MedKoo Cat#: 561735 | Name: Cryptopleurine

Description:

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

Cryptopleurine is an inhibitor of gene products associated with cell survival, proliferation, invasion, and angiogenesis. It acts by targeting the NF-κB pathway, while showing antiproliferative activity and a unique mode of action.

Chemical Structure

Cryptopleurine
Cryptopleurine
CAS#482-22-4

Theoretical Analysis

MedKoo Cat#: 561735

Name: Cryptopleurine

CAS#: 482-22-4

Chemical Formula: C24H27NO3

Exact Mass: 377.1991

Molecular Weight: 377.48

Elemental Analysis: C, 76.36; H, 7.21; N, 3.71; O, 12.71

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.
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Related CAS #
No Data
Synonym
Cryptopleurine; NSC19912; NSC-19912; NSC 19912;
IUPAC/Chemical Name
(14aR)-2,3,6-Trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizine
InChi Key
RSHYSOGXGSUUIJ-OAHLLOKOSA-N
InChi Code
InChI=1S/C24H27NO3/c1-26-16-7-8-17-19(11-16)21-13-24(28-3)23(27-2)12-20(21)18-10-15-6-4-5-9-25(15)14-22(17)18/h7-8,11-13,15H,4-6,9-10,14H2,1-3H3/t15-/m1/s1
SMILES Code
COC1=CC2=C3C=C(OC)C(OC)=CC3=C4C[C@@]5([H])CCCCN5CC4=C2C=C1
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 377.48 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: Akter KM, Kim HJ, Khalil AAK, Park WS, Lee MK, Park JH, Ahn MJ. Inner morphological and chemical differentiation of Boehmeria species. J Nat Med. 2017 Dec 19. doi: 10.1007/s11418-017-1164-8. [Epub ahead of print] PubMed PMID: 29260412. 2: Wang Y, Lee S, Ha Y, Lam W, Chen SR, Dutschman GE, Gullen EA, Grill SP, Cheng Y, Fürstner A, Francis S, Baker DC, Yang X, Lee KH, Cheng YC. Tylophorine Analogs Allosterically Regulates Heat Shock Cognate Protein 70 And Inhibits Hepatitis C Virus Replication. Sci Rep. 2017 Aug 30;7(1):10037. doi: 10.1038/s41598-017-08815-z. PubMed PMID: 28855547; PubMed Central PMCID: PMC5577180. 3: Kwon Y, Song J, Lee H, Kim EY, Lee K, Lee SK, Kim S. Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents. J Med Chem. 2015 Oct 8;58(19):7749-62. doi: 10.1021/acs.jmedchem.5b00764. Epub 2015 Sep 30. PubMed PMID: 26393416. 4: Chao MW, Wang LT, Lai CY, Yang XM, Cheng YW, Lee KH, Pan SL, Teng CM. eIF4E binding protein 1 expression is associated with clinical survival outcomes in colorectal cancer. Oncotarget. 2015 Sep 15;6(27):24092-104. PubMed PMID: 26204490; PubMed Central PMCID: PMC4695172. 5: Liéby-Muller F, Marion F, Schmitt P, Annereau JP, Kruczynski A, Guilbaud N, Bailly C. Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs. Bioorg Med Chem Lett. 2015 Jan 15;25(2):184-7. doi: 10.1016/j.bmcl.2014.11.086. Epub 2014 Dec 6. PubMed PMID: 25499434. 6: Zheng Y, Liu Y, Wang Q. Collective asymmetric synthesis of (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert-butanesulfinamide as a chiral auxiliary. J Org Chem. 2014 Apr 18;79(8):3348-57. doi: 10.1021/jo500013e. Epub 2014 Mar 28. PubMed PMID: 24679059. 7: Ying W, Herndon JW. Total synthesis of (+)-antofine and (-)-cryptopleurine. European J Org Chem. 2013 May 1;2013(15). doi: 10.1002/ejoc.201300200. PubMed PMID: 24357989; PubMed Central PMCID: PMC3864684. 8: Lai CY, Pan SL, Yang XM, Chang LH, Chang YL, Yang PC, Lee KH, Teng CM. Depletion of 4E-BP1 and regulation of autophagy lead to YXM110-induced anticancer effects. Carcinogenesis. 2013 Sep;34(9):2050-60. doi: 10.1093/carcin/bgt146. Epub 2013 Apr 30. PubMed PMID: 23633518. 