SMI-16a | CAS#587852-28-6 | Pim-1/2 kinase inhibitor

MedKoo Cat#: 562422 | Name: SMI-16a

Description:

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

SMI-16a, also known as Pim1/2 Inhibitor IV, is a potent, cell-permeable, ATP-competitive inhibitor of Pim-1/2 kinases (IC50 = 150 nM and 20 nM against Pim-1 and Pim-2, respectively).

Chemical Structure

SMI-16a

CAS#587852-28-6

Theoretical Analysis

MedKoo Cat#: 562422

Name: SMI-16a

CAS#: 587852-28-6

Chemical Formula: C13H13NO3S

Exact Mass: 263.0616

Molecular Weight: 263.31

Elemental Analysis: C, 59.30; H, 4.98; N, 5.32; O, 18.23; S, 12.18

Price and Availability

Size	Price	Availability
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 750.00	Ready to ship
500mg	USD 1,450.00	Ready to ship
1g	USD 2,250.00	Ready to ship
2g	USD 4,250.00	Ready to ship
5g	USD 6,950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Pim1/2 Inhibitor IV; PIM1/2 Kinase Inhibitor VI; Pim1/2 Kinase Inhibitor IV; SMI-16a

IUPAC/Chemical Name

(Z)-5-(4-Propoxybenzylidene)thiazolidine-2,4-dione

InChi Key

GBWOSXZUTXXXQF-FLIBITNWSA-N

InChi Code

InChI=1S/C13H13NO3S/c1-2-7-17-10-5-3-9(4-6-10)8-11-12(15)14-13(16)18-11/h3-6,8H,2,7H2,1H3,(H,14,15,16)/b11-8-

SMILES Code

O=C(NC/1=O)SC1=C/C2=CC=C(OCCC)C=C2

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

>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

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C9R10B31

QC Data

View QC data: current batch, Lot#C9R10B31

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

SMI-16a is a Pim kinase inhibitor with IC50s of 0.15, 0.02 and 48 μM for Pim1, Pim2 and PC3 cells, respectively.

In vitro activity:

Heating multiple myeloma (MM) cells to 43°C induced cell death and increased endoplasmic reticulum stress. The treatment reduced levels of survival factors Pim-2, IRF4, c-Myc, and Mcl-1. Combining with bortezomib or SMI-16a enhanced cell death. Heat treatment eradicated drug-resistant cell fractions and reduced clonogenic capacity in vitro and tumorigenicity in mice. Hyperthermia shows promise in targeting drug-resistant MM cells and improving susceptibility to chemotherapy. Reference: Oncotarget. 2017 Dec 7;9(12):10307-10316. https://pubmed.ncbi.nlm.nih.gov/29535808/

In vivo activity:

Pim-2 inhibition is a potential strategy for MM-related bone loss and tumor progression. Inhibiting Pim-2 with SMI-16a restores bone formation suppressed by MM factors in animal models. SMI-16a enhances anabolic signaling and reduces TGF-β signaling. Reference: Leukemia. 2015 Jan;29(1):207-17. doi: 10.1038/leu.2014.147. https://pubmed.ncbi.nlm.nih.gov/24787487/

	Solvent	mg/mL	mM
Solubility
	Ethanol	3.0	11.39
	DMSO	76.5	290.53

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 263.31 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

Formulation protocol:

1. Miki H, Nakamura S, Oda A, Tenshin H, Teramachi J, Hiasa M, Bat-Erdene A, Maeda Y, Oura M, Takahashi M, Iwasa M, Harada T, Fujii S, Kurahashi K, Yoshida S, Kagawa K, Endo I, Aihara K, Ikuo M, Itoh K, Hayashi K, Nakamura M, Abe M. Effective impairment of myeloma cells and their progenitors by hyperthermia. Oncotarget. 2017 Dec 7;9(12):10307-10316. doi: 10.18632/oncotarget.23121. PMID: 29535808; PMCID: PMC5828190. 2. Fujii S, Nakamura S, Oda A, Miki H, Tenshin H, Teramachi J, Hiasa M, Bat-Erdene A, Maeda Y, Oura M, Takahashi M, Iwasa M, Endo I, Yoshida S, Aihara KI, Kurahashi K, Harada T, Kagawa K, Nakao M, Sano S, Abe M. Unique anti-myeloma activity by thiazolidine-2,4-dione compounds with Pim inhibiting activity. Br J Haematol. 2018 Jan;180(2):246-258. doi: 10.1111/bjh.15033. PMID: 29327347. 3. Hiasa M, Teramachi J, Oda A, Amachi R, Harada T, Nakamura S, Miki H, Fujii S, Kagawa K, Watanabe K, Endo I, Kuroda Y, Yoneda T, Tsuji D, Nakao M, Tanaka E, Hamada K, Sano S, Itoh K, Matsumoto T, Abe M. Pim-2 kinase is an important target of treatment for tumor progression and bone loss in myeloma. Leukemia. 2015 Jan;29(1):207-17. doi: 10.1038/leu.2014.147. Epub 2014 May 2. PMID: 24787487.

