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At least 19 recordsLinked to original sources
PubMed2003

Sensory irritation due to methyl-2-cyanoacrylate, ethyl-2-cyanoacrylate, isopropyl-2-cyanoacrylate and 2-methoxyethyl-2-cyanoacrylate in mice.

The expiratory bradypnoea indicative of upper airway irritation in mice was evaluated during a period of 60 min of nasal exposure to methyl-2-cyanoacrylate, ethyl-2-cyanoacrylate, isopropyl-2-cyanoacrylate and 2-methoxyethyl-2-cyanoacrylate vapors using nose only exposure. Irritation of the upper respiratory tract caused a concentration-dependent decrease in the respiratory rate. The maximum effect occurred within the first 10 min of exposure and was followed by a drop-off in the response during the remainder of the exposure period. The airborne concentration resulting in a 50% decrease in the respiratory rate of mice (RD(50)) was calculated for each chemical. The results show that the four chemicals had similar irritant potencies. The RD(50) values of methyl-2-cyanoacrylate, ethyl-2-cyanoacrylate, isopropyl-2-cyanoacrylate and 2-methoxyethyl-2-cyanoacrylate were 1.4, 0.7, 0.6 and 1.0 p.p.m. Tentative estimates of threshold limit values showed that 0.1 RD(50) was closer to the values recommended by the American Conference of Governmental Industrial Hygienists for methyl- and ethyl-2-cyanoacrylate than 0.03 RD(50). On the basis of a threshold limit value for short-term exposure limit (TLV STEL) equal to 0.1 RD(50), the TLV STELs for the four cyanoacrylates should not exceed 0.1 or 0.2 p.p.m.

Animals↗
PubMed1999

Microcatheter adhesion of cyanoacrylates: comparison of normal butyl cyanoacrylate to 2-hexyl cyanoacrylate.

PURPOSE: To compare the catheter adhesion properties of 2-hexyl cyanoacrylate (Neuracryl M), a new agent, to those of normal butyl cyanoacrylate (Histoacryl), the most widely used liquid acrylic agent for microcatheter embolization. MATERIALS AND METHODS: 2-hexyl cyanoacrylate (Neuracryl M1) was tested in pure form and mixed with either a proprietary polymerization retardant/contrast agent (Neuracryl M2) or ethiodized oil (Ethiodol). Histoacryl was tested in pure form and mixed with Ethiodol. The cyanoacrylate mixtures were injected through microcatheters into wells partially filled with heparinized whole blood. The cyanoacrylates were allowed to polymerize around the microcatheter tips for 1-3 minutes. The microcatheters were then pulled at a constant rate until they were extracted from the polymerized cyanoacrylates. The peak forces required for extraction were recorded. RESULTS: The peak forces required to extract the microcatheters from either pure Histoacryl or Histoacryl mixed with 33% Ethiodol were significantly higher (P < .01; P < .05) than those for pure Neuracryl M1. When Neuracryl M1 and M2 were mixed together (as intended for clinical use), the force required for microcatheter extraction was significantly lower than that for either pure Histoacryl, Histoacryl mixed with 33% Ethiodol, or Neuracryl M1 alone (P < .01; P < .01; P < .01, respectively). The force required to extract microcatheters from the Neuracryl M1 and M2 mixture was not, however, significantly different from that of Histoacryl mixed with 50% Ethiodol. The force of extraction for the Neuracryl M1 and 50% Ethiodol mixture was below our ability to obtain precise measurements. CONCLUSION: When Neuracryl M1 was mixed with its proprietary polymerization retardant/contrast agent (Neuracryl M2), catheter adhesion was not significantly different from that of Histoacryl mixed with 50% Ethiodol, a mixture common in clinical use. When Neuracryl M1 was tested alone or mixed with Ethiodol (not intended by the manufacturer), catheter adhesion was significantly decreased relative to pure Histoacryl or equivalent mixtures of Histoacryl and Ethiodol.

