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Concept: Sulfoxide

167

Development of techniques to isolate, culture, and transplant human spermatogonial stem cells (SSCs) has the future potential to treat male infertility. To maximize the efficiency of these techniques, methods for SSC cryopreservation need to be developed to bank SSCs for extended periods of time. Although, it has been demonstrated that SSCs can reinitiate spermatogenesis after freezing, optimal cryopreservation protocols that maximize SSC proliferative capacity post-thaw have not been identified. The objective of this study was to develop an efficient cryopreservation technique for preservation of SSCs. To identify efficient cryopreservation methods for long-term preservation of SSCs, isolated testis cells enriched for SSCs were placed in medium containing dimethyl sulfoxide (DMSO) or DMSO and trehalose (50 mM, 100 mM, or 200 mM), and frozen in liquid nitrogen for 1 week, 1 month, or 3 months. Freezing in 50 mM trehalose resulted in significantly higher cell viability compared to DMSO at all thawing times and a higher proliferation rate compared to DMSO for the 1 week freezing period. Freezing in 200 mM trehalose did not result in increased cell viability; however, proliferation activity was significantly higher and percentage of apoptotic cells was significantly lower compared to DMSO after freezing for 1 and 3 months. To confirm the functionality of SSCs frozen in 200 mM trehalose, SSC transplantation was performed. Donor SSCs formed spermatogenic colonies and sperm capable of generating normal progeny. Collectively, these results indicate that freezing in DMSO with 200 mM trehalose serves as an efficient method for the cryopreservation of SSCs.

Concepts: Organ transplant, Food preservation, Sulfoxide, Dimethyl sulfoxide, Dimethyl sulfide, Cryopreservation, Cryobiology, Cryoprotectant

4

Polyelectrolyte complexation is critical to the formation and properties of many biological and polymeric materials, and is typically initiated by aqueous mixing followed by fluid-fluid phase separation, such as coacervation. Yet little to nothing is known about how coacervates evolve into intricate solid microarchitectures. Inspired by the chemical features of the cement proteins of the sandcastle worm, here we report a versatile and strong wet-contact microporous adhesive resulting from polyelectrolyte complexation triggered by solvent exchange. After premixing a catechol-functionalized weak polyanion with a polycation in dimethyl sulphoxide (DMSO), the solution was applied underwater to various substrates whereupon electrostatic complexation, phase inversion, and rapid setting were simultaneously actuated by water-DMSO solvent exchange. Spatial and temporal coordination of complexation, inversion and setting fostered rapid (∼25 s) and robust underwater contact adhesion (Wad ≥ 2 J m(-2)) of complexed catecholic polyelectrolytes to all tested surfaces including plastics, glasses, metals and biological materials.

Concepts: Coordination complex, Sulfoxide, Solubility, Polymer, Dimethyl sulfide, Chemistry, Dimethyl sulfoxide, Solvent

2

Technology for preserving sperm is useful for disseminating valuable male genetic traits. Cold storage is suitable for easily transporting sperm as an alternative to the shipment of live animals. However, there is a technical limitation in that the fertility of cold-stored sperm declines within 3 days. To overcome this problem, we examined the protective effects of quercetin and dimethyl sulfoxide (DMSO). DMSO and quercetin maintained the fertility and motility of cold-stored sperm for 10 days. In addition, quercetin attenuated the reduction of mitochondrial membrane potential of cold-stored sperm during sperm preincubation, allowing the induction of capacitation, and it localized to the midpiece of sperm. Furthermore, DMSO and quercetin enhanced the level of tyrosine phosphorylation of cold-stored sperm. DMSO and quercetin have life-prolonging effects on sperm during cold storage. Cold storage using DMSO and quercetin will provide a robust system for internationally transporting valuable sperm samples.

Concepts: Bacteria, Photosynthesis, Phosphorylation, Sulfoxide, Dimethyl sulfide, Sperm, Dimethyl sulfoxide, Adenosine triphosphate

1

We have developed metal-free regiocontrolled dehydrogenative C-H/C-H cross-coupling of aryl sulfoxides with phenols by means of trifluoroacetic anhydride. Since the reaction would proceed through an interrupted Pummerer reaction followed by sulfonium-tethered [3,3]-sigmatropic rear-rangement, the C-H/C-H coupling takes place exclusively between the ortho positions of both substrates. Various functional groups including carbonyl, halo, siloxy, and even boryl moieties are compatible. The biaryl products naturally possess hydroxy and sulfanyl groups, which allows the products to be useful synthetic intermediates, as evidenced by the syntheses of pi-expanded heteroarenes such as unprecedented 7,12-dioxa[8]helicene.

Concepts: Sulfoxide, Hydroxyl, Carbon, Carboxylic acid, Alcohol, Amine, Functional group, Functional groups

