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PubMed2003

Activation of spinal orexin-1 receptor produces anti-allodynic effect in the rat carrageenan test.

Orexin-A and orexin-1 receptors are found in the dorsal root ganglion cells and the spinal dorsal horn and this suggests that orexin-A is involved in the spinal nociceptive transmission. The authors examined the effect of intrathecally administered orexin-A on the level of mechanical allodynia and thermal hyperalgesia induced by paw carrageenan injection in the rat. Intrathecal injection of 0.3 and 3 nmol of orexin-A suppressed the level of mechanical allodynia, but not that of thermal hyperalgesia, and the effect of orexin-A on mechanical allodynia was antagonized by the pretreatment of 1-(2-methylbenzoxazol-6-yl)-3-[1,5]naphthyridin-4-yl urea hydrochloride, SB-334867, a selective orexin-1 receptor antagonist. These data suggest that the activation of spinal orexin-1 receptor modulates the mechanical information transmission, but not thermal information transmission, in the spinal cord during carrageenan test.

Animals↗
PubMed2005

Recently approved and investigational antibiotics for treatment of severe infections caused by Gram-positive bacteria.

The development of resistance in the major pathogenic Gram-positive genera Staphylococcus and Streptococccus has led to the need for new agents that are able to overcome existing resistance mechanisms or that have novel mechanisms of action. There is currently a dearth of new agents that are active against resistant bacterial species. Agents that have recently been approved for clinical use include linezolid, the first oxazolidinone in clinical use, daptomycin, the first lipopeptide in clinical use, and telithromycin, a ketolide that is derived from clarithromycin. Agents currently in clinical development include tigecycline, a broad-spectrum intravenous tetracycline, ceftobiprole, a broad-spectrum cephalosporin that has activity against methicillin-resistant staphylococci, DX-619 and WCK-771, which are potent quinolones that have activity against quinolone-resistant staphylococci, oritavancin and dalbavancin, both of which are new glycopeptides, and iclaprim, which is a diaminopyrimidine. Additional agents that are in preclinical development against Gram-positive pathogens include quinoline-naphthyridine agents, which target novel DNA gyrase sites, other novel quinolones that have high potency, peptide deformylase inhibitors, and new lincosamide, oxazolidinone, lipopeptide and cephalosporin derivatives. Misuse of potent new agents will, however, result in the inevitable development of resistance to these agents; responsible use of potent new agents is required to prevent continuation of this vicious cycle.

Anti-Bacterial Agents↗
PubMed2005

Structure-phototoxicity relationship in Balb/c mice treated with fluoroquinolone derivatives, followed by ultraviolet-A irradiation.

We examined the structure-phototoxicity relationship for fluoroquinolone antimicrobial agents (quinolones) using female albino Balb/c mice. First of all, to obtain an optimum dosage level for induction of phototoxicity, the prototype phototoxicant sparfloxacin was intravenously administered once at 10 mg/kg, 30 mg/kg or 100 mg/kg to female mice, followed immediately by ultraviolet-A (UVA) irradiation for 4 h (21.6J/cm2). The auricular thickness was measured at pre-dose (0 h), 4, 24, 48, 72 and 96 h post-dose, and then the histopathological examination of the auricle was performed. As results, the auricular thickness increased from 30 mg/kg, in conjunction with edema, cellular infiltration, epidermal necrosis and focal loss of the auricle. On the basis of these information, ciprofloxacin, enoxacin, fleroxacin, gatifloxacin, lomefloxacin, norfloxacin and ofloxacin were given intravenously to mice at a fixed dose of 100 mg/kg to compare their potential phototoxicities. Certain quinolones caused the auricular lesions in the following rank order (from lowest to highest): vehicle control (non-phototoxicity)=gatifloxacin=ofloxacin<ciprofloxacin=norfloxacin<enoxacin=fleroxacin<lomefloxacin=sparfloxacin. From the viewpoint of the structure-phototoxicity relationship, quinolones possessing the C-8 substituent with a fluorine or hydrogen and 1,8-naphthyridine derivative evoked phototoxicity in the mouse auricle. These results demonstrate that phototoxicity induced by quinolones would be related to the property of the eighth position.

