K145 HCl salt
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MedKoo CAT#: 558222

CAS#: 1449240-68-9 (HCl)

Description: K145 is a selective sphingosine kinase-2 (SphK2) inhibitor and anticancer agent. K145 inhibited the activity of SphK2 in a dose-dependent manner with an IC50 of 4.30±0.06 µM. K145 also exhibited inhibitory effects on the growth of U937 cells as well as apoptotic effects in U937 cells. K145 exhibits comparable in vivo anti-tumor activity to tamibarotene, while concomitantly exhibiting less toxicity in this U937 xenograft cancer model.


Chemical Structure

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K145 HCl salt
CAS# 1449240-68-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 558222
Name: K145 HCl salt
CAS#: 1449240-68-9 (HCl)
Chemical Formula: C18H24N2O3S
Exact Mass: 348.15076
Molecular Weight: 348.46
Elemental Analysis: C, 62.04; H, 6.94; N, 8.04; O, 13.77; S, 9.20

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 Same day
25.0mg USD 250.0 Same day
50.0mg USD 450.0 Same day
100.0mg USD 750.0 Same day
200.0mg USD 1250.0 Same day
500.0mg USD 2150.0 Same day
1.0g USD 3650.0 Same day
2.0g USD 5650.0 2 Weeks
5.0g USD 9950.0 2 Weeks
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Synonym: K145; K-145; K 145; K145 HCl; K145 hydrochloride.

IUPAC/Chemical Name: (Z)-3-(2-aminoethyl)-5-(3-(4-butoxyphenyl)propylidene)thiazolidine-2,4-dione hydrochloride

InChi Key: HADFDMGQKBGVAV-NKBLJONXSA-N

InChi Code: InChI=1S/C18H24N2O3S.ClH/c1-2-3-13-23-15-9-7-14(8-10-15)5-4-6-16-17(21)20(12-11-19)18(22)24-16;/h6-10H,2-5,11-13,19H2,1H3;1H/b16-6-;

SMILES Code: O=C(N(CCN)C/1=O)SC1=C/CCC2=CC=C(OCCCC)C=C2.[H]Cl

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, and in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO or water.

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

Biological target: K145 hydrochloride is a SphK2 inhibitor with an IC50 of 4.3 µM.
In vitro activity: The anti-proliferative and apoptotic effects of K145 in U937 cells were evaluated. As shown in Figure 6A, K 145 significantly inhibited the growth of U937 cells cultured in the presence of 10% serum in a concentration-dependent manner. K145 also significantly induced apoptosis in U937 cells under these experimental conditions (Figure 6B). Notably, K145 induced mainly late apoptosis with a very small percentage of necrotic cells after 24 h treatment in the presence of 10% serum. Reference: PLoS One. 2013;8(2):e56471. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3577900/
In vivo activity: The anticancer activity of K145 to inhibit the tumor growth of U937 cells was examined in nude mice (BALB/c-nu) by oral administration. As shown in Figure 10A, tumor weights of K145-treated mice were significantly less than that in vehicle-treated mice and K145 exhibited antitumor activity (TGI for K145 was 51.25%). Visual examination of the tumor samples also confirmed the significant inhibition of U937 tumor growth by K145 (Figure 10B-C). Collectively, the results of in vivo studies with K145 by oral administration demonstrated that K145 is orally available to inhibit the growth of U937 tumors at 50 mg/kg dose. Reference: PLoS One. 2013;8(2):e56471. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3577900/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 126.7 363.6
DMSO 30.0 86.09
DMSO:PBS (pH 7.2) (1:1) 0.5 1.43
DMF 10.0 28.7

