CD Exciton Chirality Method: Schiff Base and Cyanine Dye-Type Chromophores for Primary Amino Groups

Gargiulo, Dario; Ikemoto, Norihiro; Odingo, Joshua; Bozhkova, N.; Iwashita, Takashi; Berova, Nina; Nakanishi, Koji

doi:10.1021/ja00088a012

Cited by 44 publications

(23 citation statements)

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“…5 The two nitrogen atoms appended to the 1,2-diaminocyclohexyl group adopt an equatorial orientation consistent with previous observations of Kwit and Gawronski 9,10 and Hodacova et al 11 The UV studies of the complex indicate a strong absorption at 305 nm (e = 24,500 dm À3 mol À1 cm À1 ) attributed to a combination of p-p* and n-p* excitations. [12][13][14] The observed absorption proved to be broader than that observed for 2,2 0 -bipyridine, consistent with exciton coupling between the two chromophores. The existence of the restricted orientation of the two organic chromophores was confirmed by the presence of a measurable Cotton effect ( Fig.…”

Section: Resultssupporting

confidence: 64%

“…Examination of the sign of the Cotton effect and the application of exciton theory indicates that the (S,S)-configured 1,2-diaminocyclohexane gives a positive (+) orientation of the two chromophores in keeping with previous studies. 5,9,14,15 To confirm that the solution orientation is consistent with the solid state, the CD spectrum of the solid crystalline product was also recorded as a KBr disc. While the De scale is meaningless in this case, the sign remains the same (albeit slightly red shifted) indicating a similar orientation of the two chromophores in solution to those in the solid state.…”

Section: Resultsmentioning

confidence: 99%

“…Similarly, an NOE cross peak was detected between the imine proton and the cyclohexane proton H 1 , again indicating a syn-conformation, in keeping with the X-ray structure and similar to previously reported compounds. 10,14 Upon the introduction of zinc(II), cadmium(II), cobalt-(II) or iron(II) cations to ligands L1, L2 and L3, it was found that, as the ligand strands are brought together to allow inter-ligand exciton coupling, the observed Cotton effect showed a significant increase. In contrast, the addition of metal ions to L4 did not give Figure 1.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Examination of the conformational restraints to a chiral diimine bridged 2,2′-bipyridine

Prabaharan

Oakes

Fletcher

et al. 2004

Tetrahedron: Asymmetry

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Section: Resultssupporting

confidence: 64%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Examination of the conformational restraints to a chiral diimine bridged 2,2′-bipyridine

Prabaharan

Oakes

Fletcher

et al. 2004

Tetrahedron: Asymmetry

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“…The resulting precipitate ®ltered, washed with ice cold water and dried to give acid (4a) (6.7 g, 82%) crystallised from ethyl acetate:petroleum ether (9:1) as colourless compound, mp 183 C (lit. mp 182±183 C), 23,25,26 analysed Scheme 2. , 1688, 1668, 1612, 1550, 1440, 1320, 1040, 960 Preparation of 5-(4-methoxy phenyl)-2E,4E-pentadienoic acid piperidine amide (8).…”

Section: Preparation Of 5-(4-methoxy Phenyl)-2e4e-pentadienoic Acid mentioning

confidence: 99%

Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities

Koul

Taneja

et al. 2000

Bioorganic & Medicinal Chemistry

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AbstractÐInhibitors of drug metabolism have important implications in pharmaco-toxicology and agriculture. We have reported earlier that piperine, a major alkaloid of black and long peppers inhibits both constitutive and inducible cytochrome P450 (CYP)-dependent drug metabolising enzymes. In the present study, an attempt has been made to prepare several novel synthetic analogues so as to relate various modi®cations in the parent molecule to the inhibition of CYP activities. Two types of mono-oxygenase reactions arylhydrocarbon hydroxylase (AHH) and 7-methoxycoumarin-O-demethylase (MOCD) have been studied. Inhibition studies were investigated in rat microsomal fraction prepared from untreated, 3MC-and PB-treated rat liver in vitro. Modi®ca-tions were introduced into the piperine molecule: (i) in the phenyl nucleus, (ii) in the side chain and (iii) in the basic moiety. Thus, 38 compounds have been subjected to such studies, and simultaneously an attempt has also been made to arrive at the structure± activity relationship of synthetic analogues. In general, most of the inhibitory potential of the parent molecule is lost with modi®cation in either of the three components of piperine. Saturation of the side chain resulted in signi®cantly enhanced inhibition of CYP while modi®cations in the phenyl and basic moieties in few analogues oered maximal selectivity in inhibiting either constitutive or inducible CYP activities. Thus few novel analogues as CYP inactivators have been synthesized which may have important consequences in pharmacokinetics and bioavailability of drugs. #

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“…As reported in the case of Disc 2 (5), end–end adjacent dimers (such as in the duplex minor groove of AT10) could lead to a strong splitting of CD signals of dimer, which results from electronically coupled chromophores between two end–end adjacent dimers (68), whereas individual dimers (such as in AT5) could not. Similarly, in the case of DMSB, the splitting of CD signals of dimer would also be observed if end–end adjacent dimers existed in groove-elongated G-quadruplexes ( TG6T or TG8T ).…”

Section: Resultsmentioning

confidence: 69%

A dual-site simultaneous binding mode in the interaction between parallel-stranded G-quadruplex [d(TGGGGT)] 4 and cyanine dye 2,2′-diethyl-9-methyl-selenacarbocyanine bromide

Gai

Yang

Xiang

et al. 2012

Nucleic Acids Research

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G-quadruplexes have attracted growing attention as a potential cancer-associated target for both treatment and detection in recent years. For detection purpose, high specificity is one of the most important factors to be considered in G-quadruplex probe design. It is well known that end stacking and groove binding are two dominated quadruplex-ligand binding modes, and currently most reported G-quadruplex probes are designed based on the former, which has been proven to show good selectivity between quadruplexes and non-quadruplexes. Because groove of G-quadruplex also has some unique chemical properties, it could be inferred that probes that can interact with both the groove and G-tetrad site of certain G-quadruplexes simultaneously might possess higher specificity in aspects of discriminating different quadruplexes. In this article, we report a cyanine dye as a potential novel probe scaffold that could occupy both the 5′-end external G-tetrad and the corresponding groove of the G-quadruplex simultaneously. By using various spectrum and nuclear magnetic resonance techniques, we give a detailed binding characterization for this dual-site simultaneous binding mode. A preliminary result suggests that this mode might provide highly specific recognition to a parallel-stranded G-quadruplex. These findings and the structural elucidation might give some clues in aspects of developing highly specific G-quadruplex probes.

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CD Exciton Chirality Method: Schiff Base and Cyanine Dye-Type Chromophores for Primary Amino Groups

Cited by 44 publications

References 0 publications

Examination of the conformational restraints to a chiral diimine bridged 2,2′-bipyridine

Examination of the conformational restraints to a chiral diimine bridged 2,2′-bipyridine

Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities

A dual-site simultaneous binding mode in the interaction between parallel-stranded G-quadruplex [d(TGGGGT)] 4 and cyanine dye 2,2′-diethyl-9-methyl-selenacarbocyanine bromide

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