Lycobetaine acetate

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MedKoo CAT#: 525602

CAS#: 61221-41-8

Description: Lycobetaine is a selective topoisomerase II beta poison and inhibits the growth of human tumour cells. Inhibition of cell growth was studied in the clonogenic assay on 21 human tumour xenografts (mean IC(50) = 0.8 microM). The growth of human leukaemia cell lines was also potently inhibited (mean IC(50) = 1.3 microM).


Price and Availability

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Pricing updated 2020-10-26. Prices are subject to change without notice.

Lycobetaine acetate is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 525602
Name: Lycobetaine acetate
CAS#: 61221-41-8
Chemical Formula: C18H15NO5
Exact Mass:
Molecular Weight: 325.32
Elemental Analysis: C, 66.46; H, 4.65; N, 4.31; O, 24.59


Synonym: AT-1840; AT 1840; AT1840; Oxylycorine; Ungerimine acetate; Lycobetaine acetate

IUPAC/Chemical Name: 2-hydroxy-4,5-dihydro-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-6-ium acetate

InChi Key: HKIJKEFVQKXWGW-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H11NO3.C2H4O2/c18-11-3-9-1-2-17-7-10-4-14-15(20-8-19-14)6-12(10)13(5-11)16(9)17;1-2(3)4/h3-7H,1-2,8H2;1H3,(H,3,4)

SMILES Code: OC1=CC2=C([N+]3=CC4=CC5=C(OCO5)C=C42)C(CC3)=C1.CC([O-])=O


Technical Data

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, not in water

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


References

1: Zhao H, Lu H, Gong T, Zhang Z. Nanoemulsion loaded with lycobetaine-oleic acid ionic complex: physicochemical characteristics, in vitro, in vivo evaluation, and antitumor activity. Int J Nanomedicine. 2013;8:1959-73. doi: 10.2147/IJN.S43892. Epub 2013 May 21. PubMed PMID: 23723698; PubMed Central PMCID: PMC3666662.
2: Baechler SA, Fehr M, Habermeyer M, Hofmann A, Merz KH, Fiebig HH, Marko D, Eisenbrand G. Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs. Bioorg Med Chem. 2013 Feb 1;21(3):814-23. doi: 10.1016/j.bmc.2012.11.011. Epub 2012 Nov 26. PubMed PMID: 23266176.
3: Barthelmes HU, Niederberger E, Roth T, Schulte K, Tang WC, Boege F, Fiebig HH, Eisenbrand G, Marko D. Lycobetaine acts as a selective topoisomerase II beta poison and inhibits the growth of human tumour cells. Br J Cancer. 2001 Nov 16;85(10):1585-91. PubMed PMID: 11720449; PubMed Central PMCID: PMC2363954.
4: Liu J, Yang SL, Xu B. Effects of lycobetaine on chromatin structure and activity of murine hepatoma cells. Sci China B. 1990 Dec;33(12):1459-65. PubMed PMID: 2282145.
5: Liu J, Yang SL, Xu B. Characteristics of the interaction of lycobetaine with DNA. Zhongguo Yao Li Xue Bao. 1989 Sep;10(5):437-42. PubMed PMID: 2618733.
6: He HM, Weng ZY. [Structure-activity-relationship study of the new anticancer drug lycobetaine (AT-1840)]. Yao Xue Xue Bao. 1989;24(4):302-4. Chinese. PubMed PMID: 2816392.
7: Wang ZW, Shu RS, Xu B. [Nucleolus segregation of tumor cells induced by actinomycin K and lycobetaine (author's transl)]. Zhongguo Yao Li Xue Bao. 1982 Mar;3(1):48-51. Chinese. PubMed PMID: 6178253.
8: Zhang SY, Lu FL, Yang JL, Wang LJ, Xu B. [Effect on animal tumors and toxicity of lycobetaine acetate (author's transl)]. Zhongguo Yao Li Xue Bao. 1981 Mar;2(1):41-5. Chinese. PubMed PMID: 6461201.