Probing Ethanol-Induced Phospholipid Phase Transitions by the Polarity Sensitive Fluorescence Probes Prodan and Patman

Hutterer, Rudi; Hof, Martin

doi:10.1524/zpch.2002.216.3.333

Cited by 16 publications

(17 citation statements)

References 40 publications

(50 reference statements)

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“…The DMPC liposome experiences a prephase transition (T P ) and a main-phase transition (T M ) with increasing temperature. 43 The prephase transition is related to the rearrangement of the polar head groups due to the increased hydration of the lipid layer at elevated temperatures (<T M ), 10 whereas the ordered nature of the acyl chains is completely destructed after the main-phase transition. The ordered structure is referred to as solid gel (SG) phase, and the disordered structure is mentioned as liquid crystal (LC) phase.…”

Section: E E a B Smentioning

confidence: 99%

“…A large number of reported probe molecules are push–pull type organic fluorophores, such as PRODAN (6-propionyl-2-dimethylaminonaphthalene), − LAURDAN (6-lauroyl-2-dimethylaminonaphthalene), , ANS (1-anilinonaphthalene-8-sulfonate), dansyl probe, , Nile red, , and so on. , Upon photoexcitation, these molecules experience an enhancement in the dipole moment and a subsequent dipolar relaxation in the excited state depending on the nature of the immediate environment. This particular characteristic makes these molecules highly susceptible toward the environment modulation inside the biological medium.…”

Section: Introductionmentioning

confidence: 99%

“…This particular characteristic makes these molecules highly susceptible toward the environment modulation inside the biological medium. Because of the high environment susceptibility nature, PRODAN (Figure A) and its derivatives are frequently used as a biological probe, specifically for the probing of lipid bilayer systems. − However, PRODAN absorbs in the ultraviolet region, and its emission in the aqueous medium produces a significant background noise. LAURDAN, which is basically a derivative of PRODAN, exhibits a very weak aggregate emission in the aqueous medium because of its insoluble nature in water. , However, as a membrane probe, it cannot sense the prephase transition temperature of a phospholipid bilayer system .…”

Section: Introductionmentioning

confidence: 99%

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Multiparametric Sensing of Membrane Bilayer Properties with a Highly Environment-Susceptible Fluorophore

2018

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Push-pull type fluorophores are often exploited as a biological probe because of their high environment-sensitivity nature. Herein, we report the potentiality of a push-pull fluorophore, 2-formyl-5-(4'- N, N-dimethylaminophenyl)thiophene, as a membrane probe. This molecule exhibits strong absorbance in the violet region (∼400 nm) and a high emission quantum yield (≤0.6). The emission is highly sensitive to the surrounding environment, and a high Stokes shift (>7000 cm) appears in strong polar solvents. The molecule is highly susceptible to the fluorescence quenching by protic solvents. The neutral probe efficiently senses aprotic environments such as lipid bilayer membranes through all six fluorescence parameters: emission maxima, intensity, and anisotropy as well as the corresponding time-dependent parameters. The small and flat shape, nonemissive nature in the aqueous medium along with the high susceptibility to all six fluorescence parameters of the molecule strongly suggests a promising fluorescence probe for biological medium.

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Section: E E a B Smentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Multiparametric Sensing of Membrane Bilayer Properties with a Highly Environment-Susceptible Fluorophore

2018

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“…We selected the uncharged fluorophore Prodan that is known to be highly sensitive to local polarity. 56 We incubated a Comfilcon A contact lens in a solution containing a low concentration of Prodan for 1 h as mentioned in Sec. 2.…”