Animals↗
PubMed1998

Pharmacological profiles of new orally active nonpeptide tachykinin NK1 receptor antagonists.

Pharmacological profiles of new orally active amide-based tachykinin NK1 receptor antagonists, N-[3,5-bis(trifluoromethyl)benzyl]-5-(4-fluorophenyl)-7,8-dihydro-N,7-di methyl-8-oxo-1,7-naphthyridine-6-carboxamide (referred to as compound I) and two related compounds (compounds II and III), were compared with that of (+)-(2S,3S)-3-(2-methoxybenzylamino)-2-phenylpiperidine (CP-99,994), another nonpeptide tachykinin NK1 receptor antagonist. Compounds I, II, III and CP-99,994 caused parallel rightward shifts of the concentration-response curve of substance P in the guinea-pig ileum pretreated with atropine, mepyramine and indomethacin, with the pA2 values of 8.70, 7.56, 8.41 and 8.27, respectively. These antagonists did not alter the concentration-response curve of acetylcholine in the guinea-pig ileum nor that of neurokinin A in the rat vas deferens. Furthermore, contractile responses to senktide of the rat portal vein were not affected by these antagonists. In the isolated neonatal gerbil spinal cord pretreated with tetrodotoxin, substance P produced a dose-dependent depolarization of ventral roots. Compounds I, II, III and CP-99,994 caused parallel rightward shifts of the concentration-response curve of substance P in the spinal cord with the pA2 values of 7.07, 5.93, 6.40 and 7.26, respectively. In contrast, these antagonists did not affect the concentration-response curve of L-glutamate. These results suggest that compounds I, II and III are selective antagonists for tachykinin NK1 receptor both in peripheral tissues and the central nervous system.

Administration, Oral↗
PubMed1999

Phosphodiesterase 4-dependent regulation of cyclic AMP levels and leukotriene B4 biosynthesis in human polymorphonuclear leukocytes.

Several selective phosphodiesterase 4 inhibitors were found to be potent inhibitors of the N-formyl-Met-Leu-Phe (fMLP)-induced leukotriene B4 biosynthesis by human polymorphonuclear leukocytes with IC50s in the nanomolar range (0.09-26 nM). The rank order of potency was 6-(4-pyridylmethyl)-8-(3-nitrophenyl)quinoline (RS-14203) > 3-benzyl-5-phenyl-3H-imidazo[4,5-c][1,8]naphthyridin-4(5H)-one (KF18280) > 8-aza-1-(3-nitrophenyl)-3-(4-pyridylmethyl)-2,4-quinazoline dione (RS-25344) > 3-cyclo-pentyloxy-N-[3,5-dichloro-4-pyridyl]-4-methoxybenzamide (RP-73401) > R-rolipram > R-4-[2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl] pyridine (CDP840)> S-rolipram. Isoproterenol (IC50 = 350 nM) and prostaglandin E2 (IC50 = 59 nM) also suppressed leukotriene B4 biosynthesis. Inhibitors of the phosphodiesterase 1 (8-methoxymethyl-1-methyl-3-(2-methylpropyl)xanthine (8-MeOMe-IBMX)), phosphodiesterase 2 (erythro-9-(2-hydroxy-3-nonyl)adenine (EHNA)), phosphodiesterase 3 (quazinone and milrinone) and phosphodiesterase 5 (zaprinast and dipyridamole) had no inhibitory effects on the fMLP-induced leukotriene B4 biosynthesis (IC50s > 20 microM). All phosphodiesterase 4 inhibitors caused an accumulation of cellular cyclic AMP to 140-185% over the basal level of fMLP-treated control cells, comparable to that observed with high concentrations of isoproterenol and prostaglandin E2. In contrast, the complete inhibition of leukotriene B4 production by 5-lipoxygenase and 5-lipoxygenase-activating protein (FLAP) inhibitors had no effect on cyclic AMP levels. Phosphodiesterase 1, 2, 3 and 5 inhibitors had little effect on the level of cellular cyclic AMP (89-126% of the basal cyclic AMP level). Dose-dependencies for R-rolipram, RS-14203 and CDP840 indicated that the maximal accumulation of cyclic AMP occurred at concentrations of phosphodiesterase 4 inhibitors higher than those required for the inhibition of leukotriene B4 production. The presence of a mixture of 8-MeOMe-IBMX, EHNA, milrinone and zaprinast to inhibit phosphodiesterase 1, 2, 3 and 5 had little effect on the dose-dependence of R-rolipram for the inhibition of leukotriene B4 biosynthesis or cyclic AMP accumulation. These data demonstrate that selective phosphodiesterase 4 inhibitors can inhibit the fMLP-induced leukotriene B4 biosynthesis in human polymorphonuclear leukocytes with a potency similar or greater than that of potent 5-lipoxygenase or FLAP inhibitors. This inhibition is accompanied by small variations in the levels of cellular cyclic AMP and appears to proceed independently of the other phosphodiesterases.

