RAPTA-C | CAS# | antimetastatic

MedKoo Cat#: 591798 | Name: RAPTA-C

Description:

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

RAPTA-C induces apoptosis in EAC cells through mitochondrial and p53-JNK pathways.

Chemical Structure

RAPTA-C

CAS#372948-28-2

Theoretical Analysis

MedKoo Cat#: 591798

Name: RAPTA-C

CAS#: 372948-28-2

Chemical Formula: C24H36CL2N5PRu

Exact Mass: 597.1129

Molecular Weight: 597.53

Elemental Analysis: C, 48.24; H, 6.07; Cl, 11.87; N, 11.72; P, 5.18; Ru, 16.91

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 #

No Data

Synonym

RAPTA-C;

IUPAC/Chemical Name

Dichloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene](1,3,5-triaza-7-phosphatricyclo[3.3.1.13,7]decane-κP7)ruthenium

InChi Key

KRAZAAZCPOHOIH-UHFFFAOYSA-M

InChi Code

InChI=1S/C10H14.C7H15N3P.C7H6N2.2ClH.Ru/c1-8(2)10-6-4-9(3)5-7-10;1-11-5-8-2-9(6-11)4-10(3-8)7-11;1-2-4-7-6(3-1)5-8-9-7;;;/h4-8H,1-3H3;2-7H2,1H3;1-5H,(H,8,9);2*1H;/q;-1;;;;+2/p-1

SMILES Code

Cc1ccc(C(C)C)cc1.Cl[Ru]Cl.C[P-]2(CN(C3)C4)CN4CN3C2.[H][N+]5=CC6=CC=CC=C6N5

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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 597.53 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.

