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L-DON

Names

[ CAS No. ]:
157-03-9

[ Name ]:
L-DON

[Synonym ]:
(S)-2-Amino-6-diazo-5-oxocaproic acid,DON
6-DIAZO-5-OXO-L-NORLEUCINE
MFCD00037218

Biological Activity

[Description]:

L-6-Diazo-5-oxonorleucine (L-6-Diazo-5-oxonorleucine) is a glutaminases antagonist with a Ki of 6 μM. L-6-Diazo-5-oxonorleucine exhibits analgesic, antibacterial, antiviral and anticancer properties. L-6-Diazo-5-oxonorleucine displays genetic toxicity in vitro. L-6-Diazo-5-oxonorleucine decreases the self-renewal potential and metastatic ability of tumor cell[1][2][3][4].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Infection

[Target]

Ki: 6 μM (glutaminases)[4]


[References]

[1]. Kulkarni RM, et al. Evaluation of genetic toxicity of 6-diazo-5-oxo-l-norleucine (DON). Toxicol Mech Methods. 2017 Sep;27(7):518-527.

[2]. Thangavelu K, et al. Structural basis for the active site inhibition mechanism of human kidney-type glutaminase (KGA). Sci Rep. 2014 Jan 23;4:3827.

[3]. Willis RC, et al. The inhibition by 6-diazo-5-oxo-l-norleucine of glutamine catabolism of the cultured human lymphoblast. J Cell Physiol. 1977 Dec;93(3):375-82.

[4]. Sharma NS, et al. Targeting tumor-intrinsic hexosamine biosynthesis sensitizes pancreatic cancer to anti-PD1 therapy. J Clin Invest. 2019 Oct 15.

Chemical & Physical Properties

[ Density]:
1.3994 (rough estimate)

[ Boiling Point ]:
301.12°C (rough estimate)

[ Melting Point ]:
-145ºC (dec.)

[ Molecular Formula ]:
C6H9N3O3

[ Molecular Weight ]:
171.15400

[ Exact Mass ]:
171.06400

[ PSA ]:
117.78000

[ Appearance of Characters ]:
crystalline | light yellow

[ Index of Refraction ]:
1.5800 (estimate)

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RC6340000
CHEMICAL NAME :
Norleucine, 6-diazo-5-oxo, L-
CAS REGISTRY NUMBER :
157-03-9
BEILSTEIN REFERENCE NO. :
1725815
LAST UPDATED :
199706
DATA ITEMS CITED :
18
MOLECULAR FORMULA :
C6-H9-N3-O3
MOLECULAR WEIGHT :
171.18
WISWESSER LINE NOTATION :
QVYZ2V1UNN

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
80 mg/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 :
Intracerebral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>200 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 :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
76 mg/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 :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
197 mg/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 :
220 mg/kg
TOXIC EFFECTS :
Gastrointestinal - peritonitis Gastrointestinal - other changes Liver - fatty liver degeneration
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
76 mg/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 :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
100 ug/kg
SEX/DURATION :
female 7-8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
300 ug/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
400 ug/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
500 ug/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
400 ug/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

MUTATION DATA

TYPE OF TEST :
DNA damage
TEST SYSTEM :
Microorganism - not otherwise specified
DOSE/DURATION :
30 mmol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 360,95,1996 *** REVIEWS *** TOXICOLOGY REVIEW JAMAAP JAMA, Journal of the American Medical Association. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1883- Volume(issue)/page/year: 172,1765,1960 TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW ADVPA3 Advances in Pharmacology. (New York, NY) V.1-6, 1962-68. For publisher information, see AVPCAQ. Volume(issue)/page/year: 4,263,1966 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H311-H331

[ Precautionary Statements ]:
P261-P280-P301 + P310-P311

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T

[ Risk Phrases ]:
23/24/25

[ Safety Phrases ]:
S45;S36/S37/S39

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
RC6340000

[ HS Code ]:
2927000090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2927000090

[ Summary ]:
2927000090 other diazo-, azo- or azoxy-compounds。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

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