Structural, spectroscopic and theoretical studies on dixanthogens: (ROC(S)S)2, with R = n-propyl and isopropyl

Juncal, Luciana C.; Tobon, Y.; Piro, Oscar E.; Védova, Carlos O. Della; Romano, Rosana M.

doi:10.1039/c4nj00708e

Cited by 14 publications

(8 citation statements)

References 32 publications

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“…UV spectra obtained for samples at the same concentration confirmed the occurrence of dithiocarbonate groups at the end of the polymer chains (Supplementary Figure SI8). The absorption band at 280 nm related to the ππ* transition of the OC(S)S moiety 28,29 was present in the UV spectra of all samples. As expected, the intensity of this band was reduced with increased chain length.…”

Section: Synthesis and Characterization Of Chol-pnipaam-x Polymersmentioning

confidence: 92%

Evaluation of Cytotoxic Effect of Cholesterol End-Capped Poly(N-Isopropylacrylamide)s on Selected Normal and Neoplastic Cells

Misiak¹,

Niemirowicz-Laskowska²,

Markiewicz³

et al. 2020

IJN

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Purpose: Efficient intracellular delivery of a therapeutic compound is an important feature of smart drug delivery systems (SDDS). Modification of a carrier structure with a cellpenetrating ligand, ie, cholesterol moiety, is a strategy to improve cellular uptake. Cholesterol end-capped poly(N-isopropylacrylamide)s offer a promising foundation for the design of efficient thermoresponsive drug delivery systems. Methods: A series of cholesterol end-capped poly(N-isopropylacrylamide)s (PNIPAAm) with number-average molar masses ranging from 3200 to 11000 g•mol-1 were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization from original xanthate-functionalized cholesterol and self-assembled into micelles. The physicochemical characteristics and cytotoxicity of cholesterol end-capped poly(N-isopropylacrylamide)s have been thoroughly investigated. Results: Phase transition temperature dependence on the molecular weight and hydrophilic/ hydrophobic ratio in the polymers were observed in water. Biological test results showed that the obtained materials, both in disordered and micellar form, are non-hemolytic, highly compatible with fibroblasts, and toxic to glioblastoma cells. It was found that the polymer termini dictates the mode of action of the system. Conclusion: The cholesteryl moiety acts as a cell-penetrating agent, which enables disruption of the plasma membrane and in effect leads to the restriction of the tumor growth. Cholesterol end-capped PNIPAAm showing in vitro anticancer efficacy can be developed not only as drug carriers but also as components of combined/synergistic therapy.

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Section: Synthesis and Characterization Of Chol-pnipaam-x Polymersmentioning

confidence: 92%

Evaluation of Cytotoxic Effect of Cholesterol End-Capped Poly(N-Isopropylacrylamide)s on Selected Normal and Neoplastic Cells

Misiak¹,

Niemirowicz-Laskowska²,

Markiewicz³

et al. 2020

IJN

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“…Table 3 lists the wavenumbers observed in these spectra and also in the IR of an Ar-isolated matrix. The assignment of the bands has been performed with the aid of the predictions of theoretical calculations and also by the comparison with related molecules [14,[16][17][18][19][20]. Although the calculations were performed for the isolated molecule, and therefore ignoring the intermolecular interactions present in the liquid phase, the agreement between the experimental and theoretical spectra is very good.…”

Section: Theoretical Calculationsmentioning

confidence: 96%

Conformational and spectroscopic study of xanthogen ethyl formates, ROC(S)SC(O)OCH2CH3. Isolation of CH3CH2OC(O)SH

Juncal

Cozzarín

Romano

2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…The mass‐spectrographs along with the details on identifying these species are provided in Figures S2–S8 (Supporting Information). [ 43 ] The EICs show that DIXPS is composed predominantly of xanthogen polysulfides with orders ranging from 2 (disulfide) to 8 (octasulfide). Trace amounts of xanthogen decasulfide (≈1.4%) are also present as shown in Figure S9 (Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Xanthogen Polysulfides as a New Class of Electrode Material for Rechargeable Batteries

Bhargav

Manthiram

2020

Advanced Energy Materials

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electrochemical reversibility. In addition to their favorable redox behavior, these compounds are also naturally abundant, environmentally friendly, inexpensive, and easy to process into battery electrodes. [12] While sulfur offers a high energy density exceeding 2500 W h kg −1 , it is beleaguered by three major issues. First, the electrical conductivity of sulfur is extremely low, necessitating the addition of a large amount of conductive hosts (e.g., carbon) in the battery electrode. Second, the difference in density between sulfur and its discharge product, Li 2 S, is quite large. This results in a volume change of nearly 80% during cycling, thus requiring a cathode structure to accommodate the large volume fluctuation and the resulting stresses generated. Third, the lithium polysulfides formed during cycling are electrolyte-soluble and thus shuttle between the electrodes. This "shuttle effect" results in a loss of active material, poor Coulombic efficiency, and short cycle life. [8] On the other hand, organic compounds (e.g., carbonyls, organosulfides, imines, and nitriles) present three distinct advantages. First, the functional groups in the organic moieties can alter the physical properties of these materials including their electrical conductivity. [9] Second, the difference in density between the delithiated and the lithiated forms of these compounds is low, resulting in a smaller volume change and stress in the cathode. [13] Finally, the bulkiness and polarity of the organic functional groups can be used to alter their solubility in the electrolyte, thus minimizing parasitic shuttle effects. [12,14] Organosulfur compounds combine the multi-electron, highenergy-density characteristics of sulfur with the distinct advantages of organic compounds. Specifically, the ability to tune the physical and chemical properties of organosulfur materials with various functional groups allows for optimization of their conductivity, solubility, and density. [9,15-17] Recognizing these advantages, various organosulfur compounds have been reported since the late 1980s. [18,19] Early reports of such materials focused on polymers that functioned according to the disulfide-thiolate redox behavior. [19,20] More recently, polymers containing multiple SS bonds that have been synthesized through inverse vulcanization, [21,22] incorporation of covalent frameworks, [22-25] and condensation reactions have been reported. [26-29] In addition to polymers, linear compounds, [15,30,31] cyclics, [32] hybrids, [33,34] and compounds with unique functional groups have also been reported. [35-37] Organosulfides are an emerging class of alternative sulfur-based cathode materials. This work explores a new member in this family of active materials, viz., xanthogen polysulfides. Diisopropyl xanthogen polysulfide (DIXPS) is used as a model compound in a lithium battery to understand the chemical changes and the unique electrochemical behavior of this class of materials by employing various materials characterization methodologies. As a cathode ma...

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Structural, spectroscopic and theoretical studies on dixanthogens: (ROC(S)S)₂, with R = n-propyl and isopropyl

Cited by 14 publications

References 32 publications

<p>Evaluation of Cytotoxic Effect of Cholesterol End-Capped Poly(<em>N</em>-Isopropylacrylamide)s on Selected Normal and Neoplastic Cells</p>

<p>Evaluation of Cytotoxic Effect of Cholesterol End-Capped Poly(<em>N</em>-Isopropylacrylamide)s on Selected Normal and Neoplastic Cells</p>

Conformational and spectroscopic study of xanthogen ethyl formates, ROC(S)SC(O)OCH2CH3. Isolation of CH3CH2OC(O)SH

Xanthogen Polysulfides as a New Class of Electrode Material for Rechargeable Batteries

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