Adhesiveness↗
PubMed1998

Pegylated nanoparticles from a novel methoxypolyethylene glycol cyanoacrylate-hexadecyl cyanoacrylate amphiphilic copolymer.

PURPOSE: The aim of this work was to develop PEGylated poly(alkylcyanoacrylate) nanoparticles from a novel methoxypolyethyleneglycol cyanoacrylate-co-hexadecyl cyanoacrylate copolymer. METHODS: PEGylated and non-PEGylated nanoparticles were formed by nanoprecipitation or by emulsion/solvent evaporation. Nanoparticles size, zeta potential and surface hydrophobicity were investigated. Surface chemical composition was determined by X-ray photoelectron spectroscopy. Nanoparticle morphology was investigated by transmission electron microscopy after freeze-fracture. Nanoparticles cytotoxicity was assayed in vitro, onto mouse peritoneal macrophages. Cell viability was determined through cell mitochondrial activity, by a tetrazolium-based colorimetric method (MTT test). Finally, the degradation of PEGylated and non-PEGylated poly(hexadecyl cyanoacrylate) nanoparticles was followed spectrophotometrically during incubation of nanoparticles in fetal calf serum. RESULTS: Monodisperse nanoparticles with a mean diameter ranging between 100 and 200 nm were obtained using nanoprecipitation or emulsion/solvent evaporation as preparation procedures. A complete physico-chemical characterization, including surface chemical analysis, allowed to confirm the formation of PEG-coated nanoparticles. The PEGylation of the cyanoacrylate polymer showed reduced cytotoxicity towards mouse peritoneal macrophages. Furthermore, the presence of the PEG segment increased the degradability of the poly(hexadecyl cyanoacrylate) polymer in presence of calf serum. CONCLUSIONS: We succeeded to prepare PEGylated nanoparticles from a novel poly(methoxypolyethyleneglycol cyanoacrylate-co-hexadecyl cyanoacrylate) by two different techniques. Physico-chemical characterization showed the formation of a PEG coating layer. Low cytotoxicity and enhanced degradation were also shown.

Animals↗
PubMed2006

Core-shell type of nanoparticles composed of poly[(n-butyl cyanoacrylate)-co-(2-octyl cyanoacrylate)] copolymers for drug delivery application: synthesis, characterization and in vitro degradation.

Core-shell type of nanoparticles (NPs) with manipulated degradation rate and balanced hydrophilic/hydrophobic properties were designed and characterized. The NPs based on the copolymers of n-butyl cyanoacrylate (BCA) and 2-octyl cyanoacrylate (OCA) were prepared by anion emulsion polymerization in 0.01N HCl solution with pluronic F127 as the stabilizer. These NPs were spherical in shape and with size smaller than 100 nm in a narrow distribution. The particle size, zeta potential, molecular weight, hydrophobicity and degradation rate of the copolymer depended on its composition significantly. In vitro chemical hydrolytic studies indicated that the degradation rate of the NPs could be controlled over 200-fold by adjusting the BCA/OCA ratio. Differential scanning calorimetry (DSC) measurements verified the existence of copolymer with tapered structure which was induced by the reactivity difference of the monomers. A BCA/OCA core-shell structure is postulated that the OCA rich segments were mainly located in the core of the NPs. The cytotoxicity of poly(2-octyl cyanoactylate) (POCA) is quite lower than that of poly(n-butyl cyanoacrylate) (PBCA) and the toxicity of poly(BCA-co-OCA) NPs is similar to that of PBCA NPs.

Acrylates↗
PubMed2005

Body distribution and in situ evading of phagocytic uptake by macrophages of long-circulating poly (ethylene glycol) cyanoacrylate-co-n-hexadecyl cyanoacrylate nanoparticles.

