The diagnosis of invasive fungal infections from radiographic imaging is non-specific and problematic. As a first step toward increasing specificity, we describe the development of a broad-spectrum fungal-specific targeting molecule, which when modified with a fluorescent label fully retains its targeting properties, and provides a basis for future imaging applications.

A variety of contemporary analytical platforms, utilized in technical and biological applications, take advantage of labeling the objects of interest with fluorescent tracers—compounds that can be easily and sensitively detected. Here we describe the synthesis of new fluorescent quinoline and quinolone compounds, whose light emission can be conveniently tuned by simple structural modifications. Some of these compounds can be used as sensitizers for lanthanide emission in design of highly sensitive luminescent probes. In addition, we also describe simple efficient derivatization reactions that allow introduction of amine- or click-reactive cross-linking groups into the fluorophores. The reactivity of synthesized compounds was confirmed in reactions with low molecular weight nucleophiles, or alkynes, as well as with click-reactive DNA-oligonucleotide containing synthetically introduced alkyne groups. These reactive derivatives can be used for covalent attachment of the fluorophores to various biomolecules of interest including nucleic acids, proteins, living cells and small cellular metabolites. Obtained compounds are characterized using NMR, steady-state fluorescence spectroscopy as well as UV absorption spectroscopy.Electronic supplementary materialThe online version of this article (doi:10.1007/s10895-012-1039-z) contains supplementary material, which is available to authorized users.

Cleavage of disulfide bonds is a common method used in linking peptides to proteins in biochemical reactions. The structures, internal rotor potentials, bond energies, and thermochemical properties (Δ f H , S , and Cp(T)) of the S-S bridge molecules CH 3 SSOH and CH 3 SS(=O)H and the radicals CH 3 SS•=O and C•H 2 SSOH that correspond to H-atom loss are determined by computational chemistry. Structure and thermochemical parameters (S and Cp(T)) are determined using density functional Becke, three-parameter, Lee-Yang-Parr (B3LYP)/6-31++G (d, p), B3LYP/6-311++G (3df, 2p). The enthalpies of formation for stable species are calculated using the total energies at B3LYP/6-31++G (d, p), B3LYP/6-311++G (3df, 2p), and the higher level composite CBS-QB3 levels with work reactions that are close to isodesmic in most cases. The enthalpies of formation for CH 3 SSOH, CH 3 SS(=O)H are À38.3 and À16.6 kcal mol À1 , respectively, where the difference is in enthalpy RSO-H versus RS(=O)-H bonding. The C-H bond energy of CH 3 SSOH is 99.2 kcal mol À1 , and the O-H bond energy is weaker at 76.9 kcal mol À1 . Cleavage of the weak O-H bond in CH 3 SSOH results in an electron rearrangement upon loss of the CH 3 SSO-H hydrogen atom; the radical rearranges to form the more stable CH 3 SS· = O radical structure. Cleavage of the C-H bond in CH 3 SS(=O)H results in an unstable [CH 2 SS(=O)H]* intermediate, which decomposes exothermically to lower energy CH 2 = S + HSO. The CH 3 SS(=O)-H bond energy is quite weak at 54.8 kcal mol À1 with the H-C bond estimated at between 91 and 98 kcal mol À1 . Disulfide bond energies for CH 3 S-SOH and CH3S-S(=O)H are low: 67.1 and 39.2 kcal mol À1 . CH 3 S À SOH ! CH 3 S þ S À OH ΔH rxn ¼ disulfide bond energy ¼ 67:1 kcal mol À1 CH 3 S À S ¼ O ð ÞH ! CH 3 S þ HS À O ΔH rxn ¼ disulfide bond energy ¼ 39 kcal mol À1 THERMOCHEMISTRY PARAMETERS DISULFIDE -OXYGEN

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Objective:The human axilla is colonized by a wide array of microorganisms that contribute to the generation of body odour. Traditional antiperspirant/deodorant products are used to reduce perspiration in the axillary region and to treat or prevent the growth of bacteria in this region, thereby reducing or eliminating body odour. However, they may also compromise the axillary microbiome balance.The personal care industry has been seeking new ingredients, such as prebiotics or probiotics, to maintain a healthy balance of the skin microbiome by inhibiting odour-causing bacteria, whilst maintaining and promoting the growth of good bacteria. The aim of this study was to investigate the prebiotic effect of a skin-care ingredient, 2-butyloctanol, on the human axillary microbiome.Methods: An in vitro growth inhibition/promotion assay was performed to test whether 2-butyloctanol inhibited or promoted skin bacterial growth. The impact of 2-butyloctanol on the axillary microbiome was also investigated in a human clinical study using 16S rRNA gene sequencing. Results:In-vitro testing showed that 2-butyloctanol significantly inhibited the growth of corynebacteria at concentrations of 0.64%, 2.56% and 5.12%, whilst the growth of Staphylococcus epidermidis was maintained at the same concentrations. The impact of 2-butyloctanol on the axillary microbiome was also validated in a human clinical study. A deodorant roll-on product containing 3% of 2-butyloctanol significantly reduced the relative abundance of corynebacteria, whilst increasing the relative abundance of Staphylococcus and the ratio of Staphylococcus to corynebacteria after four weeks of application, whilst the placebo showed no significant change. Conclusion:For the first time, it was demonstrated that 2-butyloctanol had a potential prebiotic effect on the human underarm microbiome in inhibiting odour-causing Corynebacterium, whilst maintaining and promoting skin-friendly Staphylococcus in both in-vitro and in-vivo studies. Therefore, 2-butyloctanol could be used as a potential prebiotic ingredient in personal care products for underarm microbiome protection.