NAMI-A
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MedKoo CAT#: 206020

CAS#: 201653-76-1

Description: NAMI-A is a ruthenium anticancer agent and a metastasis inhibitor. NAMI is an acronym for "New Anti-tumour Metastasis Inhibitor", while the -A suffix indicates that this is the first of a potential series. NAMI-A is a potent agent for the treatment of solid tumor metastases as well as when these tumor lesions are in an advanced stage of growth. NAMI-A is endowed with a mechanism of action unrelated to direct tumor cell cytotoxicity, and such mechanism of action is responsible for a reduced host toxicity. NAMI-A and KP-1019 are two ruthenium anticancer agents that have entered clinical trials. (http://en.wikipedia.org/wiki/NAMI-A).


Chemical Structure

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NAMI-A
CAS# 201653-76-1

Theoretical Analysis

MedKoo Cat#: 206020
Name: NAMI-A
CAS#: 201653-76-1
Chemical Formula: C8H15Cl4N4ORuS
Exact Mass: 0.00
Molecular Weight: 458.180
Elemental Analysis: C, 20.97; H, 3.30; Cl, 30.95; N, 12.23; O, 3.49; Ru, 22.06; S, 7.00

Price and Availability

Size Price Availability Quantity
10mg USD 450 2 Weeks
50mg USD 1650 2 Weeks
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Synonym: NAMIA; ImH-trans-RuCl4(DMSO)-Im; imidazolium transimidazoledimethyl sulfoxidetetrachlororuthenat.

IUPAC/Chemical Name: Ruthenate(1-), tetrachloro(1H-imidazole-κN3)[(sulfinyl-κS)bis[methane]]-, (OC-6-11)-, hydrogen, compd. with 1H-imidazole (1:1:1).

InChi Key: HIAWXYSWERGOAJ-UHFFFAOYSA-K

InChi Code: InChI=1S/2C3H4N2.C2H6OS.4ClH.Ru/c2*1-2-5-3-4-1;1-4(2)3;;;;;/h2*1-3H,(H,4,5);1-2H3;4*1H;/q;;;;;;;+4/p-3

SMILES Code: Cl[Ru]([N]1=CNC=C1)(Cl)(Cl)(Cl)=S(C)(C)=O.C2=C[NH+]=CN2

Appearance: white 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

More Info:         

Product Data:
Biological target: NAMI-A is a ruthenium-based drug characterised by the selective activity against tumour metastases, inhibits the adhesion and migration.
In vitro activity: NAMI-A inhibits two important steps of the tumour metastatic progression of colorectal cancer, i.e. the adhesion and migration of the tumour cells on the extracellular matrix proteins. The fibronectin receptor α5β1 integrin is likely involved in the anti-adhesive effects of NAMI-A on the HCT-116 colorectal cancer cells during their interaction with the extracellular matrix. Mechanistically, NAMI-A decreases the α5β1 integrin expression, and reduces FAK (Focal Adhesion Kinase) auto-phosphorylation on Tyr397, an important signalling event, involved in α5β1 integrin activation. Reference: J Inorg Biochem. 2016 Jul;160:225-35. https://pubmed.ncbi.nlm.nih.gov/26961176/
In vivo activity: Intratumor (i.t.) injection of 35 mg/kg/day NAMI-A for six consecutive days to CBA mice bearing i.m. implants of MCa mammary carcinoma reduces primary tumor growth and particularly lung metastasis formation, causing 60% of animals to be free of macroscopically detectable metastases. Under these conditions, NAMI-A reduces the number of CD44+ tumor cells and changes tumor cell phenotype to a lower aggressive behavior, as shown by scanning electron microscopy analysis. On primary tumor site, NAMI-A causes unbalance between 2n and aneuploid cells in favor of lymphocytes. Reference: J Pharmacol Exp Ther. 2004 Aug;310(2):737-44. https://pubmed.ncbi.nlm.nih.gov/15075381/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 8.3 18.07

