Folic acid and sodium folate salts: Thermal behavior and spectroscopic (IR, Raman, and solid-state 13C NMR) characterization

Magri, Vagner R.; Rocha, Marco; Matos, Caroline Silva de; Petersen, Philippe Alexandre Divina; Leroux, F.; Petrilli, Helena Maria; Constantino, Vera Regina Leopoldo

doi:10.1016/j.saa.2022.120981

Cited by 11 publications

(6 citation statements)

References 73 publications

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“…In the case of the ball milling formulations FA:ARG-BM, a complete amorphization was achieved after eight ball milling cycles of 15 min, while the formulation FA:LYS-BM was only amorphized after 14 cycles of 15 min but showed a broad peak at 27 • , as observed in the systems prepared by solvent evaporation (ASE). The presence of this diffraction peak was previously observed, and it is interpreted, according to Magri et al, as a result of the self-assembly of dianionic folate ions through hydrogen bonds and π−π stacking [55].…”

Section: Structural Characterization By X-ray Diffraction (Xrd)supporting

confidence: 57%

“…Furthermore, some bands present in the spectra of folic acid are absent in those of folate salts, indicating deprotonation of the glutamic acid moiety and formation of an enolate group. This absence of bands and the displacement observed in others are key evidence for the formation of folate salts [55]. Thus, this spectral region was selected for analysis.…”

Section: Intermolecular Interactions Resultsmentioning

confidence: 97%

“…In both formulations, under the two types of preparation, the signals' broadening is evident, reflecting the amorphization of the samples. Following the study by Magri et al [55], the movement or absence of carboxyl group signals was analyzed, which could be interpreted as deprotonation and possible formation of a salt. When comparing the signals of 1686 cm −1 of the carboxyl of pure folic acid with the FA:AA formulations, we can observe that there is a decrease in signal intensity, and, in some cases, these signals are absent.…”

Section: Intermolecular Interactions Resultsmentioning

confidence: 99%

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Effect of Basic Amino Acids on Folic Acid Solubility

Pérez-Carreón,

Martínez,

Videa

et al. 2023

Pharmaceutics

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To prevent neural tube defects and other cardiovascular diseases in newborns, folic acid (FA) is recommended in pregnant women. A daily dose of 600 µg FA consumption is widely prescribed for women during pregnancy and 400 µg for women with childbearing potential. FA is a class IV compound according to the Biopharmaceutics Classification System (BCS) due to its low permeability (1.7 × 10−6 cm/s) and low solubility (1.6 mg/L); therefore, it must be administered via a formulation that enhances its solubility. Studies reported in the literature have proved that co-amorphization and salt formation of a poorly soluble drug with amino acids (AA) can significantly increase its solubility. Although arginine has been used with FA as a supplement, there is no information on the effect of basic AA (arginine and lysine) on the physical and chemical properties of FA-AA binary formulations. The present study implemented a conductimetric titration methodology to find the effective molar ratio to maximize FA solubility. The results showed that a 1:2.5 FA:AA molar ratio maximized solubility for arginine and lysine. Binary formulations were prepared using different methods, which led to an amorphous system confirmed by the presence of a glass transition, broad FTIR bands, and the absence of an X-ray diffraction pattern. Results of FA:AA (1:2.5) solubility increased in the range of 5500–6000 times compared with pure FA. In addition to solubility enhancement, the binary systems presented morphological properties that depend on the preparation method and whose consideration could be strategic for scaling purposes.

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Section: Structural Characterization By X-ray Diffraction (Xrd)supporting

confidence: 57%

Section: Intermolecular Interactions Resultsmentioning

confidence: 97%

Section: Intermolecular Interactions Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Effect of Basic Amino Acids on Folic Acid Solubility

Pérez-Carreón,

Martínez,

Videa

et al. 2023

Pharmaceutics

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“…The chemical structures of LS and DAL are confirmed by solid-state 13 C NMR, as depicted in Figure a. In the original LS, three peaks are observed at 139.33–119.08 ppm (I1), 73.73–53.42 ppm (I2), and 24.42–16.05 ppm (I3), corresponding to the aromatic ring in LS, the submethoxyl group or methoxy end groups (−CH 2 O–/–OCH 3 ) in the molecular chain, and the methylene (−CH 2 −) carbon in the main chain. , Notably, for DAL, new signals are observed in the range of 139.48–117.91 ppm (I4), 76.37–52.01 ppm (I5), and 26.76–15.76 ppm (I6), indicating an increase in the aromatic ring content in LS after DOPO grafting, resulting in the increase of I4. The methoxy group is replaced into a cross-linked P–C Ar bond, reducing the content of the methoxy group in the main chain, as reflected in the change of I5, which is consistent with the sharp peak of P–C Ar bond(1590 cm –1 ) in the infrared region.…”