Cyclic AMP↗
PubMed1997

Effects of vinconate on age-related alterations in [3H]MK-801, [3H]glycine, sodium-dependent D-[3H]aspartate, [3H]FK-506 and [3H]PN200-110 binding in rats.

We investigated the effects of age and (+/-)-methyl-3-ethyl-2,3,3a,4-tetrahydro-1 H-in-dolo[3,2,1-de] [1,5] naphthyridine-6-carboxylate hydrochloride (vinconate), an indolonaphthyridine derivative, on calcium channels, neurotransmitter receptor systems and immunophilin in Fischer rat brain using quantitative receptor autoradiography. [3H]MK-801, [3H]glycine, sodium-dependent D-[3H]aspartate, [3H]FK-506 and [3H]PN200-110 were used to label N-methyl-D-aspartate (NMDA) receptors, glycine receptors, excitatory amino acid transport sites, FK-506 binding proteins (FKBP) and voltage-dependent L-type calcium channels, respectively. [3H]Glycine and sodium-dependent D-[3H]aspartate binding significantly decreased in the frontal cortex, parietal cortex, striatum, nucleus accumbens, hippocampus, thalamus, substantia nigra and cerebellum of 24 month old rats in comparison with 6 month old animals. In contrast, [3H]MK-801, [3H]FK-506 and [3H]PN200-110 binding showed no significant changes in the brain of 24 month old rats. Intraperitoneal chronic treatment with vinconate (10 and 30 mg/kg, once a day for 4 weeks) dose-dependently ameliorated the significant reduction in [3H]glycine and sodium-dependent D-[3H]aspartate binding in the brain of 24 month old rats. These results demonstrate that glycine receptors and excitatory amino acid transport sites are more susceptible to aging processes than NMDA receptors, immunophilin and voltage-dependent L-type calcium channels. Furthermore, our findings suggest that vinconate may have a beneficial effect on age-related changes in glycine receptors and excitatory amino acid transport sites.

Aging↗
PubMed2002

Central administration of mCPP, a serotonin 5-HT(2B/2C) agonist, decreases water intake in rats.

In the present study, we investigated in rats the effect of third ventricle injections of 1-(3-chlorophenyl)piperazine (mCPP), a 5-HT(2) receptor agonist, on water intake induced by three different physiological stimuli: fluid deprivation, acute salt load and hypovolemia. Injections of mCPP in the doses of 80 and 160 nmol/rat were able to decrease water intake in all three conditions studied. Third ventricle injections of mCPP (160 nmol/rat) were no longer able to diminish water intake in the groups of rats pretreated with central injections of an equimolar amount of (+)-cis-4,5,7a,8,9,10,11,11a-octahydro-7H-10-methylindolo[1,7-bc][2,6]-naphthyridine (SDZ SER 082), a selective 5-HT(2B/2C) antagonist. The central administration of mCPP (160 nmol/rat) was not able to modify the intake of a 0.1% saccharin solution. It is suggested that the central activation of a 5-HT(2B/2C) component is able to impair the drive for water intake induced by the physiological stimuli represented by fluid deprivation, acute salt load and hypovolemia. This effect seems not to be consequent on a general nonspecific central nervous system depression or on a locomotor deficit, because saccharin intake is not affected by third ventricle injections of mCPP.