Preparing Stock Solutions

The following data is based on the product molecular weight 458.18 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
Formulation protocol: 1. Pelillo C, Mollica H, Eble JA, Grosche J, Herzog L, Codan B, Sava G, Bergamo A. Inhibition of adhesion, migration and of α5β1 integrin in the HCT-116 colorectal cancer cells treated with the ruthenium drug NAMI-A. J Inorg Biochem. 2016 Jul;160:225-35. doi: 10.1016/j.jinorgbio.2016.02.025. Epub 2016 Feb 27. PMID: 26961176. 2. Pillozzi S, Gasparoli L, Stefanini M, Ristori M, D'Amico M, Alessio E, Scaletti F, Becchetti A, Arcangeli A, Messori L. NAMI-A is highly cytotoxic toward leukaemia cell lines: evidence of inhibition of KCa 3.1 channels. Dalton Trans. 2014 Aug 28;43(32):12150-5. doi: 10.1039/c4dt01356e. PMID: 24975719. 3. Vadori M, Florio C, Groppo B, Cocchietto M, Pacor S, Zorzet S, Candussio L, Sava G. The antimetastatic drug NAMI-A potentiates the phenylephrine-induced contraction of aortic smooth muscle cells and induces a transient increase in systolic blood pressure. J Biol Inorg Chem. 2015 Jul;20(5):831-40. doi: 10.1007/s00775-015-1269-z. Epub 2015 May 16. PMID: 25982099. 4. Pacor S, Zorzet S, Cocchietto M, Bacac M, Vadori M, Turrin C, Gava B, Castellarin A, Sava G. Intratumoral NAMI-A treatment triggers metastasis reduction, which correlates to CD44 regulation and tumor infiltrating lymphocyte recruitment. J Pharmacol Exp Ther. 2004 Aug;310(2):737-44. doi: 10.1124/jpet.104.066175. Epub 2004 Apr 9. PMID: 15075381.
In vitro protocol: 1. Pelillo C, Mollica H, Eble JA, Grosche J, Herzog L, Codan B, Sava G, Bergamo A. Inhibition of adhesion, migration and of α5β1 integrin in the HCT-116 colorectal cancer cells treated with the ruthenium drug NAMI-A. J Inorg Biochem. 2016 Jul;160:225-35. doi: 10.1016/j.jinorgbio.2016.02.025. Epub 2016 Feb 27. PMID: 26961176. 2. Pillozzi S, Gasparoli L, Stefanini M, Ristori M, D'Amico M, Alessio E, Scaletti F, Becchetti A, Arcangeli A, Messori L. NAMI-A is highly cytotoxic toward leukaemia cell lines: evidence of inhibition of KCa 3.1 channels. Dalton Trans. 2014 Aug 28;43(32):12150-5. doi: 10.1039/c4dt01356e. PMID: 24975719.
In vivo protocol: 1. Vadori M, Florio C, Groppo B, Cocchietto M, Pacor S, Zorzet S, Candussio L, Sava G. The antimetastatic drug NAMI-A potentiates the phenylephrine-induced contraction of aortic smooth muscle cells and induces a transient increase in systolic blood pressure. J Biol Inorg Chem. 2015 Jul;20(5):831-40. doi: 10.1007/s00775-015-1269-z. Epub 2015 May 16. PMID: 25982099. 2. Pacor S, Zorzet S, Cocchietto M, Bacac M, Vadori M, Turrin C, Gava B, Castellarin A, Sava G. Intratumoral NAMI-A treatment triggers metastasis reduction, which correlates to CD44 regulation and tumor infiltrating lymphocyte recruitment. J Pharmacol Exp Ther. 2004 Aug;310(2):737-44. doi: 10.1124/jpet.104.066175. Epub 2004 Apr 9. PMID: 15075381.

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1: Novohradský V, Bergamo A, Cocchietto M, Zajac J, Brabec V, Mestroni G, Sava G. Influence of the binding of reduced NAMI-A to human serum albumin on the pharmacokinetics and biological activity. Dalton Trans. 2014 Dec 23;44(4):1905-13. doi: 10.1039/c4dt02865a. PubMed PMID: 25489765.

2: Leijen S, Burgers SA, Baas P, Pluim D, Tibben M, van Werkhoven E, Alessio E, Sava G, Beijnen JH, Schellens JH. Phase I/II study with ruthenium compound NAMI-A and gemcitabine in patients with non-small cell lung cancer after first line therapy. Invest New Drugs. 2015 Feb;33(1):201-14. doi: 10.1007/s10637-014-0179-1. Epub 2014 Oct 25. PubMed PMID: 25344453.

3: Bergamo A, Riedel T, Dyson PJ, Sava G. Preclinical combination therapy of the investigational drug NAMI-A(+) with doxorubicin for mammary cancer. Invest New Drugs. 2015 Feb;33(1):53-63. doi: 10.1007/s10637-014-0175-5. Epub 2014 Oct 23. PubMed PMID: 25338748.

4: Adigun RA, Martincigh B, Nyamori VO, Omondi B, Masimirembwa C, Simoyi RH. Kinetics and mechanistic investigation into the possible activation of imidazolium trans-[tetrachloridodimethylsulfoxideimidazoleruthenate(III)], NAMI-A, by 2-mercaptoethane sulfonate. Dalton Trans. 2014 Sep 14;43(34):12943-51. doi: 10.1039/c4dt01643b. PubMed PMID: 25026023.

5: Pillozzi S, Gasparoli L, Stefanini M, Ristori M, D'Amico M, Alessio E, Scaletti F, Becchetti A, Arcangeli A, Messori L. NAMI-A is highly cytotoxic toward leukaemia cell lines: evidence of inhibition of KCa 3.1 channels. Dalton Trans. 2014 Aug 28;43(32):12150-5. doi: 10.1039/c4dt01356e. PubMed PMID: 24975719.

6: Messori L, Merlino A. Ruthenium metalation of proteins: the X-ray structure of the complex formed between NAMI-A and hen egg white lysozyme. Dalton Trans. 2014 Apr 28;43(16):6128-31. doi: 10.1039/c3dt53582g. PubMed PMID: 24553967.

7: Sooriyaarachchi M, Wedding JL, Harris HH, Gailer J. Simultaneous observation of the metabolism of cisplatin and NAMI-A in human plasma in vitro by SEC-ICP-AES. J Biol Inorg Chem. 2014 Aug;19(6):1049-53. doi: 10.1007/s00775-014-1102-0. Epub 2014 Jan 24. PubMed PMID: 24458238.

8: Vadori M, Pacor S, Vita F, Zorzet S, Cocchietto M, Sava G. Features and full reversibility of the renal toxicity of the ruthenium-based drug NAMI-A in mice. J Inorg Biochem. 2013 Jan;118:21-7. doi: 10.1016/j.jinorgbio.2012.09.018. Epub 2012 Sep 26. PubMed PMID: 23123335.

9: Mazuryk O, Kurpiewska K, Lewiński K, Stochel G, Brindell M. Interaction of apo-transferrin with anticancer ruthenium complexes NAMI-A and its reduced form. J Inorg Biochem. 2012 Nov;116:11-8. doi: 10.1016/j.jinorgbio.2012.07.017. Epub 2012 Jul 29. PubMed PMID: 23010324.

10: 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.