Section: Resultsmentioning

confidence: 98%

Synthesis and Characterization of Sodium Lignosulfonate-Based Phosphorus-Containing Intermediates and Its Composite Si–P–C Silicone-Acrylic Emulsion Coating for Flame-Retardant Plywood

Lai,

Wang,

et al. 2024

Langmuir

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Through the substitution reaction between 9,10dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and sodium lignosulfonate (LS), a novel phosphorus-containing sodium lignosulfonate (DAL) was successfully synthesized via the solvothermal method and used as a multifunctional flame retardant to prepare a novel silicone-acrylic emulsion (SAE) composite Si− P−C coating. The structure of DAL was determined by X-ray diffraction (XRD), attenuated total reflection infrared spectroscopy (ATR-FTIR), X-ray photoelectron spectroscopy (XPS), and nuclear magnetic resonance (solid-state 13 C NMR and 31 P NMR). The results demonstrated that incorporating an appropriate dosage of DAL (0.9 g, 1.5 wt %) into SAE-based composite coatings enhances flame retardancy and reduces heat release and smoke production during burning. The peak heat release rate (p-HRR) decreases from 236.7 to 120.3 kW•m −2 , total smoke production (TSP) decreases by 71.1%, and the flame-retardant index increases from 1.00 to 4.58. Meanwhile, the coating is transformed into a dense and nonflammable vitreous polyphosphate barrier layer during the firing process to prevent heat or mass transfer. Furthermore, the pyrolysis kinetics identify that the 3D Z−L−T model governs the coatings' pyrolysis, and the appropriate DAL makes the pyrolysis E α climb from 300.98 to 331.30 kJ•mol −1 at 358−439 °C. Hence, this study presents a new synthesis method of multifunctional flame retardant DAL, studies the excellent properties and cross-linking mechanism of DAL-doped SAEcomposite Si−P−C coatings, and explores a halogen-free, low-carbon, and clean eco-technology strategy.

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“…The experimental signal in this region is very broad and bears several shoulders on the higher and lower wavenumber side. Taking into account that the band spreads from 1730-1540 cm −1 contributions from C=O carboxylic (acids, amides, or ketones), OH bending of water and also C=C stretching of aromatic rings or N-bearing aromatic heterocycles (residual pteroic acid moiety of folic acid), antisymmetric stretching of guanidyl groups coupled to NH bending and NH 2 scissoring may account for the region above 1590 cm −1 [79]. The indicated maximum may be assigned to the superimposition of water OH bending, amide I, and typical C-C stretching vibrations of heteroaromatic moieties (pteroic acid, pyridines, or pyrimidines).…”

Section: Ftir Spectrummentioning

confidence: 99%

Highly Specific Silver Ion Detection by Fluorescent Carbon Quantum Dots

et al. 2022

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Nitrogen-doped carbon quantum dots are easily obtainable nanomaterials endowed with remarkable fluorescence properties for the detection of contaminations by heavy metals. In this report, we show that nanometric particles with high specificity for silver cations can be prepared by hydrothermal synthesis starting from citric and folic acid solutions. Solutions of these N-CQDs give a strong fluorescence emission in the violet region (385 nm) when excited at 330 nm, which can be quenched selectively by silver (I) cations at sub-nanomolar concentrations, while other cations do not give any effect. This remarkable feature was tentatively correlated with the stronger interactions between silver ion and small portions of the nanomaterial surface by comparing Ag+ and the isoelectronic Cd2+.

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Folic acid and sodium folate salts: Thermal behavior and spectroscopic (IR, Raman, and solid-state 13C NMR) characterization

Cited by 11 publications

References 73 publications

Effect of Basic Amino Acids on Folic Acid Solubility

Effect of Basic Amino Acids on Folic Acid Solubility

Synthesis and Characterization of Sodium Lignosulfonate-Based Phosphorus-Containing Intermediates and Its Composite Si–P–C Silicone-Acrylic Emulsion Coating for Flame-Retardant Plywood

Highly Specific Silver Ion Detection by Fluorescent Carbon Quantum Dots

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