Ukrain

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MedKoo CAT#: 203070

CAS#: 138069-52-0

Description: Ukrain, also known as NSC-631570, is claimed to be a semisynthetic compound of thiophosphoric acid (triaziridide) and the alkaloid chelidonine derived from the common weed, Chelidonium majus (greater celandine), which grows primarily in Europe and Asia.


Price and Availability

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Pricing updated 2020-10-30. Prices are subject to change without notice.

Ukrain 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#: 203070
Name: Ukrain
CAS#: 138069-52-0
Chemical Formula: C66H75N6O18PS
Exact Mass:
Molecular Weight: 1303.3838
Elemental Analysis: C, 60.82; H, 5.80; N, 6.45; O, 22.09; P, 2.38; S, 2.46


Synonym: NSC 631570, NSC-631570, NSC631570, Ukrain

IUPAC/Chemical Name: (5bR,5b'R,6S,6'S,12bS,12b'S,13R,13'R)-13,13'-(((((2-((5bS,6S,12bS,13S)-6-hydroxy-13-methyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium-13-yl)ethyl)amino)phosphorothioyl)bis(azanediyl))bis(ethane-2,1-diyl))bis(6-hydroxy-13-methyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium) hydroxide

InChi Key: KIGCDEJCMKDBHU-DJMIMDAMSA-K

InChi Code: InChI=1S/C66H72N6O15PS.3H2O/c1-70(25-43-37(4-7-49-64(43)85-31-76-49)58-46(73)16-34-19-52-55(82-28-79-52)22-40(34)61(58)70)13-10-67-88(89,68-11-14-71(2)26-44-38(5-8-50-65(44)86-32-77-50)59-47(74)17-35-20-53-56(83-29-80-53)23-41(35)62(59)71)69-12-15-72(3)27-45-39(6-9-51-66(45)87-33-78-51)60-48(75)18-36-21-54-57(84-30-81-54)24-42(36)63(60)72;;;/h4-9,19-24,46-48,58-63,73-75H,10-18,25-33H2,1-3H3,(H3,67,68,69,89);3*1H2/q+3;;;/p-3/t46-,47-,48-,58-,59-,60+,61+,62+,63+,70-,71-,72+;;;/m0.../s1

SMILES Code: S=P(NCC[N@+]1(C)[C@]2([H])C3=CC4=C(OCO4)C=C3C[C@H](O)[C@]2([H])C5=C(C6=C(OCO6)C=C5)C1)(NCC[N@+]7(C)[C@]8([H])C9=CC%10=C(OCO%10)C=C9C[C@H](O)[C@]8([H])C%11=C(C%12=C(OCO%12)C=C%11)C7)NCC[N@@+]%13(C)[C@]%14([H])C%15=CC%16=C(OCO%16)C=C%15C[C@H](O)[C@@]%14([H])C%17=C(C%18=C(OCO%18)C=C%17)C%13.[OH-].[OH-].[OH-]


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

Shelf Life:
>5 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


Additional Information

The anticancer drug Ukrain (NSC-631570) which has been specified by the manufacturer as semisynthetic derivative of the Chelidonium majus L. alkaloid chelidonine and the alkylans thiotepa was reported to exert selective cytotoxic effects on human tumour cell lines in vitro. Few clinical trials suggest beneficial effects in the treatment of human cancer.  The potent proapoptotic effects of Ukrain are not due to the suggested "Ukrain-molecule" but to the cytotoxic efficacy of Chelidonium majus L. alkaloids including chelidonine. see http://www.ncbi.nlm.nih.gov/pubmed/16417634..
 
Ukrain is an anticancer drug based on the extract of the plant Chelidonium majus L. Numerous pre-clinical and clinical investigations seem to suggest that Ukrain is pharmacologically active and clinically effective.  Ernst E, Schmidt K critically evaluate d the clinical trial data in the form of a systematic review.    The data from randomised clinical trials suggest Ukrain to have potential as an anticancer drug. However, numerous caveats prevent a positive conclusion, and independent rigorous studies are urgently needed. see: Ernst E, Schmidt K. Ukrain - a new cancer cure? A systematic review of randomised clinical trials .BMC Cancer. 2005 Jul 1;5:69.

 


References

1: Bozeman EN, Srivatsan S, Mohammadi H, Daniels D, Shashidharamurthy R, Selvaraj P. Ukrain, a plant derived semi-synthetic compound, exerts antitumor effects against murine and human breast cancer and induce protective antitumor immunity in mice. Exp Oncol. 2012 Dec;34(4):340-7. PubMed PMID: 23302993.

2: Gagliano N, Volpari T, Clerici M, Pettinari L, Barajon I, Portinaro N, Colombo G, Milzani A, Dalle-Donne I, Martinelli C. Pancreatic cancer cells retain the epithelial-related phenotype and modify mitotic spindle microtubules after the administration of ukrain in vitro. Anticancer Drugs. 2012 Oct;23(9):935-46. doi: 10.1097/CAD.0b013e32835507bc. PubMed PMID: 22700003.

3: Gagliano N, Pettinari L, Aureli M, Martinelli C, Colombo E, Costa F, Carminati R, Volpari T, Colombo G, Milzani A, Dalle-Donne I, Gioia M. Malignant phenotype of renal cell carcinoma cells is switched by ukrain administration in vitro. Anticancer Drugs. 2011 Sep;22(8):749-62. doi: 10.1097/CAD.0b013e328346c7f7. PubMed PMID: 21799470.

