Synthesis and Aggregation Studies of Functional Binaphthyl-Bridged Chiral Phthalocyanines

Revuelta‐Maza, Miguel A.; Torres, Tomás; Torre, Gema de la

doi:10.1021/acs.orglett.9b02718

Cited by 15 publications

(25 citation statements)

References 40 publications

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“…[16] Although cationic Pcs have been also stud-ied for PDI, in many cases using alkylpyridinium motifs, [17][18][19][20] only af ew reports can be found on the preparation and biological evaluation of asymmetric systemsw ith am ore pronounced amphiphilic character arising from the asymmetric distribution of substituents in an "AABB" fashion with Aa nd B coding for differently substituted isoindoles. [21,22] On the other hand, strongly cationic nanoparticles are known to interact more favorably with the cell membranes, thereby enhancing their intracellular uptake. [10] For Gram-negative bacteria, the initial process for photodynamic eradication consists on damage to the outer membrane, allowing the drug to be incorporated in inner cellular sites.…”

Section: Introductionmentioning

confidence: 99%

“…Worth of mention is that Pors bearing cationic groups in adjacent meso positions seem to be significantly more efficient than those with the cationic groups located in opposite meso positions [16] . Although cationic Pcs have been also studied for PDI, in many cases using alkylpyridinium motifs, [17–20] only a few reports can be found on the preparation and biological evaluation of asymmetric systems with a more pronounced amphiphilic character arising from the asymmetric distribution of substituents in an “AABB” fashion with A and B coding for differently substituted isoindoles [21, 22] …”

Section: Introductionmentioning

confidence: 99%

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Self‐Assembled Binaphthyl‐Bridged Amphiphilic AABB Phthalocyanines: Nanostructures for Efficient Antimicrobial Photodynamic Therapy

Revuelta‐Maza

Heras

Agut

et al. 2021

Chemistry A European J

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Herein, the photodynamic activity of phthalocyanine (pc)‐assembled nanoparticles against bacterial strains is demonstrated. The photosensitizers (PS) studied in this work are two chiral ZnIIPcs (PS‐1 and PS‐2), with an AABB geometry (where A and B refer to differently substituted isoindole constituents). They contain differently functionalized, chiral binaphthyloxy‐linked A isoindole units, which determine the hydrophobicity of the system, and cationic methyl pyridinium moieties in the other two isoindoles to embody hydrophilicity. Both compounds have the ability to self‐assemble into nanoparticles in aqueous media and have proved efficient in the photo‐inactivation of Staphylococcus aureus and Escherichia coli, selected as models of Gram‐positive and Gram‐negative bacteria. The average size of the nanoparticles was determined by substitution at the binaphthyl core and, in turn, influences the toxicity of the PS. Thus, PS‐1, presenting a nonsubstituted binaphthyl core, forms larger nanoparticles with a larger cationic surface than the octyl‐functionalized PS‐2. Although both PSs present similar structure and photophysical features, the self‐assembled nanostructures of PS‐1 are more effective at killing both types of strain, showing an outstanding photo‐inactivation capacity with the Gram‐negative E. coli.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Self‐Assembled Binaphthyl‐Bridged Amphiphilic AABB Phthalocyanines: Nanostructures for Efficient Antimicrobial Photodynamic Therapy

Revuelta‐Maza

Heras

Agut

et al. 2021

Chemistry A European J

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“…A novel archetype of amphiphilic Pc‐based PS relies on a binaphthyloxy‐linked A 2 B 2 ZnPc core structure (with A and B coding for two differently functionalized isoindoles), [72] functionalized with pyridinium‐substituents at two of the isoindole to provide water solubility. [73] In particular, two PS endowed with different amphiphilic character were prepared, either attaching two octyl chains at the binaphthyl unit (PS‐2) or keeping the ring bare (PS‐1) (Figure 10 C).…”

Section: Nanoassemblies With Antimicrobial Activitymentioning

confidence: 99%

Self‐Assembled Porphyrinoids: One‐Component Nanostructured Photomedicines

2021

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Photodynamic therapy (PDT) is becoming a promising way to treat various kinds of cancers, with few side effects. Porphyrinoids are the most relevant photosensitizers (PS) in PDT, because they present high extinction coefficients, biocompatibility, and excellent photochemical behavior. To maximize therapeutic effects, polymer‐PS conjugates, and PS‐loaded nanoparticles have been developed, with insights in improving tumor delivery. However, some drawbacks such as non‐biodegradability, multistep fabrication, and low reagent loadings limit their clinical application. A novel strategy, noted by some authors as the “one‐for‐all” approach, is emerging to circumvent the use of additional delivery agents. This approach relies on the self‐assembly of amphiphilic PS to fabricate nanostructures with improved transport properties. In this review we focus on different rational designs of porphyrinoid PS to achieve some of the following attributes in nanoassembly: i) selective uptake, through the incorporation of recognizable biological vectors; ii) responsiveness to stimuli; iii) combination of imaging and therapeutic functions; and iv) multimodal therapy, including photothermal or chemotherapy abilities.

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“…Since then, more than 300 papers have appeared on the use of this method (Claessens et al, 2002(Claessens et al, , 2014Kobayashi, 2002). Compounds 3 and 4 containing long alkyl chains were prepared by Torres' group in order to study their aggregation (Revuelta-Maza et al, 2019). The precursor b was reported as early as 1998 as a stable phthalonitrile which does not racemize under normal Pc formation conditions (Kobayashi, 1998), so that the reaction of b and long-alkyl chain-containing phthalonitrile afforded Pc 3 preferentially, and reactions of only b produced 4 in relatively high yield.…”

Section: Binap and Binap-related Substituent-linked Systems Synthesismentioning

confidence: 99%

Recent Progress in Optically-Active Phthalocyanines and Their Related Azamacrocycles

2020

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Optically-active phthalocyanines (Pcs) and related macrocycles reported in the 2010-2020 period are introduced in this review. They are grouped into several categories: (1) chiral binaphthyl-containing Pcs, (2) optically active alkyl chain-containing Pcs, (3) chiral axial ligand-coordinated or-linked Pcs, (4) chiral subphthalocyanines (SubPcs), and (5) related azamacrocycles. For each compound, the structure and important characteristics are summarized.

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Synthesis and Aggregation Studies of Functional Binaphthyl-Bridged Chiral Phthalocyanines

Cited by 15 publications

References 40 publications

Self‐Assembled Binaphthyl‐Bridged Amphiphilic AABB Phthalocyanines: Nanostructures for Efficient Antimicrobial Photodynamic Therapy

Self‐Assembled Binaphthyl‐Bridged Amphiphilic AABB Phthalocyanines: Nanostructures for Efficient Antimicrobial Photodynamic Therapy

Self‐Assembled Porphyrinoids: One‐Component Nanostructured Photomedicines

Recent Progress in Optically-Active Phthalocyanines and Their Related Azamacrocycles

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