KP1019

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

MedKoo CAT#: 206021

CAS#: 124875-20-3

Description: KP1019 is now discontinued.


Chemical Structure

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KP1019
CAS# 124875-20-3

Theoretical Analysis

MedKoo Cat#: 206021
Name: KP1019
CAS#: 124875-20-3
Chemical Formula: C21H19Cl4N6Ru
Exact Mass:
Molecular Weight: 598.3
Elemental Analysis: C, 42.16; H, 3.20; Cl, 23.70; N, 14.05; Ru, 16.89

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Pricing updated 2021-03-02. Prices are subject to change without notice.

KP1019 is now discontinued.

Synonym: KP1019; KP 1019; KP1019; FFC14A; indazolium trans-tetrachlorobis(1H-indazole)ruthenate-(III).

IUPAC/Chemical Name: Ruthenate(1-), tetrachlorobis(1H-indazole-κN2)-, (OC-6-11)-, hydrogen, compd. with 1H-indazole (1:1:1).

InChi Key: RFCAXSUVZZSVPM-UHFFFAOYSA-K

InChi Code: InChI=1S/3C7H6N2.4ClH.Ru/c3*1-2-4-7-6(3-1)5-8-9-7;;;;;/h3*1-5H,(H,8,9);4*1H;/q;;;;;;;+4/p-3

SMILES Code: Cl[Ru-2]([N+](N1)=CC2=C1C=CC=C2)(Cl)(Cl)(Cl)[N+](N3)=CC4=C3C=CC=C4.[H][N+](N5)=CC6=C5C=CC=C6

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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 598.3 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.

Select a batch to recalculate based on the batch molecular weight:
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

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1: Jones MR, Mu C, Wang MC, Webb MI, Walsby CJ, Storr T. Modulation of the Aβ peptide aggregation pathway by KP1019 limits Aβ-associated neurotoxicity. Metallomics. 2015 Jan 24;7(1):129-35. doi: 10.1039/c4mt00252k. Epub 2014 Nov 12. PubMed PMID: 25387614.

2: Kuhn PS, Büchel GE, Jovanović KK, Filipović L, Radulović S, Rapta P, Arion VB. Osmium(III) analogues of KP1019: electrochemical and chemical synthesis, spectroscopic characterization, X-ray crystallography, hydrolytic stability, and antiproliferative activity. Inorg Chem. 2014 Oct 20;53(20):11130-9. doi: 10.1021/ic501710k. Epub 2014 Oct 7. PubMed PMID: 25290960.

3: Sadafi FZ, Massai L, Bartolommei G, Moncelli MR, Messori L, Tadini-Buoninsegni F. Anticancer ruthenium(III) complex KP1019 interferes with ATP-dependent Ca2+ translocation by sarco-endoplasmic reticulum Ca2+-ATPase (SERCA). ChemMedChem. 2014 Aug;9(8):1660-4. doi: 10.1002/cmdc.201402128. Epub 2014 Jun 11. PubMed PMID: 24920093.

4: Singh V, Azad GK, Reddy M A, Baranwal S, Tomar RS. Anti-cancer drug KP1019 induces Hog1 phosphorylation and protein ubiquitylation in Saccharomyces cerevisiae. Eur J Pharmacol. 2014 Aug 5;736:77-85. doi: 10.1016/j.ejphar.2014.04.032. Epub 2014 May 2. PubMed PMID: 24797784.

5: Heffeter P, Riabtseva A, Senkiv Y, Kowol CR, Körner W, Jungwith U, Mitina N, Keppler BK, Konstantinova T, Yanchuk I, Stoika R, Zaichenko A, Berger W. Nanoformulation improves activity of the (pre)clinical anticancer ruthenium complex KP1019. J Biomed Nanotechnol. 2014 May;10(5):877-84. PubMed PMID: 24734541.

6: Singh V, Azad GK, Mandal P, Reddy MA, Tomar RS. Anti-cancer drug KP1019 modulates epigenetics and induces DNA damage response in Saccharomyces cerevisiae. FEBS Lett. 2014 Mar 18;588(6):1044-52. doi: 10.1016/j.febslet.2014.02.017. Epub 2014 Feb 20. PubMed PMID: 24561198.

7: Fischer B, Heffeter P, Kryeziu K, Gille L, Meier SM, Berger W, Kowol CR, Keppler BK. Poly(lactic acid) nanoparticles of the lead anticancer ruthenium compound KP1019 and its surfactant-mediated activation. Dalton Trans. 2014 Jan 21;43(3):1096-104. doi: 10.1039/c3dt52388h. Epub 2013 Oct 29. PubMed PMID: 24165902.

8: Hummer AA, Heffeter P, Berger W, Filipits M, Batchelor D, Büchel GE, Jakupec MA, Keppler BK, Rompel A. X-ray absorption near edge structure spectroscopy to resolve the in vivo chemistry of the redox-active indazolium trans-[Tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019). J Med Chem. 2013 Feb 14;56(3):1182-96. doi: 10.1021/jm301648f. Epub 2013 Jan 31. PubMed PMID: 23282017; PubMed Central PMCID: PMC3579476.

