Enhancement of cell uptake and antitumor activity of selenadiazole derivatives through interaction and delivery by serum albumin

Deng, Shulin; Zeng, Delong; Luo, Yi; Zhao, Jun; Li, Xiaoling; Zhao, Zhennan; Tianfeng, Chen

doi:10.1039/c6ra28801d

Cited by 16 publications

(13 citation statements)

References 51 publications

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“…The majority of examples have the selenadiazole molecules disposed about a centre of inversion. In four examples, that is 16 [73], 19 [73], 23 [69] and 35 [77], two independent molecules comprise the crystallographic asymmetric-unit and these are connected into a supramolecular dimer. There is a single example, that is 12 [69], where there are two independent molecules and each of these selfassociates about a centre of inversion.…”

Section: Two-molecule Aggregates Featuring Two Se … N Interactions: Selenadiazole Ringsmentioning

confidence: 99%

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Tiekink

2021

Coordination Chemistry Reviews

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An evaluation of the Cambridge Structural Database for crystals containing Se … N secondary--bonding interactions was conducted. The presence of Se … N secondary-bonding interactions has been established in nearly 9% of crystals of mono-nuclear selenium compounds where such interactions can potentially form, that is, having at least one nitrogen atom. The Se … N interactions feature in 71 zero-dimensional, usually di-nuclear aggregates, 63 one-dimensional chains and tapes, and smaller numbers of two-and three-dimensional arrays, that is seven and one, respectively. Selenium(II) compounds form the majority of the dataset with only eight selenium(IV) compounds included in the survey. In most cases (112 out of 142), the selenium centre forms a single Se … N contact with 26 aggregates having a selenium atom forming two contacts and four examples where three Se … N contacts are evident. The great propensity of selenadiazole rings (75%) and selenocyanates (50%) to form Se … N secondary-bonding interactions in their crystals is particularly noteworthy.

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Section: Two-molecule Aggregates Featuring Two Se … N Interactions: Selenadiazole Ringsmentioning

confidence: 99%

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Tiekink

2021

Coordination Chemistry Reviews

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“…Furthermore, it inhibited U87 tumor (glioblastoma) spheroids growth in vitro and prolonged blood circulation time . Several alkyl benzo[ c ][1,2,5]selenadiazole-5-carboxylates were prepared and found to have a moderate activity (the lowest IC 50 being 28 μM) in several cancer cell lines . More importantly, it was found that 1,2,5-selenadiazoles bind to bovine serum albumin (BSA) through lipophilic interactions, improving cellular uptake .…”

Section: 25-selenadiazolesmentioning

confidence: 99%

Development and Therapeutic Potential of Selenazo Compounds

et al. 2019

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Incorporation of selenium (Se) atom into small molecules can substantially enhance their antioxidant, antiinflammatory, antimutagenic, antitumoral or chemopreventive, antiviral, antibacterial, antifungal, antiparasitic, and neuroprotective effects. Specifically, selenazo compounds have received great attention owing to their chemical properties, pharmaceutical applications, and low toxicity. In this Perspective, we compile extensive literature evidence with the description and discussion of the most recent advances in different selenazo and selenadiazo motifs as potential pharmacological candidates. We also provide some perspectives on the challenges and future directions in the advancement of these selenazo compounds, each of which could generate drug candidates for various diseases.

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“…Chalcogenides are compounds containing one or more chalcogen elements and have an important role to play in biology and, in particular,i nh uman health and the human body.S elenium, in the form of selenocysteine and the sec unit in the proteins (peptides), plays an important enzymatic antioxidant role in the body.R ecent advances have revealed thath eterocyclic selenium-containing compounds are important for biological activities, such as antibacterial,a nti-inflammatory,a ntitumor,a nd for ROS/RNS sensing. [29][30][31][32][33][34][35][36][37] In this part, we are reviewing recent progress to synthesize chalcogen-based chemosensors and their photophysical underpinnings. This work focuses on small chromophoric or fluorophoricm olecules, which are incorporated with organochalcogen atoms (e.g.,R -S-R, R-Se-R, R-Te-R).…”

Section: Oxidation Of Organochalogen To Their Tetravalent (E = O) Oxidesmentioning

confidence: 99%

“…Selenium, in the form of selenocysteine and the sec unit in the proteins (peptides), plays an important enzymatic antioxidant role in the body. Recent advances have revealed that heterocyclic selenium‐containing compounds are important for biological activities, such as antibacterial, anti‐inflammatory, antitumor, and for ROS/RNS sensing . In this part, we are reviewing recent progress to synthesize chalcogen‐based chemosensors and their photophysical underpinnings.…”

Section: Introductionmentioning

confidence: 99%

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

Yudhistira

Mulay

Kim

et al. 2019

Chemistry An Asian Journal

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In recent decades, HOCl research has attracted a lot of scientists from around the world. This chemical species is well known as an important player in the biological systems of eukaryotic organisms including humans. In the human body, HOCl is produced by the myeloperoxidase enzyme from superoxide in very low concentrations (20 to 400 μm); this species is secreted by neutrophils and monocytes to help fight pathogens. However, in the condition called “oxidative stress”, HOCl has the capability to attack many important biomolecules such as amino acids, proteins, nucleotides, nucleic acids, carbohydrates, and lipids; these reactions could ultimately contribute to a number of diseases such as neurodegenerative diseases (AD, PD, and ALS), cardiovascular diseases, and diabetes. In this review, we discuss recent efforts by scientists to synthesize various fluorophores which are attached to receptors to detect HOCl such as: chalcogen‐based oxidation, oxidation of 4‐methoxyphenol, oxime/imine, lactone ring opening, and hydrazine. These synthetic molecules, involving rational synthetic pathways, allow us to chemoselectively target HOCl and to study the level of HOCl selectivity through emission responses. Virtually all the reports here deal with well‐defined and small synthetic molecular systems. A large number of published compounds have been reported over the past years; this growing field has given scientists new insights regarding the design of the chemosensors. Reversibility, for example is considered important from the stand point of chemosensor reuse within the biological system; facile regenerability using secondary analytes to obtain the initial probe is a very promising avenue. Another aspect which is also important is the energy of the emission wavelength of the sensor; near‐infrared (NIR) emission is favorable to prevent autofluorescence and harmful irradiation of tissue; thus, extended applicability of such sensors can be made to the mouse model or animal model to help image internal organs. In this review, we describe several well‐known types of receptors that are covalently attached to the fluorophore to detect HOCl. We also discuss the common fluorophores which are used by chemist to detect HOCl, Apart from the chemical aspects, we also discuss the capabilities of the compounds to detect HOCl in living cells as measured through confocal imaging. The growing insight from HOCl probing suggests that there is still much room for improvement regarding the available molecular designs, knowledge of interplay between analytes, biological applicability, biological targeting, and chemical switching, which can also serve to further sensor and theurapeutic agent development alike.

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Enhancement of cell uptake and antitumor activity of selenadiazole derivatives through interaction and delivery by serum albumin

Abstract: A series of selenadiazole derivatives has been synthesized and exhibit potent anticancer efficacy through interaction and delivery by serum albumin.

Cited by 16 publications

References 51 publications

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Supramolecular aggregation patterns featuring Se⋯N secondary-bonding interactions in mono-nuclear selenium compounds: A comparison with their congeners

Development and Therapeutic Potential of Selenazo Compounds

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

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