DM-PIT-1 | CAS# 701947-53-7 | PIP3 Antagonist

MedKoo Cat#: 565112 | Name: DM-PIT-1

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Description:

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

DM-PIT-1 is a PIP3 antagonist which blocks PIP3-dependent PI3K-PDK1-Akt signaling pathway activation.

Chemical Structure

DM-PIT-1

CAS#701947-53-7

Theoretical Analysis

MedKoo Cat#: 565112

Name: DM-PIT-1

CAS#: 701947-53-7

Chemical Formula: C16H15N3O4S

Exact Mass: 345.0783

Molecular Weight: 345.37

Elemental Analysis: C, 55.64; H, 4.38; N, 12.17; O, 18.53; S, 9.28

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks
25mg	USD 1,150.00	2 Weeks

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Synonym

DM PIT-1; DM-PIT 1; DM-PIT-1; DM PIT1; 3,5-dimethyl PIT-1

IUPAC/Chemical Name

N-(((2-Hydroxy-5-nitrophenyl)amino)thioxomethyl)-3,5-dimethyl-benzamide

InChi Key

CGWBCAQMXJFWBU-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H15N3O4S/c1-9-5-10(2)7-11(6-9)15(21)18-16(24)17-13-8-12(19(22)23)3-4-14(13)20/h3-8,20H,1-2H3,(H2,17,18,21,24)

SMILES Code

O=C(NC(NC1=CC([N+]([O-])=O)=CC=C1O)=S)C2=CC(C)=CC(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

>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

Certificate of Analysis

View CoA: current batch, Lot#C23M05C23

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

DM-PIT-1 is a PIP3 antagonist which blocks PIP3-dependent PI3K-PDK1-Akt signaling pathway activation.

In vitro activity:

Among the tested compounds, PIT-1 and DM-PIT-1 showed higher Cl- ion selectivity and transport efficiency. Mechanistic studies demonstrated that the potent compounds follow the H+/Cl- transport pathway. Cellular activity studies showed that the disruption of Cl- ion homeostasis by PIT-1 and DM-PIT-1 preferentially promotes apoptotic cell death. Reference: ACS Appl Bio Mater. 2020 Feb 17;3(2):935-944. https://pubmed.ncbi.nlm.nih.gov/35019295/

In vivo activity:

An improved PIT-1 analog, DM-PIT-1, displays significant anticancer activity in the mouse syngeneic 4T1 breast cancer model in vivo. Reference: Autophagy. 2011 Jun;7(6):650-1. https://pubmed.ncbi.nlm.nih.gov/21460619/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	86.86
	DMF:PBS (pH 7.2) (1:1)	0.5	1.45
	DMSO	20.0	57.91
	Ethanol	0.2	0.58

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 345.37 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. Biswas O, Akhtar N, Vashi Y, Saha A, Kumar V, Pal S, Kumar S, Manna D. Chloride Ion Transport by PITENINs across the Phospholipid Bilayers of Vesicles and Cells. ACS Appl Bio Mater. 2020 Feb 17;3(2):935-944. doi: 10.1021/acsabm.9b00985. Epub 2020 Jan 30. PMID: 35019295. 2. Skidan I, Miao B, Thekkedath RV, Dholakia P, Degterev A, Torchilin V. In vitro cytotoxicity of novel pro-apoptotic agent DM-PIT-1 in PEG-PE-based micelles alone and in combination with TRAIL. Drug Deliv. 2009 Jan;16(1):45-51. doi: 10.1080/10717540802517951. PMID: 19555308; PMCID: PMC3071122. 3. Miao B, Degterev A. Targeting phospshatidylinositol 3-kinase signaling with novel phosphatidylinositol 3,4,5-triphosphate antagonists. Autophagy. 2011 Jun;7(6):650-1. doi: 10.4161/auto.7.6.15248. Epub 2011 Jun 1. PMID: 21460619. 4. Miao B, Skidan I, Yang J, Lugovskoy A, Reibarkh M, Long K, Brazell T, Durugkar KA, Maki J, Ramana CV, Schaffhausen B, Wagner G, Torchilin V, Yuan J, Degterev A. Small molecule inhibition of phosphatidylinositol-3,4,5-triphosphate (PIP3) binding to pleckstrin homology domains. Proc Natl Acad Sci U S A. 2010 Nov 16;107(46):20126-31. doi: 10.1073/pnas.1004522107. Epub 2010 Nov 1. PMID: 21041639; PMCID: PMC2993381.

In vitro protocol:

In vivo protocol:

1. Miao B, Degterev A. Targeting phospshatidylinositol 3-kinase signaling with novel phosphatidylinositol 3,4,5-triphosphate antagonists. Autophagy. 2011 Jun;7(6):650-1. doi: 10.4161/auto.7.6.15248. Epub 2011 Jun 1. PMID: 21460619. 2. Miao B, Skidan I, Yang J, Lugovskoy A, Reibarkh M, Long K, Brazell T, Durugkar KA, Maki J, Ramana CV, Schaffhausen B, Wagner G, Torchilin V, Yuan J, Degterev A. Small molecule inhibition of phosphatidylinositol-3,4,5-triphosphate (PIP3) binding to pleckstrin homology domains. Proc Natl Acad Sci U S A. 2010 Nov 16;107(46):20126-31. doi: 10.1073/pnas.1004522107. Epub 2010 Nov 1. PMID: 21041639; PMCID: PMC2993381.

1: Riehle RD, Cornea S, Degterev A, Torchilin V. Micellar formulations of pro-apoptotic DM-PIT-1 analogs and TRAIL in vitro and in vivo. Drug Deliv. 2013 Feb;20(2):78-85. doi: 10.3109/10717544.2013.766780. Epub 2013 Mar 16. PubMed PMID: 23495715. 2: Skidan I, Miao B, Thekkedath RV, Dholakia P, Degterev A, Torchilin V. In vitro cytotoxicity of novel pro-apoptotic agent DM-PIT-1 in PEG-PE-based micelles alone and in combination with TRAIL. Drug Deliv. 2009 Jan;16(1):45-51. doi: 10.1080/10717540802517951. PubMed PMID: 19555308; PubMed Central PMCID: PMC3071122. 3: Skidan I, Grunwald J, Thekkedath R, Degterev A, Torchilin V. A HPLC method for the quantitative determination of N-(2-hydroxy-5-nitrophenylcarbamothioyl)-3,5-dimethylbenzamide in biological samples. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Jun 1;879(19):1610-6. doi: 10.1016/j.jchromb.2011.03.055. Epub 2011 Apr 6. PubMed PMID: 21514904; PubMed Central PMCID: PMC3096932. 4: Miao B, Degterev A. Targeting phospshatidylinositol 3-kinase signaling with novel phosphatidylinositol 3,4,5-triphosphate antagonists. Autophagy. 2011 Jun;7(6):650-1. Epub 2011 Jun 1. PubMed PMID: 21460619.