The conformational effect of para-substituted C8-arylguanine adducts on the B/Z-DNA equilibrium

Vongsutilers, Vorasit; Phillips, Daniel J.; Train, Brian C.; McKelvey, Gregory R.; Thomsen, Nissa M.; Shaughnessy, Kevin H.; Lewis, James P.; Gannett, Peter M.

doi:10.1016/j.bpc.2010.12.006

Cited by 20 publications

(57 citation statements)

References 48 publications

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“…Over the years, various C8-modifications have been developed to provide B-to Z-DNA transitions, including amino fluorene, amino biphenyl and a series of C8-para-substituents containing phenylguanine (Fig. 2) [78,79]. Particularly in the case of varied C8-para-substituted phenylguanine, para-substituents not only increase steric hindrance but also lead to distortion in the helix backbone and alteration of relative hydration.…”

Section: Chemical Modificationsmentioning

confidence: 99%

Advancements in Z-DNA: Development of Inducers and Stabilizers for B to Z Transition

Yang¹,

Wang²,

Tian³

et al. 2012

CMC

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Z-DNA, an active element in genome, has drawn intense interest in chemical and biological field. Its dynamic and transient state makes it challenging to target and regulate. Thus, stabilizing and inducing Z-DNA both in vitro and in vivo is essential, so far, much many efforts have been made in these aspects. However, Z-DNA's induction and stabilization are always performed in high salt condition and sequence-dependent, limited inducers or stabilizers have been achieved with breakthrough in the aspects of real physiological condition and sequence-independence. Herein, we give a review of some typical kinds of Z-DNA inducers and stabilizers, discussing their inducing or stabilizing condition, mechanism, structural relationship and their limitation as well, attempted to get some implication and guidance for Z-DNA inducer or stabilizer design.

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Section: Chemical Modificationsmentioning

confidence: 99%

Advancements in Z-DNA: Development of Inducers and Stabilizers for B to Z Transition

Yang¹,

Wang²,

Tian³

et al. 2012

CMC

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“…There have been several amine protecting groups that have been used to protect the free amine group on the guanine ring and standard guanine phosphoramidites use an isobutyryl moiety. However the addition of a C8-aryl group onto the 2'deoxyguanosine renders the nucleoside more susceptible to acid cleavage and our group, along with another group, have demonstrated that protection using a N,N-dimethylformamidine 100,125,130 creates a more stable C8-aryl-2'-deoxyguanosine nucleoside, which is important in subsequent nucleosidic functionalization reactions as well as during DNA synthesis. Reaction with C8-aryl- Unlike the previous two reactions in the C8-aryl-2'-deoxyguanine phosphoramidite synthetic scheme, this reaction product requires purification before the phosphitylation reaction.…”

Section: B C8-aryl-2'-deoxyguanosine Protection and Functionalizationmentioning

confidence: 79%

“…Previous work in our laboratory has investigated the conformational effects of C8arylguanine modified bases on the B-/Z-DNA equilibrium. [98][99][100] In addition our group has also demonstrated expertise in the synthesis of C8-aryl-2'-deoxyguanine modified nucleoside to produce C8-aryl-2'-deoxyguanine analogs with various para-substituents on the C8-aryl modification that can be incorporated into oligonucleotide sequences. 125 In general, the C8-aryl-2'-deoxyguanine modified nucleoside synthesis begins with 8-bromo-2'-deoxyguanosine synthesis prepared from 2'-deoxyguanosine and NBS which is further used in the Suzuki coupling reaction with an arylboronic acid to make C8-aryl-2'-deoxyguanosine.…”

Section: Chapter 3: Experimental Techniques and Resultsmentioning

confidence: 99%

“…83 Recently we demonstrated that the C8-arylguanine modification shift the B-/Z-DNA equilibrium toward the Z-DNA conformation. [98][99][100] This modification was incorporated into d(CG)5 sequences (d(CGCGCG*CGCG) where G* = C8-arylguanine, Figure 1.3). The modified bases were shown to drive Z-DNA formation because they generate unfavorable steric and/or electronic interactions with the phosphate backbone when in the B-DNA conformation.…”

Section: The Effect Of Arylhydrazines On the B-/z-dna Equilibriummentioning

confidence: 99%

“…The combination of the COSY and NOESY NMR experiments can be used to assign the resonances of the B-DNA and Z-DNA conformations of C8-arylguanine modified hairpin oligonucleotides in a fashion similar to previously studied double-stranded oligonucleotides. 98,100 Hairpin oligonucleotides have also been studied in both the B-and Z-DNA conformations 120,121 and have been shown to behave similarly to their double-stranded oligonucleotides without a loop (e.g., (d(CG)n)2 vs.…”

Section: Nmr Of B-and Z-dnamentioning

confidence: 99%

See 2 more Smart Citations

C8-Arylguanine Modified Hairpin Oligonucleotides: Synthesis, Conformational Analysis, and Tools for the Investigation of Z-DNA Formation

Train¹

Self Cite

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Gannett, for helping me and guiding me throughout my dissertation work. His unyielding encouragement, patience, and understanding combined with his incredible intellect and knowledge facilitated and enhanced my comprehension of my research project. I will able to use the skills that I learned in graduate school not only in my next position but for the rest of my life. Thank you. Thank you to my dissertation committee members, Dr.

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The Cucurbit[7]Uril‐Based Supramolecular Chemistry for Reversible B/Z‐DNA Transition

Wang

et al. 2018

Advanced Science

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As a left‐handed helical structure, Z‐DNA is biologically active and it may be correlated with transcription and genome stability. Until recently, it remained a significant challenge to control the B/Z‐DNA transition under physiological conditions. The current study represents the first to reversibly control B/Z‐DNA transition using cucurbit[7]uril‐based supramolecular approach. It is demonstrated that cucurbit[7]uril can encapsulate the central butanediamine moiety [HN(CH2)4NH] and reverses Z‐DNA caused by spermine back to B‐DNA. The subsequent treatment with 1‐adamantanamine disassembles the cucurbit[7]uril/spermine complex and readily induces reconversion of B‐ into Z‐DNA. The DNA conformational change is unequivocally demonstrated using different independent methods. Direct evidence for supramolecular interactions involved in DNA conformational changes is further provided. These findings can therefore open a new route to control DNA helical structure in a reversible way.

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The conformational effect of para-substituted C8-arylguanine adducts on the B/Z-DNA equilibrium

Cited by 20 publications

References 48 publications

Advancements in Z-DNA: Development of Inducers and Stabilizers for B to Z Transition

Advancements in Z-DNA: Development of Inducers and Stabilizers for B to Z Transition

C8-Arylguanine Modified Hairpin Oligonucleotides: Synthesis, Conformational Analysis, and Tools for the Investigation of Z-DNA Formation

The Cucurbit[7]Uril‐Based Supramolecular Chemistry for Reversible B/Z‐DNA Transition

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