Fluorescent organotin compounds as dyes in silk fibroin (Bombyx mori): ultrasound-assisted synthesis, chemo-optical characterization, cytotoxicity, and confocal fluorescence microscopy

• Published in: New journal of chemistry Vol. 43; no. 13; pp. 5150 - 5158
• Main Authors: Berrones-Reyes, Jessica C., Munoz-Flores, Blanca M., Molina-Paredes, Abigail, Ibarra Rodriguez, Marisol, Rodriguez-Ortega, Alejandro, Rasika Dias, H. V., Jimenez-Perez, Victor M.
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 2019; Royal Society of Chemistry
• Subjects: Ambient temperature; Biocompatibility; Biomedical materials; Carbon 13; Chemistry; Chemistry, Multidisciplinary; Crystallography; Fluorescence; Fluorescent dyes; NMR spectroscopy; Optical properties; Organotin compounds; Physical Sciences; Science & Technology; Silk fibroin; Single crystals; Spectrum analysis; Synthesis; Tin; Tissue engineering; Toxicity; Viability; X-ray diffraction; AMINO-ACID; PRECURSOR; SONOCHEMICAL SYNTHESIS; CRYSTAL-STRUCTURES; PHOTOPHYSICAL PROPERTIES; SCAFFOLDS; DIORGANOTIN(IV) COMPLEXES; DERIVATIVES; MESENCHYMAL STEM-CELLS; SCHIFF-BASE COMPLEXES
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/c8nj05248d

The fluorescent silk fibroin (FSF) is useful in a number of biomedical applications. However, some FSFs are less useful for medical applications because they are derived from toxic compounds. Here we report for the first time a fast (similar to 20 min), ultrasonic assisted, eco-friendly synthesis of four fluorescent organotin Schiff compounds using the corresponding aldehyde, benzoic hydrazide, and diorganotin oxide (1: MeO-L-SnPh2, 2: tBu(2)-L-SnPh2, 3: HO-L-SnPh2, and 4: HO-L-SnBu2). These compounds were fully characterized by NMR spectroscopy (H-1, C-13, and Sn-119), HRMS, and UV/Vis and fluorescence spectroscopy. Single crystal X-ray diffraction investigations of complexes 1 and 2 are also reported. The as-prepared organotin Schiff compounds exhibit fluorescence at ambient temperature with good photophysical properties (fluorescence quantum yields phi: 18-55%). These organotin compounds serve as fluorescent dyes in silk fibroin (Bombyx mori). The organotin dyed fluorescent silk fibroin showed a uniform staining, high viability, and good capacity to retain organotin compounds which might be used as innocuous scaffolds in tissue engineering.