MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 527668 | Name: Apogossypolone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Apogossypolone is a potent inhibitor of Bcl-2 and Mcl-1, acting as a BH3 mimetic.

Chemical Structure

Apogossypolone
Apogossypolone
CAS#886578-07-0

Theoretical Analysis

MedKoo Cat#: 527668

Name: Apogossypolone

CAS#: 886578-07-0

Chemical Formula: C28H26O8

Exact Mass: 490.1628

Molecular Weight: 490.51

Elemental Analysis: C, 68.56; H, 5.34; O, 26.09

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Apogossypolone
IUPAC/Chemical Name
6,7,6',7'-Tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,4,1',4'-tetraone
InChi Key
GYYXKPBLWDDQQK-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H26O8/c1-9(2)17-21-13(7-15(29)27(17)35)25(33)19(11(5)23(21)31)20-12(6)24(32)22-14(26(20)34)8-16(30)28(36)18(22)10(3)4/h7-10,29-30,35-36H,1-6H3
SMILES Code
O=C1C(C(C2=O)=C(C)C(C3=C2C=C(O)C(O)=C3C(C)C)=O)=C(C)C(C4=C1C=C(O)C(O)=C4C(C)C)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 490.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: He X, Wu C, Cui Y, Zhu H, Gao Z, Li B, Hua J, Zhao B. The aldehyde group of gossypol induces mitochondrial apoptosis via ROS-SIRT1-p53-PUMA pathway in male germline stem cell. Oncotarget. 2017 Oct 24;8(59):100128-100140. doi: 10.18632/oncotarget.22044. eCollection 2017 Nov 21. PubMed PMID: 29245965; PubMed Central PMCID: PMC5725007. 2: Lin D, Li X, Xu L, Lian J, Xu Y, Meng L, Xie X, Wang X, He H, Xu D, Wang C, Zhu Y. Apogossypolone (ApoG2) induces ROS-dependent apoptosis and reduces invasiveness of PC12 cells in vitro and in vivo. Am J Transl Res. 2017 Sep 15;9(9):3990-4002. eCollection 2017. PubMed PMID: 28979675; PubMed Central PMCID: PMC5622244. 3: Zheng R, Chen K, Zhang Y, Huang J, Shi F, Wu G, Wang S. Apogossypolone induces apoptosis and autophagy in nasopharyngeal carcinoma cells in an in vitro and in vivo study. Oncol Lett. 2017 Jul;14(1):751-757. doi: 10.3892/ol.2017.6176. Epub 2017 May 16. PubMed PMID: 28693230; PubMed Central PMCID: PMC5494797. 4: Zubair H, Azim S, Khan HY, Ullah MF, Wu D, Singh AP, Hadi SM, Ahmad A. Mobilization of Intracellular Copper by Gossypol and Apogossypolone Leads to Reactive Oxygen Species-Mediated Cell Death: Putative Anticancer Mechanism. Int J Mol Sci. 2016 Jun 20;17(5). pii: E973. doi: 10.3390/ijms17060973. PubMed PMID: 27331811; PubMed Central PMCID: PMC4926505. 5: Li T, Yuan G, Zhang L, Ye L, Li S, Fan Y, Sun J. ApoG2 inhibits the antiapoptotic protein, Mcl 1, and induces mitochondria dependent apoptosis in human colorectal cancer cells. Mol Med Rep. 2015 Nov;12(5):6976-84. doi: 10.3892/mmr.2015.4299. Epub 2015 Sep 8. PubMed PMID: 26352605. 6: Sarkar S, Quinn BA, Shen XN, Dash R, Das SK, Emdad L, Klibanov AL, Wang XY, Pellecchia M, Sarkar D, Fisher PB. Therapy of prostate cancer using a novel cancer terminator virus and a small molecule BH-3 mimetic. Oncotarget. 2015 May 10;6(13):10712-27. PubMed PMID: 25926554; PubMed Central PMCID: PMC4484414. 7: Hu ZY, Xu F, Sun R, Chen YF, Zhang DS, Fan YH, Sun J. Apogossypolone induces reactive oxygen species accumulation and controls cell cycle progression in Raji Burkkit's lymphoma cells. Mol Med Rep. 2015 Jul;12(1):337-44. doi: 10.3892/mmr.2015.3404. Epub 2015 Mar 3. PubMed PMID: 25738577. 8: Li K, Liu H, Gao W, Chen M, Zeng Y, Liu J, Xu L, Wu D. Mulberry-like dual-drug complicated nanocarriers assembled with apogossypolone amphiphilic starch micelles and doxorubicin hyaluronic acid nanoparticles for tumor combination and targeted therapy. Biomaterials. 