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Biological materials fixed with an epoxy compound: Comparison of the effects with or without ionically bound heparin (1995)

Sung, Hsing-Wen ; Shih, Jeng-Shiuan

New York, NY [u.a.] : Wiley-Blackwell

Journal of Applied Biomaterials 6 (1995), S. 185-190

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ISSN: 1045-4861

Keywords: Chemistry ; Polymer and Materials Science

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Medicine , Technology

Notes: Biological materials have been used as prosthetic devices such as heart valves, vascular grafts, and pericardial patches. These biological materials have to be fixed with crosslinking reagents and sterilized subsequently before they can be implanted in humans. Recently, a new crosslinking reagent, epoxy compound, has been used to fix bioprostheses. In this fixation technique, heparin may be ionically bound on the tissue surface. It has been shown that the amount of heparin bound to the tissue surface is proportional to the quantity of protamine impregnated in the biological tissues. However, it is not known if the impregnation of protamine will affect the crosslinking density of the biological tissues. This study was designed to compare the crosslinking densities of the epoxy compound fixed biological tissues with or without heparinization. Fresh porcine aortic valves procured from a slaughter house were first impregnated in various concentrations of protamine sulfate (0, 0.5, 1.0, or 1.5%) for about 30 min. The porcine aortic valves were then crosslinked in a 4% epoxy compound solution (Denacol® EX-313). The porcine samples were taken out at various elapsed fixation periods: 18, 25, 48, 72, 96, and 120 h. Finally, the crosslinked porcine aortic valves were heparinized in a 0.5% sodium heparin solution for about 1 h. The crosslinking densities of the porcine leaflet and the aortic wall of each sample were determined by measuring their shrinkage temperatures. It was revealed that the impregnation of various concentrations of protamine did not seem to significantly alter the shrinkage temperatures of the porcine leaflet and the aortic wall throughout the entire fixation process (p 〉 0.05). This indicated that the impregnation of protamine did not significantly change the crosslinking density of the biological tissues. However, it was found that protamine tended to discolor the tissue and to stiffen the porcine leaflet and the aortic wall. Although the impregnation of protamine did not seem to significantly alter the crosslinking density of the epoxy compound fixed biological tissues, the increase of the stiffness of the heparinized tissues may cause concerns in some clinical applications. © 1995 John Wiley & Sons, Inc.

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URL: http://dx.doi.org/10.1002/jab.770060307

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Crosslinking characteristics of an epoxy-fixed porcine tendon: Effects of pH, temperature, and fixative concentration (1996)

Sung, Hsing-Wen ; Hsu, Chin-Sheng ; Lee, Yuag-Shein ; [et al.]

Hoboken, NJ : Wiley-Blackwell

Journal of Biomedical Materials Research 31 (1996), S. 511-518

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ISSN: 0021-9304

Keywords: Chemistry ; Polymer and Materials Science

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Medicine , Technology

Notes: Injury to the anterior cruciate ligament (ACL) often results in functional instability within the knee joint and may induce a severe articular deterioration. Clinically, these patients may require an ACL reconstruction. In an attempt to develop an improved ligament prosthesis, a prototype xenograft - an epoxy-fixed porcine Achilles tendon - was developed. The study was intended to investigate the crosslinking characteristics of the epoxy-fixed porcine tendons fixed at different pHs (4.0, 7.4, 9.0, and 10.5), temperatures (4, 25, and 37°C), and fixative concentrations (1, 2, or 4%). Samples of each group were taken out at various elapsed fixation periods. The crosslinking characteristics - fixation index, denaturation temperature, and moisture content - of each sample were determined. Additionally, the stiffness of the epoxy-fixed tendons under various fixation conditions was qualitatively compared. In the study it was noted that the color of porcine Achilles tendons remained natural after epoxy fixation. With increasing pH, temperature, or fixative concentration, the fixation indices and denaturation temperatures of the epoxy-fixed tendons increased. However, the fixed porcine tendons tended to be stiffer at a higher pH, temperature, or fixative concentration. The moisture contents of the epoxy-fixed tendons were relatively lower than the fresh ones, while they were approximately the same at different pHs, temperatures, and fixative concentrations. The implications of these findings for the epoxy-fixed porcine tendons in ACL reconstruction require further investigation. © 1996 John Wiley & Sons, Inc.

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Feasibility study of a natural crosslinking reagent for biological tissue fixation (1998)

Sung, Hsing-Wen ; Huang, Rong-Nan ; Huang, Lynn L. H. ; [et al.]

