Cycloleucine

Modify Date: 2024-01-02 22:27:56

Cycloleucine structure	Common Name	Cycloleucine
	CAS Number	52-52-8	Molecular Weight	129.157
	Density	1.2±0.1 g/cm3	Boiling Point	256.1±23.0 °C at 760 mmHg
	Molecular Formula	C₆H₁₁NO₂	Melting Point	320 °C (dec.)(lit.)
	MSDS	Chinese USA	Flash Point	108.7±22.6 °C
	Symbol	GHS06	Signal Word	Danger

Use of Cycloleucine

Cycloleucine is a specific inhibitor of S-adenosyl-methionine mediated methylation. Cycloleucine is antagonist of NMDA receptor associated glycine receptor, with a Ki of 600 μM. Cycloleucine is also a competitive inhibitor of ATP: L-methionine-S-adenosyl transferase in vitro. Cycloleucine has anxiolytic and cytostatic effects[1][2][3][4].

Name	1-aminocyclopentanecarboxylic acid
Synonym	More Synonyms

Description	Cycloleucine is a specific inhibitor of S-adenosyl-methionine mediated methylation. Cycloleucine is antagonist of NMDA receptor associated glycine receptor, with a Ki of 600 μM. Cycloleucine is also a competitive inhibitor of ATP: L-methionine-S-adenosyl transferase in vitro. Cycloleucine has anxiolytic and cytostatic effects[1][2][3][4].
Related Catalog	Signaling Pathways >> Neuronal Signaling >> iGluR Research Areas >> Cancer Research Areas >> Infection Research Areas >> Metabolic Disease Research Areas >> Neurological Disease Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR
Target	Ki: 600 μM (NMDA)[1][2]
In Vitro	Cycloleucine (4-40 mM; 3 h) blocks internal methylation of viral RNA in B77 transformed chick embryo fibroblasts[5]. Cycloleucine (40 mM; 24 h) blocks the formation of both m6A and the penultimate Gm in B77 38S RNA subunits by greater than 90%[5]. Cytostatic (10 µg/mL) inhibits the viability human KB and mouse L1210s leukemia cell lines[5].
In Vivo	Cycloleucine (0.5-4 µg; intracerebroventrical injection) increases time spent in open arms, open arm entries, and extreme arrivals in rats[3]. Animal Model: Male rats bilaterally cannulated into the nucleus accumbens septi (NAS)[3] Dosage: 1 µL of 0.5, 1.0, 2.0, 4 µg/µL Administration: Intracerebroventrical injection Result: Increased time spent in the open arms and extreme arrivals at all doses. Increased open arm entries at the dose of 4 μg.
References	[1]. Hood WF, et, al. 1-Aminocyclobutane-1-carboxylate (ACBC): a specific antagonist of the N-methyl-D-aspartate receptor coupled glycine receptor. Eur J Pharmacol. 1989 Feb 28;161(2-3):281-2. [2]. Caboche M, et, al. RNA methylation and control of eukaryotic RNA biosynthesis. Effects of cycloleucine, a specific inhibitor of methylation, on ribosomal RNA maturation. Eur J Biochem. 1977 Mar 15;74(1):19-29. [3]. Gargiulo API, et, al. Effects of Cycloleucine in the Nucleus Accumbens Septi on the Elevated plus Maze Test in Rats. Neuropsychobiology. 2020;79(3):191-197. [4]. Duś D, et, al. Cytostatic activity in vitro of cycloleucine, aspartic acid and glutamic acid phosphonic analogues. Arch Immunol Ther Exp (Warsz). 1980;28(3):433-8. [5]. Dimock K, et, al. Cycloleucine blocks 5'-terminal and internal methylations of avian sarcoma virus genome RNA. Biochemistry. 1978 Aug 22;17(17):3627-32.

