MN58b bromide
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MedKoo CAT#: 408112

CAS#: 203192-01-2 (bromide)

Description: MN58b bromide, or MN58b, is a selective choline kinase α (CHKα) inhibitor. MN58b is a novel anticancer drug that inhibits choline kinase, resulting in inhibition of phosphocholine synthesis. Inhibition of choline kinase by MN58b resulted in altered phospholipid metabolism both in cultured tumor cells and in vivo.


Chemical Structure

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MN58b bromide
CAS# 203192-01-2 (bromide)

Theoretical Analysis

MedKoo Cat#: 408112
Name: MN58b bromide
CAS#: 203192-01-2 (bromide)
Chemical Formula: C32H40Br2N4
Exact Mass: 0.00
Molecular Weight: 640.508
Elemental Analysis: C, 60.01; H, 6.30; Br, 24.95; N, 8.75

Price and Availability

Size Price Availability Quantity
5mg USD 150 Ready to ship
10mg USD 250 Ready to ship
25mg USD 550 Ready to ship
50mg USD 950 Ready to ship
100mg USD 1650 Ready to ship
200mg USD 2950 Ready to ship
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Related CAS #: 203192-01-2 (bromide)   730930-74-2 (cation)    

Synonym: MN58b bromide; MN58b; MN 58b; MN 58b;

IUPAC/Chemical Name: 1,1'-((butane-1,4-diylbis(4,1-phenylene))bis(methylene))bis(4-(dimethylamino)pyridin-1-ium) bromide

InChi Key: 1,1'-((butane-1,4-diylbis(4,1-phenylene))bis(methylene))bis(4-(dimethylamino)pyridin-1-ium) bromide

InChi Code: InChI=1S/C32H40N4.2BrH/c1-33(2)31-17-21-35(22-18-31)25-29-13-9-27(10-14-29)7-5-6-8-28-11-15-30(16-12-28)26-36-23-19-32(20-24-36)34(3)4;;/h9-24H,5-8,25-26H2,1-4H3;2*1H/q+2;;/p-2

SMILES Code: CN(C)C1=CC=[N+](C=C1)CC2=CC=C(CCCCC3=CC=C(C[N+]4=CC=C(N(C)C)C=C4)C=C3)C=C2.[Br-].[Br-]

Appearance: Solid powder

Purity: >97% (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: 2934.99.9001

More Info:

Biological target: The IC50s of MN58b for parental and Gemcitabine-resistant Suit2 007 cells are 3.14 µM and 0.77 µM, respectively.
In vitro activity: RA FLS were pretreated with MN58b at various concentrations and then cultured in the presence of PDGF for 3 days or 6 days for Methyl Thiazolyl Tetrazolium (MTT) assay and BrdU assay, respectively. MN58b significantly decreased cell viability (figure 3G) and cell proliferation (figure 3H) growth in a concentration-dependent manner. Reference: Ann Rheum Dis. 2015 Jul;74(7):1399-407. https://pubmed.ncbi.nlm.nih.gov/25274633/
In vivo activity: Tumors from MDA-MB-231-bearing mice were harvested for histological assessment immediately after follow-up MRI/MRS scanning (Figure 5A). Evaluation of H&E slides (Figure 5B) showed that both MN58b (P = 0.007) and JAS239 (P = 0.01) caused significant reduction in cell density. MN58b (P = 0.026) and JAS239 (P = 0.034) treatment significantly reduced the percentage of Ki67-positive cells compared to the control group (Figure 5C). Consistent with reduced cell number and proliferation, higher caspase-3 levels (Figure 5D) were detected in MN58b (P = 0.016) and JAS239 (P = 0.015) treated tumors than in controls. Reference: Oncotarget. 2017 Mar 7;8(10):16518-16530. https://pubmed.ncbi.nlm.nih.gov/28157707/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 10.0 15.60

