2697-61-2

Usage

Uses

Used in Biochemical and Biological Research:
Selenocystamine is used as a reagent for crosslinking proteins and other molecules, facilitating the study of molecular interactions and structures in biological systems.
Used in Pharmaceutical Development:
Selenocystamine is used as a potential therapeutic agent for its ability to protect cells from oxidative damage, making it a candidate for treatments aimed at reducing the impact of oxidative stress-related conditions.
Used in Anticancer Applications:
Selenocystamine is being investigated for its anti-cancer properties, suggesting its use as a potential agent in cancer therapy to combat tumor growth and progression.
Used in the Study of Selenium Roles:
Selenocystamine serves as a valuable tool in research for elucidating the roles of selenium in biological systems, contributing to the understanding of selenium's impact on health and disease.
Used in the Development of New Treatments:
Due to its potential therapeutic applications, selenocystamine is utilized in the development of new treatments for a variety of diseases, particularly those where oxidative stress plays a significant role.

Synthetic route

2-chloroethanamine hydrochloride (870-24-6) → selenocystamine (2697-61-2)

Conditions	Yield
With disodium diselenide In tetrahydrofuran; water at 20℃;	73%

C14H28N2O4Se2*2C2HF3O2 → selenocystamine (2697-61-2)

Conditions	Yield
Alkaline conditions;	68%

N,N'-(3,4-diselena-hexanediyl)-bis-phthalamic acid (112349-96-9) → selenocystamine (2697-61-2)

Conditions	Yield
With hydrogenchloride at 180℃;

N,N'-dibenzoylselenocystamine (6474-42-6) → selenocystamine (2697-61-2)

Conditions	Yield
With hydrogenchloride In ethanol

2-Amino-ethan-selenoschwefelsaeure (2697-60-1) → selenocystamine (2697-61-2)

Conditions	Yield
With hydrogenchloride
With sodium hydroxide
With hydrogen sulfide In water

2-bromoethylamine hydrobromide (2576-47-8) → selenocystamine (2697-61-2)

Conditions	Yield
With methanol; selenium; magnesium

hydrogenchloride (7647-01-0) + N,N'-(3,4-diselena-hexanediyl)-bis-phthalamic acid (112349-96-9) → selenocystamine (2697-61-2) + benzene-1,2-dicarboxylic acid (88-99-3)

Conditions	Yield
at 180℃;

selenium (7782-49-2) + 2-chloroethanamine hydrochloride (870-24-6) → selenocystamine (2697-61-2) + bis(2-aminoethyl) selenoether (27974-50-1)

Conditions	Yield
Stage #1: selenium With sodium tetrahydroborate; C12H18O12Pb3 In water at 20℃; for 1.33333h; Stage #2: 2-chloroethanamine hydrochloride With sodium hydroxide In water at 20℃; for 17h;

C2H6NSe(1-) (74178-32-8) + hemiselenocystamine → selenocystamine (2697-61-2)

Conditions	Yield
at 25℃; pH=7; Kinetics; aq. buffer; Inert atmosphere;

2-aminoethaneselenol (21681-94-7) + Cysteamine (60-23-1) → selenocystamine (2697-61-2) + 2,2'-dithio-bis[ethylamine] (51-85-4) + hemiselenocystamine

Conditions	Yield
With air pH=7;

C36H36N24O12*C4H12N2Se2 → selenocystamine (2697-61-2)

Conditions	Yield
With [D]-sodium hydroxide pH=12;

di-tert-butyl (diselanediylbis(ethane-2,1-diyl))dicarbamate → selenocystamine (2697-61-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 4h; Cooling with ice;

selenocystamine (2697-61-2) + C37H37N5O7 → C37H44N6O5Se2

Conditions	Yield
In dimethyl sulfoxide for 24h;	98%

selenocystamine (2697-61-2) + 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → di-tert-butyl (diselanediylbis(ethane-2,1-diyl))dicarbamate

Conditions	Yield
With triethylamine In water; tert-butyl alcohol Ambient temperature;	78%

selenocystamine (2697-61-2) + acryloyl chloride (814-68-6) → N,N'-bis(acryloyl)selenocystamine

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 0 - 20℃;	70%

selenocystamine (2697-61-2) + 4-(trifluoromethoxy)benzoyl chloride (36823-88-8) → C20H18F6N2O4Se2 (27914-62-1)

