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Merck

377627

Sigma-Aldrich

2-Imino-1-imidazolidineacetic acid

98%

Szinonimák:

1-Carboxymethyl-2-iminoimidazolidine, Cyclocreatine

Bejelentkezésa Szervezeti és Szerződéses árazás megtekintéséhez


About This Item

Tapasztalati képlet (Hill-képlet):
C5H9N3O2
CAS-szám:
Molekulatömeg:
143.14
MDL-szám:
UNSPSC kód:
12352100
PubChem Substance ID:
NACRES:
NA.22

Minőségi szint

Teszt

98%

Forma

solid

oldhatóság

1 M HCl: soluble 25 mg/mL, clear, colorless

funkcionális csoport

carboxylic acid

SMILES string

OC(=O)CN1CCNC1=N

InChI

1S/C5H9N3O2/c6-5-7-1-2-8(5)3-4(9)10/h1-3H2,(H2,6,7)(H,9,10)

Nemzetközi kémiai azonosító kulcs

AMHZIUVRYRVYBA-UHFFFAOYSA-N

Általános leírás

2-Imino-1-imidazolidineacetic acid (cyclocreatine) is an analog of creatine. It is reported to exhibit antitumour effect in some transplanted human and rodent tumours in vivo. It is reported as an efficient substrate for creatine kinase. It is an anticancer and neuroprotective agent. The crystal structure of cyclocreatine has been studied by X-ray diffraction methods. It is reported to crystallize as a zwitterion in the monoclinic system.

Alkalmazás

2-Imino-1-imidazolidineacetic acid (cyclocreatine) is suitable for use in a study to investigate the growth inhibitory effects of cyclocreatine on LS174T human colon adenocarcinoma implanted subdermally in nude mice. It may be used to evaluate the brain-type creatine kinase (CKB), to study the role of CKB in cigarette smoke-induced bronchial epithelial cell senescence.
Protectant against inhibition of cardiac mitochondrial respiration by methylglyoxal

Growth inhibition of Hodgkin disease-derived cell lines

Investigations into effects in rat hepatocarcinogenesis model

Biokémiai/fiziológiai hatások

Creatine analog that protects tissues from ischemic damage; decreases the rate of ATP production via creatine kinase and reduces the proliferation of tumor cell lines that are characterized by high levels of creatine kinase expression.

Piktogramok

Exclamation mark

Figyelmeztetés

Warning

Figyelmeztető mondatok

Veszélyességi osztályok

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Célzott szervek

Respiratory system

Tárolási osztály kódja

11 - Combustible Solids

WGK

WGK 3

Lobbanási pont (F)

Not applicable

Lobbanási pont (C)

Not applicable

Egyéni védőeszköz

dust mask type N95 (US), Eyeshields, Gloves


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Analitikai tanúsítványok (COA)

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Dokumentumtár megtekintése

R T Matthews et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 18(1), 156-163 (1998-01-24)
The gene defect in Huntington's disease (HD) may result in an impairment of energy metabolism. Malonate and 3-nitropropionic acid (3-NP) are inhibitors of succinate dehydrogenase that produce energy depletion and lesions that closely resemble those of HD. Oral supplementation with
R W Wiseman et al.
The Journal of biological chemistry, 270(21), 12428-12438 (1995-05-26)
The hypothesis tested was whether creatine kinase (CK) equilibrates with its substrates and products in the cytosol as if in solution. We used the creatine analogs cyclocreatine (cCr) or beta-guanidopropionate (beta GPA) to test if mass action ratios (gamma) for
C B Cuono et al.
Plastic and reconstructive surgery, 101(6), 1597-1603 (1998-05-16)
A general understanding of the pivotal role of phosphocreatine (PCr) as the principal determinant of skin flap survival is now emerging. Definitive metabolic investigations using phosphorus (31P) and proton (1H) magnetic resonance spectroscopy (MRS) have established that the inability to
J S Cantwell et al.
Biochemistry, 40(10), 3056-3061 (2001-03-22)
Creatine kinase (CK) catalyzes the reversible phosphorylation of the guanidine substrate, creatine, by MgATP. Although several X-ray crystal structures of various isoforms of creatine kinase have been published, the detailed catalytic mechanism remains unresolved. A crystal structure of the CK
P T Mulvaney et al.
International journal of cancer, 78(1), 46-52 (1998-09-02)
Cyclocreatine (1-carboxymethyl-2-iminoimidazolidine), an analog of creatine and a substrate for creatine kinase (EC 2.7.3.2), inhibits the stimulated motility of tumor cells which possess creatine kinase. A2058-055 human melanoma cells, transfected with a creatine kinase gene, showed an 80-90% reduction in

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