関: mercaptamine、mercaptoethylamine

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/22 13:48:58」(JST)

wiki en

Cysteamine is the chemical compound with the formula HSCH₂CH₂NH₂. It is the simplest stable aminothiol and a degradation product of the amino acid cysteine. It is often used as the hydrochloride salt, HSCH₂CH₂NH₃Cl. The comparatively high melting point of cysteamine (95-97 °C), indicates that it exists in a salt form.^[1]

Preparation

It can also be prepared by the reaction of ethylenimine with hydrogen sulfide.^[1]

(NHCH₂CH₂) + H₂S → HSCH₂CH₂NH₂

Reactions

It is used as the hydrochloride salt, as it readily oxidizes to the corresponding disulfide, in the presence of air. The amine portion of the molecule serves as a catalyst for this reaction.

4 HSCH₂CH₂NH₂ + O₂ → 2 NH₂CH₂CH₂SSCH₂CH₂NH₂ + 2 H₂O

Biochemical and pharmaceutical applications

Under the trade name Cystagon, cysteamine is used in the treatment of disorders of cystine excretion. Cysteamine cleaves the disulfide bond with cystine to produce molecules that can escape the metabolic defect in cystinosis and cystinuria.

It is also used for treatment of radiation sickness.^[2]

Cysteamine is used in the body to form the essential biochemical coenzyme A by combining with pantothenate and adenosine triphosphate.

In 2008, Raptor Pharmaceuticals started phase II clinical trials testing a delayed release (DR) preparation of cysteamine bitartrate for Huntington's disease. DR Cysteamine is also being investigated as a treatment for cystinosis, Batten disease, and non-alcoholic steatohepatitis.

References

^ ^a ^b Reid, E. Emmet (1958). Organic Chemistry of Bivalent Sulfur 1. New York: Chemical Publishing Company, Inc. pp. 398–399.
^ Lukashin BP, Grebeniuk AN (2001). "[Comparative study of the radiation-protective effectiveness of low doses of cysteamine, heparin, and naphtizine in experiments on mice]". Radiatsionnaia biologiia, radioecologiia / Rossiĭskaia akademiia nauk (in Russian) 41 (3): 310–2. PMID 11458646.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. シスチン蓄積症 cystinosis
2. 小児における運動減少性運動障害 bradykinetic movement disorders in children
3. 浸潤性甲状腺疾患 infiltrative thyroid disease
4. メトヘモグロビン血症の遺伝学および病因 genetics and pathogenesis of methemoglobinemia
5. 成人におけるアセトアミノフェン（パラセタモール）中毒：治療 acetaminophen paracetamol poisoning in adults treatment

English Journal

Construction of novel electrochemical immunosensor for detection of prostate specific antigen using ferrocene-PAMAM dendrimers.

Çevik E1, Bahar Ö2, Şenel M3, Abasıyanık MF2.
Biosensors & bioelectronics.Biosens Bioelectron.2016 Dec 15;86:1074-9. doi: 10.1016/j.bios.2016.07.064. Epub 2016 Jul 20.
In this study, an immunosensor was designed to utilize for the detection of prostate specific antigen (PSA) based on three different generations (G1, G2 and G3) of ferrocene (Fc) cored polyamidiamine dendrimers (Fc-PAMAM) gold (Au) electrode. The self-assembled monolayer principle (SAM) was used to
PMID 27641479

Cysteamine capped CdS quantum dots as a fluorescence sensor for the determination of copper ion exploiting fluorescence enhancement and long-wave spectral shifts.

Boonmee C1, Noipa T2, Tuntulani T3, Ngeontae W4.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2016 Dec 5;169:161-8. doi: 10.1016/j.saa.2016.05.007. Epub 2016 May 8.
We described a turn-on fluorescence sensor for the determination of Cu(2+) ions, utilizing the quantum confinement effect of cadmium sulfide quantum dots capped with cysteamine (Cys-CdS QDs). The fluorescence intensity of the Cys-CdS QDs was both enhanced and red shifted (from blue-green to yellow)
PMID 27372512

Manipulating proteostasis to repair the F508del-CFTR defect in cystic fibrosis.