Conditions	Yield
With sodium hydroxide In 1,2-dichloro-ethane

selenocystamine (2697-61-2) + calcium-N-(2,4-dihydroxy-3,3-dimethylbutyryl)-β-alaninate (137-08-6, 867-80-1, 6381-62-0, 6381-63-1, 15773-29-2, 64789-49-7, 122484-60-0, 131346-21-9) → N,N'-Dipantothenoyl-selenocystamin, Selenopantethein (110057-94-8)

Conditions	Yield
(i) Et3N, H2O, (ii) ClCO2Et, DMF, (iii) /BRN= 1698299/, AcOEt; Multistep reaction;

selenocystamine (2697-61-2) → 2-aminoethaneselenol (21681-94-7)

Conditions	Yield
With ethylenediaminetetraacetic acid; potassium chloride In water-d2 Rate constant; Hg pool cathode -1.0 V vs the saturated calomel electrode, pD=7.4;
With sodium tetrahydroborate
With water; diothiothreitol
With sodium tetrahydroborate Inert atmosphere;

selenocystamine (2697-61-2) → 2-Amino-ethanseleninsaeure, Selenohypotaurin (14499-22-0)

Conditions	Yield
With dihydrogen peroxide
With GLUTATHIONE; water; NADPH; glutathione reductase Kinetics; Reagent/catalyst;

selenocystamine (2697-61-2) → 2-aminoethaneseleninic acid (3594-82-9)

Conditions	Yield
With bromine
With dihydrogen peroxide for 1h; Kinetics;

selenocystamine (2697-61-2) + 4-trifluoromethoxybenzoic acid (330-12-1) → C20H18F6N2O4Se2 (27914-62-1)

Conditions	Yield
(i) SOCl2, (ii) /BRN= 1698299/, aq. NaOH; Multistep reaction;

selenocystamine (2697-61-2) → selenocystamine dihydrochloride (3542-13-0, 16066-41-4)

Conditions	Yield
With hydrogenchloride In methanol; diethyl ether; ethyl acetate

2-chloromethyl-3-ethoxycarbonyl-4-(o-methylthiophenyl)-5-methoxycarbonyl-6-methyl-1.4-dihydro pyridine + selenocystamine (2697-61-2) → 2-(2-aminoethyl)-selenylmethyl-3-carboethoxy-5-carbomethoxy-4-(o-methylthiophenyl)-6-methyl-1,4-dihydropyridine (120074-56-8)

Conditions	Yield
With sodium tetrahydroborate In ethanol; ethyl acetate
With sodium tetrahydroborate In ethanol; ethyl acetate
With sodium tetrahydroborate In ethanol; ethyl acetate

selenocystamine (2697-61-2) → C2H8NSe + C2H6NSe(1-) (74178-32-8)

Conditions	Yield
With formate radical In water pH=7; Kinetics;

selenocystamine (2697-61-2) → C2H8NSe + 2-Amino-ethanseleninsaeure, Selenohypotaurin (14499-22-0)

Conditions	Yield
With trichloromethylperoxyl; water pH=7; Kinetics;

selenocystamine (2697-61-2) + Cysteamine (60-23-1) → hemiselenocystamine

Conditions	Yield
at 25℃; pH=7; Kinetics; aq. buffer; Inert atmosphere;

selenocystamine (2697-61-2) + cucurbituril (80262-44-8) → C36H36N24O12*C4H12N2Se2

Conditions	Yield
In water-d2 pH=7;

selenocystamine (2697-61-2) + 3-(3-Bromo-4-hydroxy-phenyl)-2-[(E)-tetrahydro-pyran-2-yloxyimino]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester → (2E,2'E)-N,N'-[diselanediylbis(ethane-2,1-diyl)]bis[3-(3-bromo-4-hydroxyphenyl)-2-{[(tetrahydro-2H-pyran-2-yl)oxy]imino}propanamide]

Conditions	Yield
With triethylamine In 1,4-dioxane; methanol for 2h;	1.338 g

Upstream product

• 112349-96-9 N,N'-(3,4-diselena-hexanediyl)-bis-phthalamic acid 
• 6474-42-6 N,N'-dibenzoylselenocystamine 
• 2697-60-1 2-Amino-ethan-selenoschwefelsaeure 
• 2576-47-8 2-bromoethylamine hydrobromide 
• 7647-01-0 hydrogenchloride 
• 870-24-6 2-chloroethanamine hydrochloride 
• 7782-49-2 selenium 
• 21681-94-7 2-aminoethaneselenol 
• 60-23-1 Cysteamine 
• 74178-32-8 C₂H₆NSe^(1-) 

