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12542-36-8 (Gossypol (acetic acid))

1

Identification

Gossypol (acetic acid) Gossypol (acetic acid)
Name Gossypol (acetic acid)
Formula C32H34O10
MW 578.6064
CAS No. 12542-36-8
EINECS
Smiles OC1=C(C2=C(O)C(C(C=O)=C(O)C(O)=C3C(C)C)=C3C=C2C)C(C)=CC4=C(C(C)C)C(O)=C(O)C(C=O)=C41.O=C(O)C
Synonyms (±)-Gossypol-acetic aci
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)
2

Introduction

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.

Background Information

AT101, the R-(-) enantiomer of Gossypol acetic acid, binds with Bcl-2, Bcl-xL and Mcl-1 with Ki of 0.32 μM, 0.48 μM and 0.18 μM; does not inhibit BIR3 domain and BID
......by AdooQ BioScience, LLC
(S)-Gossypol acetic acid is a inhibitor of Bcl-2, potently induce cell death in Jurkat cells overexpressing Bcl-2 (IC50, 18.1μM) or Bcl-xL (IC50, 22.9μM). ......by AdooQ BioScience, LLC
Acetate gossypol, a polyphenolic compound isolated from cottonseeds, inhibits Bcl-2 by acting as a BH3 mimetic. ......by AdooQ BioScience, LLC
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. ......by BOC Sciences
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. ......by MedChemexpress Co., Ltd.
Gossypol is an orally-active polyphenolic aldehyde with potential antineoplastic activity. Derived primarily from unrefined cottonseed oil, gossypol induces cell cycle arrest at the G0/G1 phase, thereby inhibiting DNA replication and inducing apoptosis. This agent also inhibits cell-signaling enzymes, resulting in inhibition of cell growth, and may act as a male contraceptive. ......by MedKoo Biosciences, Inc.
Gossypol Acetate is a polyphenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes such as lactate dehydrogenase, NAD-linked enzymes. ......by Selleck Chemicals LLC
Gossypol-acetic acid, a polyphenolic compound isolated from cottonseeds, inhibits Bcl-2 by acting as a BH3 mimetic. ......by Target Molecule Corp.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:Light yellow to yellow Solid EBNumber:EB000012609

Storage condition

Solubility

DMSO by MedChemexpress Co., Ltd.
5

Mechanism and Indication

6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Gossypol (acetic acid) University of Michigan Comprehensive Cancer Center Larynx tumor 2012/3/31 2016/1/31 Phase 2 Clinical
Gossypol (acetic acid) University of Michigan Comprehensive Cancer Center Head and neck tumor 2010/6/30 2016/1/31 Phase 2 Clinical
Gossypol (acetic acid) Memorial Sloan-Kettering Cancer Center Metastatic non small cell lung cancer 2009/9/30 2010/5/31 Phase 2 Clinical
Gossypol (acetic acid) The Cancer Institute of New Jersey Metastatic prostate cancer 2009/7/31 2011/5/31 Phase 2 Clinical
Gossypol (acetic acid) Ascenta Therapeutics Inc Non-small-cell lung cancer 2007/9/30 2009/4/1 Phase 2 Clinical
Gossypol (acetic acid) National Cancer Institute Adrenal cortical carcinoma 2009/2/28 2012/3/1 Phase 2 Clinical
Gossypol (acetic acid) - No Development Reported
7

Safety Data of Gossypol (acetic acid)

