Chemistry and biology of N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)-labeled lipids: fluorescent probes of biological and model membranes

Chattopadhyay, Amitabha

doi:10.1016/0009-3084(90)90128-e

Cited by 317 publications

(229 citation statements)

References 221 publications

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“…This is expected, because the longer the chain, the stronger is its anchoring effect in the bilayer for corresponding positions along the former. In particular, the shorter chained derivatives NBD-diC 4 PE and NBD-diC 6 PE can only penetrate the bilayer shallowly (as visually evidenced in Fig. S3B and S3C, ESI †), and hence their ÀS CD values are the lowest among the series.…”

Section: Hydrogen Bondingmentioning

confidence: 95%

Behaviour of NBD-head group labelled phosphatidylethanolamines in POPC bilayers: a molecular dynamics study

Filipe

Santos

Ramalho

et al. 2015

Phys. Chem. Chem. Phys.

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A complete homologous series of fluorescent phosphatidylethanolamines (diC n PE), labelled at the head group with a 7-nitrobenz-2-oxa-1,3-diazo-4-yl(NBD) fluorophore and inserted in 1-palmitoyl, 2-oleoyl-snglycero-3-phosphocholine (POPC) bilayers, was studied using atomistic molecular dynamics simulations. The longer-chained derivatives of NBD-diC n PE, with n = 14, 16, and 18, are commercially available, and widely used as fluorescent membrane probes. Properties such as location of atomic groups and acyl chain order parameters of both POPC and NBD-diC n PE, fluorophore orientation and hydrogen bonding, membrane electrostatic potential and lateral diffusion were calculated for all derivatives in the series. Most of these probes induce local disordering of POPC acyl chains, which is on the whole counterbalanced by ordering resulting from binding of sodium ions to lipid carbonyl/glycerol oxygen atoms. An exception is found for NBD-diC 16 PE, which displays optimal matching with POPC acyl chain length and induces a slight local ordering of phospholipid acyl chains. Compared to previously studied fatty amines, acyl chain-labelled phosphatidylcholines, and sterols bearing the same fluorescent tag, the chromophore in NBD-diC n PE locates in a similar region of the membrane (near the glycerol backbone/carbonyl region) but adopts a different orientation (with the NO 2 group facing the interior of the bilayer). This modification leads to an inverted orientation of the P-N axis in the labelled lipid, which affects the interface properties, such as the membrane electrostatic potential and hydrogen bonding to lipid head group atoms. The implications of this study for the interpretation of the photophysical properties of NBD-diC n PE (complex fluorescence emission kinetics, differences with other NBD lipid probes) are discussed.

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Section: Hydrogen Bondingmentioning

confidence: 95%

Behaviour of NBD-head group labelled phosphatidylethanolamines in POPC bilayers: a molecular dynamics study

Filipe

Santos

Ramalho

et al. 2015

Phys. Chem. Chem. Phys.

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“…The NBD group is an extensively used fluorophore in biophysical, biochemical, and cell biological studies. NBD-labeled lipids are extensively used as fluorescent analogues of native lipids in biological and model membranes to study a variety of processes (for a review on NBD-labeled lipids, see Chattopadhyay, 1990). The NBD moiety possesses some of the most desirable properties for serving as an excellent probe for both spectroscopic and microscopic applications.…”

Section: The Wavelength-selective Fluorescence Approachmentioning

confidence: 99%

Exploring membrane organization and dynamics by the wavelength-selective fluorescence approach

Chattopadhyay

2003

Chemistry and Physics of Lipids

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144

151

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“…186 In this way, various NBD-labeled lipids and proteins have been generated and these have proved to be useful for monitoring structure and dynamics of proteins, peptides, and membranes. NBD-labeled lipids are extensively used as fluorescent analogues of native lipids in biological and model membranes to study a variety of processes.…”

Section: Extrinsic Fluorophoresmentioning

confidence: 99%

Novel Insights Into Protein Structure and Dynamics Utilizing the Red Edge Excitation Shift Approach

Raghuraman

Kelkar

Chattopadhyay

Reviews in Fluorescence 2005

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A shift in the wavelength of maximum fluorescence emission toward higher wavelengths, caused by a corresponding shift in the excitation wavelength toward the red edge of the absorption band, is termed the red edge excitation shift (REES). This effect is mostly observed with polar fluorophores in motionally restricted media such as viscous solutions or condensed phases where the dipolar relaxation time for the solvent shell around a fluorophore is comparable to or longer than its fluorescence lifetime. REES arises from slow rates of solvent relaxation (reorientation) around an excited state fluorophore which depends on the motional restriction imposed on the solvent molecules in the immediate vicinity of the fluorophore. Utilizing this approach, it becomes possible to probe the mobility parameters of the environment itself (which is represented by the relaxing solvent molecules) using the fluorophore merely as a reporter group. Further, since the ubiquitous solvent for biological systems is water, the information obtained in such cases will come from the otherwise 'optically silent' water molecules. This makes REES extremely useful since hydration plays a crucial modulatory role in the formation and maintenance of organized molecular assemblies such as folded proteins in aqueous solutions and biological membranes. The application of REES as a powerful tool to monitor the organization and dynamics of a variety of soluble, cytoskeletal, and membrane-bound proteins is discussed.

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Chemistry and biology of N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)-labeled lipids: fluorescent probes of biological and model membranes

Cited by 317 publications

References 221 publications

Behaviour of NBD-head group labelled phosphatidylethanolamines in POPC bilayers: a molecular dynamics study

Behaviour of NBD-head group labelled phosphatidylethanolamines in POPC bilayers: a molecular dynamics study

Exploring membrane organization and dynamics by the wavelength-selective fluorescence approach

Novel Insights Into Protein Structure and Dynamics Utilizing the Red Edge Excitation Shift Approach

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