Animals↗
PubMed2001

Validation of an HPLC method for the determination of urinary and plasma levels of N1-methylnicotinamide, an endogenous marker of renal cationic transport and plasma flow.

N1-Methylnicotinamide (NMN) is an endogenous cationic metabolite of nicotinamide (niacine, vitamine PP) whose renal clearance reflects both the capacity of the renal tubular transport system to secrete organic cations and renal plasma flow. NMN is present in human plasma and urine at the 1-117-ng ml(-1) and 0.5-25-microg ml(-1) concentration range, respectively, and its level depends notably on pathophysiological (age, renal or hepatic diseases) conditions. We report the optimization and validation of an HPLC method for the measurement of endogenous NMN in biological fluids after derivatization into a fluorescent compound. Plasma is first deproteinized with TCA 20% and the urine diluted 1:10 with HCI 10(-4) M prior to the derivatization procedure, which includes a condensation reaction of NMN with acetophenone in NaOH at 0 degrees C, followed by dehydration in formic acid and subsequent formation of the fluorescent 1,6-naphthyridine derivatives after heating samples in a boiling water bath. The synthetic homologous derivative N1-ethylnicotinamide (NEN) reacts similarly and is added as internal standard into the biological fluid. The reaction mixture is subjected to reverse phase high performance liquid chromatography on a Nucleosil 100-C18 column using a mobile phase (acetonitrile 22%, triethylamine 0.5%, 0.01 M sodium heptanesulfonate adjusted to pH 3.2), delivered isocratically at a flow rate of 1 ml min(-1), NMN and NEN are detected at 7.8 and 10 min by spectrofluorimetry with excitation and emission wavelengths set at 366 and 418 nm, respectively. The addition-calibration method is used with plasma and urine pools. Calibration curves (using the internal standard method) are linear (r2 > 0.997) at concentrations up to 109 ng ml(-1) and 15.7 microg ml(-1) in plasma and urine, respectively. Both intra- and inter-assay precision of plasma control samples at 10, 50 and 90 ng ml(-1) were lower than 3.3% and concentrations not deviating more than 2.7% from their nominal values. In urine intra- and inter-assay CVs of control samples at 1, 5 and 9 microg ml(-1) are lower than 8.3%, with concentrations not deviating more than -9.0 to +11.8% from their nominal values. This analytical method has therefore the required sensitivity and selectivity to measure NMN in plasma and urine, enabling the non-invasive determination of the tubular secretory capacity of the kidney and the renal plasma flow.

Biomarkers↗
PubMed1998

Use of sensitized luminescence of lanthanides in analysis of drugs.

The sensitization of the Tb(III) and Eu(III) ions luminescence by drugs, the pyrocatechol, naphthyridine and heterocyclic aromatic acid derivatives, were studied. It was shown that a result of intramolecular energy transfer from the ligand molecule to the lanthanide ion increases the luminescence intensity of the latter by 10(8)-10(10) times. The luminescence properties of the complexes in solutions were investigated. The highly sensitive methods for luminescence determination of dopegyt, levodopum, dophaminum, nevigramon, furosemidum and cinchophenum were developed. The detection limits of the drugs are 0.0005, 0.02, 0.5, 0.01, 0.05 and 0.1, respectively.

Acids, Heterocyclic↗
PubMed2002

Nonpeptide alpha(v)beta(3) antagonists. Part 2: constrained glycyl amides derived from the RGD tripeptide.