AIM: To investigate the body distribution in mice of [14C]-labeled poly methoxyethyleneglycol cyanoacrylate-co-n-hexadecyl cyanoacrylate (PEG-PHDCA) nanoparticles and in situ evading of phagocytic uptake by mouse peritoneal macrophages. METHODS: PEG-PHDCA copolymers were synthesized by condensation of methoxypolyethylene glycol cyanoacetate with [14C]-hexadecyl-cyanoacetate. [14C]-nanoparticles were prepared using the nanoprecipitation/solvent diffusion method, while fluorescent nanoparticles were prepared by incorporating rhodamine B. In situ phagocytic uptake was evaluated by flow cytometry. Body distribution in mice was evaluated by determining radioactivity in tissues using a scintillation method. RESULTS: Phagocytic uptake by macrophages can be efficiently evaded by fluorescent PEG-PHDCA nanoparticles. After 48 h, 31% of the radioactivity of the stealth [14C]-PEG-PHDCA nanoparticles after iv injection was still found in blood, whereas non-stealth PHDCA nanoparticles were cleaned up from the bloodstream in a short time. The distribution of stealth PEG-PHDCA nanoparticles and non-stealth PHDCA nanoparticals in mice was poor in lung, kidney, and brain, and a little higher in hearts. Lymphatic accumulation was unusually high for both stealth and non-stealth nanoparticles, typical of lymphatic capture. The accumulation of stealth PEG-PHDCA nanoparticles in the spleen was 1.7 times as much as that of non-stealth PHDCA (P< 0.01). But the accumulation of stealth PEG-PHDCA nanoparticles in the liver was 0.8 times as much as that of non-stealth PHDCA (P< 0.05). CONCLUSION: PEGylation leads to long-circulation of nanoparticles in the bloodstream, and splenotropic accumulation opens up the potential for further development of spleen-targeted drug delivery.

Animals↗
PubMed1976

Interfacial properties of polymethyl alpha-cyanoacrylate and polybutyl alpha-cyanoacrylate.

Several physical properties of two polyalkyl alpha-cyanoacrylates relevant to their use in pharmaceutical dosage forms have been investigated. Formation of polymer films at several oil-water interfaces reveals films of diverse morphology. The retardation of solute transfer across an oil-water interface caused by the presence of polymer films formed in situ from the monomers has revealed that the methyl derivative forms the more effective barrier to the test solute, gentian violet. The emulsion-stabilizing properties of the methyl polymer have been studied, and the film-forming properties of the monomers spread from benzene onto water surfaces have been examined using a surface balance.

Cyanoacrylates↗
PubMed1992

Alkyl cyanoacrylates as space filling bone adhesives.

Higher chained alkyl cyanoacrylates have potential to function efficiently as space filling, hydrophobic, viscoelastic, biocompatible, and rapidly polymerizing bone adhesives. Hence they may be useful in applications where a void has to be filled, such as replacement of the intervertebral disc. To assess their applicability as space filling material in such an application, three alkyl cyanoacrylates; methoxyethyl cyanoacrylate, isobutyl cyanoacrylate, and isoamyl cyanoacrylate have been evaluated in this study. The bonding strength of these cyanoacrylates to bone in a space filling situation have been measured. The results indicate the bond strength of isoamyl cyanoacrylate (0.13 MPa) to be significantly (p less than 0.05) lower compared with methoxyethyl cyanoacrylate (0.33 MPa) and isobutyl cyanoacrylate (0.37 MPa). There was no significant difference in the bond strengths of isobutyl cyanoacrylate and methoxyethyl cyanoacrylate.

Animals↗
PubMed1990

Modification of synthesis and investigation of properties for 2-cyanoacrylates.

