Analysis of structural features of bis-quaternary ammonium antimicrobial agents 4,4′-(α,ω-Polymethylenedithio)bis (1-alkylpyridinium iodide)s using computational simulation

Ohkura, Kazuto; Sukeno, Akiko; Yamamoto, Keiko; Nagamune, Hideaki; Maeda, Takuya; Kourai, Hiroki

doi:10.1016/j.bmc.2003.08.027

Cited by 18 publications

(39 citation statements)

References 18 publications

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“…22) Human growth hormone (hGH) N-terminal peptide (e.g. hGH [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] :…”

Section: )unclassified

“…The hGH [6][7][8][9][10][11][12][13] , hGH [7][8][9][10][11][12][13] , and hGH [8][9][10][11][12][13] peptides, which were derived from hGH [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] , enhanced the insulin effect on adipocytes as well as hGH [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] .…”

Section: )mentioning

confidence: 99%

“…The peptides of hGH [6][7][8][9][10] , hGH 9-13 and hGH [10][11][12][13] did not enhance the insulin effect. Based on the crystallographic geometry of hGH and its receptor complex, the amino-terminal region of hGH heavy chain contacts the receptor protein.…”

Section: )mentioning

confidence: 99%

“…Based on the crystallographic geometry of hGH and its receptor complex, the amino-terminal region of hGH heavy chain contacts the receptor protein. 24) Figure 2A shows the three-dimensional structure of hGH [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] , which was determined by the global minimum (GM) search using CONFLEX (Fujitsu Inc., Japan). The 8th-arginyl residue formed an ionic bond to the 11th-aspartic residue, and this intramolecular interaction made a macrocyclic structure comprised of a tetrapeptide, R 8 -L (bold line).…”

Section: )mentioning

confidence: 99%

“…4DTBP-m,n), which have a rigid or a flexible molecular center, were discussed 8,9) ; 5) Cell lytic protein, such as cholesterol-dependent (e.g. storeptolysin O) or -independent cytolysins (e.g.…”

Section: Introductionmentioning

confidence: 99%

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Exploring Unique Structures: Flexibility is a Significant Factor in Biological Activity

Ohkura

2007

Biological & Pharmaceutical Bulletin

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The effect of molecular flexibility on biological activity was described for soft (e.g. hGH peptides) and hard molecules (e.g. biscoclaurine-type alkaloids). These molecules had a macrocyclic structure during molecular mechanics analysis, and the minimum essential unit, which affects insulin-involved fatty acid synthesis, was observed. The flexibility of the molecular center is concerning with biological activity through the diversification of structural feature, and compared with two types of molecules which have a rigid (haloacetylcarbamoyl-2-nitroimidazole analogs: chiral-TXs) or flexible (bis-quaternary ammonium compounds: bis-QACs) molecular center. Center flexibility reflected the conformation occurrence in TXs and bis-QACs. A parameter (solvation-free energy: dGW), which reflects structural hydrophobicity, was shown, and applied to the molecular design of brefeldin A analog. This hydrophobic index was very useful, and was used for conformational analysis of chiralTXs and bis-QACs. In molecular dynamics analysis of cholesterol-dependent cytolysin (e.g. storeptolysin O) and -independent cytolysin (e.g. intermedilysin), whole molecules moved like a bow and different conformations were shown in every moment. In such situations, the membrane-associated 11mer region in these cytolysins were flexible and could always interact with extramolecular factors (e.g. membrane constitution).

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“…22) Human growth hormone (hGH) N-terminal peptide (e.g. hGH [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] :…”

Section: )unclassified

Section: )mentioning

confidence: 99%

Section: )mentioning

confidence: 99%

Section: )mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Exploring Unique Structures: Flexibility is a Significant Factor in Biological Activity

Ohkura

2007

Biological & Pharmaceutical Bulletin

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Antibacterial activity of novel insoluble bead‐shaped polymer‐supported multiquaternary ammonium salts

Murugan

Gopinath

Shanmugayya

et al. 2010

J of Applied Polymer Sci

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This study describes the effect of antibacterial activity of newly reported five different novel insoluble bead-shaped polymer-supported multiquaternary ammonium salts (PM quats) viz., bis-quat, tris-quat (2 Nos.), tetrakis-quat, hexakis-quat containing two, three, four, and six quaternary ammonium groups, respectively. The presence of number of quaternary ammonium groups in each salt was established already through Fourier-transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, and chloride ion analyzes. The antibacterial activities of these five different PM quats against three different bacteria viz., Staphylococcus aureus, Klebsiella pneumoniae, and Pseudomonas aeruginosa were investigated by serial dilution and spread plate method and compared the same with a monoquat containing single quaternary ammonium group. The extent of antibacterial activity has been measured in terms of colony forming units (CFU) at different time intervals. The observed results show that all the PM quats exhibited excellent-antibacterial activity against each bacterium. On the basis of the CFU values, the antibacterial activity was found to increase from bis-quat to hexakis-quat, which reveals that the activity of PM quats increases with increase in the number of quaternary ammonium groups. The mechanism of interaction of quats with bacterial cytoplasmic membrane has been explained as an adsorption-like phenomenon. The reusability of highly active hexakis-quat against Staphylococcus aureus was studied and the activity was found to reduce after first cycle.

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Synthesis and Microbiological Properties of Novel Bis‐Quaternary Ammonium Compounds Based on Biphenyl Spacer

et al. 2019

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Novel gemini (tail‐head‐spacer‐head‐tail) bis‐quaternary ammonium compounds (bis‐QACs) with a biphenyl spacer between two pyridinium heads were synthesized and compared with commonly used antiseptics such as benzalkonium chloride (BAC) and chlorhexidine digluconate (CHG). The series of compounds showed high inhibitory activity against five bacterial strains and two fungi. The compounds, which contain C8H17‐C10H21 aliphatic tails best within the series. A counterion change does not affect MIC in general. Cytotoxicity on human embryonic kidney cells and haemolysis were also investigated. For bis‐QACs cytotoxic effect was lower than for 3,3′‐[1,4‐phenylenebis(oxy)]bis(1‐dodecylpyridinium) dibromide (3PHBO‐12), that is their closest structural analogue, and for BAC.

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Analysis of structural features of bis-quaternary ammonium antimicrobial agents 4,4′-(α,ω-Polymethylenedithio)bis (1-alkylpyridinium iodide)s using computational simulation

Cited by 18 publications

References 18 publications

Exploring Unique Structures: Flexibility is a Significant Factor in Biological Activity

Exploring Unique Structures: Flexibility is a Significant Factor in Biological Activity

Antibacterial activity of novel insoluble bead‐shaped polymer‐supported multiquaternary ammonium salts

Synthesis and Microbiological Properties of Novel Bis‐Quaternary Ammonium Compounds Based on Biphenyl Spacer

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