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A8986

Sigma-Aldrich

Alexidine dihydrochloride

≥95% (HPLC)

Sinónimos:

1,1′-Hexamethylene-bis(5-[2-ethylhexyl]biguanide)

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About This Item

Fórmula empírica (notación de Hill):
C26H56N10 · 2HCl
Número de CAS:
1715-30-6
Peso molecular:
581.71
Número CE:
216-994-6
Número MDL:
MFCD00082369
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
329771026
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥95% (HPLC)

Formulario

powder

condiciones de almacenamiento

desiccated

color

white to off-white

solubilidad

DMSO: ≥10 mg/mL

temp. de almacenamiento

−20°C

cadena SMILES

Cl.Cl.CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC

InChI

1S/C26H56N10.2ClH/c1-5-9-15-21(7-3)19-33-25(29)35-23(27)31-17-13-11-12-14-18-32-24(28)36-26(30)34-20-22(8-4)16-10-6-2;;/h21-22H,5-20H2,1-4H3,(H5,27,29,31,33,35)(H5,28,30,32,34,36);2*1H

Clave InChI

BRJJFBHTDVWTCJ-UHFFFAOYSA-N

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Aplicación

Alexidine dihydrochloride has been used:
  • as an antiseptic to study its antimicrobial activity in saliva-derived microcosm biofilms
  • as a protein tyrosine phosphatase localized to the mitochondrion 1 (PTPMT1)-specific inhibitor to study its effects on spare respiratory capacity and viability of CD8+ T cells
  • as a PTPMT1 inhibitor to study its antiviral effect on  human cytomegalovirus (HCMV) replication in HCMV-infected human foreskin fibroblast (HFF) cells

Acciones bioquímicas o fisiológicas

Alexidine dihydrochloride is a bisbiguanide compound. It has been studied in the treatment of head and neck cancer. Alexidine dihydrochloride also exhibits antibiofilm and antifungal activity against several fungal species. It causes mitochondrial apoptosis in mammalian cells due to its anti-cancer activity. Alexidine dihydrochloride is a component of oral disinfectant and contact lens solution.
Alexidine dihydrochloride is a potent and selective PTPMT1 (Protein Tyrosine Phosphatase Localized to the Mitochondrion 1) inhibitor. Alexidine increases insulin secretion by isolated rat pancreatic islets.

Características y beneficios

This compound is featured on the Phosphoprotein Phosphatases (Tyrosine) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H315,H319,H335

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
116M4752V
076M4723V
125M4718V
015M4713V
070M4702

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Chlorhexidine ≥99.5%

Sigma-Aldrich

282227

Chlorhexidine

Chlorhexidine Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1421

Chlorhexidine

8-Aminoquinoline 98%

Sigma-Aldrich

260789

8-Aminoquinoline

Chlorhexidine digluconate solution 20% in H2O

Sigma-Aldrich

C9394

Chlorhexidine digluconate solution

J A Chawner et al.
The Journal of applied bacteriology, 66(3), 253-258 (1989-03-01)
Strains of Providencia stuartii with demonstrated resistance towards chlorhexidine did not show such resistance towards either of the related biguanide antiseptics, alexidine or vantocil. Alexidine promoted a significantly faster alteration in the permeability of Escherichia coli cell membranes towards various
Kenneth W Yip et al.
Molecular cancer therapeutics, 5(9), 2234-2240 (2006-09-21)
Despite advances in surgery, radiation, and chemotherapy, novel therapeutics are needed for head and neck cancer treatment. The objective of this current study was to evaluate alexidine dihydrochloride as a novel compound lead for head and neck cancers. Using a
Cationic antiseptics: diversity of action under a common epithet.
P Gilbert et al.
Journal of applied microbiology, 99(4), 703-715 (2005-09-16)
Hyun-Shik Kim et al.
International journal of oral science, 5(1), 26-31 (2013-03-16)
A previous study demonstrated that alexidine has greater affinity for the major virulence factors of bacteria than chlorhexidine. The aim of this study was to compare the antimicrobial activity of 1% alexidine with that of 2% chlorhexidine using Enterococcus faecalis-infected
Sophia R Schwarz et al.
Clinical oral investigations, 25(5), 2939-2950 (2020-10-10)
The aims of this study were to investigate the antimicrobial efficacy of antiseptics in saliva-derived microcosm biofilms, and to examine phenotypic adaption of bacteria upon repeated exposure to sub-inhibitory antiseptic concentrations. Saliva-derived biofilms were formed mimicking caries- or gingivitis-associated conditions
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Artículos

Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases (PTPs) and related enzymes (more than a hundred coded by the human genome) are more numerous than serine/threonine phosphatases. They belong to four families, three of which possess a conserved cysteine for catalysis and some conserved features of 3-dimensional structure. The catalytic mechanism of these PTPs involves the transient formation of a covalently phosphorylated enzyme.

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