The conventional method for synthesis of 2-cyanoacrylate monomers was modified and the adhesive properties were studied for the cyanoacrylate monomers and the resultant polymers. Toluene was found to be better as reaction solvent than methyl alcohol or xylene. The higher the molecular weight of the condensation oligomer before pyrolysis and the narrower the molecular weight distribution, the higher the yield of cyanoacrylate monomer. Ethoxyethyl cyanoacrylate with an ether side chain was shown to be a soft and biodegradable adhesive. The softening and glass transition temperatures of ethoxyethyl cyanoacrylate polymer were much lower than those of cyanoacrylate polymers with methyl, ethyl or isobutyl side chains. Hydrolysis of poly(ethoxyethyl cyanoacrylate), evaluated from formaldehyde generation and mass loss, was faster than that of ethyl cyanoacrylate and isobutyl cyanoacrylate polymer. Hydrolysis of the ethoxyethyl cyanoacrylate polymers was greatly affected by the molecular weight of the polymers. The morphological change of the cyanoacrylate polymer films was studied by scanning electron microscopy.

Adhesiveness↗
PubMed1990

In vivo evaluation of 2-cyanoacrylates as surgical adhesives.

To evaluate 2-cyanoacrylates as surgical adhesives, the bond strength in vivo as well as the tissue reaction was investigated using methyl-, ethyl-, isobutyl-, and ethoxyethyl-2-cyanoacrylate. In addition, their set time and spreading on blood were studied. When the 2-cyanoacrylates were applied to an incised site of rabbit skin, they could maintain the skin closure without suturing during the first week and the bond strength increased during the second week. Significant inflammatory response was observed around the subcutaneous tissue glued with methyl- and ethoxyethyl-2-cyanoacrylate and persisted for approximately one week. All the 2-cyanoacrylate polymers were absorbed and the tissues treated were healed two weeks after the operation. There was a mild inflammatory reaction in the tissue treated with ethyl- and isobutyl-2-cyanoacrylate, and their polymers still remained at the wound site at the second week postoperatively. The disappearance rate of the 2-cyanoacrylate polymers was roughly in proportion to the inflammatory tissue response. Ethoxyethyl-2-cyanoacrylate spread more broadly on tissues than the other 2-cyanoacrylates, while its set time was shorter than that of methyl- and ethyl-2-cyanoacrylates.

Animals↗
PubMed2005

Octyl-2-cyanoacrylate tissue adhesive in external dacryocystorhinostomy.

PURPOSE: To review our experience using octyl-2-cyanoacrylate for closing the cutaneous incision in external dacryocystorhinostomy (DCR). METHODS: A retrospective review was performed of all cases of external DCR with cyanoacrylate wound closure performed during a 12-month period. At the completion of the DCR, octyl-2-cyanoacrylate was used to close the incision. No subcutaneous sutures were placed to approximate the wound edges. Fifteen seconds of drying time elapsed before a second application of the adhesive was applied. Follow-up consisted of examinations at 1 week, 1 month, and 3 months after surgery. RESULTS: Twenty-one cases of wound closure using octyl-2-cyanoacrylate in external DCR were performed on 19 patients. Cyanoacrylate was applied to the wound without complications, and all patients had excellent closure of the wound with the cyanoacrylate at the end of the case. No wound infections were noted during the follow-up period. One patient had a wound dehiscence that was treated with forceps debridement of residual cyanoacrylate and reapplication of additional octyl-2-cyanoacrylate. One patient had hypertrophic scar formation that resolved with daily massage. In all patients, the incision was believed to be aesthetically equivalent to the expected appearance of suture closed DCR incisions. CONCLUSIONS: Closure of the DCR incision with cyanoacrylate is safe, quick, does not compromise wound integrity, and provides an aesthetic result that is equivalent to suture wound closure. Additional benefits could potentially include safer operative environment and postoperative convenience for patient and surgeon.

Adolescent↗
PubMed2003

N-2-butyl-cyanoacrylate for bleeding gastric varices: a United States pilot study and cost analysis.