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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PubMed PMID: 29146919; PubMed Central PMCID: PMC5691193. 4: Batchelor LK, Păunescu E, Soudani M, Scopelliti R, Dyson PJ. Influence of the Linker Length on the Cytotoxicity of Homobinuclear Ruthenium(II) and Gold(I) Complexes. Inorg Chem. 2017 Aug 21;56(16):9617-9633. doi: 10.1021/acs.inorgchem.7b01082. Epub 2017 Jul 31. PubMed PMID: 28758743. 5: Artner C, Holtkamp HU, Hartinger CG, Meier-Menches SM. Characterizing activation mechanisms and binding preferences of ruthenium metallo-prodrugs by a competitive binding assay. J Inorg Biochem. 2017 Dec;177:322-327. doi: 10.1016/j.jinorgbio.2017.07.010. Epub 2017 Jul 16. PubMed PMID: 28739166. 6: Michelucci E, Pieraccini G, Moneti G, Gabbiani C, Pratesi A, Messori L. Mass spectrometry and metallomics: A general protocol to assess stability of metallodrug-protein adducts in bottom-up MS experiments. Talanta. 2017 May 15;167:30-38. doi: 10.1016/j.talanta.2017.01.074. Epub 2017 Jan 26. PubMed PMID: 28340724. 7: Lu M, Chen F, Noy JM, Lu H, Stenzel MH. Enhanced Antimetastatic Activity of the Ruthenium Anticancer Drug RAPTA-C Delivered in Fructose-Coated Micelles. Macromol Biosci. 2017 Oct;17(10). doi: 10.1002/mabi.201600513. Epub 2017 Feb 24. PubMed PMID: 28234423. 8: Berndsen RH, Weiss A, Abdul UK, Wong TJ, Meraldi P, Griffioen AW, Dyson PJ, Nowak-Sliwinska P. Combination of ruthenium(II)-arene complex [Ru(η(6)-p-cymene)Cl(2)(pta)] (RAPTA-C) and the epidermal growth factor receptor inhibitor erlotinib results in efficient angiostatic and antitumor activity. Sci Rep. 2017 Feb 22;7:43005. doi: 10.1038/srep43005. PubMed PMID: 28223694; PubMed Central PMCID: PMC5320450. 9: Rojas S, Carmona FJ, Maldonado CR, Horcajada P, Hidalgo T, Serre C, Navarro JA, Barea E. Nanoscaled Zinc Pyrazolate Metal-Organic Frameworks as Drug-Delivery Systems. Inorg Chem. 2016 Mar 7;55(5):2650-63. doi: 10.1021/acs.inorgchem.6b00045. Epub 2016 Feb 17. PubMed PMID: 26886572. 10: Czerwinska I, Far J, Kune C, Larriba-Andaluz C, Delaude L, De Pauw E. Structural analysis of ruthenium-arene complexes using ion mobility mass spectrometry, collision-induced dissociation, and DFT. Dalton Trans. 2016 Apr 21;45(15):6361-70. doi: 10.1039/c6dt00080k. PubMed PMID: 26880308. 11: Lu H, Blunden BM, Scarano W, Lu M, Stenzel MH. Anti-metastatic effects of RAPTA-C conjugated polymeric micelles on two-dimensional (2D) breast tumor cells and three-dimensional (3D) multicellular tumor spheroids. Acta Biomater. 2016 Mar 1;32:68-76. doi: 10.1016/j.actbio.2015.12.020. Epub 2015 Dec 12. PubMed PMID: 26689468. 12: Weiss A, Ding X, van Beijnum JR, Wong I, Wong TJ, Berndsen RH, Dormond O, Dallinga M, Shen L, Schlingemann RO, Pili R, Ho CM, Dyson PJ, van den Bergh H, Griffioen AW, Nowak-Sliwinska P. Rapid optimization of drug combinations for the optimal angiostatic treatment of cancer. Angiogenesis. 2015 Jul;18(3):233-44. doi: 10.1007/s10456-015-9462-9. Epub 2015 Apr 1. PubMed PMID: 25824484; PubMed Central PMCID: PMC4473022. 13: Weiss A, Bonvin D, Berndsen RH, Scherrer E, Wong TJ, Dyson PJ, Griffioen AW, Nowak-Sliwinska P. Angiostatic treatment prior to chemo- or photodynamic therapy improves anti-tumor efficacy. Sci Rep. 2015 Mar 11;5:8990. doi: 10.1038/srep08990. PubMed PMID: 25758612; PubMed Central PMCID: PMC4355632. 14: Nazarov AA, Meier SM, Zava O, Nosova YN, Milaeva ER, Hartinger CG, Dyson PJ. Protein ruthenation and DNA alkylation: chlorambucil-functionalized RAPTA complexes and their anticancer activity. Dalton Trans. 2015 Feb 28;44(8):3614-23. doi: 10.1039/c4dt02764g. PubMed PMID: 25407500. 15: Blunden BM, Chapman R, Danial M, Lu H, Jolliffe KA, Perrier S, Stenzel MH. Drug conjugation to cyclic peptide-polymer self-assembling nanotubes. Chemistry. 2014 Sep 26;20(40):12745-9. doi: 10.1002/chem.201403130. Epub 2014 Aug 21. PubMed PMID: 25146103. 16: 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. 17: Blunden BM, Lu H, Stenzel MH. Enhanced delivery of the RAPTA-C macromolecular chemotherapeutic by conjugation to degradable polymeric micelles. Biomacromolecules. 2013 Dec 9;14(12):4177-88. doi: 10.1021/bm4013919. Epub 2013 Nov 22. PubMed PMID: 24266669. 18: Chakree K, Ovatlarnporn C, Dyson PJ, Ratanaphan A. Altered DNA binding and amplification of human breast cancer suppressor gene BRCA1 induced by a novel antitumor compound, [Ru(η(6)-p-phenylethacrynate)Cl(2)(pta)]. Int J Mol Sci. 2012 Oct 15;13(10):13183-202. doi: 10.3390/ijms131013183. PubMed PMID: 23202946; PubMed Central PMCID: PMC3497320. 19: Kilpin KJ, Cammack SM, Clavel CM, Dyson PJ. Ruthenium(II) arene PTA (RAPTA) complexes: impact of enantiomerically pure chiral ligands. Dalton Trans. 2013 Feb 14;42(6):2008-14. doi: 10.1039/c2dt32333h. PubMed PMID: 23187957. 20: Adeniyi AA, Ajibade PA. Effects of bidentate coordination on the molecular properties rapta-C based complex using theoretical approach. J Mol Model. 2013 Mar;19(3):1325-38. doi: 10.1007/s00894-012-1683-x. Epub 2012 Nov 28. PubMed PMID: 23187687.