Downstream Products

• 27914-62-1 C₂₀H₁₈F₆N₂O₄Se₂ 
• 21681-94-7 2-aminoethaneselenol 
• 120074-56-8 2-(2-aminoethyl)-selenylmethyl-3-carboethoxy-5-carbomethoxy-4-(o-methylthiophenyl)-6-methyl-1,4-dihydropyridine 
• 3542-13-0 selenocystamine dihydrochloride 

Relevant academic research and scientific papers

Construction of pH sensitive smart glutathione peroxidase (GPx) mimics based on pH responsive pseudorotaxanes

Two organoselenium compounds, both of which were modified with two primary amine groups, were designed and synthesized to mimic the catalytic properties of glutathione peroxidase (GPx). It was demonstrated that the catalytic mechanism of the diselenide organoselenium compound (compound 1) was a ping-pong mechanism while that of the selenide organoselenium compound (compound 2) was a sequential mechanism. The pH-controlled switching of the catalytic activities was achieved by controlling the formation and dissociation of the pseudorotaxanes based on the organoselenium compounds and cucurbit[6]uril (CB[6]). Moreover, the switching was reversible at pH between 7 and 9 for compound 1 or between 7 and 10 for compound 2.

SLAP reagents for the photocatalytic synthesis of C3/C5-substituted, N-unprotected selenomorpholines and 1,4-selenazepanes

Herein, we disclose the first set of unique selenium-containing SLAP (SiLicon Amine Protocol) reagents for the direct synthesis of C3/C5-substituted selenomorpholines and 1,4-selenazepanes fromdiverse (hetero)aldehydes under mild photocatalytic conditions. Enantiomerically pure 1,2-amino alcohol/α-amino acid versions of these heterocycles were also synthesized. Further, we have shown the late-stage modification of certain biologically active agents using the developed seleno-SLAPreagents.

Selenium and sulfur in exchange reactions: A comparative study

Cysteamine reduces selenocystamine to form hemiselenocystamine and then cystamine. The rate constants are k1 = 1.3 × 105 M-1 s-1; k-1 = 2.6 × 107 M-1 s-1; k2 = 11 M-1 s-1; and k-2 = 1.4 × 103 M-1 s-1, respectively. Rate constants for reactions of cysteine/selenocystine are similar. Reaction rates of selenium as a nucle'phile and as an electrophile are 2-3 and 4 orders of magnitude higher, respectively, than those of sulfur. Sulfides and selenides are comparable as leaving groups.

Selenium containing modifying agents and conjugates

The invention relates to a modifying agent comprising a water soluble polymer, wherein the water soluble polymer comprises at least one reactive selenium group, said reactive selenium group being capable of reacting with a thiol group thereby forming an -Se-S- bond. Furthermore, the invention relates to a method for producing said modifying agents and their use in the modification of pharmaceutically active agents, e.g. G-CSF. Additionally, the invention concerns conjugates comprising a water-soluble polymer and a pharmaceutically active agent, wherein the water-soluble polymer is linked via a S-Se-bond to agent and a method for their production and their use as medicaments. Finally, the invention concerns a pharmaceutical composition comprising the inventive conjugates.

ORGANOTELLURIUM AND SELENIUM-BASED ANTIMICROBIAL ANTIMICROBIAL FORMULATIONS AND ARTICLES

The invention provides compositions and methods for treating or preventing the spread of infectious disease through topical or cutaneous contact with a formulation or article containing an organotellurium compound, or an inorganic or organic selenium compound, or formulation thereof, capable of generating superoxide radicals in the presence of an agent of infectious disease such as bacteria, viruses, fungi and protozoa.

A facile access to chalcogen and dichalcogen bearing dialkylamines and diols

A highly practical procedure for the preparation of novel classes of chalcogen bearing diamines [{H2N(CH2)n} 2E] and diols [{HO(CH2)n}2E] (n = 2 or 3 and E = Se or Te) by the reaction of disodiumchalcogenide and haloalkylamines or haloalcohols is presented.