6708-13-0

Basic information

• Product Name: 1,2-diselenolane-3-pentanoic acid
• Synonyms: 1,2-diselenolane-3-pentanoic acid
• CAS NO: 6708-13-0
• Molecular Formula: C₈H₁₄O₂Se₂
• Molecular Weight: 300.11556
• Mol File: 6708-13-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-diselenolane-3-pentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-diselenolane-3-pentanoic acid(6708-13-0)
• EPA Substance Registry System: 1,2-diselenolane-3-pentanoic acid(6708-13-0)

Safety Data

• Hazardous Substances Data: 6708-13-0(Hazardous Substances Data)

Usage

General Description

1,2-Diselenolane-3-pentanoic acid is a chemical compound that contains a five-membered ring with selenium and oxygen atoms. It is a derivative of pentanoic acid with a selenol group attached to the second carbon atom. 1,2-Diselenolane-3-pentanoic acid has potential applications in organic synthesis and has been studied for its antioxidant and anti-inflammatory properties. It has been investigated for its potential use in the treatment of various diseases and conditions, including cancer and neurodegenerative disorders. However, further research is needed to fully understand its potential therapeutic uses and safety profile.

Upstream product

• 1070-64-0 6,8-dichlorooctanoic acid ethyl ester 
• 1451075-56-1 sodium 6,8-dichlorooctanoate 

Downstream Products

• 1456816-57-1 ethyl 5-(1,2-diselenolan-3-yl)pentanoate 
• 1456816-63-9 N'-(4-chlorobenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-64-0 N'-(furan-2-ylmethylene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-65-1 N'-(2-chlorobenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-66-2 N'-(2-hydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-67-3 N'-(4-methylbenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-68-4 N'-(3-methoxy-4-hydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-69-5 N'-(3-hydroxy-4-methoxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-70-8 N'-(4-(dimethylamino)benzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-71-9 N'-(4-methoxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-72-0 N'-(4-hydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-73-1 N'-(3,4-dihydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-58-2 5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-59-3 N'-benzylidene-5-(1,2-diselenolan-3-yl)pentanehydrazide 

Relevant articles and documents

Diselenolane-mediated cellular uptake

The emerging power of thiol-mediated uptake with strained disulfides called for a move from sulfur to selenium. We report that according to results with fluorescent model substrates, cellular uptake with 1,2-diselenolanes exceeds uptake with 1,2-dithiolanes and epidithiodiketopiperazines with regard to efficiency as well as intracellular localization. The diselenide analog of lipoic acid performs best. This 1,2-diselenolane delivers fluorophores efficiently to the cytosol of HeLa Kyoto cells, without detectable endosomal capture as with 1,2-dithiolanes or dominant escape into the nucleus as with epidithiodiketopiperazines. Diselenolane-mediated cytosolic delivery is non-toxic (MTT assay), sensitive to temperature but insensitive to inhibitors of endocytosis (chlorpromazine, methyl-β-cyclodextrin, wortmannin, cytochalasin B) and conventional thiol-mediated uptake (Ellman's reagent), and to serum. Selenophilicity, the extreme CSeSeC dihedral angle of 0° and the high but different acidity of primary and secondary selenols might all contribute to uptake. Thiol-exchange affinity chromatography is introduced as operational mimic of thiol-mediated uptake that provides, in combination with rate enhancement of DTT oxidation, direct experimental evidence for existence and nature of the involved selenosulfides.

Synthesis and Anticancer Activity of 5-(1,2-Diselenolan-3-Yl)pentanoic Acid and its Derivatives

A green and high-yielding synthetic route for the preparation of 5-(1,2-diselenolan-3-yl)pentanoic acid (SeA) was reported. Some SeA derivatives, N′-substituted benzylidene-5-(1,2-diselenolan-3-yl)pentanehydrazide, were prepared, and they were screened for their anticancer activity against human breast MCF-7, leukemia HL-60, cervixuterus Hela, and placental villus Bewo cancer cell lines. The minimum inhibitory concentrations (MICs) of the synthetic compounds showed moderate anticancer activity at low concentrations (0.5-5 μg/mL).