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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
EC Number:
216-994-6
MDL number:
MFCD00082369
UNSPSC Code:
12352200
PubChem Substance ID:
329771026
NACRES:
NA.77

Quality Level

100

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: ≥10 mg/mL

storage temp.

−20°C

SMILES string

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

InChI key

BRJJFBHTDVWTCJ-UHFFFAOYSA-N

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Application

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

Biochem/physiol Actions

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.

Features and Benefits

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Acanthamoeba keratitis (AK) is a serious ocular infection caused by a ubiquitous free-living amoeba, Acanthamoeba. This infection often results in extensive corneal damage and blindness, and is notoriously difficult to cure. While Acanthamoeba is an abundant organism, AK is most
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Invasive fungal infections due to Candida albicans, Aspergillus fumigatus, and Cryptococcus neoformans constitute a substantial threat to hospitalized immunocompromised patients. Further, the presence of drug-recalcitrant biofilms on medical devices and emergence of drug-resistant fungi, such as Candida auris, introduce treatment
J Moran et al.
Journal of periodontology, 55(5), 278-282 (1984-05-01)
The phenomenon of surface adsorption appears fundamental to the antiplaque activity of the cationic antiseptics. Moreover, reaction with chromogenic material is relevant to the local side effect of staining. The purpose of this investigation was to determine how such local
Mateja Zorko et al.
The Journal of antimicrobial chemotherapy, 62(4), 730-737 (2008-07-19)
Many antibiotics used to treat infections cause release of immunostimulatory cell wall components from bacteria. Therefore, a combination of antimicrobial and endotoxin-neutralizing activity is desired to prevent inflammation induced by destroyed bacteria. Chlorhexidine and alexidine are amphipathic bisbiguanides and could
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Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 31(3), 560-572 (2015-09-13)
Aseptic loosening and periprosthetic infection leading to inflammatory osteolysis is a major complication associated with total joint arthroplasty (TJA). The liberation of bacterial products and/or implant-derived wear particles activates immune cells that produce pro-osteoclastogenic cytokines that enhance osteoclast recruitment and
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Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases' catalytic mechanism involves transient phosphorylation.

Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases' catalytic mechanism involves transient phosphorylation.

Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases' catalytic mechanism involves transient phosphorylation.

Phosphoprotein Phosphatases (Tyrosine)

Protein tyrosine phosphatases' catalytic mechanism involves transient phosphorylation.

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