypol resulted in a significant decrease in viable ovarian follicles, especially the primary and transition follicles, and a significant increase in the number of atretic follicles after 24 hours of culture. These follicles were greatly affected when cultured with gossypol for seven days. It is concluded that gossypol present in cotton seeds directly acts on ovarian follicles in sheep to increase atresia.
Clinical Trial Information
| NCT Number | Condition Or Disease | Phase | Start Date | Sponsor | Status |
|---|---|---|---|---|---|
| NCT00544960 | Non-small Cell Lung Cancer | Phase 2 | 2010-08-27 | Ascenta Therapeutics | Completed |
| NCT02697344 | Recurrent Plasma Cell Myeloma | Phase 1 | 2021-08-18 | Mayo Clinic | Active, not recruiting |
| NCT00544596 | Extensive Stage Small Cell Lung Cancer | Phase 1 | 2014-04-02 | National Cancer Institute (NCI) | Completed |
| NCT00848016 | Recurrent Adrenocortical Carcinoma | Phase 2 | 2014-05-07 | National Cancer Institute (NCI) | Completed |
| NCT00773955 | Extensive Stage Small Cell Lung Cancer | Phase 2 | 2014-05-12 | National Cancer Institute (NCI) | Completed |
Appearance
Yellow solid
Purity
98 % by HPLC
Quantity
Grams-Kilos
Quality Standard
Enterprise Standard
Shipping
Room temperature
Storage
Store at +4 ℃, in dark place.
Pictograms
Irritant; Health Hazard
Signal Word
Warning
Boiling Point
707.9 ℃ at 760 mmHg
1.Sequential treatment with AT-101 enhances cisplatin chemosensitivity in human non-small cell lung cancer cells through inhibition of apurinic/apyrimidinic endonuclease 1-activated IL-6/STAT3 signaling pathway.
Ren T1, Shan J2, Qing Y2, Qian C2, Li Q2, Lu G2, Li M2, Li C2, Peng Y2, Luo H2, Zhang S2, Zhang W2, Wang D2, Zhou SF3. Drug Des Devel Ther. 2014 Dec 12;8:2517-29. doi: 10.2147/DDDT.S71432. eCollection 2014.
AT-101, known as R-(-)-gossypol, is a potent anticancer agent, but its chemosensitizing effects remain elusive. The present study aimed to examine whether AT-101 could increase the sensitivity of non-small cell lung cancer A549 cells to cisplatin (CDDP) and the underlying mechanisms. We evaluated the efficacy of the sequential treatment with AT-101 and CDDP using both in vitro and in vivo models. Our results showed that as compared to AT-101 or CDDP monotherapy, or AT-101 plus CDDP concurrent treatment, the sequential treatment significantly inhibited cell proliferation and migration and induced tumor cell death. Moreover, the efficacy of the sequential treatment was also confirmed in a mouse A549 xenograft model. Our study revealed that AT-101 inhibited the reduced status of apurinic/apyrimidinic endonuclease 1 (APE1) and attenuated APE1-mediated IL-6/STAT3 signaling activation by decreasing IL-6 protein expression; suppressing the STAT3-DNA binding; and reducing the expression of the downstream antiapoptotic proteins Bcl-2 and Bcl-xL.
2.Chemoresistance is associated with increased cytoprotective autophagy and diminished apoptosis in bladder cancer cells treated with the BH3 mimetic (-)-Gossypol (AT-101).
Mani J1, Vallo S2, Rakel S3, Antonietti P4, Gessler F5, Blaheta R6, Bartsch G7, Michaelis M8,9, Cinatl J10, Haferkamp A11, Kögel D12. BMC Cancer. 2015 Apr 7;15:224. doi: 10.1186/s12885-015-1239-4.
BACKGROUND: Acquired resistance to standard chemotherapy causes treatment failure in patients with metastatic bladder cancer. Overexpression of pro-survival Bcl-2 family proteins has been associated with a poor chemotherapeutic response, suggesting that Bcl-2-targeted therapy may be a feasible strategy in patients with these tumors. The small-molecule pan-Bcl-2 inhibitor (-)-gossypol (AT-101) is known to induce apoptotic cell death, but can also induce autophagy through release of the pro-autophagic BH3 only protein Beclin-1 from Bcl-2. The potential therapeutic effects of (-)-gossypol in chemoresistant bladder cancer and the role of autophagy in this context are hitherto unknown.
3.Targeting BCL2 for the treatment of lymphoid malignancies.
Anderson MA1, Huang D2, Roberts A3. Semin Hematol. 2014 Jul;51(3):219-27. doi: 10.1053/j.seminhematol.2014.05.008. Epub 2014 May 15.
The failure of apoptosis (programmed cell death) underpins the development of many tumors and often renders them resistant to cytotoxic therapies. In hematologic malignancies, this impairment of apoptosis is often caused by overexpression of the pro-survival protein BCL2. Because abnormally high levels of BCL2 sustain these tumors, there has been much interest in targeting BCL2 as a novel approach to treating various hematologic malignancies. One such approach is the development of BH3 mimetic compounds, small molecules that mimic the action of the BH3-only proteins, natural antagonists of BCL2 and its pro-survival relatives. These compounds act by restoring the ability of a cell to undergo apoptotic cell death. Some of them have shown very encouraging results in early-phase clinical trials that are currently underway, particularly in patients with chronic lymphocytic leukemia and some non-Hodgkin lymphomas, diseases marked by BCL2 overexpression.
4.Toxicity of Gossypol from Cottonseed Cake to Sheep Ovarian Follicles.
Câmara AC1, Gadelha IC1, Borges PA1, de Paiva SA1, Melo MM2, Soto-Blanco B2. PLoS One. 2015 Nov 24;10(11):e0143708. doi: 10.1371/journal.pone.0143708. eCollection 2015.
Gossypol, a polyphenol compound produced by cotton plant, has proven reproductive toxicity, but the effects of gossypol on sheep ovaries are unknown. This study was aimed to determine the in vitro and in vivo effects of gossypol on the ovarian follicles of sheep. This trial was divided into two experiments. In the first one, we used twelve non-pregnant, nulliparous, Santa Inês crossbred ewes, which were randomly distributed into two equal groups and fed diets with and without cottonseed cake. Feed was offered at 1.5% of the animal's body weight for 63 days. The concentrations of total and free gossypol in the cottonseed cake were 3.28 mg/g and 0.11 mg/g, respectively. Throughout the trial period, no animal showed clinical signs of toxicity and no effects on body weight were observed. However, there was a significantly lower number of viable ovarian follicles (20.6%) and higher number of atretic follicles (79.4%) in the gossypol-fed sheep compared to the control (85.
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