Biguanide hydrochloride

Ernst, S. R.

doi:10.1107/s0567740877003203

Cited by 27 publications

(28 citation statements)

References 2 publications

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“…1 and 2) are very similar to those previously reported for the chloride BIGH.C1 (Ernst, 1977), the carbonate (BIGH)2CO3 and the sulfates (BIGH)2SO4.2H20 and (BIGH2)SO4.H20 (Pinkerton & Schwarzenbach, 1978). Both cations are composed of two planar halves with one atom in common.…”

Section: Bigh22+supporting

confidence: 75%

Energetic Materials: the Biguanidium Nitrates

Martin¹,

Pinkerton²,

Schiemann³

1996

Acta Crystallogr C

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Section: Bigh22+supporting

confidence: 75%

Energetic Materials: the Biguanidium Nitrates

Martin¹,

Pinkerton²,

Schiemann³

1996

Acta Crystallogr C

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“…This geometry is enforced by an intramolecular NHLN hydrogen bond, with NLH distances of normal values (1.993(5)-2.263(5) Å). Similar features appear in all previous structural studies of neutral biguanides (4,(9)(10)(11), so a nearly planar geometry and an intramolecular hydrogen bond appear to be structural features of biguanides that can be used reliably by crystal engineers. The average Fig.…”

Section: Crystal Structure Of Bis(biguanide)supporting

confidence: 57%

“…3a). The NLN distance in these cationic pairs is 3.033(3) Å. Intercationic hydrogen bonding is inhibited by coulombic repulsion and is absent in most biguanidinium salts (4,11,14,15,17,(19)(20)(21), although it has previously been observed in a few cases (12,13,18). Slightly offset face-to-face aromatic interactions are also observed in the structure of salt 2·2HCl (Fig.…”

Section: Crystal Structure Of the Dihydrochloride Salt Of Bis(biguanimentioning

confidence: 64%

“…It is noteworthy that this uncommon hydrogen-bonded dimeric motif is observed in the structures of both bis(biguanidinium) salts, despite its coulombic disadvantage. Nevertheless, its absence in the structures of most other biguanidinium salts (4,11,14,15,17,(19)(20)(21) suggests that it does not define a motif that can be used reliably in supramolecular construction.…”

Section: Crystal Structure Of the Dihydrochloride Salt Of Bis(biguanimentioning

confidence: 95%

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Hydrogen-bonded networks in crystals built from bis(biguanides) and their salts

Lebel¹,

Maris²,

Wuest³

2006

Can. J. Chem.

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Biguanide groups and biguanidinium cations incorporate multiple sites that can donate or accept hydrogen bonds. To assess their ability to associate and to direct the formation of extended hydrogen-bonded networks, we examined the structure of crystals of four compounds in which two neutral biguanide groups or the corresponding cations are attached to the 1,4-and 1,3-positions of phenylene spacers. As expected, all four structures incorporate extensive networks of hydrogen bonds and reveal other reliable features. In particular, (1) neutral biguanide groups favor a roughly planar conformation with an intramolecular hydrogen bond, and they associate as hydrogen-bonded pairs, (2) despite coulombic repulsion, biguanidinium cations can also associate as hydrogen-bonded pairs, and (3) the 1,3-phenylenebis(biguanidinium) dication favors a pincerlike conformation that allows chelation of suitable counterions. However, the precise patterns of hydrogen bonding in the structures vary substantially, limiting the usefulness of biguanide and biguanidinium as groups for directing supramolecular assembly. Résumé :Des groupes biguanide et des cations biguanidinium incorporent de multiples sites qui peuvent donner ou accepter des liaisons hydrogène. Dans le but d'évaluer la capacité d'associer et de diriger la formation de réseaux étendus de liaisons hydrogène, on a étudié la structure cristalline de quatre composés dans lesquels deux groupes biguanide neutres, ou les cations correspondants, sont attachés aux positions 1,4-et 1,3-de groupes phénylènes. Comme prévu, les quatre structures permettent d'incorporer des réseaux de liaisons hydrogène et mettent en évidence d'autres caracté-ristiques fiables. En particulier, 1) les groupes biguanide neutres favorisent une conformation pratiquement plane avec une liaison hydrogène intramoléculaire et s'associent sous la forme de paires réunies par des liaisons hydrogène, 2) malgré une répulsion coulombique, les cations biguanidinium peuvent aussi former des paires associées par des liaisons hydrogène et 3) le dication phénylène-1,3-bis(biguanidinium) favorise une conformation en forme de pince qui permet d'effectuer une chélation avec des contre-ions appropriés. Toutefois, les régimes précis des liaisons hydrogène varient d'une façon substantielle, ce qui limite l'utilité des groupes biguanide et biguanidinium comme unités pouvant orienter un assemblage supramoléculaire.

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“…The first transition step can be attributed to the protonation equilibrium of phenanthridine nitrogen (pKa  6), 17,18 with well separated protonated (max = 462 nm) and non-protonated nitrogen species (max = 399 nm), whereas latter transition step can be attributed to the protonation equilibrium of biguanide moiety. 28 Consequently, at acidic pH (pH 5.0, citric acid/NaOH buffer, I=0.03 mol dm -3 ) phenanthridine nitrogen of 5 and 6 is mostly protonated (76%), consequently 5 is characterized by two positive charges and 6 (with two biguanide groups) has three positive charges. On the other hand, at neutral conditions (pH 7.0, buffer sodium cacodylate, I = 0.05 mol dm -3 ) phenanthridines of 5 and 6 are not protonated and compounds are characterized by one or two positively charged biguanides, respectively.…”

Section: Spectroscopymentioning

confidence: 99%

The phenanthridine biguanides efficiently differentiate between dGdC, dAdT and rArU sequences by two independent, sensitive spectroscopic methods

et al. 2011

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At submicromolar concentrations two novel phenanthridine biguanides exhibit distinctly different spectroscopic signals for dGdC and dAdT sequences, respectively, by opposite fluorimetric changes (quenching for dGdC and increase for dAdT) and especially bis -biguanide derivative gives opposite ICD response (negative ICD for dGC and strong positive for dAdT). This speci fic signalling was explained by ability of compounds to switch binding mode from intercalation into dGdC to minor groove binding into dAdT sequences. Both compounds bind to rArU by intercalation, yielding different fluorimetric and CD response in compariso n to any of aforementioned ds-DNA. Moreover, both compounds revealed significantly higher affinity toward ds-polynucleotides in comparison to previously studied alkylamine-and urea-analogues. Furthermore, DNA/RNA binding properties of novel compounds could be controlled by pH, due to the protonation of heterocyclic nitrogen. Low in vitro cytotoxicity of both compounds against human cell lines makes them interesting spectrophotometric probes.

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Biguanide hydrochloride

Cited by 27 publications

References 2 publications

Energetic Materials: the Biguanidium Nitrates

Energetic Materials: the Biguanidium Nitrates

Hydrogen-bonded networks in crystals built from bis(biguanides) and their salts

The phenanthridine biguanides efficiently differentiate between dGdC, dAdT and rArU sequences by two independent, sensitive spectroscopic methods

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