SMI-16a
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MedKoo CAT#: 562422

CAS#: 587852-28-6

Description: 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

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SMI-16a
CAS# 587852-28-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 562422
Name: SMI-16a
CAS#: 587852-28-6
Chemical Formula: C13H13NO3S
Exact Mass: 263.06
Molecular Weight: 263.310
Elemental Analysis: C, 59.30; H, 4.98; N, 5.32; O, 18.23; S, 12.18

Price and Availability

Size Price Availability Quantity
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 450 Ready to ship
200mg USD 750 Ready to ship
500mg USD 1450 Ready to ship
1g USD 2250 Ready to ship
2g USD 4250 Ready to ship
5g USD 6950 2 Weeks
Bulk inquiry

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:

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/

Solubility Data

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

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.

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. 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: 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.
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.

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1: 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.