Enzymatic Aminopropylation of Certain Secondary Amines.

Shirahata, Akira; Hosoda, Harumi; Takahashi, Norio; Beppu, Takanobu; Niitsu, Masaru; Samejima, Keijiro

doi:10.1248/bpb.18.355

Cited by 4 publications

(2 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…, as well as 1,19-diamino-5,10,15-triazanonadecane (4-4-4-4) were synthesized as described earlier (29)(30)(31). The structures of all spermidine analogs were confirmed by elemental analysis as well as NMR, HPLC and Mass spectrometry.…”

Section: Chemicals and Oligonucleotidesmentioning

confidence: 99%

Effects of natural and synthetic polyamines on the conformation of an oligodeoxyribonucleotide with the estrogen response element

Thomas

Kulkarni²,

Gallo

et al. 1997

Nucleic Acids Research

View full text Add to dashboard Cite

We studied the effects of natural and synthetic polyamines on the conformation of an oligodeoxyribonucleotide (ODN1) harboring the estrogen response element (ERE) by circular dichroism (CD) spectroscopy and polyacrylamide gel electrophoresis. Putrescine and spermidine had no marked effect on the CD spectrum of ODN1. In contrast, spermine provoked and stabilized two characteristic changes in the CD spectrum. The first change was indicated by an increase in the intensity of the CD band at 280 nm at 0.5 mM spermine in Tris-HCl buffer containing 50 mM NaCl. This change appears to be related to changes in base tilt and conformational alterations similar to A-DNA. At 1-2 mM spermine, the CD spectrum was characterized by a loss of positive bands at 220 and 270 nm. This change might have contributions from polyamine-induced condensation/aggregation of DNA. Spectral measurements were also conducted in Tris-HCl buffer containing 150 mM NaCl to minimize contributions from condensation and aggregation of ODN1. Under these conditions, CD spectral changes were retained by (ODN1), although the magnitude of the change was diminished. In contrast, a control oligdeoxyribonucleotide (ODN2) having similar base composition did not show any significant change in the CD spectrum in the presence of 150 mM NaCl and 2 mM spermine. The changes in the CD spectrum of ODN1 were highly sensitive to polyamine structure, as evidenced by experiments using spermine analogs with altered number of -CH2- groups separating the amino and imino groups. Electrophoretic mobility shift analysis further showed ODN1 stabilization by spermine and its analogs. These data demonstrate the ability of an ODN containing ERE to undergo conformational transitions in the presence of polyamines and suggest a possible mechanism for polyamine-mediated alterations in the interaction of estrogen receptor with ERE.

show abstract

Section: Chemicals and Oligonucleotidesmentioning

confidence: 99%

Effects of natural and synthetic polyamines on the conformation of an oligodeoxyribonucleotide with the estrogen response element

Thomas

Kulkarni²,

Gallo

et al. 1997

Nucleic Acids Research

View full text Add to dashboard Cite

show abstract

“…(4-N-3-APAMPP) were synthesized by us [24][25][26]. Others were synthesized according to the method for spermidine using N-methyl- Figure 1 Chemical structures of spermidine and its analogues used in this study N-(3-bromopropyl)toluene sulphamide (for N"-methylspermidine) or cyclohexylamine instead of benzylamine (for N%-cyclohexylspermidine).…”

Section: Experimental Polyaminesmentioning

confidence: 99%

Structural specificity effects of trivalent polyamine analogues on the stabilization and conformational plasticity of triplex DNA

Kulkarni¹,

Greenfield

Shirahata

et al. 1996

Biochemical Journal

Self Cite

View full text Add to dashboard Cite

Natural polyamines, i.e. putrescine, spermidine and spermine, are excellent promoters of triplex DNA. Using melting temperature (Tm) measurements and CD spectroscopy, we found that structural alterations on spermidine backbone, including methylation, or acetylation at the N1-, N4- and/or N8-positions had a profound influence on the stability and conformation of poly(dA).2poly(dT) triplex. The conformation of the polynucleotide complex underwent sequential changes from B-DNA to triplex DNA as the concentration of spermidine increased from 0 to 50 microM in a buffer containing 10 mM sodium cacodylate and 1 mM EDTA (pH 7.2). At 60 microM spermidine, the CD spectrum of triplex DNA was comparable with that of psi-DNA, with a strong positive band centred around 260 nm. A negative band was also found at 295 nm. At higher concentrations of spermidine, however, the intensity of the positive band progressively decreased and the peak intensity was found at a 1:0.3 molar ratio of DNA phosphate:spermidine. Temperature-dependent CD analysis showed that the psi-DNA structure melted to single-stranded DNA at temperatures above the Tm determined from the absorbance versus temperature profile. Comparable effects were exerted on the conformation of triplex DNA by Co(NH3)6(3+), an inorganic trivalent cation. Substitution of the N4-hydrogen of spermidine by a cyclohexyl ring or the fusion of the N4-nitrogen in a cyclic ring system, as in piperidine, enhanced the ability of spermidine analogues to stabilize triplex and psi-DNA forms over a wider concentration range compared with spermidine. These data demonstrate a differential effect of trivalent cations in stabilizing triplex DNA and provoking unusual conformations such as psi-DNA. Synthetic homologues of spermidine that stabilize triplex DNA over a wider range of concentrations than that stabilized by spermidine itself might have potential therapeutic applications in the development of an anti-gene strategy against several diseases, including cancer and AIDS.

show abstract

1H, 13C, 15N NMR and nJ(C, H) coupling constants investigation of 3-piperidino-propylamine: A combined experimental and theoretical study

Şenyel

Alver

Parlak

2008

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

View full text Add to dashboard Cite

Enzymatic Aminopropylation of Certain Secondary Amines.

Cited by 4 publications

References 1 publication

Effects of natural and synthetic polyamines on the conformation of an oligodeoxyribonucleotide with the estrogen response element

Effects of natural and synthetic polyamines on the conformation of an oligodeoxyribonucleotide with the estrogen response element

Structural specificity effects of trivalent polyamine analogues on the stabilization and conformational plasticity of triplex DNA

1H, 13C, 15N NMR and nJ(C, H) coupling constants investigation of 3-piperidino-propylamine: A combined experimental and theoretical study

Contact Info

Product

Resources

About