Esposito S1, Tosco A2, Villella VR1, Raia V3, Kroemer G4,5,6,7,8,9,10, Maiuri L11,12.
Molecular and cellular pediatrics.Mol Cell Pediatr.2016 Dec;3(1):13. doi: 10.1186/s40348-016-0040-z. Epub 2016 Mar 14.
Cystic fibrosis (CF) is a lethal monogenic disease caused by mutations in the cystic fibrosis transmembrane conductance regulator (CFTR) gene that entails the (diagnostic) increase in sweat electrolyte concentrations, progressive lung disease with chronic inflammation and recurrent bacterial infecti
PMID 26976279

Japanese Journal

Electrochemical Determination of Dopamine in the Presence of Ascorbic Acid and Uric Acid Using the Synergistic Effect of Gold Nanoflowers and L-Cysteamine Monolayer at the Surface of a Gold Electrode

Li Yongxin,Lu Qiufang,Shi Aibin [他],CHEN Yuanli,WU Shengnan,WANG Lun
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 27(9), 921-927, 2011-09-10
NAID 10029761107

Identification of N-homocysteinylated apolipoprotein AI in normal human serum

Ishimine N,Usami Y,Nogi S,Sumida T,Kurihara Y,Matsuda K,Nakamura K,Yamauchi K,Okumura N,Tozuka M,山内一由
Annals of clinical biochemistry 47, 453-459, 2010-09-00
… The present study strives to develop detection and potential semi-quantification methods for N-homocysteinylated apolipoprotein AI (N-Hcy-apoAI) in human serum.Methods: Serum treated with or without cysteamine was supplied to isoelectric focusing (IEF) followed by an immunoblot using an anti-apoAI antibody. … Cysteamine treatment increased the isoelectric point for N-Hcy-apoAI, but not for unmodified apoAI, due to the presence of -SH group(s) derived from Hcy and the absence of a cysteine residue in the apoAI molecule. …
NAID 120002598897

Intestinal Metaplasia : The Effect of Acid on the Gastric Mucosa and Gastric Carcinogenesis

Watanabe Hiromitsu,ワタナベヒロミツ,渡邊敦光
Journal of toxicologic pathology 23(3), 115-123, 2010
… Alkaline phosphatase (ALP) positive metaplastic foci were increased by administration of ranitidine (H2 receptor antagonist), crude stomach antigens or subtotal resection of the fundus and decreased by cysteamine (gastric acid secretion stimulator), histamine or removal of the submandibular glands. …
NAID 130000450737

Related Pictures

★リンクテーブル★

リンク元	「システアミン」「mercaptoethylamine」「mercaptamine」

「システアミン」

Cysteamine
Names
	IUPAC name 2-aminoethanethiol
	Other names β-mercaptoethylamine; 2-aminoethanethiol; 2-mercaptoethylamine; decarboxycysteine; thioethanolamine; mercaptamine
Identifiers
CAS Registry Number	60-23-1 ; 156-57-0 (HCl)
ATC code	A16AA04; S01XA21
ChEBI	CHEBI:17141
ChEMBL	ChEMBL602
ChemSpider	5834
DrugBank	DB00847
	InChI InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2 ; Key: UFULAYFCSOUIOV-UHFFFAOYSA-N ; InChI=1/C2H7NS/c3-1-2-4/h4H,1-3H2; Key: UFULAYFCSOUIOV-UHFFFAOYAX ;
IUPHAR/BPS	7440
Jmol-3D images	Image
KEGG	D03634
PubChem	6058
	SMILES SCCN ;
UNII	5UX2SD1KE2
Properties
Chemical formula	C2H7NS
Molar mass	77.15 g·mol−1
Melting point	95 to 97 °C (203 to 207 °F; 368 to 370 K)
Hazards
Safety data sheet	External MSDS
EU classification	Xn
S-phrases	S26 S36
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is: /?)
	Infobox references

　　[★]

英: cysteamine
関: メルカプタミン、メルカプトエチルアミン

「mercaptoethylamine」

　　[★]

メルカプトエチルアミン

関: cysteamine、mercaptamine

「mercaptamine」

　　[★]

メルカプタミン

関: cysteamine、mercaptoethylamine

[Reid-1] Reid, E. Emmet (1958). Organic Chemistry of Bivalent Sulfur 1. New York: Chemical Publishing Company, Inc. pp. 398–399.

[pmid11458646-2] Lukashin BP, Grebeniuk AN (2001). "[Comparative study of the radiation-protective effectiveness of low doses of cysteamine, heparin, and naphtizine in experiments on mice]". Radiatsionnaia biologiia, radioecologiia / Rossiĭskaia akademiia nauk (in Russian) 41 (3): 310–2. PMID 11458646.

匿名

検索

案内

案内

cysteamine