9: Stevens SK, Strehle AP, Miller RL, Gammons SH, Hoffman KJ, McCarty JT, Miller ME, Stultz LK, Hanson PK. The anticancer ruthenium complex KP1019 induces DNA damage, leading to cell cycle delay and cell death in Saccharomyces cerevisiae. Mol Pharmacol. 2013 Jan;83(1):225-34. doi: 10.1124/mol.112.079657. Epub 2012 Oct 22. PubMed PMID: 23090979.

10: Dömötör O, Hartinger CG, Bytzek AK, Kiss T, Keppler BK, Enyedy EA. Characterization of the binding sites of the anticancer ruthenium(III) complexes KP1019 and KP1339 on human serum albumin via competition studies. J Biol Inorg Chem. 2013 Jan;18(1):9-17. doi: 10.1007/s00775-012-0944-6. Epub 2012 Oct 18. PubMed PMID: 23076343.

11: Aitken JB, Antony S, Weekley CM, Lai B, Spiccia L, Harris HH. Distinct cellular fates for KP1019 and NAMI-A determined by X-ray fluorescence imaging of single cells. Metallomics. 2012 Oct;4(10):1051-6, 1007. Epub 2012 Aug 20. PubMed PMID: 22907648.

12: Büchel GE, Stepanenko IN, Hejl M, Jakupec MA, Keppler BK, Arion VB. En route to osmium analogues of KP1019: synthesis, structure, spectroscopic properties and antiproliferative activity of trans-[Os(IV)Cl4(Hazole)2]. Inorg Chem. 2011 Aug 15;50(16):7690-7. doi: 10.1021/ic200728b. Epub 2011 Jul 8. PubMed PMID: 21739939; PubMed Central PMCID: PMC3152248.

13: Bartel C, Egger AE, Jakupec MA, Heffeter P, Galanski M, Berger W, Keppler BK. Influence of ascorbic acid on the activity of the investigational anticancer drug KP1019. J Biol Inorg Chem. 2011 Dec;16(8):1205-15. doi: 10.1007/s00775-011-0809-4. Epub 2011 Jun 26. PubMed PMID: 21706338.

14: Heffeter P, Böck K, Atil B, Reza Hoda MA, Körner W, Bartel C, Jungwirth U, Keppler BK, Micksche M, Berger W, Koellensperger G. Intracellular protein binding patterns of the anticancer ruthenium drugs KP1019 and KP1339. J Biol Inorg Chem. 2010 Jun;15(5):737-48. doi: 10.1007/s00775-010-0642-1. Epub 2010 Mar 11. PubMed PMID: 20221888; PubMed Central PMCID: PMC3371400.

15: Bergamo A, Masi A, Jakupec MA, Keppler BK, Sava G. Inhibitory Effects of the Ruthenium Complex KP1019 in Models of Mammary Cancer Cell Migration and Invasion. Met Based Drugs. 2009;2009:681270. doi: 10.1155/2009/681270. Epub 2009 Sep 17. PubMed PMID: 19789639; PubMed Central PMCID: PMC2748298.

16: Cetinbas N, Webb MI, Dubland JA, Walsby CJ. Serum-protein interactions with anticancer Ru(III) complexes KP1019 and KP418 characterized by EPR. J Biol Inorg Chem. 2010 Feb;15(2):131-45. doi: 10.1007/s00775-009-0578-5. Epub 2009 Aug 26. PubMed PMID: 19707803.

17: Lentz F, Drescher A, Lindauer A, Henke M, Hilger RA, Hartinger CG, Scheulen ME, Dittrich C, Keppler BK, Jaehde U; Central European Society for Anticancer Drug Research-EWIV. Pharmacokinetics of a novel anticancer ruthenium complex (KP1019, FFC14A) in a phase I dose-escalation study. Anticancer Drugs. 2009 Feb;20(2):97-103. doi: 10.1097/CAD.0b013e328322fbc5. PubMed PMID: 19209025.

18: Hartinger CG, Jakupec MA, Zorbas-Seifried S, Groessl M, Egger A, Berger W, Zorbas H, Dyson PJ, Keppler BK. KP1019, a new redox-active anticancer agent--preclinical development and results of a clinical phase I study in tumor patients. Chem Biodivers. 2008 Oct;5(10):2140-55. doi: 10.1002/cbdv.200890195. Review. PubMed PMID: 18972504.

19: Hartinger CG, Zorbas-Seifried S, Jakupec MA, Kynast B, Zorbas H, Keppler BK. From bench to bedside--preclinical and early clinical development of the anticancer agent indazolium trans-[tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019 or FFC14A). J Inorg Biochem. 2006 May;100(5-6):891-904. Epub 2006 Feb 28. Review. PubMed PMID: 16603249.

20: Jakupec MA, Arion VB, Kapitza S, Reisner E, Eichinger A, Pongratz M, Marian B, Graf von Keyserlingk N, Keppler BK. KP1019 (FFC14A) from bench to bedside: preclinical and early clinical development--an overview. Int J Clin Pharmacol Ther. 2005 Dec;43(12):595-6. PubMed PMID: 16372531.



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