DC Chemicals Limited
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Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: Ethanethiol, 2-((3-aminopropyl)amino)-, dihydrochloride
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Purity: 98.0%
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14653-77-1

14653-77-1 structure

14653-77-1 structure

Name: WR-1065
Chemical Name: Amifostine Thiol Dihydrochloride
CAS Number: 14653-77-1
Molecular Formula: C₅H₁₆Cl₂N₂S
Molecular Weight: 207.16
Catalog: Signaling Pathways Apoptosis MDM-2/p53
Create Date: 2018-05-07 08:00:00
Modify Date: 2024-01-03 07:03:16
WR-1065 dihydrochloride can protect normal tissues from the toxic effects of certain cancer drugs and activate p53 through a JNK-dependent signaling pathway.

Name	Amifostine Thiol Dihydrochloride
Synonyms	Ethanethiol, 2-[(3-aminopropyl)amino]-, hydrochloride (1:1) 2-(3-aminopropylamino)ethanethiol,dihydrochloride 2-[(3-Aminopropyl)amino]ethanethiol hydrochloride (1:1) 2-[(3-Aminopropyl)amino]ethanethiol dihydrochloride WR-1065 dihydrochloride WR-1065 dihydrochloride

Description	WR-1065 dihydrochloride can protect normal tissues from the toxic effects of certain cancer drugs and activate p53 through a JNK-dependent signaling pathway.
Related Catalog	Signaling Pathways >> Apoptosis >> MDM-2/p53 Research Areas >> Cancer
Target	p53[1]
In Vitro	The DNA-binding activity is increased in a WR-1065 dihydrochloride (WR-1065) concentration-dependent manner. Cells treated with 1 mM WR-1065 dihydrochloride for 24 h reveal that all of the p53-induced genes analyzed are transactivated following WR-1065 dihydrochloride treatment, in a p53-dependent manner. Significantly, treatment with WR-1065 dihydrochloride leads to a 3-fold increase in luciferase expression driven by AP-1, and a 5-fold increase when this reporter gene is driven by NF-κB, when these values are normalized to the level of the cotransfected β-galactosidase gene[2].
In Vivo	The results show that wR-1065 dihydrochloride (WR-1065) attenuates the severity of 6-OHDA-induced catalepsy (P<0.001) when compare with 6-OHDA-lesioned rats. Also it has been observed that WR-1065 dihydrochloride improves catalepsy in dose dependent manner (P<0.001). Pretreatment with three different doses of WR-1065 dihydrochloride (20, 40 and 80 μg/2 μL/rat) for 3 days before 6-OHDA administration, significantly (P<0.001) elevates SOD activity and restores it to normal range compare with 6-OHDA lesioned rats[3].
Kinase Assay	For Western analysis, cells are treated with 1 mM WR-1065 dihydrochloride (WR-1065) for 24 h, and subconfluent cultures of cells are harvested and lysed in RIPA buffer supplemented with protease inhibitors. Protein concentrations are determined by a detergent-compatible assay. Western blots are blocked and incubated in antibody in PBS/0.2% Tween 20/5% nonfat dry milk. Blots are incubated with 1 μg/mL antibody for 1 h at room temperature, followed by washing in PBS/0.2% Tween 20 and incubation in peroxidase-conjugated secondary antibody and chemiluminescence detection[2].
Cell Assay	To test the effects of paclitaxel in the presence or absence of WR-1065 dihydrochloride (WR-1065) on cell growth, cells are seeded in 96-well tissue culture dishes at 20% confluence and allowed to attach and recover for at least 24 h. Varying combinations of paclitaxel alone or in combination with a 60 min pretreatment with 1 mM WR-1065 dihydrochloride are then added to each well, and the plates are incubated for an additional 48 h or 72 h. The number of surviving cells is determined by staining. The percentage of cells killed by paclitaxel and/or WR-1065 dihydrochloride is calculated as the percentage decrease in sulforhodamine B binding compare with control cells[2].
Animal Admin	Seventy two rats are divided randomly into 9 equal groups: 1) Control group receives no injection and is left untreated for the entire period of the experiment as intact animals; 2) Sham operated group is subjected only to surgical procedure; 3) Vehicle (saline)-treated group receives 2 μL saline (intra-SNc); 4) Lesioned group receives 6-hydroxydopamine; 5) Vehicle+6OHDA group receives saline as a vehicle 3 days once daily (2 μL/rat) before 6-OHDA injection; 6 to 8) Rats in these groups are pretreated with intra-SNc injection of WR-1065 dihydrochloride (WR-1065) (20, 40 and 80 μg/2 μL/rat) 3 days before 6-OHDA injection; 9) Non-lesioned animals receive intra-SNc injection of WR-1065 dihydrochloride (80 μg/2 μL/rat) for three days[3].
References	[1]. Pluquet O, et al. The cytoprotective aminothiol WR1065 activates p53 through a non-genotoxic signaling pathway involving c-Jun N-terminal kinase. J Biol Chem. 2003 Apr 4;278(14):11879-87. [2]. Shen H, et al. Binding of the aminothiol WR-1065 to transcription factors influences cellular response to anticancer drugs. J Pharmacol Exp Ther. 2001 Jun;297(3):1067-73. [3]. Afshin Kheradmand, et al. Effect of WR-1065 on 6-hydroxydopamine-induced catalepsy and IL-6 level in rats. Iran J Basic Med Sci. 2016 May; 19(5): 490-496.

Density	0.975g/cm3
Boiling Point	218.6ºC at 760 mmHg
Molecular Formula	C₅H₁₆Cl₂N₂S
Molecular Weight	207.16
Flash Point	86ºC
PSA	76.85000
LogP	1.74780
Vapour Pressure	0.124mmHg at 25°C
Index of Refraction	1.496
Storage condition	2-8℃

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KJ0203000

CHEMICAL NAME :: Ethanethiol, 2-((3-aminopropyl)amino)-, dihydrochloride

CAS REGISTRY NUMBER :: 14653-77-1

LAST UPDATED :: 199707

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C5-H14-N2-S.2Cl-H

MOLECULAR WEIGHT :: 207.19

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 24,48,1989

Symbol	GHS05, GHS07
Signal Word	Danger
Hazard Statements	H302-H318
Precautionary Statements	P280-P305 + P351 + P338
RIDADR	NONH for all modes of transport