Hazard Symbols : Xn
Risk Statements : R22;R40
Safety Statements : S22;S36
RTECS : MD7360000
WGKGermany : 3
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
AdooQ BioScience, LLC USA
AdooQ BioScience, LLC USA
AdooQ BioScience, LLC USA
Alfa Chemistry USA
Apexbio Technology LLC USA
Ark Pharm, Inc. USA
BOC Sciences
Biochempartner Co., Ltd China
CHEMSCENE, LLC 200mg/USD114();500mg/USD210() USA
Carbosynth Limited 5g/USD325()
MedChemexpress Co., Ltd. 200mg/USD114();500mg/USD210() USA
MedKoo Biosciences, Inc. USA
Santa Cruz Biotechnology, Inc. 250mg/USD120() USA
Selleck Chemicals LLC USA
Shanghai Haoyuan Chemexpress Co., Ltd. 200mg/USD114();500mg/USD210() China
Sigma-Aldrich, Inc. 250mg/USD126() USA
Target Molecule Corp. 5mg/USD24();10mg/USD45();20mg/USD88();100mg/USD198();250mg/USD329() USA
Wuhan ChemFaces Biochemical Co., Ltd. 20mg/USD100() China
Zhejiang Yixin Pharmaceutical Co., Ltd. China
10

Related Products

Other Forms of 12542-36-8

Name CAS No Formula MW
Gossypol 303-45-7 C30H30O8 518.55

Recommended Compounds in Bcl-2 Family

Name CAS No Formula MW
MIM1 509102-00-5 C17H21N3O3S 347.43
713492-66-1
Marinopyrrole A 1227962-62-0 C22H12Cl4N2O4 510.15
WEHI-539 1431866-33-9 C31H29N5O3S2 583.72
Gambogic Acid 2752-65-0 C38H44O8 628.75
ABT-199 1257044-40-8 C45H50ClN7O7S 868.44
(±)-Apogossypol 475-56-9 C28H30O6 462.5342
Gossypol 303-45-7 C30H30O8 518.55
AT-101 90141-22-3 C30H30O8 518.55
BAM7 331244-89-4 C21H19N5O2S 405.47
SZ4TA2 406231-90-1 C28H32N4O5S2 568.71
TW-37 877877-35-5 C33H35NO6S 573.7
HA14-1 65673-63-4 C17H17BrN2O5 409.23
Obatoclax 803712-79-0 C21H23N3O4S 413.49
ABT-737 852808-04-9 C42H45ClN6O5S2 813.43
Navitoclax 923564-51-6 C47H55ClF3N5O6S3 974.61
Bax inhibitor peptide V5 579492-81-2 C27H50N6O6S 586.79
A-1331852 1430844-80-6 C38H38N6O3S 658.81
A-1155463 1235034-55-5 C35H32FN5O4S2 669.79
Bz 423 216691-95-1 C27H21ClN2O2 440.92

Recommended Compounds in Same Indication

Name CAS No Formula MW
LDK378 1032900-25-6 C28H36ClN5O3S 558.14
Pemetrexed (disodium) 150399-23-8 C20H19N5Na2O6 471.37
Volasertib 755038-65-4 C34H50N8O3 618.81
ALK inhibitor 1 761436-81-1 C23H28BrN7O3S 562.48
Olaparib 763113-22-0 C24H23FN4O3 434.46
Afatinib (dimaleate) 850140-73-7 C32H33ClFN5O11 718.08
MGCD-265 analog 875337-44-3 C26H20FN5O2S2 517.5977
Crizotinib 877399-52-5 C21H22Cl2FN5O 450.34
AT-101 90141-22-3 C30H30O8 518.55
Bicalutamide 90357-06-5 C18H14F4N2O4S 430.37
Tivantinib 905854-02-6 C23H19N3O2 369.42
Enzalutamide 915087-33-1 C21H16F4N4O2S 464.44
Dovitinib 405169-16-6 C21H21FN6O 392.43
Tivozanib 475108-18-0 C22H19ClN4O5 454.86
Nordihydroguaiaretic acid 500-38-9 C18H22O4 302.36
Sunitinib 557795-19-4 C22H27FN4O2 398.47
Orteronel 566939-85-3 C18H17N3O2 307.35
Linsitinib 867160-71-2 C26H23N5O 421.49
Leuprolide (Acetate) 74381-53-6 C61H88N16O14 1269.45
TAK-700 (R-form) 752243-39-3 C18H17N3O2 307.35
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Route of Synthesis

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References

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More Information

Gossypol (acetic acid)

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