UV Resonance Raman Finds Peptide Bond−Arg Side Chain Electronic Interactions

Sharma, Bhavya; Asher, Sanford A.

doi:10.1021/jp112174s

Cited by 7 publications

(10 citation statements)

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“…A positive broad peak around 195-200 nm along with a negative peak at 226-229 nm indicate the presence of a β-sheet like arrangement. The red-shifted β-sheet signal has been previously observed and it has been shown to π* transitions of the peptide bonds [39,40] and the carboxylic acid moieties in the peptide [41,42]. The absorption peak at 280 nm is attributed to the aromatic side chains of Trp, with a less intense π The light-absorption properties of the pentapeptide hydrogel were in recording its UV-Vis spectrum in aqueous medium (Figure 8A).…”

Section: Optical Properties Structural Conformation and Crystallinity...mentioning

confidence: 73%

“…The most characteristic absorption features of the pentapeptide were observed in the far-UV (<220 nm) and the near-UV regions (280 nm). In particular, the strong absorption peak observed below 220 nm is attributed to the π↔π* transitions of the peptide bonds [39,40] and the carboxylic acid moieties in the peptide [41,42]. The absorption peak at 280 nm is attributed to the aromatic side chains of Trp, with a less intense π↔π* transition identified as a shoulder at 292 nm.…”

Section: Optical Properties Structural Conformation and Crystallinity...mentioning

confidence: 99%

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NGIWY-Amide: A Bioinspired Ultrashort Self-Assembled Peptide Gelator for Local Drug Delivery Applications

et al. 2022

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Fibrillar structures derived from plant or animal origin have long been a source of inspiration for the design of new biomaterials. The Asn-Gly-Ile-Trp-Tyr-NH2 (NGIWY-amide) pentapeptide, isolated from the sea cucumber Apostichopus japonicus, which spontaneously self-assembles in water to form hydrogel, pertains to this category. In this study, we evaluated this ultra-short cosmetic bioinspired peptide as vector for local drug delivery applications. Combining nuclear magnetic resonance, circular dichroism, infrared spectroscopy, X-ray diffraction, and rheological studies, the synthesized pentapeptide formed a stiff hydrogel with a high β-sheet content. Molecular dynamic simulations aligned well with scanning electron and atomic-force microscopy studies, revealing a highly filamentous structure with the fibers adopting a helical-twisted morphology. Model dye localization within the supramolecular hydrogel provided insights on the preferential distribution of hydrophobic and hydrophilic compounds in the hydrogel network. That was further depicted in the diffusion kinetics of drugs differing in their aqueous solubility and molecular weight, namely, doxorubicin hydrochloride, curcumin, and octreotide acetate, highlighting its versatility as a delivery vector of both hydrophobic and hydrophilic compounds of different molecular weight. Along with the observed cytocompatibility of the hydrogel, the NGIWY-amide pentapeptide may offer new approaches for cell growth, drug delivery, and 3D bioprinting tissue-engineering applications.

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Section: Optical Properties Structural Conformation and Crystallinity...mentioning

confidence: 73%

Section: Optical Properties Structural Conformation and Crystallinity...mentioning

confidence: 99%

NGIWY-Amide: A Bioinspired Ultrashort Self-Assembled Peptide Gelator for Local Drug Delivery Applications

et al. 2022

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“…Recently, we studied the excitation profiles of arg and found that the overtone of the CN 3 out-of-plane vibration is enhanced as the excitation wavelength is tuned into resonance. 30 …”

Section: Resultsmentioning

confidence: 99%

UV Resonance Raman and DFT Studies of Arginine Side Chains in Peptides: Insights into Arginine Hydration

2013

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We examined the UV resonance Raman (UVRR) spectra of four models of the arg side chain, guanidinium (gdn), ethylguanidinium (EG), arginine (arg) and Ac-arg-OMe (AAO) in H2O and D2O, in order to identify spectral markers that report on the environment of the arg side chain. To elucidate the resonance Raman enhancement mechanism of the arg side chain, we used DFT to calculate the equilibrium geometries of the electronic ground state and the first excited state. We determined the vibrational mode frequencies of the ground state and the first derivative of the first electronic excited state potential energy with respect to each vibrational normal mode of the electronic ground state at the electronic ground state equilibrium geometry. The DFT calculations and the potential energy distributions reveal that, in addition to the gdn group C-N stretching vibrations, the C-N bond stretching vibration of the gdn group-methylene linkage is also strongly resonance enhanced in EG, arg and AAO. From the UVRR spectra, we find that the Raman cross section and frequency of the ~1170 cm−1 vibration of the arg side chain depends on its hydration state and can be used to determine the hydration state of the arg side chain in peptides and proteins. We examined the hydration of the arg side chain in two polyala peptides and found that in the α-helical conformation the arg side chain in the AEP peptide (sequence: A9RA3EA4RA2) is less hydrated than that in the AP peptide (sequence: A8RA4RA4RA2).

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“…3A). 25,26 The structure of the wild-type EGFR kinase domain has been previously determined in both active and inactive conformations. 27,28 The L858R mutation lies in the N-terminal portion of the activation loop.…”

Section: Raman and Ihc Analyses Of Egfr Status In Nsclc Patientsmentioning

confidence: 99%

Evaluation of Raman spectroscopy for diagnosing EGFR mutation status in lung adenocarcinoma

Wang

Zhang

Huang

et al. 2014

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Somatic mutations in the epidermal growth factor receptor (EGFR) gene were associated with sensitivity to small molecule tyrosine kinase inhibitors for patients with lung adenocarcinomas. In this research, EGFR mutation status was analyzed by DNA sequencing in 153 lung adenocarcinoma tissues. Of these, 75 samples carried EGFR mutations, including 29 with E19del mutation, 33 with L858R mutation, 7 with T790M mutation, and 6 with multiple mutations. Then, 30 samples including 10 with wild type (wt)-EGFR, 10 with L858R and 10 with E19del mutations were selected for Raman and immunohistochemistry (IHC) analyses. After removing the spectra from normal and non-mutated regions, 441 spectra were found appropriate for Raman analysis: 149 from wt-EGFR, 135 from L858R and 157 from E19del mutations. The Raman peaks at 675, 1107, 1127 and 1582 cm(-1) were significantly increased in wt-EGFR tissues which can be attributed to specific amino acids and DNA. The Raman peaks at 1085, 1175 and 1632 cm(-1) assigned to arginine were slightly increased in L858R tissues. The overall intensity of E19del tissues was weaker than others due to exon 19 deletion that removes residues 746-750 of the expressed protein. Principal component analysis (PCA) and support vector machine (SVM) were applied for final prediction. The PCA/SVM algorithm yielded an overall accuracy of 87.8% for diagnosing L858R or E19del from wt-EGFR tissues. Finally, RS provides a simple, rapid and low-cost procedure based upon the molecular signatures for predicting EGFR mutation status.

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UV Resonance Raman Finds Peptide Bond−Arg Side Chain Electronic Interactions

Cited by 7 publications

References 51 publications

NGIWY-Amide: A Bioinspired Ultrashort Self-Assembled Peptide Gelator for Local Drug Delivery Applications

NGIWY-Amide: A Bioinspired Ultrashort Self-Assembled Peptide Gelator for Local Drug Delivery Applications

UV Resonance Raman and DFT Studies of Arginine Side Chains in Peptides: Insights into Arginine Hydration

Evaluation of Raman spectroscopy for diagnosing EGFR mutation status in lung adenocarcinoma

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