2015 Jan;39:131-44. doi: 10.1016/j.biomaterials.2014.10.073. Epub 2014 Nov 16. PubMed PMID: 25477180. 9: Zhang H, Wang J, Deng F, Huang E, Yan Z, Wang Z, Deng Y, Zhang Q, Zhang Z, Ye J, Qiao M, Li R, Wang J, Wei Q, Zhou G, Luu HH, Haydon RC, He TC, Deng F. Canonical Wnt signaling acts synergistically on BMP9-induced osteo/odontoblastic differentiation of stem cells of dental apical papilla (SCAPs). Biomaterials. 2015 Jan;39:145-54. doi: 10.1016/j.biomaterials.2014.11.007. Epub 2014 Nov 22. PubMed PMID: 25468367; PubMed Central PMCID: PMC4258144. 10: Zhang X, Hu X, Mu S, Zhan Y, An Q, Liu Z, Huang X. Apogossypolone inhibits the proliferation of LNCaP cells in vitro and in vivo. Mol Med Rep. 2014 Sep;10(3):1184-94. doi: 10.3892/mmr.2014.2379. Epub 2014 Jul 14. PubMed PMID: 25060748; PubMed Central PMCID: PMC4121422. 11: He JH, Liao XL, Wang W, Li DD, Chen WD, Deng R, Yang D, Han ZP, Jiang JW, Zhu XF. Apogossypolone, a small-molecule inhibitor of Bcl-2, induces radiosensitization of nasopharyngeal carcinoma cells by stimulating autophagy. Int J Oncol. 2014 Sep;45(3):1099-108. doi: 10.3892/ijo.2014.2497. Epub 2014 Jun 11. PubMed PMID: 24919770. 12: Mellon JE, Dowd MK, Beltz SB, Moore GG. Growth inhibitory effects of gossypol and related compounds on fungal cotton root pathogens. Lett Appl Microbiol. 2014 Aug;59(2):161-8. doi: 10.1111/lam.12262. Epub 2014 Apr 29. PubMed PMID: 24713043. 13: Billard C. BH3 mimetics: status of the field and new developments. Mol Cancer Ther. 2013 Sep;12(9):1691-700. doi: 10.1158/1535-7163.MCT-13-0058. Epub 2013 Aug 23. Review. PubMed PMID: 23974697. 14: Zhan YH, Huang XF, Hu XB, An QX, Liu ZX, Zhang XQ. Growth inhibition and apoptosis induction of human umbilical vein endothelial cells by apogossypolone. Asian Pac J Cancer Prev. 2013;14(3):1791-5. PubMed PMID: 23679275. 15: Mellon JE, Dowd MK, Beltz SB. Effects of temperature and medium composition on inhibitory activities of gossypol-related compounds against aflatoxigenic fungi. J Appl Microbiol. 2013 Jul;115(1):179-86. doi: 10.1111/jam.12219. Epub 2013 May 16. PubMed PMID: 23594138. 16: Xin J, Zhan Y, Liu M, Hu H, Xia L, Nie Y, Wu K, Liang J, Tian J. ApoG2 induces ER stress-dependent apoptosis in gastric cancer cells in vitro and its real-time evaluation by bioluminescence imaging in vivo. Cancer Lett. 2013 Aug 19;336(2):260-9. doi: 10.1016/j.canlet.2013.03.019. Epub 2013 Mar 21. PubMed PMID: 23523614. 17: Cheng P, Ni Z, Dai X, Wang B, Ding W, Rae Smith A, Xu L, Wu D, He F, Lian J. The novel BH-3 mimetic apogossypolone induces Beclin-1- and ROS-mediated autophagy in human hepatocellular carcinoma [corrected] cells. Cell Death Dis. 2013 Feb 7;4:e489. doi: 10.1038/cddis.2013.17. Erratum in: Cell Death Dis. 2013;4:e598. PubMed PMID: 23392177; PubMed Central PMCID: PMC3734844. 18: Anderson MA, Huang DC, Roberts AW. BH3 mimetic therapy: an emerging and promising approach to treating chronic lymphocytic leukemia. Leuk Lymphoma. 2013 May;54(5):909-11. doi: 10.3109/10428194.2013.769223. Epub 2013 Feb 1. PubMed PMID: 23339446. 19: Xin J, Zhan YH, Xia LM, Zhu HW, Nie YZ, Liang JM, Tian J. ApoG2 as the most potent gossypol derivatives inhibits cell growth and induces apoptosis on gastric cancer cells. Biomed Pharmacother. 2013 Feb;67(1):88-95. doi: 10.1016/j.biopha.2012.10.016. Epub 2012 Nov 19. PubMed PMID: 23201009. 20: Balakrishnan K, Aggarwal S, Wierda W, Gandhi V. Bax and Bak are required for apogossypolone, a BH3-mimetic, induced apoptosis in chronic lymphocytic leukemia cells. Leuk Lymphoma. 2013 May;54(5):1097-100. doi: 10.3109/10428194.2012.718344. Epub 2012 Sep 4. PubMed PMID: 22866921; PubMed Central PMCID: PMC4123740.