OBJECTIVES: N-butyl-2-cyanoacrylate has been reported to be effective for bleeding varices but is not available in the United States. We report the initial US experience with cyanoacrylate in this prospective trial and evaluate its safety, efficacy, and relative costs. METHODS: Patients with active or recent gastric variceal bleeding were eligible. Cyanoacrylate therapy was performed until variceal occlusion was achieved. Rebleeding was assessed at 72 h (acute phase), 6 wk (subacute phase), and 1 yr (chronic phase). Survival was assessed at 3 months and 1 yr. Cost analysis was performed comparing the first 17 patients to historical control patients not treated with cyanoacrylate. RESULTS: A total of 44 patients were enrolled, 37 with cirrhosis and seven with noncirrhotic portal hypertension (NCPH). In cirrhotic patients, rebleeding was seen in two of 37 (5%) at 72 h, one of 30 (3%) at 6 wk, and five of 28 (18%) at 1 yr. Survival without shunt at 3 months was 30 of 34 (88%) and at 1 yr was 24 of 31 (77%). In NCPH patients, rebleeding was seen in two of seven (29%) at 72 h. These patients received definitive therapy for NCPH after diagnosis. Mortality and costs were substantially higher in the non-cyanoacrylate group. The odds of death were greater by 7-fold in the non-cyanoacrylate group than within the cyanoacrylate group (95% CI = 1.18-41.36, p = 0.0318). At 3 months, there was a 3.18-fold difference (95% CI = 1.05-9.64, p = 0.0411) in accrued costs; at 1 yr, the difference was 2.55-fold (95% CI = 0.96-6.94, p = 0.0585). The cost-effective ratio was estimated as 108,237 US dollars/death averted, reflecting marked cost reduction with improved survival in the cyanoacrylate-treated group. This is believed to result largely from avoidance of shunt interventions. CONCLUSIONS: Cyanoacrylate treatment of gastric varices is safe, clinically effective, and cost effective.

Adult↗
PubMed2002

Cyanoacrylate embolization of experimental aneurysms.

BACKGROUND AND PURPOSE: Cyanoacrylates are effective occlusive agents in neurovascular interventions. To study their potential to improve long-term results of endovascular treatment of aneurysms, we conducted experimental studies in canine aneurysm models. METHODS: Venous pouch carotid aneurysms were constructed in dogs. Results of coil embolization of lateral wall and bifurcation aneurysms were compared. A lateral wall model of embolization with gelatin sponges was used to study the effects of coating sponges with cyanoacrylate on angiographic results and neointima thickness at 3 and 12 weeks. These models were also used to investigate the control of endovascular cyanoacrylate deposition, alone or over a coil placed at the neck of the treated lesions. The results of endovascular cyanoacrylate embolization of bifurcation aneurysms were compared with those of coil embolization at 3 months. RESULTS: Bifurcation aneurysms treated with coils showed more frequent recurrences (P <.01) and thinner neointimas (P <.01) at 3 months than did lateral wall aneurysms. Cyanoacrylate-coated sponges improved angiographic results (P <.05) and led to thicker neointimas at 3 and 12 weeks (P <.05) as compared with uncoated sponges. Endovascular cyanoacrylate deposition with microcatheters led to stray emboli in all cases. Cyanoacrylate delivery was improved by a single coil positioned at the neck of the aneurysm, but parent vessel embolization still occurred in 25% of the animals. Cyanoacrylate embolization of bifurcation aneurysms improved angiographic results at 3 months as compared with coil embolization (P <.01). CONCLUSION: Cyanoacrylate embolization is currently difficult to control. It has the potential to decrease recurrences after endovacular treatment of aneurysms, but a safe method for endovascular delivery has yet to be developed.

Animals↗
PubMed2002

Quantitative assessment of polymerization-binding mechanics of cyanoacrylates: model development and validation.

