Dependence of hydrophobicity of apolar molecules on their molecular volume

Leo, Albert J.; Hansch, Corwin; Jow, P. Y. C.

doi:10.1021/jm00227a007

Cited by 93 publications

(28 citation statements)

References 1 publication

(1 reference statement)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The lipophilicity of a physicochemical characteristic of a compound depends on other characteristics as well, such as polarity, solubility and density (Leo et al 1976). For information on the lipophilic character of carvacrol, Ultee et al (2002) evaluated its partitioning behaviour in a mixture of octanol and water.…”

Section: Neoformans Lm-22mentioning

confidence: 99%

Investigation of the antifungal activity of carvacrol against strains ofCryptococcus neoformans

Nóbrega¹,

Teixeira

Oliveira

et al. 2016

Pharmaceutical Biology

View full text Add to dashboard Cite

Background: Cryptococcus neoformans is the etiologic agent of opportunistic systemic fungal infection cryptococcosis, which affects individuals with compromised immune systems. Thus, natural products research has become important, since monoterpenes such as carvacrol, a promising molecule in the search antifungal agents, have shown significant biological activity. Objective: The study aimed to investigate the antifungal activity and mode of action of carvacrol against strains of C. neoformans. Methods: The minimum inhibitory concentration (MIC) was determined by microdilution method. Minimum fungicidal concentration (MFC) was performed by seeding technique on solid media. Studying the mode of action was performed using broth microdilution. Results: The MIC ranged from 25 to 81 lg/mL and the MFC ranged from 25 to 102 lg/mL. Carvacrol bonded to exogenous ergosterol and cholesterol. Discussion: The results suggest that carvacrol has antifungal activity against C. neoformans and its mode of action is related to fungal membrane instability. Conclusions: The phytoconstituent carvacrol may eventually become a drug; however, further studies are needed to elucidate its mechanism.

show abstract

Section: Neoformans Lm-22mentioning

confidence: 99%

Investigation of the antifungal activity of carvacrol against strains ofCryptococcus neoformans

Nóbrega¹,

Teixeira

Oliveira

et al. 2016

Pharmaceutical Biology

View full text Add to dashboard Cite

show abstract

“…According to the relation ∆G ) ∆H -T∆S, some authors ascribe the hydrophobic effect to an unfavorable enthalpycontrolled process related to the formation of a cavity to host the solute molecule, [9][10][11]14,[26][27][28][29][30][31][32][33][34][35][36][37][38][39] whereas others attribute it to an essentially entropy-governed mechanism emphasizing the ordering or structuring of the water molecules around the apolar solute. Both kinds of explanation generally start from the fact that to dissolve a substance, a cavity of suitable size must first be created within the solvent to accommodate the solute, and this particular process perturbs the three-dimensional net of H-bonds of associated solvents, such as water.…”

Section: Introductionmentioning

confidence: 99%

The Hydrophobic Effect. 1. A Consequence of the Mobile Order in H-Bonded Liquids

Ruelle

Kesselring

1998

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

The hydrophobic effect has an entropic nature that cannot be explained by classical multicomponent treatments that do not explicitly take into account both the mobility and the nonergodicity of the H-bonds in amphiphilic liquids. The nonergodic thermodynamics of mobile order in H-bonded liquids based on time fractions rather than on concentrations provides a novel qualitative and quantitative explanation for the molecular origin of the hydrophobic effect. Chiefly, this effect corresponds to the loss of the mobile order entropy of associated molecules by dilution with foreign substances. Not being a unique property of water, the propensity of an amphiphilic solvent to induce a solvophobic effect increases primarily as its structuration factor increases, and secondarity as the solute/solvent molar volume ratio increases. On this basis, it can be expected that in the absence of strong solute-solvent specific interactions, the solubility of nonelectrolytes will generally decrease in the following order: butanol > propanol > ethanol > methanol > propylene glycol > ethylene glycol > formamide > water.

show abstract

“…A 0 is slightly higher for the methyl and chloro derivatives than for PTCA, whereas it is smaller for the fluorosubstituted compound. Taking into account CPK volume values (19), one should expect that A 0 values for PTCA and its substituted derivatives would increase in the following order: -H, -F, -CH 3 , -Cl. Although there is no significant difference in geometrical areas for fluorocarbon amphiphiles in comparison to hydrocarbon amphiphiles bearing the same head group (20), the former are known to occupy a larger area on the water surface than their hydrocarbon analogues (21,22), possibly due to electrostatic repulsion forces between film-forming molecules, caused by the presence of strong electronegative fluorine substituents.…”

Section: Discussionmentioning

confidence: 99%