Synonym
SRPIN340; SRPIN-340; SRPIN 340.
IUPAC/Chemical Name
N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)isonicotinamide
InChi Key
DWFGGOFPIISJIT-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H18F3N3O/c19-18(20,21)14-4-5-16(24-10-2-1-3-11-24)15(12-14)23-17(25)13-6-8-22-9-7-13/h4-9,12H,1-3,10-11H2,(H,23,25)
SMILES Code
O=C(C1=CC=NC=C1)NC2=CC(C(F)(F)F)=CC=C2N3CCCCC3
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
Biological target:
SRPIN340 is an ATP-competitive serine-arginine-rich protein kinase (SRPK) inhibitor, with a Ki of 0.89 μM for SRPK1.
In vitro activity:
SRPIN340 prevented nuclear translocation of SRPKs in 5-FU and cisplatin-treated cells, reducing drug cytotoxicity. Inhibition of SRPK1 by SRPIN340 or trifluoromethyl arylamides kept SRPK1 mainly in the cytoplasm when stimulated with EGF in melanoma cells. Similarly, SRPIN340 inhibition of SRPK1 and SRPK2 protected cardiomyocytes from oxidative stress-induced apoptosis and cell death.
Reference: Cells. 2021 Apr; 10(4): 759. https://pubmed.ncbi.nlm.nih.gov/33808326/
In vivo activity:
Daily subcutaneous injection of SRPIN340 near the tumor site significantly decreased human melanoma tumor growth compared to control. Post-tumor analysis revealed reduced total VEGF expression in SRPIN340-treated tumors, with no impact on anti-angiogenic VEGFxxxb isoforms. Unlike knockdown, tumors were large enough for CD31 staining to assess microvascular density (MVD), showing a significant reduction with SRPIN340 treatment compared to vehicle.
Reference: Br J Cancer. 2014 Jul 29; 111(3): 477–485. https://pubmed.ncbi.nlm.nih.gov/25010863/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSI |
40.5 |
115.90 |
|
| DMF |
15.0 |
42.94 |
|
| Ethanol |
47.5 |
135.97 |
|
| Ethanol:PBS (pH 7.2) (1:4) |
0.2 |
0.57 |
|
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
349.35
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. Sigala I, Koutroumani M, Koukiali A, Giannakouros T, Nikolakaki E. Nuclear Translocation of SRPKs Is Associated with 5-FU and Cisplatin Sensitivity in HeLa and T24 Cells. Cells. 2021 Mar 30;10(4):759. doi: 10.3390/cells10040759. PMID: 33808326; PMCID: PMC8065462.
2. Siqueira RP, Barbosa Éde A, Polêto MD, Righetto GL, Seraphim TV, Salgado RL, Ferreira JG, Barros MV, de Oliveira LL, Laranjeira AB, Almeida MR, Júnior AS, Fietto JL, Kobarg J, de Oliveira EB, Teixeira RR, Borges JC, Yunes JA, Bressan GC. Potential Antileukemia Effect and Structural Analyses of SRPK Inhibition by N-(2-(Piperidin-1-yl)-5-(Trifluoromethyl)Phenyl)Isonicotinamide (SRPIN340). PLoS One. 2015 Aug 5;10(8):e0134882. doi: 10.1371/journal.pone.0134882. PMID: 26244849; PMCID: PMC4526641.
3. Gammons MV, Lucas R, Dean R, Coupland SE, Oltean S, Bates DO. Targeting SRPK1 to control VEGF-mediated tumour angiogenesis in metastatic melanoma. Br J Cancer. 2014 Jul 29;111(3):477-85. doi: 10.1038/bjc.2014.342. Epub 2014 Jul 10. PMID: 25010863; PMCID: PMC4119992.
4. Dong Z, Noda K, Kanda A, Fukuhara J, Ando R, Murata M, Saito W, Hagiwara M, Ishida S. Specific inhibition of serine/arginine-rich protein kinase attenuates choroidal neovascularization. Mol Vis. 2013;19:536-43. Epub 2013 Mar 5. PMID: 23559848; PMCID: PMC3611948.
In vitro protocol:
1. Sigala I, Koutroumani M, Koukiali A, Giannakouros T, Nikolakaki E. Nuclear Translocation of SRPKs Is Associated with 5-FU and Cisplatin Sensitivity in HeLa and T24 Cells. Cells. 2021 Mar 30;10(4):759. doi: 10.3390/cells10040759. PMID: 33808326; PMCID: PMC8065462.
