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執大象，天下往，往而無害，安平泰
WEB: www.eosmedchem.com
EMAIL: info@eosmedchem.com; eosmedchem@gmail.com; eosmedchem@qq.com
TEL: 0086-531-69905422
GMP PLANT: No. 37, Yulong Road, Qufu City, Shandong Province.
Description: CD437 is a synthetic retinoid that is an RARγ-selective agonist. It displays RARγ-dependent and -independent effects on differentiation and apoptosis.
Name: CD437
CAS#: 125316-60-1
Chemical Formula: C27H26O3
Exact Mass: 398.1882
Molecular Weight: 398.5
Elemental Analysis: C, 81.38; H, 6.58; O, 12.04
Synonym: CD437; CD 437; CD-437; Ro-472077; Ro 472077; Ro472077; AHPN.
IUPAC/Chemical Name: 6-[3-(1-adamantyl)-4-hydroxyphenyl]naphthalene-2-carboxylic acid
InChi Key: LDGIHZJOIQSHPB-UHFFFAOYSA-N
InChi Code: InChI=1S/C27H26O3/c28-25-6-5-22(20-1-2-21-11-23(26(29)30)4-3-19(21)10-20)12-24(25)27-13-16-7-17(14-27)9-18(8-16)15-27/h1-6,10-12,16-18,28H,7-9,13-15H2,(H,29,30)
SMILES Code: O=C(C1=CC=C2C=C(C3=CC=C(O)C(C45CC6CC(C5)CC(C6)C4)=C3)C=CC2=C1)O
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).
Harmonized System Code: 293490
REFERENCES
1: Han T, Goralski M, Capota E, Padrick SB, Kim J, Xie Y, Nijhawan D. The antitumor toxin CD437 is a direct inhibitor of DNA polymerase α. Nat Chem Biol. 2016 Jul;12(7):511-5. doi: 10.1038/nchembio.2082. Epub 2016 May 16. PubMed PMID: 27182663; PubMed Central PMCID: PMC4912453.
2: Magnussen GI, Ree Rosnes AK, Shahzidi S, Dong HP, Emilsen E, Engesæter B, Flørenes VA. Synthetic retinoid CD437 induces apoptosis and acts synergistically with TRAIL receptor-2 agonist in malignant melanoma. Biochem Biophys Res Commun. 2012 Apr 13;420(3):516-22. doi: 10.1016/j.bbrc.2012.03.023. Epub 2012 Mar 13. PubMed PMID: 22446330.
3: Mishur RJ, Griffin ME, Battle CH, Shan B, Jayawickramarajah J. Molecular recognition and enhancement of aqueous solubility and bioactivity of CD437 by β-cyclodextrin. Bioorg Med Chem Lett. 2011 Jan 15;21(2):857-60. doi: 10.1016/j.bmcl.2010.11.073. Epub 2010 Nov 21. PubMed PMID: 21185186; PubMed Central PMCID: PMC3057113.
4: Hashiguchi K, Tsuchiya H, Tomita A, Ueda C, Akechi Y, Sakabe T, Kurimasa A, Nozaki M, Yamada T, Tsuchida S, Shiota G. Involvement of ETS1 in thioredoxin-binding protein 2 transcription induced by a synthetic retinoid CD437 in human osteosarcoma cells. Biochem Biophys Res Commun. 2010 Jan 1;391(1):621-6. doi: 10.1016/j.bbrc.2009.11.109. Epub 2009 Nov 20. PubMed PMID: 19932085.
5: Matsuoka S, Tsuchiya H, Sakabe T, Watanabe Y, Hoshikawa Y, Kurimasa A, Itamochi H, Harada T, Terakawa N, Masutani H, Yodoi J, Shiota G. Involvement of thioredoxin-binding protein 2 in the antitumor activity of CD437. Cancer Sci. 2008 Dec;99(12):2485-90. doi: 10.1111/j.1349-7006.2008.00979.x. Epub 2008 Nov 17. PubMed PMID: 19018770.
6: Pan M, Geng S, Xiao S, Ren J, Liu Y, Li X, Li Z, Peng Z. Apoptosis induced by synthetic retinoic acid CD437 on human melanoma A375 cells involves RIG-I pathway. Arch Dermatol Res. 2009 Jan;301(1):15-20. doi: 10.1007/s00403-008-0902-x. Epub 2008 Oct 21. PubMed PMID: 18936944.
7: Valli C, Paroni G, Di Francesco AM, Riccardi R, Tavecchio M, Erba E, Boldetti A, Gianni' M, Fratelli M, Pisano C, Merlini L, Antoccia A, Cenciarelli C, Terao M, Garattini E. Atypical retinoids ST1926 and CD437 are S-phase-specific agents causing DNA double-strand breaks: significance for the cytotoxic and antiproliferative activity. Mol Cancer Ther. 2008 Sep;7(9):2941-54. doi: 10.1158/1535-7163.MCT-08-0419. PubMed PMID: 18790775.
