Polydiacetylenes (PDAs) are conjugated polymers that can form highly ordered structures with unique chromatic features. PDAs are typically obtained by polymerisation of diacetylene (DA) monomers using ultraviolet (UV) light irradiation without the need of any initiators, which generates a polymeric backbone with alternating C=C and C≡C bonds (one-yne), giving a blue non-fluorescent PDAs. Several stimuli, such as pH, temperature and ligand-receptor interaction, can induce a red-shift and weakly fluorescent colorimetric transition that makes PDAs a very interesting system in the field of sensors and drug delivery systems [1,2]. PDAs systems are usually prepared using amphiphilic commercial monomers like 10,12 - pentacosadyinoic acid (PCDA) and 10,12 - tricosadyinoic acid (TCDA), with the addition in the final formulation of phospholipids [3] and/or water-soluble polymers [4], that can influence PDAs system sensitivity, stability and drug-released properties. In the present project, we selected poly(glycerol adipate) (PGA) as a novel greener polymeric alternative to develop PDAs mixed-micelles. The addition of PGA will confer to the final formulations biodegradability and biocompatibility [5]. Furthermore, PGA can self-assembly into nanoparticles (NPs) in aqueous media using nanoprecipitation method, which is highly compatible with traditional process for the formation of PDAs [6]. Due to PGA low toxicity and possibility to produce active polymeric prodrugs by drug coupling to the PGA backbone, PDA/PGA mixed-micelles can be considered a potential platform intrinsically biodegradable which may facilitate in vivo and in vitro tracking of delivery systems [7]. [1] X. Qian and B. Stadler, Chem. Mater. 2019, 31(4), 1196-1222. [2] F. Fang, F. Meng, L. Luo, Mater. Chem. Front. 2020, 4(4), 1089,1104 [3] G.P. Camilloto, C.G. Otoni, G.W.R. de Almeida, I.R.N de Oliveira, L.H.M. da Silva, A.C. dos Santos Pires, N. De F.F. Soares. ACS Food Sci. Technol. 2021, 1(5), 745-753. [4] A. Pankaew, N. Traiphol, R. Traiphol, Colloids Surf. Physicochem. Eng. Asp. 2021, 608, 125626. [5] P.L. JacobsL.A. Ruiz Cantu, A.K. Pearce, Y. He, J.C. Lentz, J.C. Moore, F.Machado, G.Rivers, E. Apebende, M.R. Fernandenz, I. Francolini, R. Wildman, S.M. Howdle, V. Taresco, Poly (Glycerol Adipate) (PGA) Backbone Modifications with a Library of Functional Diols: Chemical and Physical Effects. Polymer, 228, 123912 [6] P. Kallinteri, S. Higgins, G.A. Hutcheon, C.B. St Pourcain, M.C. Garnett. Biomacromolecules.
Development Of Smart Polydiacetylene Micelles For In Vitro And In Vivo Tracking / Brugnoli, Benedetta; Jacob, Philippa L.; Howdle, Steve M.; Francolini, Iolanda; Taresco, Vincenzo. - (2022). (Intervento presentato al convegno First Symposium for Young Chemists (SYNC2022) tenutosi a Sapienza University of Rome).
Development Of Smart Polydiacetylene Micelles For In Vitro And In Vivo Tracking
Benedetta Brugnoli;Iolanda Francolini;Vincenzo Taresco
2022
Abstract
Polydiacetylenes (PDAs) are conjugated polymers that can form highly ordered structures with unique chromatic features. PDAs are typically obtained by polymerisation of diacetylene (DA) monomers using ultraviolet (UV) light irradiation without the need of any initiators, which generates a polymeric backbone with alternating C=C and C≡C bonds (one-yne), giving a blue non-fluorescent PDAs. Several stimuli, such as pH, temperature and ligand-receptor interaction, can induce a red-shift and weakly fluorescent colorimetric transition that makes PDAs a very interesting system in the field of sensors and drug delivery systems [1,2]. PDAs systems are usually prepared using amphiphilic commercial monomers like 10,12 - pentacosadyinoic acid (PCDA) and 10,12 - tricosadyinoic acid (TCDA), with the addition in the final formulation of phospholipids [3] and/or water-soluble polymers [4], that can influence PDAs system sensitivity, stability and drug-released properties. In the present project, we selected poly(glycerol adipate) (PGA) as a novel greener polymeric alternative to develop PDAs mixed-micelles. The addition of PGA will confer to the final formulations biodegradability and biocompatibility [5]. Furthermore, PGA can self-assembly into nanoparticles (NPs) in aqueous media using nanoprecipitation method, which is highly compatible with traditional process for the formation of PDAs [6]. Due to PGA low toxicity and possibility to produce active polymeric prodrugs by drug coupling to the PGA backbone, PDA/PGA mixed-micelles can be considered a potential platform intrinsically biodegradable which may facilitate in vivo and in vitro tracking of delivery systems [7]. [1] X. Qian and B. Stadler, Chem. Mater. 2019, 31(4), 1196-1222. [2] F. Fang, F. Meng, L. Luo, Mater. Chem. Front. 2020, 4(4), 1089,1104 [3] G.P. Camilloto, C.G. Otoni, G.W.R. de Almeida, I.R.N de Oliveira, L.H.M. da Silva, A.C. dos Santos Pires, N. De F.F. Soares. ACS Food Sci. Technol. 2021, 1(5), 745-753. [4] A. Pankaew, N. Traiphol, R. Traiphol, Colloids Surf. Physicochem. Eng. Asp. 2021, 608, 125626. [5] P.L. JacobsL.A. Ruiz Cantu, A.K. Pearce, Y. He, J.C. Lentz, J.C. Moore, F.Machado, G.Rivers, E. Apebende, M.R. Fernandenz, I. Francolini, R. Wildman, S.M. Howdle, V. Taresco, Poly (Glycerol Adipate) (PGA) Backbone Modifications with a Library of Functional Diols: Chemical and Physical Effects. Polymer, 228, 123912 [6] P. Kallinteri, S. Higgins, G.A. Hutcheon, C.B. St Pourcain, M.C. Garnett. Biomacromolecules.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
