“…Axial binding of cytosine via N3 (Chart , structure c) to Rh 2 (HNCOCH 3 ) 4 units is stabilized by formation of hydrogen bonds between the exocyclic NH 2 (4), O2 sites, and the tetraamidate cage . Similarly, in diplatinum(III,III)−guanine ax adducts, the guanine O6 and the NH 3 groups of the dimetal unit engage in hydrogen bonding interactions (Figure ). − Axial binding of adenine and adenosine via N9/N3 and N7, respectively, has been proposed for their adducts with tetraacetatodiruthenium(II,III), but the compounds have not been structurally characterized 2 3 Molecular structure of Rh 2 (μ-O 2 CCH 3 ) 4 (1-MeAdo) 2 . 4 Molecular structure of trans- [Rh 2 (μ-O 2 CCH 3 ) 2 (μ-NHCOCF 3 ) 2 (9-EtGuaH) 2 ].…”
Section: Interactions With Nucleobases and Nucleos(t)idesmentioning
This Account summarizes the DNA binding properties of anticancer active dinuclear Rh, Re, and Ru compounds. The combined results of NMR spectroscopy, X-ray crystallography, and various biochemical tools provide incontrovertible evidence that dinuclear complexes are favorably poised to bind to purine nucleobases, DNA fragments, and double-stranded DNA. Moreover, direct DNA photocleavage in vitro is effected by dirhodium compounds in the presence of electron acceptors in solution or directly attached to the dirhodium core. This research has provided valuable insight in the interactions of dinuclear compounds with DNA, knowledge that is an excellent backdrop for rational design of promising dinuclear drugs.
“…Axial binding of cytosine via N3 (Chart , structure c) to Rh 2 (HNCOCH 3 ) 4 units is stabilized by formation of hydrogen bonds between the exocyclic NH 2 (4), O2 sites, and the tetraamidate cage . Similarly, in diplatinum(III,III)−guanine ax adducts, the guanine O6 and the NH 3 groups of the dimetal unit engage in hydrogen bonding interactions (Figure ). − Axial binding of adenine and adenosine via N9/N3 and N7, respectively, has been proposed for their adducts with tetraacetatodiruthenium(II,III), but the compounds have not been structurally characterized 2 3 Molecular structure of Rh 2 (μ-O 2 CCH 3 ) 4 (1-MeAdo) 2 . 4 Molecular structure of trans- [Rh 2 (μ-O 2 CCH 3 ) 2 (μ-NHCOCF 3 ) 2 (9-EtGuaH) 2 ].…”
Section: Interactions With Nucleobases and Nucleos(t)idesmentioning
This Account summarizes the DNA binding properties of anticancer active dinuclear Rh, Re, and Ru compounds. The combined results of NMR spectroscopy, X-ray crystallography, and various biochemical tools provide incontrovertible evidence that dinuclear complexes are favorably poised to bind to purine nucleobases, DNA fragments, and double-stranded DNA. Moreover, direct DNA photocleavage in vitro is effected by dirhodium compounds in the presence of electron acceptors in solution or directly attached to the dirhodium core. This research has provided valuable insight in the interactions of dinuclear compounds with DNA, knowledge that is an excellent backdrop for rational design of promising dinuclear drugs.
“…During 2015, six compounds which corresponded to the 5'-(N-aminoacyl)-sulfonamido-5'-deoxyadenosine (aaSoA) series (47-52), analogous to the aminoacyl-sulfamoyl adenosine compounds (aaSAs) and their peptidyl conjugates, were synthesized. The synthesis was based on coupling reactions ( via Mitsonobu reaction [61]), ammonolysis and oxidative chlorination, for obtain the different sulfamides that were used as precursors for the condensation and hydrogenolysis reactions, obtaining 5'- O -(N-L-aminoacyl)-sulfamoyl adenosines (aaSAs) (Fig. 12 ).…”
Section: Methods Of Synthesis Of Adenosine Derivatives Interaction Wmentioning
confidence: 99%
“…The reactions included couplings of glycosyl donor with 6-chloropurine giving rise to the first derivatives of such condensation. Then, these derivatives were subjected to condensation with 2,6-dichloro purine under Mitsunobu conditions [61] to produce derivatives of 2,6-dichloro purine, which were treated with 3-halobenzyl amines to give the corresponding products regioselectively substituted, resulting in the synthesis of homologated apio analogues of IB-MECA and Cl-IBMECA [60].…”
Section: Methods Of Synthesis Of Adenosine Derivatives Interaction Wmentioning
confidence: 99%
“…Chemical structure of adenosine derivative of tetraacetatodiruthenium (II, III) chloride (Source: Gangopadhyay et al [61]).…”
Since 1929, several researchers have conducted studies in relation to the nucleoside of adenosine (1) mainly distribution identifying, characterizing their biological importance and synthetic chemistry to which this type of molecule has been subjected to obtain multiple of its derivatives. The receptors that interact with adenosine and its derivatives, called purinergic receptors, are classified as A1, A2A, A2B and A3. In the presence of agonists and antagonists, these receptors are involved in various physiological processes and diseases. This review describes and compares some of the synthetic methods that have been developed over the last 30 years for obtaining some adenosine derivatives, classified according to substitution processes, complexation, mating and conjugation. Finally, we mention that although the concentrations of these nucleosides are low in normal tissues, they can increase rapidly in pathophysiological conditions such as hypoxia, ischemia, inflammation, trauma and cancer. In particular, the evaluation of adenosine derivatives as adjunctive therapy promises to have a significant impact on the treatment of certain cancers, although the transfer of these results to clinical practice requires a deeper understanding of how adenosine regulates the process of tumorigenesis.
“…For example, its reactions with adenine and adenosine were studied in aqueous solutions, and it was found that they yield the adducts of this metal scaffold with adenine (1 : 1) and adenosine (1 : 2). 16 The metalation of adenine pro-…”
This article provides an overview on the application of diruthenium(II,III) paddlewheel complexes for anticancer purposes. The use of this coordinative construct is indeed attractive because it provides for an excellent...
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