1,1′-{[3,5-Bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] Dibromide
A synthesis of a cationic moiety and fluorescent moieties containing amphiphilic 1,4-dihydropyridine (1,4-DHP) derivatives was performed starting with the Hantzsch-type cyclization of dodecyl acetoacetate, phenylaldehyde and ammonium acetate. Bromination of the 2,6-dimethyl groups of a parent 1,4-DH...
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MDPI AG
2022-09-01
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| Online Access: | https://www.mdpi.com/1422-8599/2022/3/M1438 |
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| author | Reinis Ozolins Mara Plotniece Karlis Pajuste Reinis Putralis Nadiia Pikun Arkadij Sobolev Aiva Plotniece Martins Rucins |
| author_facet | Reinis Ozolins Mara Plotniece Karlis Pajuste Reinis Putralis Nadiia Pikun Arkadij Sobolev Aiva Plotniece Martins Rucins |
| author_sort | Reinis Ozolins |
| collection | DOAJ |
| description | A synthesis of a cationic moiety and fluorescent moieties containing amphiphilic 1,4-dihydropyridine (1,4-DHP) derivatives was performed starting with the Hantzsch-type cyclization of dodecyl acetoacetate, phenylaldehyde and ammonium acetate. Bromination of the 2,6-dimethyl groups of a parent 1,4-DHP compound, followed by nucleophilic substitution of bromine with 4-(anthracen-9-yl)pyridine, produced the desired 1,1′-{[3,5-bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] dibromide. The obtained target compound was fully characterized by the IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR and HRMS data. Studies of the self-assembling properties and characterization of the nanoparticles obtained by the ethanol injection method were performed using dynamic light scattering (DLS) measurements. DLS measurement data showed that 1,1′-{[3,5-bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] dibromide produced liposomes that had average diameters of 200 nm when the samples were freshly prepared, and 140 nm after 7 days or 1 month storage. The PDI values of the samples were approximately 0.50 and their zeta-potential values were approximately 41 mV when the samples were freshly prepared, and 33 mV after storage. The obtained nanoparticles were stored at room temperature for one month and remained stable during that period. The mean molecular area of the cationic 1,4-DHP-anthracene hybrid <b>4</b> was 118 Å<sup>2</sup>, while the mean molecular area of the cationic 1,4-DHP <b>5</b> without anthracene substituents was only 83 Å<sup>2</sup>. The photoluminescence quantum yield (PLQY) value for the EtOH solution of the 1,4-DHP derivative <b>4</b> was 10.8%, but for the 1,4-DHP derivative <b>5</b> it was only 1.8%. These types of compounds could be used as synthetic lipids in the further development of prospective theranostic delivery systems. |
| first_indexed | 2024-03-09T23:02:43Z |
| format | Article |
| id | doaj.art-2104371383274a49a5813a833e166842 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T23:02:43Z |
| publishDate | 2022-09-01 |
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| spelling | doaj.art-2104371383274a49a5813a833e1668422023-11-23T17:57:53ZengMDPI AGMolbank1422-85992022-09-0120223M143810.3390/M14381,1′-{[3,5-Bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] DibromideReinis Ozolins0Mara Plotniece1Karlis Pajuste2Reinis Putralis3Nadiia Pikun4Arkadij Sobolev5Aiva Plotniece6Martins Rucins7Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, LatviaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Riga Stradiņš University, Dzirciema 16, LV-1007 Riga, LatviaLatvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, LatviaLatvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, LatviaLatvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, LatviaLatvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, LatviaLatvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, LatviaLatvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, LatviaA synthesis of a cationic moiety and fluorescent moieties containing amphiphilic 1,4-dihydropyridine (1,4-DHP) derivatives was performed starting with the Hantzsch-type cyclization of dodecyl acetoacetate, phenylaldehyde and ammonium acetate. Bromination of the 2,6-dimethyl groups of a parent 1,4-DHP compound, followed by nucleophilic substitution of bromine with 4-(anthracen-9-yl)pyridine, produced the desired 1,1′-{[3,5-bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] dibromide. The obtained target compound was fully characterized by the IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR and HRMS data. Studies of the self-assembling properties and characterization of the nanoparticles obtained by the ethanol injection method were performed using dynamic light scattering (DLS) measurements. DLS measurement data showed that 1,1′-{[3,5-bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] dibromide produced liposomes that had average diameters of 200 nm when the samples were freshly prepared, and 140 nm after 7 days or 1 month storage. The PDI values of the samples were approximately 0.50 and their zeta-potential values were approximately 41 mV when the samples were freshly prepared, and 33 mV after storage. The obtained nanoparticles were stored at room temperature for one month and remained stable during that period. The mean molecular area of the cationic 1,4-DHP-anthracene hybrid <b>4</b> was 118 Å<sup>2</sup>, while the mean molecular area of the cationic 1,4-DHP <b>5</b> without anthracene substituents was only 83 Å<sup>2</sup>. The photoluminescence quantum yield (PLQY) value for the EtOH solution of the 1,4-DHP derivative <b>4</b> was 10.8%, but for the 1,4-DHP derivative <b>5</b> it was only 1.8%. These types of compounds could be used as synthetic lipids in the further development of prospective theranostic delivery systems.https://www.mdpi.com/1422-8599/2022/3/M14381,4-dihydropyridinepyridiniumanthraceneself-assembling propertiesnanoparticlesDLS |
| spellingShingle | Reinis Ozolins Mara Plotniece Karlis Pajuste Reinis Putralis Nadiia Pikun Arkadij Sobolev Aiva Plotniece Martins Rucins 1,1′-{[3,5-Bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] Dibromide Molbank 1,4-dihydropyridine pyridinium anthracene self-assembling properties nanoparticles DLS |
| title | 1,1′-{[3,5-Bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] Dibromide |
| title_full | 1,1′-{[3,5-Bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] Dibromide |
| title_fullStr | 1,1′-{[3,5-Bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] Dibromide |
| title_full_unstemmed | 1,1′-{[3,5-Bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] Dibromide |
| title_short | 1,1′-{[3,5-Bis((dodecyloxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]bis(methylene)}bis[4-(anthracen-9-yl)pyridin-1-ium] Dibromide |
| title_sort | 1 1 3 5 bis dodecyloxycarbonyl 4 phenyl 1 4 dihydropyridine 2 6 diyl bis methylene bis 4 anthracen 9 yl pyridin 1 ium dibromide |
| topic | 1,4-dihydropyridine pyridinium anthracene self-assembling properties nanoparticles DLS |
| url | https://www.mdpi.com/1422-8599/2022/3/M1438 |
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