Superstructures with cyclodextrins: Chemistry and applications IV

• Gerhard Wenz

Beilstein J. Org. Chem. 2017, 13, 2157–2159, doi:10.3762/bjoc.13.215

• nanoparticles with the sensitizer Zn-phthalocyanine and the antineoplastic drug docetaxel. These materials might be applicable for dual cancer therapy [15]. Another self-assembled CD nanocarrier for the photoreactive dye squaraine that is useful for photodynamic therapy is described in this Thematic Series [16

Direct catalytic arylation of heteroarenes with meso-bromophenyl-substituted porphyrins

• Alexei N. Kiselev,
• Olga K. Grigorova,
• Alexei D. Averin,
• Sergei A. Syrbu,
• Oskar I. Koifman and
• Irina P. Beletskaya

Beilstein J. Org. Chem. 2017, 13, 1524–1532, doi:10.3762/bjoc.13.152

• developed for guided photodynamic therapy [3]. On the other hand, various heterocycles also find multiple medical applications: bis(benzimidazoles), bis(benzoxazoles) and benzothiazoles display anticancer activities [4], 2-arylbenzothiazole is a privileged scaffold in drug discovey, and the main areas of

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• aqueous medium, which precludes any response to light excitation. Keywords: β-cyclodextrins; fluorescence; photodynamic therapy; photosensitizers; singlet oxygen; xanthene; Introduction Cyclodextrins (CDs) are cyclic oligosaccharides able to form host–guest inclusion complexes with drugs and this

• successfully utilized in photodynamic therapy (PDT). This minimally invasive therapeutic approach has proven to be very well-suited for cancer and bacterial diseases treatment. The PDT is based on the combination of three main components: visible light, a photosensitizer (PS) and molecular oxygen [4][5]. After

A self-assembled cyclodextrin nanocarrier for photoreactive squaraine

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248

• significant potential for photodynamic therapy. Herein we report that squaraines can be immobilized on a self-assembled nanocarrier composed of amphiphilic cyclodextrins to enhance their photochemical activity. To this end, a squaraine was equipped with two adamantane moieties that act as anchors for the

• cyclodextrin vesicle surface. The supramolecular immobilization was monitored by using fluorescence spectroscopy and microscopy and the photochemistry of the squaraine was investigated by using absorption spectroscopy. Keywords: cyclodextrin; host–guest chemistry; photodynamic therapy; self-assembly

• ; squaraine; Introduction Photodynamic therapy (PDT) has become a very attractive alternative to traditional cancer therapies due to its efficiency and selectivity [1][2][3][4]. PDT is based on a photosensitizer (PS), which is delivered to cancerous tissue followed by the irradiation with light of an

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• chelation [1][2][3][4]. BF2+-chelated ADP derivatives (Figure 1b) in particular have drawn interest for photodynamic therapy, bio-imaging and light harvesting applications [5][6][7][8]. We have shown that derivatives of Zn(ADP)2 are promising electron acceptors for organic photovoltaics (OPVs) [9][10]. A

Superstructures with cyclodextrins: chemistry and applications III

• Gerhard Wenz and
• Eric Monflier

Beilstein J. Org. Chem. 2016, 12, 937–938, doi:10.3762/bjoc.12.91

• role. As exemplified in the following, CD chemistry has developed into a very attractive field of research. The cell-penetrating peptide octa-arginine was conjugated to methylated β-CD. The resulting biofunctionalized host was able to transport a porphyrin sulfonate into HeLa cells used in photodynamic

• therapy [1]. Furthermore, it was found that lactose-appended β-CD lowers the cholesterol level in HepG2 cells – a result that is relevant for the treatment of Niemann–Pick-type C disease [2]. Metal-organic frameworks (MOFs) created from native CDs can be applied for the separation of isomeric xylenes or

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

• Vito Rizzi,
• Sergio Matera,
• Paola Semeraro,
• Paola Fini and
• Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

• appears to be 1:1 for all examined CDs. Keywords: cyclodextrins; inclusion complex; photodynamic therapy; Introduction Since several years, supramolecular chemistry has been considered the chemistry of the intermolecular bonds inducing the association of several chemical species with the formation of

• photodynamic therapy (PDT) applications [19]. Some authors of this paper have extensively studied the behavior of several PSs in the presence of CDs [19][20] highlighting the important role of the latter. Interestingly, among PSs the use of thiobases has emerged as a novel approach for PDT applications in

• potential method to improve/change the photochemical behavior of the thiobase. In particular, the protection of S4TdR, as photosensitizer, from degradation through reactive oxygen species during photodynamic therapy applications could be attained in the presence of all analyzed CDs. A study in this

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• sorting, in photodynamic therapy and in colorimetric enzymatic tests (ELISA). Although it is possible to modify xanthene dyes with specific functional groups (e.g., isothiocyanates, maleimide, succinimidyl), enabling them to react with amine groups, such chemical modifications dramatically affect the cost

Smart molecules for imaging, sensing and health (SMITH)

• Bradley D. Smith

Beilstein J. Org. Chem. 2015, 11, 2540–2548, doi:10.3762/bjoc.11.274

• led us to pursue molecular imaging of microbial infection, an unsolved research problem of high biomedical significance. We demonstrated targeted optical imaging of bacterial infection in animal models and subsequently developed optical probes for photodynamic therapy of bacterial infection [19][20

• receptors on the surface of cancer cells. We are hopeful that the probes will be useful for therapeutic applications such as fluorescence-guided surgery and intra-operative photodynamic therapy. Life as an academic supramolecular chemist This is my 25th year at the University of Notre Dame, which is located

Synthesis and spectroscopic properties of β-triazoloporphyrin–xanthone dyads

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2015, 11, 1434–1440, doi:10.3762/bjoc.11.155