Preparing Stock Solutions

The following data is based on the product molecular weight 640.51 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. Guma M, Sanchez-Lopez E, Lodi A, Garcia-Carbonell R, Tiziani S, Karin M, Lacal JC, Firestein GS. Choline kinase inhibition in rheumatoid arthritis. Ann Rheum Dis. 2015 Jul;74(7):1399-407. doi: 10.1136/annrheumdis-2014-205696. Epub 2014 Oct 1. PMID: 25274633; PMCID: PMC4382461. 2. Kumar M, Arlauckas SP, Saksena S, Verma G, Ittyerah R, Pickup S, Popov AV, Delikatny EJ, Poptani H. Magnetic resonance spectroscopy for detection of choline kinase inhibition in the treatment of brain tumors. Mol Cancer Ther. 2015 Apr;14(4):899-908. doi: 10.1158/1535-7163.MCT-14-0775. Epub 2015 Feb 5. PMID: 25657334; PMCID: PMC4394035. 3. Arlauckas SP, Kumar M, Popov AV, Poptani H, Delikatny EJ. Near infrared fluorescent imaging of choline kinase alpha expression and inhibition in breast tumors. Oncotarget. 2017 Mar 7;8(10):16518-16530. doi: 10.18632/oncotarget.14965. PMID: 28157707; PMCID: PMC5369982. 4. Guma M, Sanchez-Lopez E, Lodi A, Garcia-Carbonell R, Tiziani S, Karin M, Lacal JC, Firestein GS. Choline kinase inhibition in rheumatoid arthritis. Ann Rheum Dis. 2015 Jul;74(7):1399-407. doi: 10.1136/annrheumdis-2014-205696. Epub 2014 Oct 1. PMID: 25274633; PMCID: PMC4382461.
In vitro protocol: 1. Guma M, Sanchez-Lopez E, Lodi A, Garcia-Carbonell R, Tiziani S, Karin M, Lacal JC, Firestein GS. Choline kinase inhibition in rheumatoid arthritis. Ann Rheum Dis. 2015 Jul;74(7):1399-407. doi: 10.1136/annrheumdis-2014-205696. Epub 2014 Oct 1. PMID: 25274633; PMCID: PMC4382461. 2. Kumar M, Arlauckas SP, Saksena S, Verma G, Ittyerah R, Pickup S, Popov AV, Delikatny EJ, Poptani H. Magnetic resonance spectroscopy for detection of choline kinase inhibition in the treatment of brain tumors. Mol Cancer Ther. 2015 Apr;14(4):899-908. doi: 10.1158/1535-7163.MCT-14-0775. Epub 2015 Feb 5. PMID: 25657334; PMCID: PMC4394035.
In vivo protocol: 1. Arlauckas SP, Kumar M, Popov AV, Poptani H, Delikatny EJ. Near infrared fluorescent imaging of choline kinase alpha expression and inhibition in breast tumors. Oncotarget. 2017 Mar 7;8(10):16518-16530. doi: 10.18632/oncotarget.14965. PMID: 28157707; PMCID: PMC5369982. 2. Guma M, Sanchez-Lopez E, Lodi A, Garcia-Carbonell R, Tiziani S, Karin M, Lacal JC, Firestein GS. Choline kinase inhibition in rheumatoid arthritis. Ann Rheum Dis. 2015 Jul;74(7):1399-407. doi: 10.1136/annrheumdis-2014-205696. Epub 2014 Oct 1. PMID: 25274633; PMCID: PMC4382461.

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1: Al-Saffar NM, Troy H, Ramírez de Molina A, Jackson LE, Madhu B, Griffiths JR, Leach MO, Workman P, Lacal JC, Judson IR, Chung YL. Noninvasive magnetic resonance spectroscopic pharmacodynamic markers of the choline kinase inhibitor MN58b in human carcinoma models. Cancer Res. 2006 Jan 1;66(1):427-34. doi: 10.1158/0008-5472.CAN-05-1338. PMID: 16397258.


