Methoxypropyl cyanoacrylate

The addition of certain members of the family of gel-formers to methoxypropyl cyanoacrylate yields a series of tissue adhesive formulations, which can be used a effectively as ... 

Early demonstration that the absorption of poly(methoxypropyl cyanoacrylate) can be accelerated in the presence of hquid absorbable oxalate polymers led Shalaby to develop a new family of methoxypropyl cyanoacrylate (MFC)/polyester formulations as tissue adhesives with a broad range of properties. These formulations were tailored to produce absorbable tissue adhesives with a range of adhesive properties and compositionally controlled compliance depending on the type and content of the absorbable polyester component in the formulation. 

In response to these concerns, and particularly the ones associated with tire nonabsorbable cyanoacrylates that are used clinically. Linden and Shalaby disclosed a novel, absorbable tissue adhesive composition that addressed, to a practical extent, the drawbacks of the absorbable bioadhesive as well as nonabsorbable cyanoacrylates. In effect, these absorbable tissue adhesive compositions were based (1) primarily on methoxyalkyl cyanoacrylates and preferably methoxypropyl cyanoacrylate as the precursor of an absorbable tissue adhesive polymer and (2) on a polymeric, highly absorbable, liquid comprising an oxalate ester of triethylene glycol as a modifier to modulate the viscosity of the overall composition, lower the heat of polymerization, and increase the compliance and absorption rate of the cured adhesive joint. In a more recent disclosure by Shalaby, a number of other useful modifiers were described and the functional performance of the new adhesive compositions was reported. ... 

Based on the design criteria noted above, the evolution of the absorbable cyanoacrylate-based system commenced with methoxypropyl cyanoacrylate (MFC) and was followed by formulation of MFC with polyether oxalate or polyester carbonate. Figure 5.1 outlines a polymerization scheme and designation of the final polymer. Both V-100 and V-150 tissue adhesives contain the same components but in different proportions. 

Methoxypropyl cyanoacrylate/poly(trioxyethylene oxalate) tissue adhesive provides an alternative to the traditional methods of wound closure. 

Shalaby S. W., Linden, C. L., Jr. and Shalaby M., Absorption of radiolabeUed methoxypropyl cyanoacrylate tissue adhesive composition in rats, Trans. Soc. Biomater., 26, 293, 2003. 

Trimethylene carbonate (TMC) and glycolide (G) were purchased from Boehringer Ingelheim Chemicals, Inc. (Virginia). Polyethylene glycol-400 (PEG-400) was purchased from Sigma-Aldrich (Missouri). Modified/stabilized methoxypropyl cyanoacrylate tissue adhesive (MS-MPC) was prepared at Poly-Med, Inc. (South Carolina). 

Methoxypropyl cyanoacrylate tissue adhesive (C-TA) as a positive control... 

Cyanoacrylate monomers are generally low viscosity, colorless liquids that are unstable in the absence of acidic stabilizers. The commercially important materials are lower alkyl esters of 2-cyanoacrylic acid including methyl, ethyl, n-propyl, al-lyl, n-butyl, isobutyl, 2-methoxyethyl, 2-methoxypropyl, and n-octyl derivatives. The structures of some of these monomers are shown in Figure 1. The physical properties of these and related monomers are reported in detail in several previous... 

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