In vitro protocol:

In vivo protocol:

1. Fujii S, Nakamura S, Oda A, Miki H, Tenshin H, Teramachi J, Hiasa M, Bat-Erdene A, Maeda Y, Oura M, Takahashi M, Iwasa M, Endo I, Yoshida S, Aihara KI, Kurahashi K, Harada T, Kagawa K, Nakao M, Sano S, Abe M. Unique anti-myeloma activity by thiazolidine-2,4-dione compounds with Pim inhibiting activity. Br J Haematol. 2018 Jan;180(2):246-258. doi: 10.1111/bjh.15033. PMID: 29327347. 2. Hiasa M, Teramachi J, Oda A, Amachi R, Harada T, Nakamura S, Miki H, Fujii S, Kagawa K, Watanabe K, Endo I, Kuroda Y, Yoneda T, Tsuji D, Nakao M, Tanaka E, Hamada K, Sano S, Itoh K, Matsumoto T, Abe M. Pim-2 kinase is an important target of treatment for tumor progression and bone loss in myeloma. Leukemia. 2015 Jan;29(1):207-17. doi: 10.1038/leu.2014.147. Epub 2014 May 2. PMID: 24787487.

1: Köttner L, Wolff F, Mayer P, Zanin E, Dube H. Rhodanine-Based Chromophores: Fast Access to Capable Photoswitches and Application in Light-Induced Apoptosis. J Am Chem Soc. 2024 Jan 24;146(3):1894-1903. doi: 10.1021/jacs.3c07710. Epub 2024 Jan 11. PMID: 38207286. 2: Wang Y, Xiu J, Ren C, Yu Z. Protein kinase PIM2: A simple PIM family kinase with complex functions in cancer metabolism and therapeutics. J Cancer. 2021 Mar 5;12(9):2570-2581. doi: 10.7150/jca.53134. PMID: 33854618; PMCID: PMC8040705. 3: Miki H, Nakamura S, Oda A, Tenshin H, Teramachi J, Hiasa M, Bat-Erdene A, Maeda Y, Oura M, Takahashi M, Iwasa M, Harada T, Fujii S, Kurahashi K, Yoshida S, Kagawa K, Endo I, Aihara K, Ikuo M, Itoh K, Hayashi K, Nakamura M, Abe M. Effective impairment of myeloma cells and their progenitors by hyperthermia. Oncotarget. 2017 Dec 7;9(12):10307-10316. doi: 10.18632/oncotarget.23121. PMID: 29535808; PMCID: PMC5828190. 4: Fujii S, Nakamura S, Oda A, Miki H, Tenshin H, Teramachi J, Hiasa M, Bat- Erdene A, Maeda Y, Oura M, Takahashi M, Iwasa M, Endo I, Yoshida S, Aihara KI, Kurahashi K, Harada T, Kagawa K, Nakao M, Sano S, Abe M. Unique anti-myeloma activity by thiazolidine-2,4-dione compounds with Pim inhibiting activity. Br J Haematol. 2018 Jan;180(2):246-258. doi: 10.1111/bjh.15033. PMID: 29327347. 5: Hiasa M, Teramachi J, Oda A, Amachi R, Harada T, Nakamura S, Miki H, Fujii S, Kagawa K, Watanabe K, Endo I, Kuroda Y, Yoneda T, Tsuji D, Nakao M, Tanaka E, Hamada K, Sano S, Itoh K, Matsumoto T, Abe M. Pim-2 kinase is an important target of treatment for tumor progression and bone loss in myeloma. Leukemia. 2015 Jan;29(1):207-17. doi: 10.1038/leu.2014.147. Epub 2014 May 2. PMID: 2478748 6: Kreuz S, Holmes KB, Tooze RM, Lefevre PF. Loss of PIM2 enhances the anti-proliferative effect of the pan-PIM kinase inhibitor AZD1208 in non-Hodgkin lymphomas. Mol Cancer. 2015 Dec 8;14:205. doi: 10.1186/s12943-015-0477-z. PubMed PMID: 26643319; PubMed Central PMCID: PMC4672512.