2. Siqueira RP, Barbosa Éde A, Polêto MD, Righetto GL, Seraphim TV, Salgado RL, Ferreira JG, Barros MV, de Oliveira LL, Laranjeira AB, Almeida MR, Júnior AS, Fietto JL, Kobarg J, de Oliveira EB, Teixeira RR, Borges JC, Yunes JA, Bressan GC. Potential Antileukemia Effect and Structural Analyses of SRPK Inhibition by N-(2-(Piperidin-1-yl)-5-(Trifluoromethyl)Phenyl)Isonicotinamide (SRPIN340). PLoS One. 2015 Aug 5;10(8):e0134882. doi: 10.1371/journal.pone.0134882. PMID: 26244849; PMCID: PMC4526641.
In vivo protocol:
1. Gammons MV, Lucas R, Dean R, Coupland SE, Oltean S, Bates DO. Targeting SRPK1 to control VEGF-mediated tumour angiogenesis in metastatic melanoma. Br J Cancer. 2014 Jul 29;111(3):477-85. doi: 10.1038/bjc.2014.342. Epub 2014 Jul 10. PMID: 25010863; PMCID: PMC4119992.
2. Dong Z, Noda K, Kanda A, Fukuhara J, Ando R, Murata M, Saito W, Hagiwara M, Ishida S. Specific inhibition of serine/arginine-rich protein kinase attenuates choroidal neovascularization. Mol Vis. 2013;19:536-43. Epub 2013 Mar 5. PMID: 23559848; PMCID: PMC3611948.
1: Gammons MV, Lucas R, Dean R, Coupland SE, Oltean S, Bates DO. Targeting SRPK1 to control VEGF-mediated tumour angiogenesis in metastatic melanoma. Br J Cancer. 2014 Jul 29;111(3):477-85. doi: 10.1038/bjc.2014.342. Epub 2014 Jul 10. PubMed PMID: 25010863; PubMed Central PMCID: PMC4119992.
2: Gammons MV, Dick AD, Harper SJ, Bates DO. SRPK1 inhibition modulates VEGF splicing to reduce pathological neovascularization in a rat model of retinopathy of prematurity. Invest Ophthalmol Vis Sci. 2013 Aug 27;54(8):5797-806. doi: 10.1167/iovs.13-11634. PubMed PMID: 23761094.
3: Dong Z, Noda K, Kanda A, Fukuhara J, Ando R, Murata M, Saito W, Hagiwara M, Ishida S. Specific inhibition of serine/arginine-rich protein kinase attenuates choroidal neovascularization. Mol Vis. 2013;19:536-43. Epub 2013 Mar 5. PubMed PMID: 23559848; PubMed Central PMCID: PMC3611948.
4: Ogawa Y, Hagiwara M. Challenges to congenital genetic disorders with "RNA-targeting" chemical compounds. Pharmacol Ther. 2012 Jun;134(3):298-305. doi: 10.1016/j.pharmthera.2012.02.001. Epub 2012 Feb 9. Review. PubMed PMID: 22342810.
5: Karakama Y, Sakamoto N, Itsui Y, Nakagawa M, Tasaka-Fujita M, Nishimura-Sakurai Y, Kakinuma S, Oooka M, Azuma S, Tsuchiya K, Onogi H, Hagiwara M, Watanabe M. Inhibition of hepatitis C virus replication by a specific inhibitor of serine-arginine-rich protein kinase. Antimicrob Agents Chemother. 2010 Aug;54(8):3179-86. doi: 10.1128/AAC.00113-10. Epub 2010 May 24. PubMed PMID: 20498328; PubMed Central PMCID: PMC2916360.
6: Fukuhara T, Hosoya T, Shimizu S, Sumi K, Oshiro T, Yoshinaka Y, Suzuki M, Yamamoto N, Herzenberg LA, Herzenberg LA, Hagiwara M. Utilization of host SR protein kinases and RNA-splicing machinery during viral replication. Proc Natl Acad Sci U S A. 2006 Jul 25;103(30):11329-33. Epub 2006 Jul 13. PubMed PMID: 16840555; PubMed Central PMCID: PMC1544086.
