CAS 23261-20-3|VAL-083

Introduction：Basic information about CAS 23261-20-3|VAL-083, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Common NameVAL-083
CAS Number23261-20-3Molecular Weight146.14100
Density1.567Boiling Point348ºC at 760mmHg
Molecular FormulaC6H10O4Melting Point/
MSDS/Flash Point164.3ºC

Names

Name1,2-bis(oxiran-2-yl)ethane-1,2-diol
SynonymMore Synonyms

VAL-083 BiologicalActivity

DescriptionVAL-083 is an alkylating agent that creates N7 methylation on DNA, with antitumor activity.
Related CatalogSignaling Pathways >>Cell Cycle/DNA Damage >>DNA Alkylator/CrosslinkerResearch Areas >>Cancer
Target

DNA Alkylator[1]

In VitroVAL-083 is an alkylating agent that creates N7 methylation on DNA. VAL-083 suppresses U251 and SF188 cell growth and induces apoptosis after 72 h. VAL-083 (5 μM) inhibits the growth of SF188 by ∼95%. VAL-083 inhibits T98G cells growth in a dose-dependent manner (IC50 <5 μM)[1]. VAL-083 (Dianhydrogalactitol) inhibits the proliferation of HUVEC and U251 cells at doses of more than 12.5 μg/mL. VAL-083 (3.125, 6.25, 12.5 μg/mL) also suppresses the migration and invasion, and reduces MMP2, VEGF, VEGFR2, and FGF2 expression in HUVEC and U251 cells[2]. VAL-083 (1,2:5,6-dianhydrogalactitol, 1, 2, 5 μM) dose-dependently induces cell cycle arrest at G2/M phase in the 3 glioma cell lines. VAL-083 activates two parallel signaling cascades, the p53-p21 and the CDC25C-CDK1 cascade. In addition, VAL-083 significantly enhances the radiosensitivity of LN229 cells[3].
In VivoVAL-083 (Dianhydrogalactitol; 25, 50, 100 μg/mL) dose-dependently inhibits angiogenesis in zebrafish model. VAL-083 considerably reduces VEGF, VEGFR2, and FGF2 expression at 25 μg/mL, and further causes reduction in FGFR2 expression at 50 μg/mL[2]. VAL-083 (1,2:5,6-dianhydrogalactitol; 5 mg/kg, iv, twice per week for 6 weeks) significantly blocks the growth of LN229 cells in mice with the relative tumor growth rate (T/C) of 22.38%, and the tumor growth inhibitory rate (TGI) of 83.58%. Moreover, VAL-083 dramatically activates the CDC25C-CDK1 cascade in the xenografted tumor moedl[3].
Cell AssayThe effects of VAL-083 in HUVEC and U251 cellHUVEC and U251 cell proliferation are measured by the CCK8 assay. Cells are seeded into 96-well plates at a destiny of 1 × 104 cells per well. After overnight incubation, cell attachment is followed by the addition of VAL-083 in various concentrations for 24 h; then 10 μL CCK8 is added to each well and incubated at 37°C for 2 h. Optical density is measured at 450 nm[2].
Animal AdminMice[3] LN229 cells are suspended in MEM, and 2 × 106 cells per mouse are subcutaneously injected into the flank of BALB/c nude mice at 6-8 weeks old. The tumor volume is calculated as follows: 0.5×L×W2. Tumor-bearing mice are divided into two groups (n = 8) with similar average volumes (vehicle: 108 ± 4 mm3 vs VAL-083: 107 ± 4 mm3). Then, both groups undergo the following treatment: The VAL-083 treatment group receives VAL-083 at 5 mg/kg or 10 μL/g, iv, twice per week for 6 weeks. The vehicle group receives saline at 10 μL/g, iv, three times per week for 6 weeks. Tumor volumes are measured twice per week[3].
References

[1]. Kaiji Hu, et al. Abstract 811: VAL083, a novel N7 alkylating agent, surpasses temozolomide activity and inhibits cancer stem cells providing a new potential treatment option for glioblastoma multiforme. Cancer Research. 2012 Mar 31-Apr 4.

[2]. Jiang X, et al. Dianhydrogalactitol, a potential multitarget agent, inhibits glioblastoma migration, invasion, and angiogenesis. Biomed Pharmacother. 2017 Jul;91:1065-1074.

[3]. Peng C, et al. 1,2:5,6-dianhydrogalactitol inhibits human glioma cell growth in vivo and in vitro by arresting the cell cycle at G2/M phase. Acta Pharmacol Sin. 2017 Apr;38(4):561-570.

Chemical & Physical Properties

Density1.567
Boiling Point348ºC at 760mmHg
Molecular FormulaC6H10O4
Molecular Weight146.14100
Flash Point164.3ºC
Exact Mass146.05800
PSA65.52000
InChIKeyAAFJXZWCNVJTMK-GUCUJZIJSA-N
SMILESOC(C1CO1)C(O)C1CO1
Storage condition2-8℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LW5320000
CAS REGISTRY NUMBER :
23261-20-3
LAST UPDATED :
199703
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C6-H10-O4
MOLECULAR WEIGHT :
146.16
WISWESSER LINE NOTATION :
T3OTJ BYQYQ- BT3OTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
14 mg/kg
TOXIC EFFECTS :
Gastrointestinal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
11 mg/kg
TOXIC EFFECTS :
Gastrointestinal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Gastrointestinal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
7899 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
15 mg/kg
TOXIC EFFECTS :
Gastrointestinal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
16500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
21 mg/kg
TOXIC EFFECTS :
Gastrointestinal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
14 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
20 mg/kg/5D-I
TOXIC EFFECTS :
Blood - agranulocytosis Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
20 mg/kg/5D-I
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
87500 ug/kg/70D-I
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified)
TYPE OF TEST :
DNA adduct
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
DNA inhibition

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - rabbit Bone marrow
DOSE/DURATION :
136 umol/L
REFERENCE :
BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 25,1705,1976

Safety Information

HS Code2910900090

Customs

HS Code2910900090
Summary2910900090. epoxides, epoxyalcohols, epoxyphenols and epoxyethers, with a three-membered ring, and their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

Synonyms

Galactitol,1,2:5,6-dianhydro
1,2:5,6-Diepoxydulcitol
Dulcitoldiepoxide
5,6-Diepoxydulcitol
Dianhydrogalactitol
1,2,5,6-dianhydro-galactitol
1,2-5,6-dianhydro-dulcitol
Dianhydrodulcitol
VAL-083
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