Preparing Stock Solutions

The following data is based on the product molecular weight 348.46 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. Shi Y, Qiao J, Mu B, Zuo B, Yuan J. 3-(2-amino-ethyl)-5-[3-(4-butoxyl-phenyl)-propylidene]-thiazolidine-2,4-dione (K145) ameliorated dexamethasone induced hepatic gluconeogenesis through activation of Akt/FoxO1 pathway. Biochem Biophys Res Commun. 2017 Nov 4;493(1):286-290. doi: 10.1016/j.bbrc.2017.09.029. Epub 2017 Sep 11. PMID: 28911865. 2. Liu K, Guo TL, Hait NC, Allegood J, Parikh HI, Xu W, Kellogg GE, Grant S, Spiegel S, Zhang S. Biological characterization of 3-(2-amino-ethyl)-5-[3-(4-butoxyl-phenyl)-propylidene]-thiazolidine-2,4-dione (K145) as a selective sphingosine kinase-2 inhibitor and anticancer agent. PLoS One. 2013;8(2):e56471. doi: 10.1371/journal.pone.0056471. Epub 2013 Feb 20. PMID: 23437140; PMCID: PMC3577900.
In vitro protocol: 1. Shi Y, Qiao J, Mu B, Zuo B, Yuan J. 3-(2-amino-ethyl)-5-[3-(4-butoxyl-phenyl)-propylidene]-thiazolidine-2,4-dione (K145) ameliorated dexamethasone induced hepatic gluconeogenesis through activation of Akt/FoxO1 pathway. Biochem Biophys Res Commun. 2017 Nov 4;493(1):286-290. doi: 10.1016/j.bbrc.2017.09.029. Epub 2017 Sep 11. PMID: 28911865. 2. Liu K, Guo TL, Hait NC, Allegood J, Parikh HI, Xu W, Kellogg GE, Grant S, Spiegel S, Zhang S. Biological characterization of 3-(2-amino-ethyl)-5-[3-(4-butoxyl-phenyl)-propylidene]-thiazolidine-2,4-dione (K145) as a selective sphingosine kinase-2 inhibitor and anticancer agent. PLoS One. 2013;8(2):e56471. doi: 10.1371/journal.pone.0056471. Epub 2013 Feb 20. PMID: 23437140; PMCID: PMC3577900.
In vivo protocol: 1. Shi Y, Qiao J, Mu B, Zuo B, Yuan J. 3-(2-amino-ethyl)-5-[3-(4-butoxyl-phenyl)-propylidene]-thiazolidine-2,4-dione (K145) ameliorated dexamethasone induced hepatic gluconeogenesis through activation of Akt/FoxO1 pathway. Biochem Biophys Res Commun. 2017 Nov 4;493(1):286-290. doi: 10.1016/j.bbrc.2017.09.029. Epub 2017 Sep 11. PMID: 28911865. 2. Liu K, Guo TL, Hait NC, Allegood J, Parikh HI, Xu W, Kellogg GE, Grant S, Spiegel S, Zhang S. Biological characterization of 3-(2-amino-ethyl)-5-[3-(4-butoxyl-phenyl)-propylidene]-thiazolidine-2,4-dione (K145) as a selective sphingosine kinase-2 inhibitor and anticancer agent. PLoS One. 2013;8(2):e56471. doi: 10.1371/journal.pone.0056471. Epub 2013 Feb 20. PMID: 23437140; PMCID: PMC3577900.

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 1: Liu K, Guo TL, Hait NC, Allegood J, Parikh HI, Xu W, Kellogg GE, Grant S, Spiegel S, Zhang S. Biological characterization of 3-(2-amino-ethyl)-5-[3-(4-butoxyl-phenyl)-propylidene]-thiazolidine-2,4-dione (K145) as a selective sphingosine kinase-2 inhibitor and anticancer agent. PLoS One. 2013;8(2):e56471. doi: 10.1371/journal.pone.0056471. Epub 2013 Feb 20. PubMed PMID: 23437140; PubMed Central PMCID: PMC3577900.



Additional Information

 Related CAS#:
CAS#1449240-68-9 (K145 HCl salt);
CAS#1309444-75-4 (K145 free base)