Accessory gland secretions of male insects have many important functions including the formation of spermatophores. We used light and electron microscopy to investigate the structure of the accessory glands and posterior vasa deferentia of the carabid beetle Pterostichus nigrita to try to determine where spermatophore material is produced. Each accessory gland and posterior vas deferens had an outer layer of longitudinal muscle, beneath which was a layer of connective tissue and a thin band of circular muscle, all of which surrounded a layer of epithelial cells lining the lumen of the ducts. Based on the ultrastructure of the epithelial cells, and their secretory products, we identified two epithelial cell types in each region (distal and proximal) of the accessory glands and four types in the posterior vas deferens. Most secretory products, which stained positively for proteins and some mucins, were released into the lumen of the ducts by apocrine secretion. The accessory glands produced one type of secretory product whereas in posterior vasa deferentia, four types of secretory products were found layered in the lumen. Our results suggest that most of the structural material used to construct a spermatophore is produced by the cells of the posterior vasa deferentia.

A novel alternative route to access rhenium(V)−phthalocyanine complexes through direct metalation of metal‐free phthalocyanines (H2Pcs) with a rhenium(VII) salt in the presence of various two‐electron reducing agents is presented. Direct ion metalation of tetraamino‐ or tetranitrophthalocyanine with perrhenate (ReO4−) in the presence of triphenylphosphine led to oxidative decomposition of the H2Pcs, giving their respective phthalonitriles. Conversely, treatment of H2Pcs with ReO4− employing sodium metabisulfite yielded the desired ReVO−Pc complex. Finally, reaction of H2Pcs with ReO4− and NaBH4 as reducing agent led to the formation of rhenium oxide (RexOy) nanoparticles (NPs). The NP synthesis was optimised, and the RexOy NPs were capped with folic acid (FA) conjugated with tetraaminophthalocyanine (TAPc) to enhance their cancer cell targeting ability. The cytotoxicity profile of the resultant RexOy−TAPc−FA NPs was assessed and found to be greater than 80 % viability in four cell lines, namely, MDA−MB‐231, HCC7, HCC1806 and HEK293T. Non‐cytotoxic concentrations were determined and employed in cancer cell localization studies. The particle size effect on localization of NPs was also investigated using confocal fluorescence and transmission electron microscopy. The smaller NPs (≈10 nm) were found to exhibit stronger fluorescence properties than the ≈50 nm NPs and exhibited better cell localization ability than the ≈50 nm NPs.