Density	1.2±0.1 g/cm3
Boiling Point	256.1±23.0 °C at 760 mmHg
Melting Point	320 °C (dec.)(lit.)
Molecular Formula	C₆H₁₁NO₂
Molecular Weight	129.157
Flash Point	108.7±22.6 °C
Exact Mass	129.078979
PSA	63.32000
LogP	-0.05
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.522
Water Solubility	5 g/100 mL

Cycloleucine MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GY2625000

CHEMICAL NAME :: Cyclopentanecarboxylic acid, 1-amino-

CAS REGISTRY NUMBER :: 52-52-8

BEILSTEIN REFERENCE NO. :: 0636626

LAST UPDATED :: 199701

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C6-H11-N-O2

MOLECULAR WEIGHT :: 129.18

WISWESSER LINE NOTATION :: L5TJ AZ AVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Behavioral - anorexia (human) Gastrointestinal - nausea or vomiting

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 290 mg/kg

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

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 340 mg/kg

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

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 309 mg/kg

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

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 119 mg/kg

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

REFERENCE :: NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. (Bethesda, MD 20205) Volume(issue)/page/year: JAN1986

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 375 mg/kg

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

REFERENCE :: NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. (Bethesda, MD 20205) Volume(issue)/page/year: JAN1986

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 300 mg/kg

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

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 300 mg/kg

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

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 4 gm/kg

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

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 18,469,1971

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 140 mg/kg

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

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: >316 mg/kg

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

REFERENCE :: EESADV Ecotoxicology and Environmental Safety. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1977- Volume(issue)/page/year: 6,149,1982 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4200 mg/kg/4W-C

TOXIC EFFECTS :: Blood - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 948 mg/kg/30D-I

TOXIC EFFECTS :: Behavioral - food intake (animal) Musculoskeletal - other changes

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 900 mg/kg/15D-I

TOXIC EFFECTS :: Behavioral - muscle weakness Gastrointestinal - other changes Blood - hemorrhage

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 7200 mg/kg/30D-I

TOXIC EFFECTS :: Behavioral - muscle weakness Related to Chronic Data - death

REFERENCE :: JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301
Precautionary Statements	P301 + P310
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes	Xn:Harmful
Risk Phrases	R22
Safety Phrases	S22-S24/25
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	GY2625000
Packaging Group	III
Hazard Class	6.1
HS Code	2922499990

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Literature: Zelinsky; Annenkow; Kulikow Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1911 , vol. 43, p. 1095 Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1911 , vol. 73, p. 463 Full Text Show Details Zelinsky; Stadnikow Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1911 , vol. 75, p. 350

Precursor 8
CAS#:699-51-4 1,3-Diazaspiro[... CAS#:120-92-3 Cyclopentanone CAS#:2627-43-2 Cyclopentanecar... CAS#:1192-28-5 cyclopentanone oxime
CAS#:99848-19-8 1-hydroxyamino-... CAS#:89985-89-7 1-(benzhydrylid... CAS#:49830-37-7 1-Aminocyclopen... CAS#:151-50-8 POTASSIUM CYANIDE
DownStream 10
CAS#:3400-45-1 Cyclopentanecar... CAS#:35264-09-6 Boc-Cyclolencine CAS#:14855-33-5 7,14-diazadispi... CAS#:145122-55-0 6,9-DIAZA-SPIRO...
CAS#:141745-71-3 N-[(2'-Cyano[1,... CAS#:17193-28-1 1-amino-1-cyclo... CAS#:22649-36-1 1-(methylamino)... CAS#:22649-37-2 Cyclopentanecar...
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HS Code	2922499990
Summary	HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

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1-Aminocyclopentanecarboxylicacid

1-aminocyclopentane-1-carboxylic acid

1-Aminocyclopropane-1-carboxylic acid

EINECS 200-144-6

1-amino-1-carboxylic cyclopentane

1-Amino-1-cyclopentanecarboxylic acid

ACPC

Cyclopentanecarboxylic acid, 1-amino-

MFCD00001381

Cycloleucine

1-amino-1-carboxycyclopentane

Cyclolencine

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1-Amino-1-cyclopentanecarboxylate

1-aminocyclopentane-1-carboxylicacid

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