4: Venkatesh K, Govindaraj S, Ramachandran A, Kalimuthu S, Perumal E, Velayutham S, Jagadeesan A. Effect of ukrain on cell survival and apoptosis in the androgen-independent prostate cancer cell line PC-3. J Environ Pathol Toxicol Oncol. 2011;30(1):11-9. PubMed PMID: 21609312.

5: Funel N, Costa F, Pettinari L, Taddeo A, Sala A, Chiriva-Internati M, Cobos E, Colombo G, Milzani A, Campani D, Dalle-Donne I, Gagliano N. Ukrain affects pancreas cancer cell phenotype in vitro by targeting MMP-9 and intra-/extracellular SPARC expression. Pancreatology. 2010;10(5):545-52. doi: 10.1159/000266127. Epub 2010 Oct 23. PubMed PMID: 20975318.

6: Skivka L, Susak Y, Trompak O, Kudryavets Y, Bezdeneznikh N, Semesiuk N, Lykhova O. The effect of monotherapy and combined therapy with NSC-631570 (ukrain) on growth of low- and high-metastasizing B16 melanoma in mice. J Oncol Pharm Pract. 2011 Dec;17(4):339-49. doi: 10.1177/1078155210382470. Epub 2010 Sep 3. PubMed PMID: 20817651.

7: Susak YM, Skivka LM, Rudik MP, Pozur VV, Liubunya AV. Comparative investigation of the effect of ukrain on growth of ascites and solid forms of Ehrlich's carcinoma. Exp Oncol. 2010 Jul;32(2):107-10. PubMed PMID: 20693973.

8: Skivka LM, Trompak OO, Kudryavets YI, Bezdenezhnykh NA, Susak YM. The effect of NSC-631570 (ukrain) alone and in combination with pathogen-associated molecules on cell cycle distribution and apoptosis induction of mouse melanoma cells with different biological properties. Exp Oncol. 2010 Jul;32(2):92-6. PubMed PMID: 20693969.

9: Gagliano N, Moscheni C, Torri C, Donetti E, Magnani I, Costa F, Nowicky W, Gioia M. Ukrain modulates glial fibrillary acidic protein, but not connexin 43 expression, and induces apoptosis in human cultured glioblastoma cells. Anticancer Drugs. 2007 Jul;18(6):669-76. PubMed PMID: 17762395.

10: Lanvers-Kaminsky C, Nolting DM, Köster J, Schröder A, Sandkötter J, Boos J. In-vitro toxicity of Ukrain against human Ewing tumor cell lines. Anticancer Drugs. 2006 Oct;17(9):1025-30. PubMed PMID: 17001175.

11: Mendoza J, Zamora R, Gallardo JC, Ceballos G, Aldana A, Espinosa M, Maldonado V, Melendez-Zajgla J. NF-kappaB does not influence the induction of apoptosis by Ukrain. Cancer Biol Ther. 2006 Jul;5(7):788-93. Epub 2006 Jul 26. PubMed PMID: 16721042.

12: Mozhenok TP, Beliaeva TN, Leont'eva EA, Faddeeva MD. [Effect of alkaloid sanguinarine and a pharmaceutical preparation ukrain on modulation of vesicular membrane fusion and actin cytoskeleton of macrophages]. Tsitologiia. 2005;47(10):860-5. Russian. PubMed PMID: 16711384.

13: Gagliano N, Moscheni C, Torri C, Magnani I, Bertelli AA, Nowicky W, Gioia M. Effect of Ukrain on matrix metalloproteinase-2 and Secreted Protein Acidic and Rich in Cysteine (SPARC) expression in human glioblastoma cells. Anticancer Drugs. 2006 Feb;17(2):189-94. PubMed PMID: 16428937.

14: Habermehl D, Kammerer B, Handrick R, Eldh T, Gruber C, Cordes N, Daniel PT, Plasswilm L, Bamberg M, Belka C, Jendrossek V. Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway. BMC Cancer. 2006 Jan 17;6:14. PubMed PMID: 16417634; PubMed Central PMCID: PMC1379651.

15: Ernst E, Schmidt K. Ukrain - a new cancer cure? A systematic review of randomised clinical trials. BMC Cancer. 2005 Jul 1;5:69. Review. PubMed PMID: 15992405; PubMed Central PMCID: PMC1180428.

16: Grinevich Y, Shalimov S, Bendyuh G, Zahriychuk O, Hodysh Y. Effect of Ukrain on the growth and metastasizing of Lewis carcinoma in C57BL/6 mice. Drugs Exp Clin Res. 2005;31(2):59-70. PubMed PMID: 15929607.

17: Cordes N, Blaese MA, Plasswilm L, Rodemann HP, Van Beuningen D. Fibronectin and laminin increase resistance to ionizing radiation and the cytotoxic drug Ukrain in human tumour and normal cells in vitro. Int J Radiat Biol. 2003 Sep;79(9):709-20. PubMed PMID: 14703944.

18: Zemskov V, Prokopchuk O, Susak Y, Zemskov S, Tkachenko O, Hodysh Y, Nowicky W. Efficacy of ukrain in the treatment of pancreatic cancer. Langenbecks Arch Surg. 2002 Jun;387(2):84-9. Epub 2002 Jun 19. PubMed PMID: 12111260.

19: Gansauge F, Ramadani M, Pressmar J, Gansauge S, Muehling B, Stecker K, Cammerer G, Leder G, Beger HG. NSC-631570 (Ukrain) in the palliative treatment of pancreatic cancer. Results of a phase II trial. Langenbecks Arch Surg. 2002 Mar;386(8):570-4. Epub 2002 Feb 13. PubMed PMID: 11914932.

20: Nowicky W. Clinical testing of Ukrain. Lancet Oncol. 2001 Jan;2(1):10. PubMed PMID: 11905612.