1,1′-{[3,5-Bis(dodecyloxycarbonyl)-4-(naphthalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide

Abstract

Synthesis of a double-charged cationic amphiphilic 1,4-dihydropyridine derivative with dodecyl ester groups at positions 3 and 5 of the 1,4-DHP ring was performed starting from Hantzsch type cyclization of dodecyl acetoacetate, 2-naphthaldehyde and ammonium acetate. Bromination of this compound followed by nucleophilic substitution of bromine with (E)-4-(2-(naphthalen-2-yl)vinyl)pyridine gave the desired cationic amphiphilic 1,1′-{[3,5-bis(dodecyloxycarbonyl)-4-(naphthalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium}dibromide. The obtained target compound was fully characterized by IR, UV, 1H-NMR, 13C-NMR, HRMS and microanalysis. The characterization of the cationic 1,4-DHP nanoparticles in an aqueous solution was performed by DLS measurements. The obtained results showed that the compound formed nanoparticles with an average diameter of around 300 nm, a PDI value of around 490 and a zeta-potential of around 20 mV for freshly prepared samples. However, after one week of storage at room temperature, an aggregation of nanoparticles was detected.

Synthesis and Characterization of Novel Amphiphilic N-Benzyl 1,4-Dihydropyridine Derivatives—Evaluation of Lipid Monolayer and Self-Assembling Properties

“…Thus, amphiphilic 1,4-DHP-anthracene hybrid signals of 1,4-DHP 4-H were observed at 5.15 ppm, and the 2,6-methylene group AB-system signals were observed at 5.89 and 6.39 ppm [ 25 ]. The 1 H NMR spectra of amphiphilic 1,4-DHP derivative having 4-(naphthalen-2-yl)-substituent at position 4 and ( E )-4-(2-(naphthalen-2-yl)vinyl)pyridinium substituents at positions 2 and 6 of 1,4-DHP cycle demonstrated signals at 6.50 ppm for 4-H proton and 4.67 and 5.44 ppm for 2,6-methylene group protons [ 24 ].…”

“…The ability to form nanoparticles by the amphiphilic 1,4-DHP is highly influenced by the substituents of its ring, which can be observed in our previous studies for the structurally related compounds. Thus, particles formed by 1,4-DHP amphiphile 1 had an average diameter of 110 nm and a PDI value of 0.345 [ 17 ], and particles formed by 1,1′-{[3,5-bis(dodecyloxycarbonyl)-4-(naphthalen-2-yl)-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis{4-[(E)-2-(naphthalen-2-yl)vinyl]pyridin-1-ium} dibromide had an average diameter of approximately 300 nm and a PDI value of 0.491 for the freshly prepared sample [ 24 ]. According to the literature, the size and homogeneity of samples also depend on the preparation method.…”

Styrylpyridinium Derivatives for Fluorescent Cell Imaging

“…The PLQY values for the SP derivatives 6d , e (each with a julolidinyl moiety) were 0.5% and 0.7%, respectively. Previously, we designed naphthalene-2-yl)vinyl)pyridinium groups containing 1,4-dihydropyridine amphiphile, for which the PLQY value for the EtOH solution was 1% [ 20 ].…”

“…The approach is rapid, simple, and can be easily scaled up [ 51 ]. This method was previously used successfully for the preparation and characterisation of lipid-like pyridinium amphiphiles [ 20 , 52 , 53 ]. The obtained results are summarised in Table 4 .…”

“…The long π conjugation style, length of the conjugated bridge, and molecular planarity are essential preconditions for the design of functional chromophores [ 17 , 18 , 19 ]. The synthesis and evaluation of the physicochemical and self-assembling properties of styrylpyridinium moieties containing a 1,4-DHP amphiphile as a prospective delivery system were demonstrated by our research group [ 20 ]. It was demonstrated that the structure of SP or related derivatives affected their properties.…”