2: Li Y, Kinting S, Höppner S, Forstner ME, Uhl O, Koletzko B, Griese M. Metabolic labelling of choline phospholipids probes ABCA3 transport in lamellar bodies. Biochim Biophys Acta Mol Cell Biol Lipids. 2019 Dec;1864(12):158516. doi: 10.1016/j.bbalip.2019.158516. Epub 2019 Aug 29. PMID: 31473345.


3: Kumar M, Arlauckas SP, Saksena S, Verma G, Ittyerah R, Pickup S, Popov AV, Delikatny EJ, Poptani H. Magnetic resonance spectroscopy for detection of choline kinase inhibition in the treatment of brain tumors. Mol Cancer Ther. 2015 Apr;14(4):899-908. doi: 10.1158/1535-7163.MCT-14-0775. Epub 2015 Feb 5. PMID: 25657334; PMCID: PMC4394035.


4: Guma M, Sanchez-Lopez E, Lodi A, Garcia-Carbonell R, Tiziani S, Karin M, Lacal JC, Firestein GS. Choline kinase inhibition in rheumatoid arthritis. Ann Rheum Dis. 2015 Jul;74(7):1399-407. doi: 10.1136/annrheumdis-2014-205696. Epub 2014 Oct 1. PMID: 25274633; PMCID: PMC4382461.


5: Zimmerman T, Moneriz C, Diez A, Bautista JM, Gómez Del Pulgar T, Cebrián A, Lacal JC. Antiplasmodial activity and mechanism of action of RSM-932A, a promising synergistic inhibitor of Plasmodium falciparum choline kinase. Antimicrob Agents Chemother. 2013 Dec;57(12):5878-88. doi: 10.1128/AAC.00920-13. Epub 2013 Sep 16. PMID: 24041883; PMCID: PMC3837925.


6: Mazarico JM, Sánchez-Arévalo Lobo VJ, Favicchio R, Greenhalf W, Costello E, Carrillo-de Santa Pau E, Marqués M, Lacal JC, Aboagye E, Real FX. Choline Kinase Alpha (CHKα) as a Therapeutic Target in Pancreatic Ductal Adenocarcinoma: Expression, Predictive Value, and Sensitivity to Inhibitors. Mol Cancer Ther. 2016 Feb;15(2):323-33. doi: 10.1158/1535-7163.MCT-15-0214. Epub 2016 Jan 14. PMID: 26769123.


7: Arlauckas SP, Kumar M, Popov AV, Poptani H, Delikatny EJ. Near infrared fluorescent imaging of choline kinase alpha expression and inhibition in breast tumors. Oncotarget. 2017 Mar 7;8(10):16518-16530. doi: 10.18632/oncotarget.14965. PMID: 28157707; PMCID: PMC5369982.


8: Gallego-Ortega D, Gómez del Pulgar T, Valdés-Mora F, Cebrián A, Lacal JC. Involvement of human choline kinase alpha and beta in carcinogenesis: a different role in lipid metabolism and biological functions. Adv Enzyme Regul. 2011;51(1):183-94. doi: 10.1016/j.advenzreg.2010.09.010. Epub 2010 Oct 28. PMID: 21035492.


9: Rodríguez-González A, Ramírez de Molina A, Bañez-Coronel M, Megias D, Lacal JC. Inhibition of choline kinase renders a highly selective cytotoxic effect in tumour cells through a mitochondrial independent mechanism. Int J Oncol. 2005 Apr;26(4):999-1008. PMID: 15753995.


10: Rodríguez-González A, Ramírez de Molina A, Fernández F, Ramos MA, del Carmen Núñez M, Campos J, Lacal JC. Inhibition of choline kinase as a specific cytotoxic strategy in oncogene-transformed cells. Oncogene. 2003 Dec 4;22(55):8803-12. doi: 10.1038/sj.onc.1207062. PMID: 14654777.