Douglas Gamba

Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones

This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF(3).Et(2)O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested.

The effect of sterilization methods on electronspun poly(lactide‐co‐glycolide) and subsequent adhesion efficiency of mesenchymal stem cells

The sterilization of scaffolds is an essential step for tissue engineering in vitro and, mainly, clinical biomaterial use. However, this process can cause changes in the structure and surface of the scaffolds. Therefore, the objective of this study was to investigate the effect of sterilization by ethanol, ultraviolet radiation (UVR) or antimicrobial solution (AMS) on poly(lactide-co-glycolide) (PLGA) scaffolds produced by the electrospinning technique. The properties of nanofibers and the cellular adhesion of mesenchymal stem cells to the scaffolds were analyzed after the treatments. All methods generated sterile scaffolds but showed some kind of damage to the scaffolds. Ethanol and AMS caused changes in the morphology and scaffold dimensions, which were not observed when using the UVR method. However, UVR caused a greater reduction in polymeric molecular weight, which increased proportionally with exposure time of treatment. Nanofibers sterilized with AMS for 1 h and 2 h showed greater cellular adhesion than the other methods, demonstrating their potential as a method for sterilizing PLGA nanofibers.

InCl3/NaClO: a reagent for allylic chlorination of terminal olefins

Tricloreto de indio na presenca de hipoclorito de sodio promove a cloracao alilica de olefinas terminais em meio bifasico (diclorometano/agua) com bons rendimentos. Para estabelecer um procedimento geral, escolheu-se a carvona como composto modelo e otimizou-se a estequiometria, temperatura, e tempo de conversao para o respectivo cloreto alilico. Tratando-se b-pineno com tricloreto de indio/hipoclorito de sodio obteve-se seletivamente o cloreto perilico, um precursor importante para a obtencao de derivados de limoneno oxigenados no carbono C-7.

Electrospun scaffolds functionalized with heparin and vascular endothelial growth factor increase the proliferation of endothelial progenitor cells.

In severe cases of peripheral arterial disease, tissue loss can occur and the use of vascular grafts can be necessary. However, currently, there are no suitable substitutes for application in small diameter vessels. The aim of this work has been to produce scaffolds with adequate properties for application as vascular substitutes. Polycaprolactone scaffolds were produced by the electrospinning technique. The surface of the scaffolds was functionalized with heparin and vascular endothelial growth factor (VEGF) and their physical-chemical properties were characterized. Human endothelial progenitor cells (EPCs) or mesenchymal stem cells (MSCs) were seeded onto the surface of the scaffolds in order to create an endothelial layer. The electrospun scaffolds exhibited mechanical properties compatible with the native arteries. The presence of heparin prevented blood coagulation on the scaffold surface. The presence of heparin and VEGF favored the adaptation of MSCs and EPCs on the scaffolds in relation to the non functionalized scaffolds. In addition, the EPCs cultivated on the scaffolds maintained the expression of CD31, CD34 and VE-cadherin genes. The results obtained in the present study suggest that electrospun scaffolds functionalized with heparin and VEGF can be applied in vascular tissue engineering. These scaffolds exhibited antithrombogenic properties and favored the development of cells on their surface. The association of heparin and VEGF with electrospun scaffolds increased EPC proliferation, favoring the formation of the endothelial layer and the regeneration of damaged vessels.

Effect of feeder free poly(lactide-co-glycolide) scaffolds on morphology, proliferation, and pluripotency of mouse embryonic stem cells.

The aim of the study has been to evaluate the morphology, proliferation, and pluripotency maintenance of mouse embryonic stem cells (mESCs) cultivated on poly(lactic-co-glycolic acid) scaffolds. The scaffolds were hydrolyzed with NaOH (treated) and nonhydrolyzed (untreated). Morphological and mechanical characterization of the scaffolds was performed. mESC were evaluated for cell viability, cytotoxicity, expression of pluripotency markers, colony morphology, and overall distribution. The treatment generated a reduction in the hydrophobic characteristics of the scaffolds, leading to a higher wettability compared to the untreated group. The viability, cytotoxicity, number of colonies, and the thickness of the cell layer presented similar results between the scaffold groups. The viability test showed that it was possible to cultivate the mESCs on the scaffolds. The cytotoxicity analysis showed that the PLGA scaffolds were not harmful for the cells. The cells maintained the expression of the pluripotency markers Oct4 and Sox2. The number of colonies and the thickness of the cell layer on the scaffold showed that they were not able to colonize the entire volume of the scaffolds. The area occupied by the mESCs was the same between the treated and untreated groups after 14 days in culture. It is possible to conclude that both conditions are equally suitable for maintaining mESC culture.

Enantioselective synthesis of (R)-isocarvone from (S)-perillaldehyde

This work describes the enantioselective preparation of (R)-(+)-isocarvone, (S)-(-)-5-isopropenylcyclohex-2-enone and (S)-(-)-3-isopropenylcyclohexanone starting from (S)-(-)-perillaldehyde. These compounds hold the prospect of serving as useful chiral building blocks or intermediates in organic synthesis.