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52-52-8

52-52-8 structure
52-52-8 structure
  • Name: Cycloleucine
  • Chemical Name: 1-aminocyclopentanecarboxylic acid
  • CAS Number: 52-52-8
  • Molecular Formula: C6H11NO2
  • Molecular Weight: 129.157
  • Catalog: Biochemical Common amino acids and protein drugs
  • Create Date: 2018-09-20 18:21:45
  • Modify Date: 2024-01-02 22:27:56
  • 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
Synonyms 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
1-Aminocyclopentanecarboxylic acid
1-Amino-1-cyclopentanecarboxylate
1-aminocyclopentane-1-carboxylicacid
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
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

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
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
699-51-4 structure

699-51-4

~75%

52-52-8 structure

52-52-8

Literature: Tsang, Joseph W.; Schmied, Bernhard; Nyfeler, Rolf; Goodman, Murray Journal of Medicinal Chemistry, 1984 , vol. 27, # 12 p. 1663 - 1668
120-92-3 structure

120-92-3

~%

52-52-8 structure

52-52-8

Literature: Kovachev; Ivanov; Buyukliev; Konstantinov; Karaivanova Pharmazie, 1996 , vol. 51, # 1 p. 25 - 27
2627-43-2 structure

2627-43-2

~%

52-52-8 structure

52-52-8

Literature: Neelakantan; Hartung Journal of Organic Chemistry, 1958 , vol. 23, p. 964,967
1192-28-5 structure

1192-28-5

~%

52-52-8 structure

52-52-8

Literature: Neelakantan; Hartung Journal of Organic Chemistry, 1958 , vol. 23, p. 964,967
99848-19-8 structure

99848-19-8

~%

52-52-8 structure

52-52-8

Literature: Neelakantan; Hartung Journal of Organic Chemistry, 1958 , vol. 23, p. 964,967
89985-89-7 structure

89985-89-7

~%

52-52-8 structure

52-52-8

Literature: O'Donnell, Martin J.; Bruder, William A.; Eckrich, Thomas M.; Shullenberger, Daniel F.; Staten, Gilbert S. Synthesis, 1984 , # 2 p. 127 - 128
49830-37-7 structure

49830-37-7

~%

52-52-8 structure

52-52-8

Literature: Sudo,R.; Ichihara,S. Bulletin of the Chemical Society of Japan, 1963 , vol. 36, p. 34 - 37
151-50-8 structure

151-50-8

120-92-3 structure

120-92-3

~%

52-52-8 structure

52-52-8

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
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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