• photoelectric materials [7][8]. In addition, porphyrins are potentially used as photosensitizers in photodynamic therapy to treat various types of tumors [9][10]. In recent years, many hybrid molecules including porphyrin–C60 [11], porphyrin–quinones [12] and porphyrin–cyclodextrin [13] conjugates were

• xanthones, it was contemplated to incorporate these heterocyclic scaffolds in a single molecular framework to construct novel β-triazolo–porphyrin–xanthone conjugates and their diporphyrin analogues which may prove useful as photosensitizers for photodynamic therapy applications. Results and Discussion In

Efficient deprotection of F-BODIPY derivatives: removal of BF₂ using Brønsted acids

• Mingfeng Yu,
• Joseph K.-H. Wong,
• Cyril Tang,
• Peter Turner,
• Matthew H. Todd and
• Peter J. Rutledge

Beilstein J. Org. Chem. 2015, 11, 37–41, doi:10.3762/bjoc.11.6

• ; Findings Compounds incorporating the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (F-BODIPY) motif 1 have found widespread use in fluorescent molecular probes [1][2], photovoltaic devices [3][4] and photodynamic therapy agents [5][6][7][8]. Accordingly, there is considerable interest in extending and

A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry

• Chrysie Aggelidou,
• Theodossis A. Theodossiou,
• Antonio Ricardo Gonçalves,
• Mariza Lampropoulou and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 2414–2420, doi:10.3762/bjoc.10.251

• , molecular/drug carrier with the capacity to undergo intracellular transformation into protoporphyrin IX (PpIX), an endogenous powerful photosensitizer for photodynamic therapy (PDT). The water-soluble derivative 2 was prepared by esterifying δ-azidolevulinic acid with heptakis(6-hydroxyethylamino-6-deoxy)-β

• in terms of water solubility and lack of aggregation. Keywords: cyclodextrins; PDT; protoporphyrin IX; prodrug; δ-aminolevulinic acid; Introduction Porphyrins have long been used as agents for tumor photodiagnosis (PDD) and photodynamic therapy (PDT) because of their preferential accumulation in

First synthesis of meso-substituted pyrrolo[1,2-a]quinoxalinoporphyrins

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2014, 10, 808–813, doi:10.3762/bjoc.10.76

• of biologically important functional groups were also introduced on the periphery of meso-substituted porphyrins to develop efficient photosensitizers for photodynamic therapy applications [41][42][43]. However, the porphyrins with a pyrrolo[1,2-a]quinoxaline moiety at the meso-positions have not

From porphyrin benzylphosphoramidate conjugates to the catalytic hydrogenation of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin

• Marcos C. de Souza,
• Leandro F. Pedrosa,
• Géssica S. Cazagrande,
• Vitor F. Ferreira,
• Maria G. P. M. S. Neves and
• José A. S. Cavaleiro

Beilstein J. Org. Chem. 2014, 10, 628–633, doi:10.3762/bjoc.10.54

• hydrogenation; chlorin; isobacteriochlorin; phosphoramidate; porphyrin; Introduction The use of porphyrin derivatives as photosensitizers is considered for the photodynamic therapy (PDT) of malignant tumors and the treatment of age-related macular degeneration in several countries [1][2]. It is already known

Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins

• Satyasheel Sharma and
• Mahendra Nath

Beilstein J. Org. Chem. 2013, 9, 496–502, doi:10.3762/bjoc.9.53

• derivatives has emerged as one of the major areas of research due to the success of these molecules for the eradication of malignant cells by photodynamic therapy (PDT) after their selective accumulation [7][8][9][10] in neoplastic tissues. In addition, the low dark-toxicity profile, easy removal from the

Molecular solubilization of fullerene C₆₀ in water by γ-cyclodextrin thioethers

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2012, 8, 1644–1651, doi:10.3762/bjoc.8.188

• synthesized and utilized for the inhibition of therapeutically important enzymes, such as HIV-1 protease [12], for the prevention of bacterial growth [13][14], or for photodynamic therapy of cancer by scission of DNA [3]. Despite these successes, there are still several issues relating to the chemical

• solvents will hopefully find interesting applications in biomedicine, such as in photodynamic therapy or HIV-protease inhibition. Experimental General Unless otherwise stated, all chemicals were used as received. Powdered fullerene C60 (> 99%) was purchased from Sigma Aldrich. Teflon syringe filters from

Fine-tuning alkyne cycloadditions: Insights into photochemistry responsible for the double-strand DNA cleavage via structural perturbations in diaryl alkyne conjugates

• Wang-Yong Yang,
• Samantha A. Marrone,
• Nalisha Minors,
• Diego A. R. Zorio and
• Igor V. Alabugin

Beilstein J. Org. Chem. 2011, 7, 813–823, doi:10.3762/bjoc.7.93

• time. Such selectivity is particularly useful in biological applications such as cancer therapy where it accounts for the increasing importance of photodynamic therapy and related methods [1][2][3][4][5][6][7][8][9][10][11]. Previously, we expanded our studies of alkyne reactivity [12][13][14][15][16

Surfactant catalyzed convenient and greener synthesis of tetrahydrobenzo[a]xanthene-11-ones at ambient temperature

• Pravin V. Shinde,
• Amol H. Kategaonkar,
• Bapurao B. Shingate and
• Murlidhar S. Shingare

Beilstein J. Org. Chem. 2011, 7, 53–58, doi:10.3762/bjoc.7.9

• application as antagonists for inhibiting the action of zoxalamine and in photodynamic therapy [9][10]. In addition, their derivatives can be used as dyes [11][12], pH sensitive fluorescent materials for the visualization of biomolecular assemblies [13] and in laser technologies [14][15]. Among the xanthene

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32