Mimetics of the RGD tripeptide are described that are potent, selective antagonists of the integrin receptor, alpha(v)beta(3). The use of the 5,6,7,8-tetrahydro[1,8]naphthyridine group as a potency-enhancing N-terminus is demonstrated. Two 3-substituted-3-amino-propionic acids previously contained in alpha(IIb)beta(3) antagonists were utilized to enhance binding affinity and functional activity for the targeted receptor. Further affinity increases were then achieved through the use of cyclic glycyl amide bond constraints.

Amides↗
PubMed1998

Photocleavage of DNA by the fluoroquinolone antibacterials.

We have determined the relative efficiencies for the formation of single strand breaks (ssbs) after the UVA irradiation of pBR322 DNA and various fluoroquinolone (fleroxacin, lomefloxacin, norfloxacin) and naphthyridine (nalidixic acid, enoxacin) antibacterials. After correcting for the differences in absorption, the relative order for DNA photocleaving activity under anaerobic conditions is: fleroxacin, lomefloxacin > nalidixic acid >> norfloxacin > enoxacin. In general, fluoroquinolones having fluorine substituents at the C-6 and C-8 positions (lomefloxacin and fleroxacin) are 10-fold more efficient in generating ssbs than those having only a C-6 fluorine atom (norfloxacin). The effect of oxygen on photoinduced DNA damage caused by these antibacterials is complex, but our data imply that active oxygen species are not necessary for DNA scission by these molecules, and indeed, may sometimes inhibit it. Lomefloxacin ethyl ester, which cannot undergo decarboxylation, is as active as lomefloxacin itself. Thus the free radical generated by decarboxylation is unlikely to be the active species involved in photoinduced fluoroquinolone DNA cleavage. For lomefloxacin and fleroxacin, DNA damage probably results from the generation of a carbene at C-8 as a result of photoinduced loss of their F8 atom as fluoride upon UVA irradiation. Fluoroquinolones lacking a C-8 fluorine atom must operate by a different mechanism. While photocleavage of pBR322 DNA does not necessarily mean that duplex DNA will be cleaved under the same conditions, nevertheless lomefloxacin and fleroxacin, the two most photogenotoxic fluoroquinolones, did cause the most damage to the plasmid DNA.

Anti-Infective Agents↗
PubMed2000

Reactivity of mu-hydroxodizinc(II) centers in enzymatic catalysis through model studies.

The stable dinuclear complex [Zn2(BPAM)(mu-OH)(mu-O2PPh2)](ClO4)2, where BPAN = 2,7-bis[2-(2-pyridylethyl)-aminomethyl]-1,8-naphthyridine, was chosen as a model to investigate the reactivity of (mu-hydroxo)dizinc(II) centers in metallohydrolases. Two reactions, the hydrolysis of phosphodiesters and the hydrolysis of beta-lactams, were studied. These two processes are catalyzed in vivo by zinc(II)-containing enzymes: P1 nucleases and beta-lactamases, respectively. The former catalyzes the hydrolysis of single-stranded DNA and RNA. beta-Lactamases, expressed in many types of pathogenic bacteria, are responsible for the hydrolytic degradation of beta-lactam antibiotic drugs. In the first step of phosphodiester hydrolysis promoted by the dinuclear model complex, the substrate replaces the bridging diphenylphosphinate. The bridging hydroxide serves as a general base to deprotonate water, which acts as a nucleophile in the ensuing hydrolysis. The dinuclear model complex is only 1.8 times more reactive in hydrolyzing phosphodiesters than a mononuclear analogue, Zn(bpta)(OTf)2, where bpta = N,N-bis(2-pyridylmethyl)-tert-butylamine. Hydrolysis of nitrocefin, a beta-lactam antibiotic analogue, catalyzed by [Zn2(BPAN)(mu-OH)(mu-O2PPh2)](ClO4)2 involves monodentate coordination of the substrate via its carboxylate group, followed by nucleophilic attack of the zinc(II)-bound terminal hydroxide at the beta-lactam carbonyl carbon atom. Collapse of the tetrahedral intermediate results in product formation. Mononuclear complexes Zn(cyclen)-(NO3)2 and Zn(bpta)(NO3)2, where cyclen = 1,4,7,10-tetraazacyclododecane, are as reactive in the beta-lactam hydrolysis as the dinuclear complex. Kinetic and mechanistic studies of the phosphodiester and beta-lactam hydrolyses indicate that the bridging hydroxide in [Zn2(BPAN)(mu-OH)(mu-O2PPh2)](ClO4)2 is not very reactive, despite its low pKa value. This low reactivity presumably arises from the two factors. First, the briding hydroxide and coordinated substrate in [Zn2(BPAN)(mu-OH)(substrate)]2+ are not aligned properly to favor nucleophilic attack. Second, the nucleophilicity of the bridging hydroxide is diminished because it is simultaneously bound to the two zinc(II) ions.