9: Wang Y, Wong HC, Gullen EA, Lam W, Yang X, Shi Q, Lee KH, Cheng YC. Cryptopleurine analogs with modification of e ring exhibit different mechanism to rac-cryptopleurine and tylophorine. PLoS One. 2012;7(12):e51138. doi: 10.1371/journal.pone.0051138. Epub 2012 Dec 10. PubMed PMID: 23251437; PubMed Central PMCID: PMC3519526. 10: Yang X, Shi Q, Lai CY, Chen CY, Ohkoshi E, Yang SC, Wang CY, Bastow KF, Wu TS, Pan SL, Teng CM, Yang PC, Lee KH. Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies. J Med Chem. 2012 Aug 9;55(15):6751-61. doi: 10.1021/jm3001218. Epub 2012 Jul 23. PubMed PMID: 22823514; PubMed Central PMCID: PMC3422873. 11: Pansare SV, Dyapa R. Enantioselective approach to functionalized quinolizidines: synthesis of (+)-julandine and (+)-cryptopleurine. Org Biomol Chem. 2012 Sep 7;10(33):6776-84. doi: 10.1039/c2ob25689d. Epub 2012 Jul 20. PubMed PMID: 22821193. 12: Jin HR, Jin SZ, Cai XF, Li D, Wu X, Nan JX, Lee JJ, Jin X. Cryptopleurine targets NF-κB pathway, leading to inhibition of gene products associated with cell survival, proliferation, invasion, and angiogenesis. PLoS One. 2012;7(6):e40355. doi: 10.1371/journal.pone.0040355. Epub 2012 Jun 29. PubMed PMID: 22768286; PubMed Central PMCID: PMC3386984. 13: Yang X, Shi Q, Yang SC, Chen CY, Yu SL, Bastow KF, Morris-Natschke SL, Wu PC, Lai CY, Wu TS, Pan SL, Teng CM, Lin JC, Yang PC, Lee KH. Antitumor agents 288: design, synthesis, SAR, and biological studies of novel heteroatom-incorporated antofine and cryptopleurine analogues as potent and selective antitumor agents. J Med Chem. 2011 Jul 28;54(14):5097-107. doi: 10.1021/jm200330s. Epub 2011 Jun 28. PubMed PMID: 21668000; PubMed Central PMCID: PMC3141083. 14: Cui M, Song H, Feng A, Wang Z, Wang Q. Asymmetric synthesis of (R)-antofine and (R)-cryptopleurine via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde. J Org Chem. 2010 Oct 15;75(20):7018-21. doi: 10.1021/jo101510x. PubMed PMID: 20843097. 15: Yang X, Shi Q, Bastow KF, Lee KH. Antitumor agents. 274. A new synthetic strategy for E-ring SAR study of antofine and cryptopleurine analogues. Org Lett. 2010 Apr 2;12(7):1416-9. doi: 10.1021/ol902819j. PubMed PMID: 20196574; PubMed Central PMCID: PMC2849728. 16: Chemler SR. Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkaloids for Anti-Cancer Therapy. Curr Bioact Compd. 2009 Mar 1;5(1):2-19. PubMed PMID: 20160962; PubMed Central PMCID: PMC2759725. 17: Kim S, Lee YM, Lee J, Lee T, Fu Y, Song Y, Cho J, Kim D. Expedient syntheses of antofine and cryptopleurine via intramolecular 1,3-dipolar cycloaddition. J Org Chem. 2007 Jun 22;72(13):4886-91. Epub 2007 May 25. PubMed PMID: 17523674. 18: Yang CW, Chuang TH, Wu PL, Huang WH, Lee SJ. Anti-inflammatory effects of 7-methoxycryptopleurine and structure-activity relations of phenanthroindolizidines and phenanthroquinolizidines. Biochem Biophys Res Commun. 2007 Mar 23;354(4):942-8. Epub 2007 Jan 22. PubMed PMID: 17274949. 19: Fürstner A, Kennedy JW. Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C. Chemistry. 2006 Sep 25;12(28):7398-410. PubMed PMID: 16881031. 20: Cai XF, Jin X, Lee D, Yang YT, Lee K, Hong YS, Lee JH, Lee JJ. Phenanthroquinolizidine alkaloids from the roots of Boehmeria pannosa potently inhibit hypoxia-inducible factor-1 in AGS human gastric cancer cells. J Nat Prod. 2006 Jul;69(7):1095-7. PubMed PMID: 16872154.