Studies on structure of kinetin riboside and its analogues by variable-temperature NMR

Baranowski, Daniel; Framski, Grzegorz; Wyszko, Eliza; Ostrowski, Tomasz

doi:10.1016/j.molstruc.2019.05.112

Cited by 5 publications

(9 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The KR derivatives were synthesized according to the protocol described by Baranowski et al [33]. Chemical structures of the compounds were drawn using ACD/ChemSketch (2017) Freeware.…”

Section: Synthesis Of 8-azakr and 7-deazakrmentioning

confidence: 99%

“…The presence of the furfuryl group at N 6 of 8-azaKR would most likely prevent the deamination reaction, which could contribute to increased potency of 8-azaKR inside the cells in comparison to 8-azaadenosine. Derivatives of KR were obtained according to the previously reported procedure for the synthesis [33] (Figure 2C-E).…”

Section: Determination Of Kr Analogues Showing Similar Affinity For Adkmentioning

confidence: 99%

See 1 more Smart Citation

Implications of Oxidative Stress in Glioblastoma Multiforme Following Treatment with Purine Derivatives

et al. 2021

Self Cite

View full text Add to dashboard Cite

Recently, small compound-based therapies have provided new insights into the treatment of glioblastoma multiforme (GBM) by inducing oxidative impairment. Kinetin riboside (KR) and newly designed derivatives (8-azaKR, 7-deazaKR) selectively affect the molecular pathways crucial for cell growth by interfering with the redox status of cancer cells. Thus, these compounds might serve as potential alternatives in the oxidative therapy of GBM. The increased basal levels of reactive oxygen species (ROS) in GBM support the survival of cancer cells and cause drug resistance. The simplest approach to induce cell death is to achieve the redox threshold and circumvent the antioxidant defense mechanisms. Consequently, cells become more sensitive to oxidative stress (OS) caused by exogenous agents. Here, we investigated the effect of KR and its derivatives on the redox status of T98G cells in 2D and 3D cell culture. The use of spheroids of T98G cells enabled the selection of one derivative—7-deazaKR—with comparable antitumor activity to KR. Both compounds induced ROS generation and genotoxic OS, resulting in lipid peroxidation and leading to apoptosis. Taken together, these results demonstrated that KR and 7-deazaKR modulate the cellular redox environment of T98G cells, and vulnerability of these cells is dependent on their antioxidant capacity.

show abstract

“…The KR derivatives were synthesized according to the protocol described by Baranowski et al [33]. Chemical structures of the compounds were drawn using ACD/ChemSketch (2017) Freeware.…”

Section: Synthesis Of 8-azakr and 7-deazakrmentioning

confidence: 99%

Section: Determination Of Kr Analogues Showing Similar Affinity For Adkmentioning

confidence: 99%

Implications of Oxidative Stress in Glioblastoma Multiforme Following Treatment with Purine Derivatives

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…A convenient method for the preparation of triazolo [4,5-d]pyrimidine-7-amine 105 was heating aminonitrile 104 in an excess of diethylme-thylamine (DEMA) followed by the treatment with ammonia in MeOH (Scheme 35) [67].…”

Section: The Cyclocondensation Of Triazolilaminonitritesmentioning

confidence: 99%

1,2,3-Triazole-4(5)-amines – Convenient Synthetic Blocks for the Construction of Triazolo-Annulated Heterocycles

СИРОТА

Kemskiy

Saliyeva

et al. 2022

J. Org. Pharm. Chem.

View full text Add to dashboard Cite

Aim. To analyze and summarize the synthetic potential of 1,2,3-triazole-4(5)-amines as efficient building blocks in the synthesis of triazolo-annulated pyridine, azine and azepine systems.Results and discussion. Original literature sources revealing the synthetic potential of 4(5)-amino functionalized 1,2,3-triazoles as convenient and available building blocks for the preparation of triazolo-annulated pyridines, azines and azepines were analyzed and systematized. Condensation of 1,2,3-triazole-4(5)-amines with methylene active compounds was shown to be a powerful tool for the synthesis of versatile triazolo[4,5-b]pyridines. In turn, the cyclocondensation based on 5-amino-1,2,3-triazole-4-carboxylic acids and their structurally modified derivatives was proven to be a general way for obtaining a number of triazolo[4,5-d]pyrimidine systems. Few representatives of triazolo-annulated pyridazines, 1,3-oxazines and 1,3-thiazines were synthesized by the intramolecular cyclization of the corresponding 4-aryl(carboxy-, aminomethyl)-5-amino-1,2,3-triazoles. The cyclocondensation involving 4,5-diamino-, 4-carbofunctionalized 5-amino-1,2,3-triazoles and 4-amino-5-thiocarboxamido-1,2,3-triazoles was successful for the construction of di-, oxa- and thiazepino-annulated triazoles.Conclusions. The analysis, systematization and summary of the literature regarding the synthetic potential of 1,2,3-triazole-4(5)-amines conclusively demonstrate that these structures are easily available and convenient molecular blocks for the construction of triazolo-annulated pyridine, azine and azepine systems that are important for synthetic and biomedical research.

show abstract

“…N 6 -substituted adenines and adenosine nucleosides are characterized by the phenomenon of amino-imino tautomerism (Figure 1) [6][7][8][9][10]. It has been reported that the amino form of adenine is absolutely dominant in solution; however, additional substitution can shift the tautomeric amino-imino equilibrium [11]. The introduction of an electronwithdrawing substituent at the C2 position of the purine shifts the equilibrium towards the amino form.…”

Section: Introductionmentioning

confidence: 99%

“…The presence of the second form in NMR was detected for kinetin and its derivatives [11,12]. Novotna et al suggested that 2-chloro-N 6 -furfuryl-adenosine exists in two forms: amino and imino tautomers at room temperature in a solution.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Hydrogen Bonding in N6-Substituted 2-Chloroadenosines: Evidence from NMR Spectroscopy

Berzina,

Eletskaya,

Kayushin

et al. 2023

IJMS

View full text Add to dashboard Cite

Two forms were found in the NMR spectra of N6-substituted 2-chloroadenosines. The proportion of the mini-form was 11–32% of the main form. It was characterized by a separate set of signals in COSY, 15N-HMBC and other NMR spectra. We assumed that the mini-form arises due to the formation of an intramolecular hydrogen bond between the N7 atom of purine and the N6–CH proton of the substituent. The 1H,15N-HMBC spectrum confirmed the presence of a hydrogen bond in the mini-form of the nucleoside and its absence in the main form. Compounds incapable of forming such a hydrogen bond were synthesized. In these compounds, either the N7 atom of the purine or the N6–CH proton of the substituent was absent. The mini-form was not found in the NMR spectra of these nucleosides, confirming the importance of the intramolecular hydrogen bond in its formation.

show abstract

Studies on structure of kinetin riboside and its analogues by variable-temperature NMR

Cited by 5 publications

References 19 publications

Implications of Oxidative Stress in Glioblastoma Multiforme Following Treatment with Purine Derivatives

Implications of Oxidative Stress in Glioblastoma Multiforme Following Treatment with Purine Derivatives

1,2,3-Triazole-4(5)-amines – Convenient Synthetic Blocks for the Construction of Triazolo-Annulated Heterocycles

Intramolecular Hydrogen Bonding in N6-Substituted 2-Chloroadenosines: Evidence from NMR Spectroscopy

Contact Info

Product

Resources

About