Design of a Gd‐<scp>DOTA</scp>‐Phthalocyanine Conjugate Combining <scp>MRI</scp> Contrast Imaging and Photosensitization Properties as a Potential Molecular Theranostic

Tekdaş, Duygu Aydın; Garifullin, Ruslan; Şentürk, Berna; Zorlu, Yunus; Gundogdu, Umut; Atalar, Ergin; Tekinay, Ayşe B.; Chernonosov, Alexander А.; Yerli, Yusuf; Dumoulin, Fabienne; Güler, Mustafa O.; Ahsen, Vefa; Gürek, Ayşe Gül

doi:10.1111/php.12332

Cited by 43 publications

(22 citation statements)

References 78 publications

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“…The amide-bond formation allows rapid access to Gd(III) complex functionalization but it strongly induces reduced thermodynamic stability while maintaining the same kinetic inertness as the GdDOTA complex [43]. The phthalocyanine-based PS has been linked to one particular GdDO3A-amide complex, ZnPht-1Gd (Figure 2a) [44]. This complex has exhibited low relaxivity (1.43 mM −1 •s −1 at 128 MHz) and the authors have proposed that this weak value could be due to the presence of the amide function on the arm that could block water access to the metallic center.…”

Section: Molecular Theranostic Agents With Combined Pdt and Mri Studiesmentioning

confidence: 99%

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Molecular Theranostic Agents for Photodynamic Therapy (PDT) and Magnetic Resonance Imaging (MRI)

Jenni

Sour

2019

Inorganics

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Magnetic resonance imaging (MRI) is a powerful non-invasive diagnostic tool that can provide important insights for medical treatment monitoring and optimization. Photodynamic therapy (PDT), a minimally invasive treatment for various types of tumors, is drawing increasing interest thanks to its temporal and spatial selectivity. The combination of MRI and PDT offers real-time monitoring of treatment and can give significant information for drug-uptake and light-delivery parameters optimization. In this review we will give an overview of molecular theranostic agents that have been designed for their potential application in MRI and PDT.

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Section: Molecular Theranostic Agents With Combined Pdt and Mri Studiesmentioning

confidence: 99%

“…Chemical structure of (a) ZnPht-1Gd[44] and (b) ZnPz-1Gd[45]; (c) phototoxic effect in WI-38 VA13 cells incubated with Zn-Pz-nGd (n = 1, 4, 8; 50 µM, 24 h) and irradiated by white light for 0 or 10 min. The same protocol was realized with Photofrin as a positive control.…”

mentioning

confidence: 99%

Molecular Theranostic Agents for Photodynamic Therapy (PDT) and Magnetic Resonance Imaging (MRI)

Jenni

Sour

2019

Inorganics

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“…Molecules of the tetrapyrrole family (e.g., porphyrin and phthalocyanine derivatives) are probably the most appealing chromophores for a vast array of photoactivated processes, such as phototherapy [1][2][3], photodiagnosis [4][5][6], photocatalysis [7,8], solar energy conversion [9,10], and also as photomaterials [11][12][13]. In particular, phthalocyanines largely fulfil a crucial optical requisite, necessary for photomedicinal applications, which is a strong absorption in near-infrared (NIR) spectral region (600-900 nm), as light in this region affords the deepest penetration in soft tissue.…”

Section: Introductionmentioning

confidence: 99%

“…Palladium-catalyzed carbonylation reactions were first described by Heck almost 40 years ago [38]. Since then, many developments have been reported [6,[39][40][41][42][43][44][45][46] and nowadays carbonylation has become an indispensable alternative to the classic organic synthesis of carbonyl compounds, including carboxylic acid derivatives (e.g., amides, esters) with valuable application in both industrial and fine chemistry. Among these reactions, aminocarbonylation [47][48][49][50], carried out using Ar-X substrates (X = I, Br, Cl, OTf, OTs, etc.…”

Section: Introductionmentioning

confidence: 99%

A New Tool in the Quest for Biocompatible Phthalocyanines: Palladium Catalyzed Aminocarbonylation for Amide Substituted Phthalonitriles and Illustrative Phthalocyanines Thereof

et al. 2018

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The amide peptide bond type linkage is one of the most natural conjugations available, present in many biological synthons and pharmaceutical drugs. Hence, aiming the direct conjugation of potentially biologically active compounds to phthalocyanines, herein we disclose a new strategy for direct modulation of phthalonitriles, inspired by an attractive synthetic strategy for the preparation of carboxamides based on palladium-catalyzed aminocarbonylation of aryl halides in the presence of carbon monoxide (CO) which, to our knowledge, has never been used to prepare amide-substituted phthalonitriles, the natural precursors for the synthesis of phthalocyanines. Some examples of phthalocyanines prepared thereof are also reported, along with their full spectroscopic characterization and photophysical properties initial assessment.

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“…The magnetization hysteresis loop further indicated the superparamagnetic nature of Gd/HA-SWCNTs ( Figure 4B). Chelated Gd compounds have been widely used as T 1 -CA in MRI; 8,9 owing to the presence of Gd on HA-SWCNTs, the nanocomposites can act as a T 1 CA for MRI.…”

Section: +mentioning

confidence: 99%

Hyaluronic acid-functionalized single-walled carbon nanotubes as tumor-targeting MRI contrast agent

Hou¹,

Zhang²,

Wang³

et al. 2015

IJN

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A tumor-targeting carrier, hyaluronic acid (HA)-functionalized single-walled carbon nanotubes (SWCNTs), was explored to deliver magnetic resonance imaging (MRI) contrast agents (CAs) targeting to the tumor cells specifically. In this system, HA surface modification for SWCNTs was simply accomplished by amidation process and could make this nanomaterial highly hydrophilic. Cellular uptake was performed to evaluate the intracellular transport capabilities of HA-SWCNTs for tumor cells and the uptake rank was HA-SWCNTs> SWCNTs owing to the presence of HA, which was also evidenced by flow cytometry. The safety evaluation of this MRI CAs was investigated in vitro and in vivo. It revealed that HA-SWCNTs could stand as a biocompatible nanocarrier and gadolinium (Gd)/HA-SWCNTs demonstrated almost no toxicity compared with free GdCl 3 . Moreover, GdCl 3 bearing HA-SWCNTs could significantly increase the circulation time for MRI. Finally, to investigate the MRI contrast enhancing capabilities of Gd/HA-SWCNTs, T 1 -weighted MR images of tumor-bearing mice were acquired. The results suggested Gd/HA-SWCNTs had the highest tumor-targeting efficiency and T 1 -relaxivity enhancement, indicating HA-SWCNTs could be developed as a tumor-targeting carrier to deliver the CAs, GdCl 3 , for the identifiable diagnosis of tumor.

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Design of a Gd‐DOTA‐Phthalocyanine Conjugate Combining MRI Contrast Imaging and Photosensitization Properties as a Potential Molecular Theranostic

Cited by 43 publications

References 78 publications

Molecular Theranostic Agents for Photodynamic Therapy (PDT) and Magnetic Resonance Imaging (MRI)

Molecular Theranostic Agents for Photodynamic Therapy (PDT) and Magnetic Resonance Imaging (MRI)

A New Tool in the Quest for Biocompatible Phthalocyanines: Palladium Catalyzed Aminocarbonylation for Amide Substituted Phthalonitriles and Illustrative Phthalocyanines Thereof

Hyaluronic acid-functionalized single-walled carbon nanotubes as tumor-targeting MRI contrast agent

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