8: Gonda K, Tsuchiya H, Sakabe T, Akechi Y, Ikeda R, Nishio R, Terabayashi K, Ishii K, Matsumi Y, Ashla AA, Okamoto H, Takubo K, Matsuoka S, Watanabe Y, Hoshikawa Y, Kurimasa A, Shiota G. Synthetic retinoid CD437 induces mitochondria-mediated apoptosis in hepatocellular carcinoma cells. Biochem Biophys Res Commun. 2008 Jun 13;370(4):629-33. doi: 10.1016/j.bbrc.2008.04.008. Epub 2008 Apr 10. PubMed PMID: 18406343.
9: Pan M, Peng ZH, Xiao SX, Li XL, Liu Y, Li ZX, Ren JW. [A novel retinoid CD437 induces apoptosis of human epidermoid carcinoma A431 cells]. Nan Fang Yi Ke Da Xue Xue Bao. 2008 Mar;28(3):305-8. Chinese. PubMed PMID: 18359678.
10: Watanabe Y, Tsuchiya H, Sakabe T, Matsuoka S, Akechi Y, Fujimoto Y, Yamane K, Ikeda R, Nishio R, Terabayashi K, Ishii K, Gonda K, Matsumi Y, Ashla AA, Okamoto H, Takubo K, Tomita A, Hoshikawa Y, Kurimasa A, Itamochi H, Harada T, Terakawa N, Shiota G. CD437 induces apoptosis in ovarian adenocarcinoma cells via ER stress signaling. Biochem Biophys Res Commun. 2008 Feb 15;366(3):840-7. Epub 2007 Dec 17. PubMed PMID: 18082618.
11: Jiang T, Soprano DR, Soprano KJ. GADD45A is a mediator of CD437 induced apoptosis in ovarian carcinoma cells. J Cell Physiol. 2007 Sep;212(3):771-9. PubMed PMID: 17474084.
12: Parrella E, Giannì M, Fratelli M, Barzago MM, Raska I Jr, Diomede L, Kurosaki M, Pisano C, Carminati P, Merlini L, Dallavalle S, Tavecchio M, Rochette-Egly C, Terao M, Garattini E. Antitumor activity of the retinoid-related molecules (E)-3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid (ST1926) and 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid (CD437) in F9 teratocarcinoma: Role of retinoic acid receptor gamma and retinoid-independent pathways. Mol Pharmacol. 2006 Sep;70(3):909-24. Epub 2006 Jun 20. PubMed PMID: 16788091.
13: Zou C, Zhou J, Qian L, Feugang JM, Liu J, Wang X, Wu S, Ding H, Zou C, Liebert M, Grossman HB. Comparing the effect of ATRA, 4-HPR, and CD437 in bladder cancer cells. Front Biosci. 2006 Sep 1;11:2007-16. PubMed PMID: 16720286.
14: Jin F, Liu X, Zhou Z, Yue P, Lotan R, Khuri FR, Chung LW, Sun SY. Activation of nuclear factor-kappaB contributes to induction of death receptors and apoptosis by the synthetic retinoid CD437 in DU145 human prostate cancer cells. Cancer Res. 2005 Jul 15;65(14):6354-63. PubMed PMID: 16024638.
15: Boisvieux-Ulrich E, Sourdeval M, Marano F. CD437, a synthetic retinoid, induces apoptosis in human respiratory epithelial cells via caspase-independent mitochondrial and caspase-8-dependent pathways both up-regulated by JNK signaling pathway. Exp Cell Res. 2005 Jul 1;307(1):76-90. Epub 2005 Apr 18. PubMed PMID: 15922728.
16: Kim HJ, Lotan R. Identification of protein modulation by the synthetic retinoid CD437 in lung carcinoma cells using high throughput immunoblotting. Int J Oncol. 2005 Feb;26(2):483-91. PubMed PMID: 15645134.
17: Holmes WF, Soprano DR, Soprano KJ. Early events in the induction of apoptosis in ovarian carcinoma cells by CD437: activation of the p38 MAP kinase signal pathway. Oncogene. 2003 Sep 25;22(41):6377-86. PubMed PMID: 14508518.
18: Rishi AK, Zhang L, Boyanapalli M, Wali A, Mohammad RM, Yu Y, Fontana JA, Hatfield JS, Dawson MI, Majumdar AP, Reichert U. Identification and characterization of a cell cycle and apoptosis regulatory protein-1 as a novel mediator of apoptosis signaling by retinoid CD437. J Biol Chem. 2003 Aug 29;278(35):33422-35. Epub 2003 Jun 18. PubMed PMID: 12816952.
19: Holmes WF, Soprano DR, Soprano KJ. Comparison of the mechanism of induction of apoptosis in ovarian carcinoma cells by the conformationally restricted synthetic retinoids CD437 and 4-HPR. J Cell Biochem. 2003 May 15;89(2):262-78. PubMed PMID: 12704790.
20: Joseph B, Marchetti P, Lefebvre O, Schraen-Maschke S, Méreau-Richard C, Formstecher P. The novel retinoid AHPN/CD437 induces a rapid but incomplete apoptotic response in human myeloma cells. Biochim Biophys Acta. 2003 Feb 17;1593(2-3):277-82. PubMed PMID: 12581872.
