15894-70-9

Basic information

• Product Name: 1,6-Bis(cyano-guanidino)hexane
• Synonyms: HMBCG;1,6-HEXAMETHYLENE-BIS-CYANOGUANIDINE;N,N'''-1,6-hexanediylbis[N'-cyanoguanidine];1,6-Bis(cyano-guanidino)-hexane;Guanidine, N,N-1,6-hexanediylbisN-cyano-;1,6-Hexamethylenebis-(dicyanamide);NN-Dicyano-N,Nhexanediyl-di-guanidine;1,6-Bis(3-cyanoguanidino)hexane
• CAS NO: 15894-70-9
• Molecular Formula: C₁₀H₁₈N₈
• Molecular Weight: 250.3
• EINECS: 240-032-4
• Product Categories: Small molecule;Aliphatics;Metabolites & Impurities
• Mol File: 15894-70-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: >2950C
• Boiling Point: 437.7 °C at 760 mmHg
• Flash Point: 218.5 °C
• Appearance: White Solid
• Density: 1.25 g/cm³
• Vapor Pressure: 0Pa at 95℃
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Very Slightly), Water (Very Slightly, Heated)
• PKA: 3.21±0.70(Predicted)
• Water Solubility: 7.05mg/L at 25℃
• CAS DataBase Reference: 1,6-Bis(cyano-guanidino)hexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Bis(cyano-guanidino)hexane(15894-70-9)
• EPA Substance Registry System: 1,6-Bis(cyano-guanidino)hexane(15894-70-9)

Safety Data

• Hazardous Substances Data: 15894-70-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Flammability and Explosibility

Nonflammable

Upstream product

• 124-09-4 1,6-Hexanediamine 
• 1934-75-4 sodium dicyanamide 
• 6055-52-3 hexane-1,6-diamine dihydrochloride 

Downstream Products

• 22573-93-9 alexidine 
• 55-56-1 chlorhexidine 
• 59470-54-1 C₂₂H₃₀Br₂N₁₀ 
• 53416-52-7 C₂₂H₃₀F₂N₁₀ 
• 114278-67-0 5,5'-bis-(3,4-dichloro-phenyl)-1,1'-hexanediyl-bis-biguanide; dihydrochloride 
• 124106-36-1 5,5'-bis-(2,4-dichloro-benzyl)-1,1'-hexanediyl-bis-biguanide; tetrahydrochloride 
• 123936-96-9 5,5'-bis-(2,6-dichloro-benzyl)-1,1'-hexanediyl-bis-biguanide; dihydrochloride 
• 65568-72-1 5,5'-bis-(4-carboxy-phenyl)-1,1'-hexanediyl-bis-biguanide; dihydrochloride 
• 114398-73-1 5,5'-bis-(4-methyl-benzyl)-1,1'-hexanediyl-bis-biguanide; dihydrochloride 
• 120176-57-0 5,5'-diphenethyl-1,1'-hexanediyl-bis-biguanide 
• 111937-02-1 5,5'-bis-(3-chloro-phenyl)-1,1'-hexanediyl-bis-biguanide; dihydrochloride 
• 50765-39-4 5,5'-dicyclohexyl-1,1'-hexanediyl-bis-biguanide; dihydrochloride 

Relevant articles and documents

Synthesis and biochemical evaluation of highly enantiomerically pure (R,R)- and (S,S)-alexidine

Alexidine is in everyday human use as oral disinfectant and contact lens disinfectant. It is used as a mixture of stereoisomers. Since all of alexidine's known biological targets are chiral, the biological activity of any of its chiral stereoisomers could be significantly higher than that of the mixture of stereoisomers. This makes a synthetic methodology for obtaining the individual enantiomers of the chiral diastereoisomer highly desirable. Here, we describe the first synthesis of both enantiomers of alexidine in high enantiomeric purity, and demonstrate their activity against the protein-protein interaction between the anti-apoptotic protein Bcl-xL and the pro-apoptotic protein Bak.

Discovery of Novel Inhibitors Targeting Human O-GlcNAcase: Docking-Based Virtual Screening, Biological Evaluation, Structural Modification, and Molecular Dynamics Simulation

β-N-Acetylhexosaminidases have emerged as promising targets for drug and pesticide discovery due to their critical physiological functions in various cellular processes. In particular, human O-GlcNAcase (hOGA) from the glycoside hydrolase family 84 (GH84) has gained significant attention. This enzyme was found to be linked to various diseases such as diabetes, cancer, and Alzheimer's disease (AD). In this study, to develop novel hOGA inhibitors with suitable pharmaceutical properties, virtual screening of the Drugbank database was performed using a docking-based approach targeting hOGA. Chlorhexidine (4, Ki = 4.0 μM) was identified as a potent hOGA inhibitor with excellent selectivity (Ki > 200 μM against human β-N-acetylhexosaminidase B) and subjected to structural modifications and SAR studies. Furthermore, molecular dynamics simulations as well as binding free energy and free energy decomposition calculations were carried out to investigate the basis for the efficiency of potent inhibitors against hOGA. This present work revealed the new application of the disinfectant chlorhexidine and provided useful information for the future design of hOGA inhibitors.

Oral disinfectants inhibit protein-protein interactions mediated by the anti-apoptotic protein Bcl-xL and induce apoptosis in human oral tumor cells

Chlorhexidine and alexidine have long been used as oral disinfectants by humans. Both compounds inhibit protein-protein interactions mediated by the anti-apoptotic protein Bcl-xL at physiologically relevant concentrations and induce apoptosis in a series of tumor cell lines derived from the tongue and pharynx (see picture). Inhibition of protein-protein interactions is a potential mode of action of drugs in current human use. Copyright