Hoboken, NJ : Wiley-Blackwell

Journal of Biomedical Materials Research 42 (1998), S. 560-567

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ISSN: 0021-9304

Keywords: biological tissue ; crosslinking reagent ; genipin ; cytotoxicity ; enzymatic degradation ; Chemistry ; Polymer and Materials Science

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Medicine , Technology

Notes: Bioprostheses derived from biological tissues must be chemically modified and subsequently sterilized before they can be implanted in humans. Various crosslinking reagents, including formaldehyde, glutaraldehyde, dialdehyde starch, and epoxy compound, have been used to chemically modify biological tissues. However, these synthetic crosslinking reagents are all highly (or relatively highly) cytotoxic. It is therefore desirable to provide a crosslinking reagent suitable for use in biomedical applications that is of low cytotoxicity and that forms stable and biocompatible crosslinked products. This study evaluates the feasibility of using a naturally occurring crosslinking reagent - genipin - to chemically modify biological tissues. Genipin and its related iridoid compounds, extracted from gardenia fruits, have been used in traditional Chinese medicine for the treatments of jaundice and various inflammatory and hepatic diseases. In this feasibility study, the cytotoxicity of genipin and the crosslinking characteristics of genipin-fixed biological tissues were investigated. Fresh porcine pericardia procured from a slaughterhouse were used as raw materials. Glutaraldehyde and an epoxy compound (ethylene glycol diglycidyl ether), which has been used extensively in developing bioprostheses, were used as controls. It was found that the cytotoxicity of genipin was significantly lower than that of glutaraldehyde and the epoxy compound. The amino acid residues in the porcine pericardium that may react with genipin were lysine, hydroxylysine, and arginine. Additionally, the genipin-fixed tissue had a mechanical strength and resistance against enzymatic degradation comparable to the glutaraldehyde-fixed tissue. This suggests that genipin can form stable crosslinked products. The results of this in vitro study demonstrate that genipin is an effective crosslinking reagent for biological tissue fixation. © 1998 John Wiley & Sons, Inc. J Biomed Mater Res, 42, 560-567, 1998.

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Effects of various chemical sterilization methods on the crosslinking and enzymatic degradation characteristics of an epoxy-fixed biological tissue (1997)

Sung, Hsing-Wen ; Hsu, Hung-Liang ; Hsu, Chin-Sheng

Hoboken, NJ : Wiley-Blackwell

Journal of Biomedical Materials Research 37 (1997), S. 376-383

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ISSN: 0021-9304

Keywords: chemical sterilization ; bioprostheses ; glutaraldehyde ; epoxy compound ; propylene oxide ; ethanol ; crosslinking characteristics ; degradation rate ; Chemistry ; Polymer and Materials Science

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Medicine , Technology

Notes: Due to the nature of bioprostheses, which are mainly biological tissues that cannot be sterilized with heat or irradiation, the sterilization method by choice is generally liquid chemicals. It is known that a number of liquid chemicals can have rapid germicidal effect and can be used to sterilize bioprostheses. The study was to evaluate the effects of various chemical sterilization methods on the crosslinking and enzymatic degradation characteristics of an epoxy-fixed biological tissue. The chemical sterilants employed were: a 70% ethanol solution (EtOH), a 2% epoxy compound + 20% ethanol solution (EX-810), a 2% propylene oxide + 20% ethanol solution (PO), and a 0.625% glutaraldehyde + 20% ethanol + 0.2% polysorbate solution (GA). Both masking and crosslinking of the free amino groups within the epoxy-fixed tissue were observed subsequent to sterilization with GA or EX-810. This improved the resistance of the GA or EX-810 sterilized tissues against collagenase degradation as compared to its nonsterilized counterpart. However, subsequent to sterilization with PO, only masking of the free amino groups within the epoxy-fixed tissue was noted. The inhibition of the collagenase degradation by masking of the free amino groups was traded off by the more random molecular packing of the PO sterilized sample due to the introduction of the side branches. Sterilization of the epoxy-fixed tissue with EtOH may increase its denaturation temperature and tensile strength, while neither masking nor crosslinking of free amino groups within the tissue took place. The resistance to degradation of the EtOH sterilized tissue, however, did not improve as compared to its nonsterilized counterpart. © 1997 John Wiley & Sons, Inc. J Biomed Mater Res, 37, 376-383, 1997.

