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MedKoo Cat#: 328024 | Name: Tylophorine

Description:

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

Tylophorine is a natural product and a major alkaloid of Tylophora indica. Tylophorine is known to possess anti-inflammatory and antitumor activity. Tylophorine arrests carcinoma cells at G1 phase by downregulating cyclin A2 expression.

Chemical Structure

Tylophorine
Tylophorine
CAS#482-20-2 (free base)

Theoretical Analysis

MedKoo Cat#: 328024

Name: Tylophorine

CAS#: 482-20-2 (free base)

Chemical Formula: C24H27NO4

Exact Mass: 393.1940

Molecular Weight: 393.48

Elemental Analysis: C, 73.26; H, 6.92; N, 3.56; O, 16.26

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 #
1035188-49-8 (HCl) 1035188-56-7 (HBr) 1035188-58-9 (HI) 482-20-2 (free base) 25908-92-3 (racemate)
Synonym
Tylophorine; Tylophorin; NSC 76387; NSC-76387; NSC76387;
IUPAC/Chemical Name
(S)-2,3,6,7-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline
InChi Key
SSEUDFYBEOIWGF-AWEZNQCLSA-N
InChi Code
InChI=1S/C24H27NO4/c1-26-21-9-16-15-8-14-6-5-7-25(14)13-20(15)19-12-24(29-4)23(28-3)11-18(19)17(16)10-22(21)27-2/h9-12,14H,5-8,13H2,1-4H3/t14-/m0/s1
SMILES Code
COC1=C(OC)C=C2C3=CC(OC)=C(OC)C=C3C4=C(CN5[C@](CCC5)([H])C4)C2=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 393.48 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: Wang Y, Lam W, Chen SR, Guan FL, Dutchman GE, Francis S, Baker DC, Cheng YC. Tylophorine Analog DCB-3503 Inhibited Cyclin D1 Translation through Allosteric Regulation of Heat Shock Cognate Protein 70. Sci Rep. 2016 Sep 6;6:32832. doi: 10.1038/srep32832. PubMed PMID: 27596272; PubMed Central PMCID: PMC5011780. 2: Yao T, Zhang H, Zhao Y. Synthesis of 9,10-Phenanthrenes via Palladium-Catalyzed Aryne Annulation by o-Halostyrenes and Formal Synthesis of (±)-Tylophorine. Org Lett. 2016 Jun 3;18(11):2532-5. doi: 10.1021/acs.orglett.6b00558. PubMed PMID: 27188401. 3: Wen T, Wang Z, Meng X, Wu M, Li Y, Wu X, Zhao L, Wang P, Yin Z, Li-Ling J, Wang Q. Synthesis of novel tylophorine derivatives and evaluation of their anti-inflammatory activity. ACS Med Chem Lett. 2014 Jul 23;5(9):1027-31. doi: 10.1021/ml500255j. PubMed PMID: 25221661; PubMed Central PMCID: PMC4160763. 4: Su B, Zhang H, Deng M, Wang Q. An enantioselective strategy for the total synthesis of (S)-tylophorine via catalytic asymmetric allylation and a one-pot DMAP-promoted isocyanate formation/Lewis acid catalyzed cyclization sequence. Org Biomol Chem. 2014 Jun 14;12(22):3616-21. doi: 10.1039/c4ob00200h. PubMed PMID: 24756131. 5: 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. PubMed PMID: 24679059. 6: Saraswati S, Kanaujia PK, Kumar S, Kumar R, Alhaider AA. Tylophorine, a phenanthraindolizidine alkaloid isolated from Tylophora indica exerts antiangiogenic and antitumor activity by targeting vascular endothelial growth factor receptor 2-mediated angiogenesis. Mol Cancer. 2013 Jul 29;12:82. doi: 10.1186/1476-4598-12-82. PubMed PMID: 23895055; PubMed Central PMCID: PMC3733984. 7: Yang CW, Lee YZ, Hsu HY, Wu CM, Chang HY, Chao YS, Lee SJ. c-Jun-mediated anticancer mechanisms of tylophorine. Carcinogenesis. 2013 Jun;34(6):1304-14. doi: 10.1093/carcin/bgt039. PubMed PMID: 23385061. 