0

Compartmental models were used to investigate the pharmacokinetics of intravenous (i.v.), oral (p.o.), and topical (TOP) administration of dimethyl sulfoxide (DMSO). The plasma concentration-time curve following a 15-min i.v. infusion of DMSO was described by a two-compartment model. Median and range of alpha (t1/2α ) and beta (t1/2β ) half-lives were 0.029 (0.026-0.093) and 14.1 (6.6-16.4) hr, respectively. Plasma concentration-time curves of DMSO following p.o. and TOP administration were best described by one-compartment absorption and elimination models. Following the p.o. administration, median absorption (t1/2ab ) and elimination (t1/2e ) half-lives were 0.15 (0.01-0.77) and 15.5 (8.5-25.2) hr, respectively. The plasma concentrations of DMSO were 47.4-129.9 μg/ml, occurring between 15 min and 4 hr. The fractional absorption (F) during a 24-hr period was 47.4 (22.7-98.1)%. Following TOP administrations, the median t1/2ab and t1/2e were 1.2 (0.49-2.3) and 4.5 (2.1-11.0) hr, respectively. Plasma concentrations were 1.2-8.2 μg/ml occurring at 2-4 hr. Fractional absorption following TOP administration was 0.48 (0.315-4.4)% of the dose administered. Clearance (Cl) of DMSO following the i.v. administration was 3.2 (2.2-6.7) ml hr-1  kg-1 . The corrected clearances (ClF ) for p.o. and TOP administrations were 2.9 (1.1-5.5) and 4.5 (0.52-18.2) ml hr-1  kg-1 .

Concepts: Sulfur, Highland Clearances, Sulfoxides, Sulfoxide, Dimethyl sulfide, Intravenous therapy, Dimethyl sulfoxide, Pharmacokinetics

0

Morphology regulation is vital to obtain high-performance perovskite films. Vapor-assisted deposition provides a simple approach to prepare perovskite films with controlled vapor-solid reaction. However, dense PbI2 precursor films with large crystal grains make it difficult for organic molecules to diffuse and interact with inner PbI2 frame. Here, a surface modification process is developed to optimize the surface layer morphology of PbI2 precursor films and lower the resistance of induced period in crystallization. The vapor optimization time is shortened to several-second level and the intermediate phase forms on the surface layer of PbI2 films. We achieve porous PbI2 surface with smaller grains through dimethyl sulfoxide (DMSO) vapor treatment, which promotes migration and reaction rate between CH3NH3I vapor and PbI2 layer. The PbI2 precursor films emerge dramatic morphological evolution, due to the formed intermediate phase on PbI2 surface layer. Taking advantage of the proposed surface modification process, we achieve high quality uniform perovskite films with larger crystal grains and without residual PbI2. The repeatable perovskite solar cells (PSCs) with modified films exhibit power conversion efficiency (PCE) up to 18.43% for planar structure. Moreover, the devices show less hysteresis because of improved films quality and reduced films density states. Our work expands the application of morphology control through forming intermediate phase and demonstrates an effective way to enhance the performance of the PSCs.

Concepts: Chemical engineering, Density, Sulfoxide, Energy conversion, Solar cell, Dimethyl sulfoxide, Dimethyl sulfide, Energy conversion efficiency

0

Homoisoflavonoids were formed in DMSO exclusively, and flavones were formed in t-AmOH when salicylaldehyde and alkynoic acids reacted with [Ru(p-cymene)Cl2]2 and CsOAc. They were formed through C-H activation of salicylaldehyde and decarboxylative coupling of alkynoic acid. This reaction system showed good yields, broad substrate scope, and good functional group tolerance. It was found that chalcone was an intermediate in the formation of both homoisoflavonoid and flavone.

Concepts: Sulfoxide, Organic chemistry, Methylsulfonylmethane, Alcohol, Carbonyl, Acetic acid, Amine, Chemical reaction

0

A convenient strategy for the synthesis of sulfur ylides via rhodium-catalyzed coupling of in situ generated iodonium ylides with sulfides or sulfoxides has been developed. A wide range of sulfur ylides were obtained in moderate to good yields from inexpensive sulfur compounds and active methylene compounds with a short reaction time (MW, 5-10 min) or 12-16 h at rt. Furthermore, these sulfoxonium ylides were used as novel acceptor/acceptor carbenes for N-H insertion reactions.

Concepts: Dimethyl sulfoxide, Sulfoxide, Pyrite, Sulfide, Hydrogen sulfide, Chemical reaction, Functional groups, Sulfur

0

Algae collection and chlorophyll extraction are two troublesome steps in the traditional methods used for the determination of chlorophyll concentration in natural water. A new method was established in this study for fast collection and extraction of chlorophyll. Based on our results, the optimum centrifugation condition for collecting algae was determined as: 5000 g for 15 min at 4 °C, and the optimum dilution ratio of dimethyl sulfoxide: 90% acetone was 1:4. The specific steps were as follows: the algae in water samples were collected by centrifugation at 5000 g at 4 °C for 15 min. The precipitated algae were suspended with 2 mL DMSO. Then the sample was transferred to a 15 mL centrifuge tube, and the tube was incubated at 65 °C for 1-2 h in the dark until the sample turned white. After cooling, the chlorophyll extract was diluted with 8 mL 90% acetone, before centrifugation at 5000 g for 5 min. The absorbance values of the supernatants at 750, 664, 647 and 630 nm were used for the calculation of chlorophyll concentrations by the trichromatic equations. This new method saved the filter cost, simplified the extraction process, improved the algae acquisition efficiency, and accelerated the chlorophyll extraction rate.

Concepts: Sulfoxide, Solvent, Photosynthesis, Algae, Dimethyl sulfide, Dimethyl sulfoxide, Plant

0

Live peripheral blood mononuclear cells (PBMCs) can be frozen and thawed for later analyses by adding and removing a cryoprotectant, such as dimethyl sulfoxide (DMSO). Laboratories across the world use various procedures, but published evidence of optimal thawing procedures is scarce.

Concepts: Sulfoxide, Dimethyl sulfide, Cryoprotectant, Cell biology, Hematology, Flow cytometry, PBMC, Dimethyl sulfoxide