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Crosslinking characteristics of porcine tendons: Effects of fixation with glutaraldehyde or epoxy (1996)

Sung, Hsing-Wen ; Shih, Jeng-Shiuan ; Hsu, Chin-Sheng

Hoboken, NJ : Wiley-Blackwell

Journal of Biomedical Materials Research 30 (1996), S. 361-367

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ISSN: 0021-9304

Keywords: Chemistry ; Polymer and Materials Science

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Medicine , Technology

Notes: Anterior cruciate ligament (ACL) injuries, if left untreated, often produce significant disability in the athletically active population. Currently, autogenous tissue is the most commonly used substitute for ACL reconstruction because its immunogenicity is virtually nonexistent. However, the functional amount of autogenous tissue available for transplantation is limited. Additionally, this transplantation procedure may create a defect at the donor site, which can result in functional disability. To address these concerns, a prototype xenograft ligament prosthesis, epoxy-fixed porcine Achilles tendon, was developed. This study was intended to investigate the crosslinking characteristics of the epoxy-fixed porcine tendon. The fresh and glutaraldehyde-fixed porcine Achilles tendons were used as controls. Fresh porcine Achilles tendons procured from a slaughterhouse were used to fabricate the ligament prostheses. A 4% epoxy (ethylene glycol diglycidyl ether) solution or a 0.625% glutaraldehyde solution was employed to fix the porcine tendons. Samples of each group were taken out at various elapsed fixation periods. The crosslinking characteristics - denaturation temperature, moisture content, and fixation index - of each sample were then determined. In the study, it was learned that the crosslinking rate for the glutaraldehyde fixation was faster than that for the epoxy fixation. While the denaturation temperatures and the fixation indices for both studied groups were higher than for the fresh one, the denaturation temperature of the glutaraldehyde-fixed tendon was relatively higher than its epoxy-fixed counterpart. However, the fixation index and the moisture content for both studied groups were comparable. Also, it was noted that the epoxy-fixed tendon appeared more natural as compared to its glutaraldehyde-fixed counterpart. The implications of these findings for the epoxy-fixed tendon in the clinical ACL reconstruction require further investigation. © 1996 John Wiley & Sons, Inc.

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Studies on epoxy compound fixation (1996)

Sung, Hsing-Wen ; Cheng, Wen-Huey ; Chiu, Ing-Sh ; [et al.]

Hoboken, NJ : Wiley-Blackwell

Journal of Biomedical Materials Research 33 (1996), S. 177-186

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ISSN: 0021-9304

Keywords: Chemistry ; Polymer and Materials Science

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Medicine , Technology

Notes: Bioprostheses derived from collagenous tissues have to be fixed and subsequently sterilized before they can be implanted in humans. Clinically, the most commonly used fixative is glutaraldehyde. However, the tendency for glutaraldehyde to markedly alter tissue stiffness and promote tissue calcification are well-recognized drawbacks of this fixative. To address the deficiencies with the glutaraldehyde-fixed tissue, a new fixative, epoxy compound, was used to fix biological prostheses. The study was undertaken to investigate the fixation rates and crosslinking densities of biological tissues fixed with various epoxy compounds. These epoxy compounds are different in their chemical structures. Glutaraldehyde was used as a control. The fixation rates and crosslinking densities of the fixed tissues were determined by measuring their fixation indices and denaturation temperatures, respectively. Generally, the epoxy-fixed tissues were more pliable than the glutaraldehyde-fixed one. Furthermore, the tissues fixed with monofunctional epoxy compound were more pliable than those fixed with multifunctional epoxy compounds. With increasing pH or temperature, the fixation rate of epoxy compound increased. However, the number of epoxide functional groups did not seem to affect the fixation rate of the epoxy compound. The fixation rate of glutaraldehyde was faster than that of epoxy compounds. Additionally, the crosslinking density of the glutaraldehyde-fixed tissue was greater than that of the epoxy-fixed counterparts. Moreover, it was noted that the denaturation temperatures of the tissues fixed with glutaraldehyde or multifunctional epoxy compounds were significantly higher than the fresh ones (p 〈 0.05), while that fixed with monofunctional epoxy compound stayed roughly the same throughout the entire fixation process (p 〉 0.05). The results obtained in this study may be used to optimize the fixation process for developing bioprostheses fixed with epoxy compounds. © 1996 John Wiley & Sons, Inc.

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Degradation potential of biological tissues fixed with various fixatives: An in vitro study (1997)

Sung, Hsing-Wen ; Hsu, Chin-Sheng ; Wang, Sheng-Ping ; [et al.]

