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W2020

Sigma-Aldrich

WR-1065

≥98% (HPLC)

Synonym(s):

2-[(3-Aminopropyl)amino]ethanethiol dihydrochloride, WR-1065 dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C5H14N2S · 2HCl
CAS Number:
14653-77-1
Molecular Weight:
207.16
MDL number:
MFCD00460339
UNSPSC Code:
12352200
PubChem Substance ID:
329830444
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

H2O: ≥20 mg/mL

storage temp.

−20°C

SMILES string

Cl.Cl.NCCCNCCS

InChI

1S/C5H14N2S.2ClH/c6-2-1-3-7-4-5-8;;/h7-8H,1-6H2;2*1H

InChI key

XDRLRDHLCIFZIW-UHFFFAOYSA-N

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Biochem/physiol Actions

WR-1065 is cytoprotective cell-permeable reactive oxygen species scavenger and p53 activator and re-activator. Recently shown to have antiretroviral activity and an active metabolite of Amifostine which selectively protects normal tissues from the damaging effects of anti-neoplastic radiation therapy.
WR-1065 is the active metabolite of the prodrug amifostine, generated by alkaline phosphatase. It is found to accumulate in many epithelial tissues. WR-1065 protects cellular membranes and DNA from free radical induced damage.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Radiotherapy alone, versus radiotherapy with amifostine 3 times weekly, versus radiotherapy with amifostine 5 times weekly: A prospective randomized study in squamous cell head and neck cancer
Jellema AP, et al.
Cancer, 107(3), 544-553 (2006)
Caroline Prouillac et al.
Free radical biology & medicine, 46(8), 1139-1148 (2009-05-15)
Thiol and aminothiol compounds are among the most efficient chemical radioprotectors. To increase their efficiency, we synthesized two new classes of thiol and aminothiol compounds derived from benzothiazole (T1, T2, AM1, AM2) and thiadiazole (T3, T4, AM3) structures. We examined
Jeffrey S Murley et al.
Radiation research, 167(4), 465-474 (2007-03-29)
RKO36 cells, a subclone of RKO colorectal carcinoma cells that have been stably transfected with the pCMV-EGFP2Xho vector, were grown to confluence and then exposed to either the radioprotector WR-1065, i.e. the active thiol form of amifostine, for 30 min
Sara Ibrahim Omar et al.
Chemical biology & drug design, 86(2), 163-172 (2014-11-20)
The guardian of the genome, p53, is the most mutated protein found in all cancer cells. Restoration of wild-type activity to mutant p53 offers promise to eradicate cancer cells using novel pharmacological agents. Several molecules have already been found to
Jeffrey S Murley et al.
Radiation research, 175(1), 57-65 (2010-12-24)
RKO36 cells exposed to either WR1065 or 10 cGy X rays show elevated SOD2 gene expression and SOD2 enzymatic activity. Cells challenged at this time with 2 Gy exhibit enhanced radiation resistance. This phenomenon has been identified as a delayed
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