8: Su B, Chen F, Wang Q. An enantioselective strategy for the synthesis of (S)-tylophorine via one-pot intramolecular Schmidt/Bischler-Napieralski/imine-reduction cascade sequence. J Org Chem. 2013 Mar 15;78(6):2775-9. doi: 10.1021/jo302725q. PubMed PMID: 23373672. 9: Stoye A, Peez TE, Opatz T. Left, right, or both? On the configuration of the phenanthroindolizidine alkaloid tylophorine from Tylophora indica. J Nat Prod. 2013 Feb 22;76(2):275-8. doi: 10.1021/np300838w. PubMed PMID: 23369033. 10: 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. PubMed PMID: 23251437; PubMed Central PMCID: PMC3519526. 11: Lee YZ, Yang CW, Hsu HY, Qiu YQ, Yeh TK, Chang HY, Chao YS, Lee SJ. Synthesis and biological evaluation of tylophorine-derived dibenzoquinolines as orally active agents: exploration of the role of tylophorine e ring on biological activity. J Med Chem. 2012 Dec 13;55(23):10363-77. doi: 10.1021/jm300705j. PubMed PMID: 23167614. 12: Meng X, Zhang Y, Jia Z, Huo X, He X, Tian G, Wu M, Wang Z, Zhou X, Xiong S, Gao X, Wu Z, Han J, Zhao L, Wang P, Hong Z, Wang Q, Yin Z. A novel tylophorine analog W-8 up-regulates forkhead boxP3 expression and ameliorates murine colitis. J Leukoc Biol. 2013 Jan;93(1):83-93. doi: 10.1189/jlb.0812402. PubMed PMID: 23142729. 13: Wen T, Li Y, Wu M, Chen X, Han L, Bao X, Wang Z, Wang K, Hu Y, Zhou X, Wu Z, Wang P, Hong Z, Zhao L, Wang Q, Yin Z. A novel tylophorine analog NK-007 ameliorates colitis through inhibition of innate immune response. Int Immunopharmacol. 2012 Dec;14(4):487-94. doi: 10.1016/j.intimp.2012.08.008. PubMed PMID: 22929538. 14: Niphakis MJ, Gay BC, Hong KH, Bleeker NP, Georg GI. Synthesis and evaluation of the anti-proliferative and NF-κB activities of a library of simplified tylophorine analogs. Bioorg Med Chem. 2012 Oct 1;20(19):5893-900. doi: 10.1016/j.bmc.2012.07.044. PubMed PMID: 22910225. 15: Xu X, Liu Y, Park CM. Rhodium(III)-catalyzed intramolecular annulation through C-H activation: total synthesis of (±)-antofine, (±)-septicine, (±)-tylophorine, and rosettacin. Angew Chem Int Ed Engl. 2012 Sep 10;51(37):9372-6. doi: 10.1002/anie.201204970. PubMed PMID: 22907635. 16: Lahm G, Stoye A, Opatz T. A five-step synthesis of (±)-tylophorine via a nitrile-stabilized ammonium ylide. J Org Chem. 2012 Aug 3;77(15):6620-3. doi: 10.1021/jo3011045. PubMed PMID: 22783990. 17: Wen T, Li Y, Wu M, Sun X, Bao X, Lin Y, Hao J, Han L, Cao G, Wang Z, Liu Y, Wu Z, Hong Z, Wang P, Zhao L, Li Z, Wang Q, Yin Z. Therapeutic effects of a novel tylophorine analog, NK-007, on collagen-induced arthritis through suppressing tumor necrosis factor α production and Th17 cell differentiation. Arthritis Rheum. 2012 Sep;64(9):2896-906. doi: 10.1002/art.34528. PubMed PMID: 22576707. 18: Wang K, Hu Y, Liu Y, Mi N, Fan Z, Liu Y, Wang Q. Design, synthesis, and antiviral evaluation of phenanthrene-based tylophorine derivatives as potential antiviral agents. J Agric Food Chem. 2010 Dec 8;58(23):12337-42. doi: 10.1021/jf103440s. PubMed PMID: 21058739. 19: Wang Y, Gao W, Svitkin YV, Chen AP, Cheng YC. DCB-3503, a tylophorine analog, inhibits protein synthesis through a novel mechanism. PLoS One. 2010 Jul 15;5(7):e11607. doi: 10.1371/journal.pone.0011607. PubMed PMID: 20657652; PubMed Central PMCID: PMC2904705. 20: Stoye A, Opatz T. Racemization-free synthesis of (S)-(+)-tylophorine from L-proline by radical cyclization. Org Lett. 2010 May 7;12(9):2140-1. doi: 10.1021/ol100652b. PubMed PMID: 20377275.

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