Spectroscopic and In Vitro Investigations of Boron(III) Complex with Meso-4-Methoxycarbonylpropylsubstituted Dipyrromethene for Fluorescence Bioimaging Applications

Abstract

This study focuses on the behavior of a new fluorescent marker for labeling individual biomolecules and staining cell organelles developed on a meso-substituted BODIPY platform. Boron(III) complex with meso-4-methoxycarbonylpropylsubstituted 3,3’,5,5’-tetramethyl-2,2′-dipyrromethene has been synthesized and identified via visible, UV-, NMR- and MS-spectra X-ray. The behavior of fluorophore in solutions has been studied with various experimental techniques. It has been found that luminophore exhibits a high quantum yield (almost ~100–75%) in the blue-green region (513–520 nm) and has high photostability. In addition, biological analysis indicates that the fluorophore exhibits a tendency to effectively penetrate into cell membranes. On the other hand, the proposed BODIPY can be used to study the significant differences among a large number of pathogens of mycotic infections, as well as to visualize structural changes in the plasma membrane, which is necessary for the clearance of mammalian cells undergoing apoptotic cell death.

Design, Spectral Characteristics, and Possibilities for Practical Application of BODIPY FL-Labeled Monoterpenoid

“…The observed effect can be due to the formation of additional hydrogen bonds between the protons of the alcohols’ hydroxyl groups or chloroform and the fluorine atoms or carbonyl oxygen of the conjugate 3 . The introduction of a myrtenyl butanoate substituent into the meso -position of the luminophore has no visible effect on the φ value of compound 3 as it is observed for the structurally related BODIPY 1 . The maximal fluorescence of BODIPYmyrt (∼100%) was in cyclohexane, toluene, and chloroform (Table ).…”

“…It is noteworthy that molecule 3 includes a planar symmetric conjugated BODIPY fragment, a chiral terpene backbone, and an achiral spacer connecting them. The geometry of the BODIPY fragment is typical for compounds based on it . In contrast to the mobile spacer, the conjugated fragment and the terpene backbone are conformationally rigid.…”

“…BF 2 complex with ms -methoxycarbonylpropyl-substituted dipyrromethene 1 was synthesized according to the procedure previously reported. − …”

“…In our recent studies, we described the biomarkers based on the BODIPYs with an ester group ((−(CH 2 ) n COOCH 3 ), n = 3 or 4) into dipyrromethene meso -spacer ( [BF 2 dpm] ). , The meso-substituted BODIPYs preferentially stained Gram-positive bacteria and were suggested to be useful in distinguishing between Gram-positive bacteria and Gram-negative bacteria in mixed cultures . We showed that these luminophores accumulate in the cytoplasm of mammalian cells and exhibit a polar micro-speckled staining pattern that is more intensive in tumor cells compared to the nontransformed fibroblasts. , Moreover, [BF 2 dpm] can be used as a fluorescent marker when assessing the features and structural changes of cellular membranes of mammalian and fungal cells.…”

“…11 We showed that these luminophores accumulate in the cytoplasm of mammalian cells and exhibit a polar micro-speckled staining pattern that is more intensive in tumor cells compared to the nontransformed fibroblasts. 11,12 Moreover, [BF 2 dpm] can be used as a fluorescent marker when assessing the features and structural changes of cellular membranes of mammalian and fungal cells.…”