Hoboken, NJ : Wiley-Blackwell

Journal of Biomedical Materials Research 35 (1997), S. 147-155

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ISSN: 0021-9304

Keywords: biological tissue ; epoxy compound ; bacterial collagenase ; pronase ; in vitro degradation ; Chemistry ; Polymer and Materials Science

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Medicine , Technology

Notes: The purpose of this study was to investigate the in vitro degradation potential of porcine pericardia fixed with various aldehyde or epoxy compound (EC) fixatives, using bacterial collagenase and pronase. The fixatives investigated were formaldehyde (FA), glutaraldehyde (GA), monofunctional EC (EX-131), and multifunctional ECs (EX-810, EX-313, and EX-512). Fresh porcine pericardium was used as a control. The test samples were well immersed in a 20-U/mL collagenase solution or a 10-U/ml pronase solution and incubated at 37°C at pH 7.5 for 24 h. The extent of degradation of each test sample was determined by measuring its increment in free amino group content and changes in collagen structure, denaturation temperature, and tensile stress after degradation. In general, the extent of tissue degradation with pronase was more notable than with collagenase. As observed with fresh tissue, the EX-131 EC fixed tissue radically disintegrated after either collagenase or pronase degradation, whereas the other test samples remained intact. The reason for this may reside in the more random molecular packing of the EX-131 EC-fixed tissue, which led to some loss in its helical integrity. This made penetration of enzymes into biological tissue easier. Of the multifunctional EC test groups, tissues fixed with tetrafunctional EC (EX-521) or trifunctional EC (EX-313) had relatively better resistance to degradation than those fixed with bifunctional EC (EX-810). The extent of degradation for the EX-313 or EX-512 EC fixed tissues was similar to that observed for the FA- or GA-fixed tissues. The results of this study indicated that the biological tissue fixed with monofunctional EC (EX-131) cannot resist bacterial collagenase or pronase degradation. However, resistance to degradation of the multifunctional EC (EX-313 or EX-152)-fixed tissues was comparable to that of the aldehyde (FA or GA)-fixed tissues. Therefore, of various EC fixatives, the EC with a greater number of functional groups should be chosen for tissue fixation to increase its resistance to enzymatic degradation. © 1997 John Wiley & Sons, Inc. J Biomed Mater Res, 35, 147-155, 1997

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Biocompatibility study of a biological tissue fixed with a naturally occurring crosslinking reagent (1998)

Huang, Lynn L. H. ; Sung, Hsing-Wen ; Tsai, Chen-Chi ; [et al.]

Hoboken, NJ : Wiley-Blackwell

Journal of Biomedical Materials Research 42 (1998), S. 568-576

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ISSN: 0021-9304

Keywords: biological tissue ; crosslinking reagent ; genipin ; subcutaneous implant ; biocompatibility ; Chemistry ; Polymer and Materials Science

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Medicine , Technology

Notes: A recognized disadvantage of the currently available chemical reagents used to fix bioprostheses is the potential toxic effects a recipient may be exposed to from residues. It is therefore desirable to provide a crosslinking reagent that is of low cytotoxicity and can form stable and biocompatible crosslinked products. To achieve this goal, a naturally occurring crosslinking reagent - genipin - was used by our group to fix biological tissues. Genipin can be obtained from its parent compound geniposide, which can be isolated from the fruits of Gardenia jasminoides ELLIS. In our previous feasibility study, it was found that the cytotoxicity of genipin is significantly lower than both glutaraldehyde and an epoxy compound. Additionally, it was shown that genipin can form stable crosslinked products. The present study further investigates the biocompatibility of a genipin-fixed porcine pericardium implanted subcutaneously in a growing rat model. The fresh, glutaraldehyde-, and epoxy-fixed counterparts were used as controls. It was noted that the inflammatory reaction of the genipin-fixed tissue was significantly less than its glutaraldehyde- and epoxy-fixed counterparts. Also, the genipin-fixed tissue has tensile strength and resistance against in vivo degradation comparable to the glutaraldehyde-fixed tissue. Additionally, the calcium content of the genipin-fixed tissue measured throughout the entire course of the study was minimal. Nevertheless, further study in calcification for the genipin-fixed tissue should be conducted in a blood-contact environment. The results obtained in this subcutaneous study indicate that genipin is a promising crosslinking reagent for biological tissue fixation. However, further durability testing in vitro and in vivo are needed to determine the relative functional merits of this new crosslinker. © 1998 John Wiley & Sons, Inc. J Biomed Mater Res, 42, 568-576, 1998.

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