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Propidium iodide (PI) is a red-fluorescent nuclear and chromosome counterstain which can bind to double stranded DNA by intercalating between base pairs.

Synonyms: PI

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Quality Control of Propidium Iodide Purity: 95% SDS Specification

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Product Citations

Synthesis of Novel Chloro-Benzo [d] imidazole Regioisomers as Selective CB2 Receptor Agonists: Indirect Functional Evaluation and Molecular Insights

Salazar, Valeria Zuñiga ; Ravanal, Renato Burgos ; Soto-Flores, Jonathan ; Sabadini, Gianfranco ; González, José Vicente ; Mella, Jaime , et al.

DOI: 10.3390/ph18111599 Pharmaceuticals,2025,18(11):1599.

Abstract: Background/Objectives: The cannabinoid type 2 receptor (CB₂ receptor) has been extensively studied in recent years due to the benefits associated with its modulation, including the regulation of the inflammatory response, neuroimmunomodulatory properties, and antitumor effects, all with the advantage of lacking significant psychoactive effects. Herein, we report the design, synthesis, characterization, biological assays, and molecular modelling analyses of novel (5/6-chloro-2-aryl-1H-benzo [d]imidazol-1-yl)(4-methoxyphenyl)methanone and 5/6-chloro-1-(4-methoxybenzyl)-2-aryl-1H-benzo [d]imidazole regioisomers as potential cannabinoid type 2 receptor ligands. Methods: The compounds were evaluated for their presumed CB₂ agonist activity using an indirect receptor-dependent apoptotic cell death assay exerted by cannabinoids, using the cell lines HEK293 (low CB₁/CB₂ expression), U-87 MG (high CB₁ expression), and HL-60 (exclusive CB₂ expression), and including the known cannabinoid ligands WIN-55,212-2 and AM630 as reference ligands. Flow cytometry was performed to assess apoptosis. Molecular docking and molecular dynamics simulations were used to explore ligand-receptor interactions at the CB₂ active site. Results: Compounds 3a, 3b’, 3c, and 4b selectively reduced HL-60 cell viability, similar to WIN-55,212-2, while showing no toxicity toward HEK293 or U-87 MG cells. Flow cytometry indicated that compounds 3a and 3c induced apoptosis in HL-60 cells comparable to WIN-55,212-2. Computational studies suggested that both compounds bind within the CB₂ receptor active site predominantly through π–π and hydrophobic interactions involving their benzo [d]imidazole cores, 2-aryl moieties, and 4-methoxybenzoyl scaffolds, resembling the binding patterns of established CB₂ ligands. Conclusions: Compounds 3a and 3c exert selective cytotoxicity against HL-60 cells, likely via a CB₂ agonist-mediated apoptotic mechanism. The applied combined experimental and computational approach provides a rapid, informative strategy for preliminary evaluation of CB₂ ligands and guides subsequent detailed pharmacological studies.

Keywords: cannabinoids ; benzo[d]imidazole ; cytotoxic studies ; flow cytometry ; indirectagonism ; docking ; molecular dynamics

Purchased from AmBeed: 25535-16-4

Product Details of Propidium Iodide

CAS No. :	25535-16-4
Formula :	C₂₇H₃₄I₂N₄
M.W :	668.39
SMILES Code :	C[N+](CCC[N+]1=C(C2=CC=CC=C2)C3=CC(N)=CC=C3C4=C1C=C(N)C=C4)(CC)CC.[I-].[I-]
Synonyms :	PI
English Name :	3,8-Diamino-5-(3-(diethyl(methyl)ammonio)propyl)-6-phenylphenanthridin-5-ium iodide
MDL No. :	MFCD00011921

Safety of Propidium Iodide

GHS Pictogram:
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Application In Synthesis of Propidium Iodide

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 25535-16-4 ]

[ 25535-16-4 ] Synthesis Path-Downstream 1~8

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid anschliessend mit wss. NH₃ und KI;

2
[ 18643-08-8 ]
[ 25535-16-4 ]
[ 847068-11-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In DMF (N,N-dimethyl-formamide)	1.A A. Synthesis of BDMODS-PI. Hydrophobic modification of propidium iodide (95%, Aldrich Chemical Company) was accomplished by treating propidium iodide with an excess of DMODSiCl (6 molar equivalents, Aldrich) in anhydrous N,N-dimethylformamide (DMF, Aldrich) or dimethyl sulfoxide (DMSO, Aldrich), with K2CO3 as a base, and activated 3A molecular sieves present as a water scavenger, to form BDMODS-PI (FIG. 2A). Prior to use, the BDMODS-PI is filtered through a 0.20 μm sterile Nylon filter, which removes the solids and the hydrolysis products of the DMODSiCl (which are not DMF soluble). Although DMF and other amides are known to react with chlorosilanes, no evidence of the imidate (or products arising from the imidate) have been observed under these reaction conditions (79-82). In order to verify the structural assignments, several additional controls (silylations and alkylations) were also conducted on related aniline ring systems (including aniline and 3,8-diamino-6-phenylphenanthridine). All products were analyzed by 1H NMR (250 MHz, N,N-dimethylformamide-d7), and support the structural assignments. The NMR indicated the addition of two alkylsilane groups to the PI based on integration and a corresponding loss of two aniline protons. The effective rate of hydrolysis of the BDMODS-PI also was too rapid to be tested by NMR.

References: [1]Current Patent Assignee: ROCHE MADISON - US2005/54612, 2005, A1 Location in patent: Page/Page column 7; 8.

3
[ 639066-08-3 ]
[ 25535-16-4 ]
[ 847068-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃;	1.B B. Synthesis of CDMC12-PI. Propidium iodide was also modified with the cyclic anhydride CDMC 12 to form the bis-maleamic acid derivative CDMC 12-PI (FIG. 2A). The reaction of a maleic anhydride and an amine is a reversible reaction, favoring the acylation (the maleamic acid) under basic conditions. Upon acidification, maleamic acids are know to undergo ring closure to yield the original amine and the original anhydride. This ring closure reaction of maleamic acids is generally slow under neutral conditions. However, in the case of aniline-like nitrogens, as found in propidium iodide, the hydrolytic lability of the bond is predicted to be much more facile under neutral conditions than what would be found with a normal amine. Aniline nitrogens are generally less reactive (and have lower pKa's) than other amines due to delocalization of electron density with the aromatic ring. In the current modification reaction with propidium iodide (not optimized), CDMC12 (3 eq) was added together with K2CO3 in DMF or DMSO at 60° C. Analysis of the reaction by 1H NMR (250 MHz, N,N-dimethylformamide-d7) indicates the loss of the amine protons of propidium iodide and the appearance of the amide protons from the bis-maleamic acid. Control reactions have been conducted with both aniline and 3,8-diamino-6-phenylphenanthridine in order to verify structural assignments.

References: [1]Current Patent Assignee: ROCHE MADISON - US2005/54612, 2005, A1 Location in patent: Page/Page column 8.

4
[ 25535-16-4 ]
[ 36015-30-2 ]