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MedKoo Cat#: 462709 | Name: Tylophorine HCl

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 HCl
Tylophorine HCl
CAS#1035188-49-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 462709

Name: Tylophorine HCl

CAS#: 1035188-49-8 (HCl)

Chemical Formula: C24H28ClNO4

Exact Mass: 393.1940

Molecular Weight: 429.94

Elemental Analysis: C, 67.05; H, 6.56; Cl, 8.25; N, 3.26; O, 14.88

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 HCl, Tylophorine hydrochloride,
IUPAC/Chemical Name
(S)-2,3,6,7-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline hydrochloride,
InChi Key
PDABAAPXQRBTMM-UQKRIMTDSA-N
InChi Code
InChI=1S/C24H27NO4.ClH/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;1H/t14-;/m0./s1
SMILES Code
COC1=C(OC)C=C2C3=CC(OC)=C(OC)C=C3C4=C(CN5[C@](CCC5)([H])C4)C2=C1.[H]Cl
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
>3 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 429.94 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: Lee YZ, Guo HC, Zhao GH, Yang CW, Chang HY, Yang RB, Chen L, Lee SJ. Tylophorine-based compounds are therapeutic in rheumatoid arthritis by targeting the caprin-1 ribonucleoprotein complex and inhibiting expression of associated c-Myc and HIF-1α. Pharmacol Res. 2020 Feb;152:104581. doi: 10.1016/j.phrs.2019.104581. Epub 2019 Nov 30. PMID: 31794869. 2: Pratama NP, Wulandari S, Nugroho AE, Fakhrudin N, Astuti P, Sudarsono. Tylophorine Abrogates G2/M Arrest Induced by Doxorubicine and Promotes Increased Apoptosis in T47D Breast Cancer Cells. Asian Pac J Cancer Prev. 2018 Nov 29;19(11):3065-3069. doi: 10.31557/APJCP.2018.19.11.3065. PMID: 30485942; PMCID: PMC6318386. 3: 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. PMID: 28855547; PMCID: PMC5577180. 4: Joa H, Blažević T, Grojer C, Zeller I, Heiss EH, Atanasov AG, Feldler I, Gruzdaitis P, Czaloun C, Proksch P, Messner B, Bernhard D, Dirsch VM. Tylophorine reduces protein biosynthesis and rapidly decreases cyclin D1, inhibiting vascular smooth muscle cell proliferation in vitro and in organ culture. Phytomedicine. 2019 Jul;60:152938. doi: 10.1016/j.phymed.2019.152938. Epub 2019 Apr 23. PMID: 31078367. 5: Wu CM, Yang CW, Lee YZ, Chuang TH, Wu PL, Chao YS, Lee SJ. Tylophorine arrests carcinoma cells at G1 phase by downregulating cyclin A2 expression. Biochem Biophys Res Commun. 2009 Aug 14;386(1):140-5. doi: 10.1016/j.bbrc.2009.05.138. Epub 2009 Jun 6. PMID: 19501048. 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. PMID: 23895055; 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. Epub 2013 Feb 5. PMID: 23385061. 8: Gao W, Lam W, Zhong S, Kaczmarek C, Baker DC, Cheng YC. Novel mode of action of tylophorine analogs as antitumor compounds. Cancer Res. 2004 Jan 15;64(2):678-88. doi: 10.1158/0008-5472.can-03-1904. PMID: 14744785. 9: Xi Z, Zhang R, Yu Z, Ouyang D. The interaction between tylophorine B and TMV RNA. Bioorg Med Chem Lett. 2006 Aug 15;16(16):4300-4. doi: 10.1016/j.bmcl.2006.05.059. Epub 2006 Jun 12. PMID: 16759858. 10: 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. Epub 2013 Jan 31. PMID: 23369033. 11: 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. PMID: 27596272; PMCID: PMC5011780. 12: 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. Epub 2012 Dec 4. PMID: 23167614. 13: 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. Epub 2012 Aug 3. PMID: 22910225. 14: 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. PMID: 20657652; PMCID: PMC2904705. 15: 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. Epub 2012 Aug 25. PMID: 22929538. 16: 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. PMID: 25221661; PMCID: PMC4160763. 17: Qiu YQ, Yang CW, Lee YZ, Yang RB, Lee CH, Hsu HY, Chang CC, Lee SJ. Targeting a ribonucleoprotein complex containing the caprin-1 protein and the c-Myc mRNA suppresses tumor growth in mice: an identification of a novel oncotarget. Oncotarget. 2015 Feb 10;6(4):2148-63. doi: 10.18632/oncotarget.3236. Erratum in: Oncotarget. 2019 Aug 06;10(47):4919. PMID: 25669982; PMCID: PMC4385842. 18: 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. PMID: 23251437; PMCID: PMC3519526. 19: Xi Z, Zhang R, Yu Z, Ouyang D, Huang R. Selective interaction between tylophorine B and bulged DNA. Bioorg Med Chem Lett. 2005 May 16;15(10):2673-7. doi: 10.1016/j.bmcl.2005.02.022. PMID: 15863340. 20: 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. Epub 2012 Nov 9. PMID: 23142729.