An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (Kassoc approximately 5 x 10(7) M(-1)) for the UG.DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (Kdimer< 10 M(-1)) and UG (Kdimer ca. 200-300 M(-1)) means that the UG.DAN complex forms with unparalleled fidelity.

The butyl urea of guanosine (UG) presents an ADDA hydrogen-bonding array that is complementary to the DAAD array of 2,7-diamido-1,8-naphthyridine (DAN). The stability of the DAN.UG complex was measured by fluorimetry using the fluorescence resonance energy transfer (FRET) from the naphthyridine ring to a coumarin 343 moiety linked covalently to the UG unit. The quadruply hydrogen-bonded complex is extremely stable with a measured association constant, Kassoc, of 3 x 108 M-1. Unlike related hydrogen-bonding modules, the guanosine urea, UG, contains a relatively fixed tautomeric form and only weakly self-associates (Kdimer = ca. 200 M-1). The DAN unit was linked to a styrene-based monomer and copolymerized with styrene to form a polymer (PS-DAN) containing a controlled number of the DAAD recognition units. Likewise, a methacrylate monomer containing the UG unit was copolymerized with butyl methacrylate to form a polymer (PBMA-UG). Blends formed from PS-DAN and PBMA-UG were characterized by DSC, SEC, and viscometry. The importance of selective heterocomplexation and weak self-association in forming the blended networks was demonstrated by using a ureidopyrimidinone (UPy) unit, which also forms strong heterocomplexes with DAN but is able to strongly self-associate.

Novel deoxyadenosine derivatives tethering a phenyl or naphthyl group by means of an amido linker have been synthesized, and these derivatives, stacking on the 5' end of a DNA duplex, provide free energy contributions equal to or greater than that of the Watson-Crick A/T base pair.

[structure; see text] An iterative synthetic route to organic-soluble ureido-naphthyridine oligomers has been developed. Use of this protocol allowed synthesis of a short ureido-naphthyridine oligomer, which presents a self-complementary DDAADDAA hydrogen bonding array (D = hydrogen bond donor, A = hydrogen bond acceptor). Strong self-association via eight hydrogen bonds was observed in organic solution.

Remineralization treatment, which offers the advantage of being non-invasive, is increasingly being used as a minimal intervention treatment in managing incipient enamel caries. The aim of this review was to develop EBM guideline for optimized strategies for non-invasive treatment of incipient enamel caries. Japanese Society of Conservative Dentistry (JSCD) guideline committee formulated a Guideline for treating incipient enamel caries using the GRADE system, which is the global, mainstream standard for guideline development. The committee selected the most frequent clinical questions (CQs) in treating incipient enamel caries and identified clinically important outcomes in evaluating the efficacy of treatments. Using extensive electronic and manual searches, relevant randomized controlled trials and controlled clinical trials were identified. Based on evidence profiles produced by the committee, the panel discussed the effects, benefits and disadvantages of the selected treatments, as well as their cost effectiveness and feasibility, in order to achieve a consensus in treating incipient enamel caries non-invasively. A recommendation was made for each clinical question after voting by the panel members. Based on the evidence profile and panel discussions for each CQ, the experts strongly recommended application of topical fluoride to inhibit cavitation of incipient enamel caries, and to diminish white spot lesions.