Section: Fluorophore Binding To An Sihg Contact Lensmentioning

confidence: 99%

Glucose-sensitive silicone hydrogel contact lens toward tear glucose monitoring

2018

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Accurate and reliable monitoring of blood glucose is needed for the treatment of diabetes, which has many challenges, including lack of patient compliance. Measuring tear glucose is an alternative to traditional finger-stick tests used to track blood sugar levels, but glucose sensing using tears has yet to be achieved. We report a methodology for possible tear glucose monitoring using glucose-sensitive silicone hydrogel (SiHG) contact lenses, the primary type of lenses available in today's market. Initially, we assessed the interpenetrating polymer network, with nearly pure silicone and water regions, existing in the SiHGs using a polarity-sensitive probe Prodan. We then synthesized a glucose-sensitive fluorophore Quin-C18 with a hydrophobic side chain for localization of probe at the interfacial region. Using our glucose-sensing contact lens, we were able to measure varying concentrations of glucose in an in-vitro system. The Quin-C18 strongly bound to the lenses with insignificant leaching even after multiple rinses. The lenses displayed a similar response to glucose after three months of storage in water. This study demonstrates that it may be possible to develop a contact lens for continuous glucose monitoring in the near term, using our concept of fluorophore binding at the silicone-water interface.

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“…10 Numerous structural analogues of PRODAN, which substitute its naphthalene core with other conjugated systems while keeping the electron donor/acceptor flanking groups, have been synthesized and possess even more desirable photophysical properties. For example, synthesis of the amino acid Aladan 11 (also known as DANA 12 ), which bears the PRODAN side chain, has allowed for its introduction into peptides during solid phase peptide synthesis (SPPS) (via the corresponding Fmoc derivative) and into proteins by means of nonsense suppression.…”

Section: Introductionmentioning

confidence: 99%

PHOXI: A High Quantum Yield, Solvent-Sensitive Blue Fluorescent 5-Hydroxytryptophan Derivative Synthesized within Ten Minutes under Aqueous, Ambient Conditions

Grigoryan¹,

Eisenberg

Juszczak

2017

J. Phys. Chem. B

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Multiple tryptophan (Trp) proteins are not amenable to fluorescence study because individual residue emission is not resolvable. Biosynthetic incorporation of an indole analogue such as 5-hydroxyindole has not provided sufficient spectroscopic resolution because of low quantum yield and small emission shift. Here, 5-hydroxyindole is used as the starting framework for building a blue emitting fluorophore of high quantum yield, 2-phenyl-6H-oxazolo[4,5-e]indole (PHOXI). This is a three reagent reaction completed in 10 min under ambient conditions in borate buffer at pH 8. Reaction conditions have been optimized using 5-hydroxyindole. Derivatization is demonstrated on tryptophanyl 5-hydroxytryptophan (5-HTP) and a stable β-hairpin “zipper” peptide with four tryptophan residues, TrpZip2, where Trp 4 has been replaced with 5-HTP, W4 → 5-HTP. Reaction optimization yields a PHOXI fluorophore that is essentially free of byproducts. Reaction specificity is demonstrated by the lack of reaction with N-acetyl-cysteine and amyloid β-40, a peptide containing all amino acids except tryptophan, proline, and cysteine and lacking 5-HTP. Fluorescence study of PHOXI-derivatized 5-hydroxyindole in different solvents reveals the sensitivity of PHOXI to solvent polarity with a remarkable 87 nm red-shift in water relative to cyclohexane while maintaining high quantum yield. Thus, PHOXI joins the ranks of solvatochromic fluorophores such as PRODAN. Surprisingly, DFT calculations reveal coplanarity of the oxazolo/indole extended ring system and the phenyl substituent for both the HOMO and LUMO orbitals. Despite the crowded environment of three additional Trps in TrpZip2, CD spectroscopy shows that the TrpZip2 β-hairpin structure is partially retained upon PHOXI incorporation. In an environment of smaller residues, PHOXI incorporation can be less disruptive of protein secondary structure, especially at molecular interfaces and other environments where there is typically less steric hindrance.

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Probing Ethanol-Induced Phospholipid Phase Transitions by the Polarity Sensitive Fluorescence Probes Prodan and Patman

Cited by 16 publications

References 40 publications

Multiparametric Sensing of Membrane Bilayer Properties with a Highly Environment-Susceptible Fluorophore

Multiparametric Sensing of Membrane Bilayer Properties with a Highly Environment-Susceptible Fluorophore

Glucose-sensitive silicone hydrogel contact lens toward tear glucose monitoring

PHOXI: A High Quantum Yield, Solvent-Sensitive Blue Fluorescent 5-Hydroxytryptophan Derivative Synthesized within Ten Minutes under Aqueous, Ambient Conditions

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