SRPIN340
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MedKoo CAT#: 406657

CAS#: 218156-96-8

Description: SRPIN340 is a selective serine arginine protein kinase (SRPK) 1 inhibitor with Ki = 0.89 μM. SRPK1 is a common binding partner of the E1^E4 protein of diverse human papillomavirus types. SRPK1 selective inhibitors could be a potentially novel topical (eye drop) therapeutic for wet AMD.

Chemical Structure

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SRPIN340
CAS# 218156-96-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 406657
Name: SRPIN340
CAS#: 218156-96-8
Chemical Formula: C18H18F3N3O
Exact Mass: 349.14
Molecular Weight: 349.350
Elemental Analysis: C, 61.88; H, 5.19; F, 16.31; N, 12.03; O, 4.58

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 350 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 3850 Ready to ship
5g USD 5950 Ready to ship
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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

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, 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

More Info:         

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
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

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.

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. 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.

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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.