DPTIP | CAS#351353-48-5 | neutral sphingomyelinase 2 (N-SMase 2) inhibitor

MedKoo Cat#: 585022 | Name: DPTIP

Description:

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

DPTIP is a potent and selective N-SMase2 inhibitor and brain penetrant.

Chemical Structure

DPTIP

CAS#351353-48-5 (free base)

Theoretical Analysis

MedKoo Cat#: 585022

Name: DPTIP

CAS#: 351353-48-5 (free base)

Chemical Formula: C21H18N2O3S

Exact Mass: 378.1038

Molecular Weight: 378.45

Elemental Analysis: C, 66.65; H, 4.79; N, 7.40; O, 12.68; S, 8.47

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 650.00	2 Weeks
100mg	USD 1,050.00	2 Weeks
200mg	USD 1,850.00	2 Weeks

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Related CAS #

2361799-64-4 (HCl) 351353-48-5 (free base)

Synonym

DPTIP

IUPAC/Chemical Name

2,6-Dimethoxy-4-[4-phenyl-5-(2-thienyl)-1H-imidazol-2-yl]phenol

InChi Key

JMXVHYPSBANVAQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H18N2O3S/c1-25-15-11-14(12-16(26-2)20(15)24)21-22-18(13-7-4-3-5-8-13)19(23-21)17-9-6-10-27-17/h3-12,24H,1-2H3,(H,22,23)

SMILES Code

OC1=C(OC)C=C(C2=NC(C3=CC=CC=C3)=C(C4=CC=CS4)N2)C=C1OC

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

>3 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

Instruction

View handling instruction

Biological target:

DPTIP is a potent brain penetrant neutral sphingomyelinase 2 (N-SMase 2) inhibitor (exosome inhibitor), with an IC50 of 30 nM.

In vitro activity:

Even more, DPTIP showed potent antiviral activity against both viruses with half-maximal effective concentrations (EC50) of 0.26 µM in Vero cells and 2.81 µM in HeLa cells for WNV. Reference: Int J Mol Sci. 2022 Nov 11;23(22):13935. https://pubmed.ncbi.nlm.nih.gov/36430407/

In vivo activity:

Male mice treated with D-DPTIP had significant and robust reduction of hippocampal nSMase2 activity (dark red vs. dark blue; p = 4.5 × 10−7) (Figure 7B). Similarly, female mice treated with D-DPTIP had significantly reduced nSMase2 activity (light red vs. light blue; p = 0.0013). Reference: Pharmaceutics. 2022 Sep 28;14(10):2066. https://pubmed.ncbi.nlm.nih.gov/36297501/

	Solvent	mg/mL	mM
Solubility
	DMSO	143.9	380.29

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 378.45 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. Álvarez-Fernández H, Mingo-Casas P, Blázquez AB, Caridi F, Saiz JC, Pérez-Pérez MJ, Martín-Acebes MA, Priego EM. Allosteric Inhibition of Neutral Sphingomyelinase 2 (nSMase2) by DPTIP: From Antiflaviviral Activity to Deciphering Its Binding Site through In Silico Studies and Experimental Validation. Int J Mol Sci. 2022 Nov 11;23(22):13935. doi: 10.3390/ijms232213935. PMID: 36430407; PMCID: PMC9697135. 2. Rojas C, Barnaeva E, Thomas AG, Hu X, Southall N, Marugan J, Chaudhuri AD, Yoo SW, Hin N, Stepanek O, Wu Y, Zimmermann SC, Gadiano AG, Tsukamoto T, Rais R, Haughey N, Ferrer M, Slusher BS. DPTIP, a newly identified potent brain penetrant neutral sphingomyelinase 2 inhibitor, regulates astrocyte-peripheral immune communication following brain inflammation. Sci Rep. 2018 Dec 7;8(1):17715. doi: 10.1038/s41598-018-36144-2. PMID: 30531925; PMCID: PMC6286365. 3. Tallon C, Bell BJ, Sharma A, Pal A, Malvankar MM, Thomas AG, Yoo SW, Hollinger KR, Coleman K, Wilkinson EL, Kannan S, Haughey NJ, Kannan RM, Rais R, Slusher BS. Dendrimer-Conjugated nSMase2 Inhibitor Reduces Tau Propagation in Mice. Pharmaceutics. 2022 Sep 28;14(10):2066. doi: 10.3390/pharmaceutics14102066. PMID: 36297501; PMCID: PMC9609094. 4. Pal A, Gori S, Yoo SW, Thomas AG, Wu Y, Friedman J, Tenora L, Bhasin H, Alt J, Haughey N, Slusher BS, Rais R. Discovery of Orally Bioavailable and Brain-Penetrable Prodrugs of the Potent nSMase2 Inhibitor DPTIP. J Med Chem. 2022 Aug 25;65(16):11111-11125. doi: 10.1021/acs.jmedchem.2c00562. Epub 2022 Aug 5. PMID: 35930706.

In vitro protocol:

In vivo protocol:

1. Tallon C, Bell BJ, Sharma A, Pal A, Malvankar MM, Thomas AG, Yoo SW, Hollinger KR, Coleman K, Wilkinson EL, Kannan S, Haughey NJ, Kannan RM, Rais R, Slusher BS. Dendrimer-Conjugated nSMase2 Inhibitor Reduces Tau Propagation in Mice. Pharmaceutics. 2022 Sep 28;14(10):2066. doi: 10.3390/pharmaceutics14102066. PMID: 36297501; PMCID: PMC9609094. 2. Pal A, Gori S, Yoo SW, Thomas AG, Wu Y, Friedman J, Tenora L, Bhasin H, Alt J, Haughey N, Slusher BS, Rais R. Discovery of Orally Bioavailable and Brain-Penetrable Prodrugs of the Potent nSMase2 Inhibitor DPTIP. J Med Chem. 2022 Aug 25;65(16):11111-11125. doi: 10.1021/acs.jmedchem.2c00562. Epub 2022 Aug 5. PMID: 35930706.

Rojas et al (2018) DPTIP, a newly identified potent brain penetrant neutral sphingomyelinase 2 inhibitor, regulates astrocyte-peripheral immune communication following brain inflammation. Sci.Rep. 8 17715 PMID: 30531925