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Blower, Philip J.

doi:10.1039/b103007h

Cited by 10 publications

(5 citation statements)

References 174 publications

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“…However, there were no silver(I) compounds that combine light and thermal stability, chemical inertness, water insolubility and show antimicrobial activity. Thus, the greatest challenge with common silver(I) inorganic compounds known for their antimicrobial properties is a reduction back to elemental silver upon exposure to light and heat [14]. Nevertheless, there is one particular class of low molecular weight organic compounds that can act as ligands for binding silver(I) cations and will form complexes that satisfy the specific requirements outlined above.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of two cyanoxime ligands, their precursors, and light insensitive antimicrobial silver(I) cyanoximates

Riddles

Whited

Lotlikar

et al. 2014

Inorganica Chimica Acta

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High-yield syntheses of N-piperidine-cyanacetamide (1), N-morpholyl-cyanacetamide (4) and their oxime derivatives N-piperidine-2-cyano-2-oximino-acetamide (HPiPCO, 2) and N-morpholyc-2-cyano-2-oximino-acetamide (HMCO, 5) were developed using two-step preparations. At first, the reactions of neat cyanoacetic acid esters and the respective cyclic secondary amines such as piperideine and morpholine afforded pure cyanacetamides, which were converted into cyanoximes at room temperature using the nitrosation reaction with gaseous CH3ONO. The synthesized compounds were investigated by means of IR, 1H, 13C and UV-visible spectroscopy. Crystal structures of two starting substituted cyan-acetamides and two target cyanoximes were determined. Silver(I) complexes of AgL composition (L = PipCO, 3; MCO, 6) were prepared in high yield. Both metal complexes are thermally stable above 100oC, and remarkably stable to high intensity visible light. The stability of dried AgL compounds towards short wavelength UV-radiation (a frequently used germicidal light) was examined using diffusion reflectance spectroscopy. Both complexes demonstrate slow photoreduction within ~3 hrs, observable as a gradual color change and darkening due to the formation of fine (nano-scale) particles of metallic silver. The complex Ag(MCO), 6, is about 2.6 times less stable towards UV-radiation than its more lypophyllic analog Ag(PipCO), 3. Antimicrobial and biofilm growth inhibition properties of the prepared solid acrylate-based polymeric composites containing embedded silver(I) cyanoximates were investigated using three human pathogens: P. aeruginosa PAO1 (wound isolate), S. aureus NRS70 (methicillin resistant respiratory isolate), and S. mutans UA159 (cariogenic dental isolate). Studies showed that both 3 and 6 compounds completely abolished the growth of PAO1 at 0.5 weight % concentration, and the growth of UA159 and NRS70 at 1% concentration. Moreover, data demonstrates that complexes 3 and 6 also inhibit both planktonic and biofilm growth of Gram-positive and Gram-negative bacterial pathogens. The demonstrated thermal stability and pronounced antimicrobial activity of both silver(I) cyanoximates indicates the strong potential for the studied complexes to be used as light insensitive antimicrobial additives to light-curable adhesives that set indwelling devices in place.

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of two cyanoxime ligands, their precursors, and light insensitive antimicrobial silver(I) cyanoximates

Riddles

Whited

Lotlikar

et al. 2014

Inorganica Chimica Acta

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“…The booming application of metal complexes in the treatment of numerous human diseases is a vigorously expanding area in biomedical and inorganic chemistry [1,2]. The variation in coordination number, geometries, accessible redox states, thermodynamic and kinetic characteristics, and the intrinsic properties of the metal ion are some special characteristics of organometallic complexes that offer the medicinal chemists to employ different strategies for their exploitation.…”

Section: Introductionmentioning

confidence: 99%

Organotin(IV) 4-nitrophenylethanoates: Synthesis, structural characteristics and intercalative mode of interaction with DNA

Muhammad

Shah

Rehman

et al. 2009

Journal of Organometallic Chemistry

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“…The successful application of metal complexes in the treatment of numerous human diseases is a vigorously expanding area in biomedical and inorganic chemistry research. , Cancer is the primary target in the proposed research because it is the leading cause of premature deaths in the world. There are several ways to induce irreparable DNA damage, which may cause the arrest of its replication and create conditions for apoptosis (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Tin(IV) Cyanoximates: Synthesis, Characterization, and Cytotoxicity

et al. 2007

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In recent years, numerous organotin(IV) derivatives have exhibited remarkable cytotoxicity against several types of cancer. However, the properties of the cyanoxime-containing organotin(IV) complexes are unknown. Previously, it has been shown that cyanoximes displayed an interesting spectrum of biological activity ranging from growth-regulation to antimicrobial and pesticide detoxification actions. The work presented here attempts to combine the useful properties of both groups of compounds and investigate the likely antiproliferating activity of the new substances. A series of 19 organotin(IV) complexes, with nine different cyanoxime ligands, were anaerobically prepared by means of the heterogeneous metathesis reaction between the respective organotin(IV) halides (Cl, Br) and ML (M=Ag, Tl; L=cyanoximate anion), using an ultrasound in the CH3CN at room temperature. The compounds were characterized using spectroscopic methods (UV-visible, IR, 1H,13C NMR, 119Sn Mössbauer) and X-ray analysis. The crystal structures of the complexes revealed the formation of two types of tin(IV) cyanoximates: mononuclear five-coordinated compounds of R4-xSnLx composition (R=Me, Et, n-Bu, Ph; x=1, 2; L=cyanoximate anion), and the tetranuclear R8Sn4(OH)2O2L2 species (R=n-Bu, Ph). The latter complex contains a planar [Sn4(OH)2O2]2- core, consisting of three adjacent rhombs with bridging oxo and hydroxo groups. The tin(IV) atoms are five-coordinated and have distorted trigonal-pyramidal surrounding. This is the first instance when the organic anions were found to act as monodentate O-bound planar oxime ligands. All of the compounds were studied in vitro for antiproliferating activity, using human cervical cancer HeLa and WiDR colon cancer cell lines; cisplatin was used as a positive control substance. The two dibutyltin(IV) cyanoximates showed cytotoxicity similar and greater to that of cisplatin.

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Cited by 10 publications

References 174 publications

Synthesis and characterization of two cyanoxime ligands, their precursors, and light insensitive antimicrobial silver(I) cyanoximates

Synthesis and characterization of two cyanoxime ligands, their precursors, and light insensitive antimicrobial silver(I) cyanoximates

Organotin(IV) 4-nitrophenylethanoates: Synthesis, structural characteristics and intercalative mode of interaction with DNA

Tin(IV) Cyanoximates: Synthesis, Characterization, and Cytotoxicity

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