Catalysis↗
PubMed2006

Photosensitizers containing the 1,8-naphthyridyl moiety and their use in dye-sensitized solar cells.

Using a Friedländer condensation approach, we prepared a series of 2-(pyrid-2'-yl)-1,8-naphthyridines containing a carboethoxy group appended at the 4- and 4'-positions. Complexation of these ligands with Ru(II) and NaNCS led to the complexes [Ru(L)2(NCS)2], and subsequent hydrolysis of the ester groups afforded the carboxylic acid dyes 13b-15b. The more delocalized and electronegative nature of the 1,8-naphthyridyl moiety lowers the energy of the ligand pi*-level and extends the absorption envelope of these complexes well into the red. The system lacking a 4-carboxypyridine moiety shows poor absorbance in the blue region of the spectrum. Solar cells involving thin films of anatase TiO2 impregnated with these dyes were prepared, and their photovoltaic performance was evaluated. The incident photon-to-current efficiencies in the region beyond 625 nm were considerably greater than those of the prototype N3 dye.

Journal Article↗
PubMed2006

Even-numbered metal chain complexes: synthesis, characterization, and DFT analysis of [Ni4(mu4-Tsdpda)4(H2O)2] (Tsdpda2- = N-(p-toluenesulfonyl)dipyridyldiamido), [Ni4(mu4-Tsdpda)4]+, and related Ni4 string complexes.

The synthesis and the X-ray structure of two complexes exhibiting a linear chain of four nickel atoms is reported, following Ni4(mu4-phdpda)4 (1), which had been characterized previously. [Ni4(mu4-Tsdpda)4(H2O)2], where H2Tsdpda is N-(p-toluenesulfonyl)dipyridyldiamine (2), is axially coordinated to two water molecules, at variance with 1. One-electron oxidation of 2 resulted in the loss of the axial ligands, yielding [Ni4(mu4-Tsdpda)4]+, [3]+, which was also structurally characterized. Finally, we report the structure of Ni4(mu4-DAniDANy)4 (4), a complex synthesized starting from the new ligand N,N'-bis-p-anisyl-2,7-diamino-1,8-naphthyridine. Magnetic measurements concluded that 4 is diamagnetic, like 1, whereas 2 is antiferromagnetic (-2J(14) = 80 cm(-)(1), using the Heisenberg Hamiltonian H = -2J(14) S(1).S(4)), as are other axially coordinated chains with an odd number of nickel atoms. DFT calculations are reported on these complexes in order to rationalize their electronic structure and their magnetic behavior. The magnetic properties of the [Ni4]8+ complexes are governed by the electronic state of the Ni(II) atoms, which may be either low-spin (S = 0), or high-spin (S = 1). DFT calculations show that the promotion to high spin of two Ni atoms in the chain, either external or internal, depends on the interplay between axial and equatorial coordination. The synergy between axial coordination and the presence of electron-withdrawing toluenesulfonyl substituents in 2 favors the promotion to the high-spin state of the terminal Ni atoms, thus yielding an antiferromagnetic ground state for the complex. This is at variance with complexes 1 and 4, for which the lowest quintet state results from the promotion to high spin of the internal nickel atoms, together with an important ligand participation, and is destabilized by 9 to 16 kcal mol(-1) with respect to the diamagnetic ground state.