BACKGROUND AND PURPOSE: Although commonly acknowledged as paramount in significance, the mechanics of cyanoacrylate polymerization remain poorly characterized and quantified for clinical applications. This prompted development of a simplistic model for the systematic study of polymerization and binding behaviors of cyanoacrylates. METHODS: A sliding bed apparatus was constructed that linked a strain gage with a vessel that could be filled with liquid medium, cyanoacrylate, and a microcatheter. As the cyanoacrylate polymerized, the microcatheter was mechanically drawn away very slowly from the fixed vessel, resulting in the development of forces that were recorded to characterize the dynamics of polymerization and binding. Optimization of the model required manipulation of several variables that could influence polymerization. Three different formulations of cyanoacrylate were also tested to determine whether there are significant differences in polymerization dynamics. RESULTS: After experimenting with a few basic physical parameters of the test apparatus, consistent measurements of binding forces during cyanoacrylate polymerization could be recorded and measured. Polymerization produced a multiphasic pattern of binding forces, in which three distinct phases were observed. Furthermore, the rates of polymerization were significantly influenced by a variety of parameters, including the type of fluid within the model vessel, geometry of the model vessel, and rate of injection of acrylic into the well. Furthermore, there were significant differences in the pattern of dynamic binding forces among the various formulations of cyanoacrylate tested. CONCLUSIONS: A standardized bench top testing apparatus has been developed, which can consistently show dynamic binding related to polymerization of cyanoacrylates. This preliminary study shows a clear multiphasic pattern of polymerization binding, which may have important clinical implications. The apparatus may be useful for gaining better insight into a variety of clinically important phenomena related to cyanoacrylate polymerization.

Cyanoacrylates↗
PubMed1990

[Biochemical study on the application of alpha-cyanoacrylate instant adhesives in dentistry].

The author biochemically evaluated the possible application of 4 types of alpha-cyanoacrylate adhesive agents (methyl, ethyl, isopropyl and isobutyl) in dentistry. A semiconductor temperature sensor was used to measure alpha-cyanoacrylate polymerization-temperature maximum heat, and an oscilloscope was employed to measure heat value. Amounts of formaldehyde eluted from the soluble component of alpha-cyanoacrylate was measured colorimetrically. In addition, to evaluate the effects of alpha-cyanoacrylate on pulp tissue, the soluble component of alpha-cyanoacrylate polymer was added to mouse macrophages. Changes in the numbers and morphology of macrophages and their glucose consumption in the supernatant medium were studied and compared with corresponding data obtained when formaldehyde alone was used. (1) During the polymerization of alpha-cyanoacrylate, when a glass fiber disc filter was used, the temperature increased by 19.1 degrees C in 1 microliter with methyl and by 8.6 degrees C with isobutyl. Even with the same alkyl, however, polymerization heat differed depending on the structure and constitution of the adhesive material and varied widely according to experimental conditions. (2) A mean maximum temperature of 1.7 degrees C in the dentin floor during polymerization of 10 microliters of alpha-cyanoacrylate monomer with methyl suggests no thermal injury to the pulp. (3) Formaldehyde was detected in all 4 adhesives when alpha-cyanoacrylate was dropped into distilled water for polymerization. Since, with each alkyl, the amount of eluted formaldehyde reached a maximum after 1 day of immersion, continuous elution of formaldehyde by hydrolysis was negligible. (4) A greater amount of formaldehyde was eluted from the polymer with methyl and ethyl, which have less Cs, than from the polymer with isopropyl and isobutyl, which have more Cs. These findings suggest that alkyl type affects the amount of eluted formaldehyde. (5) The soluble component of the alpha-cyanoacrylate polymer, either methyl or ethyl, had no effect on the number or morphology of mouse macrophages, as compared with corresponding data obtained when sterilized distilled water was used as a control. Isopropyl and isobutyl, however, decreased cell count and inhibited the extension of the sell soma. (6) The effects of isopropyl and isobutyl on the numbers and morphology of macrophages were similar to those of formaldehyde used alone at a concentration of 8 ppm or more. These findings suggest that, under the present experimental conditions, the above-mentioned changes in macrophages are the effects of about 8 ppm of formaldehyde. (7) The rate of glucose consumption by macrophages with methyl or ethyl was as high as that with the control.(ABSTRACT TRUNCATED AT 400 WORDS)

Adhesives↗