Journal Article↗
PubMed2003

Hydrazide-based quadruply hydrogen-bonded heterodimers. Structure, assembling selectivity, and supramolecular substitution.

This paper describes the synthesis, self-assembly, and characterization of a new class of highly stable hydrazide-based quadruply hydrogen-bonded heterodimers. All of the hydrazide-derived heterodimers possess the complementary ADDA-DAAD hydrogen-bonding sequences. Hydrazide derivatives 1, which has two intramolecular S(6) RO.H-N hydrogen bonds, and 2 complex to afford two fastly exchanging isomeric heterodimers 1.2 and 1.2' in chloroform, as a result of two different conformational arrangements of 2. An average binding constant K(assoc) of 4.7 x 10(4) M(-)(1) was determined for heterodimer 1.2 and 1.2' by (1)H NMR titration of 1 with changing 2 in chloroform-d. In contrast, 1 binds 11 and 12, both of which are introduced with two intramolecular S(6) hydrogen bonds, to exclusively afford heterodimers 1.11 and 1.12, with K(assoc) values of 1.8 x 10(4) and 5.0 x 10(2) M(-)(1), respectively. Fluorine-containing 19, which has a hydrazide skeleton identical to that of 1 but two intramolecular S(6) F.H-N hydrogen bonds, can also complex with 2, 11, and 12, to afford heterodimers 19.2, 19.2', 19.11, and 19.12, with K(assoc) values of of 1.2 x 10(4) (average value for 19.2 and 19.2'), 5.4 x 10(3), and 1.9 x 10(2) M(-)(1), respectively. The structures of the new heterodimers have been proven with NOESY, IR, and VPO (for some of the heterodimers) experiments. Moreover, 1 and 19 can also strongly bind 2,7-dilauroylamido-1,8-naphthyridine 23 to afford dimers 1.23 and 19.23 with K(assoc) values of 6.0 x 10(5) and 1.4 x 10(5) M(-)(1), respectively. Adding 1 to the 1:1 solution of 23 and 1-octyl-3-(4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-yl)urea 24 or 1-octyl-3-(4-oxo-1,4-dihydro-pyrimidin-2-yl)urea 25, which had been developed initially by Zimmerman and Meijer, respectively, induces dimers 23.24 and 23.25 to dissociate, leading to the formation of dimers 1.23 and 24.24 or 25.25, respectively. The new hydrazide-based hydrogen-bonding modules described are useful building blocks for self-assembly and open a new avenue to recognition between discrete supramolecular species.

Journal Article↗
PubMed2005

Complementary quadruple hydrogen bonding in supramolecular copolymers.

This paper describes a supramolecular copolymer based on quadruple hydrogen bonding between self-complementary ureido-pyrimidinones and complementary 2,7-diamido-1,8-naphthyridines. In contrast to previously reported polymer systems solely based on complementary hydrogen-bonding units, these polymers retain a high DP over a broad composition range.

Journal Article↗
PubMed2004

Formation of branched calixarene aggregates-a time-resolved static light scattering study.

Mixtures of a calix[4]arene and a naphthyridine derivative dissolved in 1,2-dichlorobenzene form thermoreversible aggregates. The aggregation process was followed by means of time-resolved multiangle light scattering at two different mixing ratios, 1:3 and 1:4, yielding a detailed record of the relative mass, the radius of gyration, and the particle scattering function of the growing aggregates. On the basis of these data, a conclusive model of the structure is presented for the developing aggregates: monomers aggregate to wormlike filaments which form branching points. Formation of branching points proceeds in a frequency and distribution which is similar to the polycondensation of ABC monomers toward non-randomly branched macromolecules (Burchard, W. Macromolecules 1977, 10, 919-927). Thus, aggregation results in hyperbranched-like particles with striking analogies to the polymerization of glucose to amylopectin.

Journal Article↗