US3331814A - Synthetic polypeptides of an l-imino acid and an l-amino acid - Google Patents
Synthetic polypeptides of an l-imino acid and an l-amino acid Download PDFInfo
- Publication number
- US3331814A US3331814A US295223A US29522363A US3331814A US 3331814 A US3331814 A US 3331814A US 295223 A US295223 A US 295223A US 29522363 A US29522363 A US 29522363A US 3331814 A US3331814 A US 3331814A
- Authority
- US
- United States
- Prior art keywords
- acid
- imino
- polypeptide
- amino acid
- synthetic polypeptides
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/68—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyaminoacids or polypeptides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
- A61L17/06—At least partially resorbable materials
- A61L17/08—At least partially resorbable materials of animal origin, e.g. catgut, collagen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
- A61L17/06—At least partially resorbable materials
- A61L17/10—At least partially resorbable materials containing macromolecular materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/06—Wet spinning methods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Definitions
- a strand or filament used to sew together the open parts of a Wound is referred to as a suture; when used to tie blood vessels it is known as a ligature.
- suture is used in this specification to refer to both sutures and ligatures.
- Sutures are either absorbable or non-absorbable.
- the only completely absorbable suture is of animal origin and is known, generically, as cat-gut.
- This material is composed largely of the protein collagen, which is absorbed o digested, during the healing process, by the tissues in which it is embedded. The absorption is brought about by proteolytic enzymes in the tissues which hydrolyse the collagen into its component amino acids which are readily metabolised.
- the present invention is a polypeptide subject to proteolysis, comprising a copolymer of an L-imino acid and an L-amino acid.
- L-proline and L-hydroxyproline are the preferred imino acids and they may be used in conjunction with such amino acids as L-glutamic acid and L-alanine in forming the polypeptide.
- the rate of proteolysis of the polypeptide increases with the proportion of the imino acid component and it is merely a matter of experiment to discover the ratio of imino acid to amino acid residues which endows the polypeptide with a desirable resistance or susceptibility to proteolysis.
- the polypeptide need contain no more than from 5 to 15 percent of the imino acid, but it is also possible to slow the rate of proteolysis of the polypeptide containing this amount or more of the imino acid by tanning, as is done for cat-gut by transforming it to chromicised cat-gut for example.
- polypeptide from a mixture of the N-carboxyanhydride derivatives of the amino-acid and the imino acid.
- the mixture is reacted in an inert solvent for the polypeptide to form a viscous solution with evolution of carbon dioxide.
- the solution of polypeptide may then be extruded to form filaments or films by contact with a coagulant o1- evaporation of the solvent, i.e. using ice wet spinning or dry-spinning techniques.
- the films and filaments are strengthened and rendered less soluble by stretching.
- the filaments are useful sutures and the films may be sliced to form sutures or used as absorbable panels in surgery.
- the invention is illustrated by the following example.
- the polypeptide solution could be cast into films or spun into filaments by extrusion into coagulants such as ether or ether/ acetone mixtures.
- the unstretched filaments were found to be insoluble in water, readily soluble in dichloroacetic acid and trifluoracetic acid, and sparingly soluble in glacial acetic acid, formic acid, chloroform, methylene chloride and N,N-dimethyl formamide.
- the filaments were stretched by 400 percent and this has the effect of reducing their solubility in all the above-mentioned solvents, as well as increasing the filament tenacity to 1.6- gram/ denier.
- the absovbability of the sutures of the filamentary polypeptide was tested in vitro by incubation in media containing proteolytic enzymes such as trypsin and papain.
- proteolytic enzymes such as trypsin and papain.
- the method used was that employed by Lennox & Forss (Journal of the Society of Leather Trades Chemists, 36, 322) in their examination of the digestion of tanned collagen by enzymes. The results of these determinations showed that the polypeptide had a rate of proteolysis similar to that of chromicised cat-gut.
- a solid, fiber forming, water insoluble polypeptide copolymer capable of proteolysis consisting essentially of an L-imino acid selected from the group consisting of L-proline and L-hydroxy proline and an L-amino acid selected from the group consisting of L-glutamic acid and L-alanine.
Description
United States Patent 3,331,814 SYNTHETIC POLYPEPTTDES OF AN L-IMINO ACID AND AN L-AMINO ACID Alan Arthur Randall, Maidenhead, England, assignor to Courtaulds Limited, London, England, a British com- P y N0 Drawing. Filed July 15, 1963, Ser. No. 295,223 Claims priority, application Great Britain, Aug. 24, 1962, 32,561/62 4 Claims. (Cl. 260-78) This invention is concerned with synthetic polypeptides which are hydrolysable by enzymes and which may be formed into filaments or films.
In the practice of surgery, a strand or filament used to sew together the open parts of a Wound, is referred to as a suture; when used to tie blood vessels it is known as a ligature. The word suture is used in this specification to refer to both sutures and ligatures.
Sutures are either absorbable or non-absorbable. The only completely absorbable suture is of animal origin and is known, generically, as cat-gut. This material is composed largely of the protein collagen, which is absorbed o digested, during the healing process, by the tissues in which it is embedded. The absorption is brought about by proteolytic enzymes in the tissues which hydrolyse the collagen into its component amino acids which are readily metabolised.
The rate of proteolysis of collagen can be slowed by tanning the protein, as is done, for example, in the production of chromicised cat-gut. In this way, a number of sutures having difierent life-spans in proteolytic environments, may be derived :from a single sample of raw cat-gut, simply by varying the severity of the tanning process.
We have made a fibre-forming synthetic polypeptide which has a property similar to that of collagen, in that it is subject to proteolysis.
Accordingly, the present invention is a polypeptide subject to proteolysis, comprising a copolymer of an L-imino acid and an L-amino acid.
L-proline and L-hydroxyproline are the preferred imino acids and they may be used in conjunction with such amino acids as L-glutamic acid and L-alanine in forming the polypeptide.
The rate of proteolysis of the polypeptide increases with the proportion of the imino acid component and it is merely a matter of experiment to discover the ratio of imino acid to amino acid residues which endows the polypeptide with a desirable resistance or susceptibility to proteolysis.
For use in sutures, the polypeptide need contain no more than from 5 to 15 percent of the imino acid, but it is also possible to slow the rate of proteolysis of the polypeptide containing this amount or more of the imino acid by tanning, as is done for cat-gut by transforming it to chromicised cat-gut for example.
We have made the polypeptide from a mixture of the N-carboxyanhydride derivatives of the amino-acid and the imino acid. The mixture is reacted in an inert solvent for the polypeptide to form a viscous solution with evolution of carbon dioxide. The solution of polypeptide may then be extruded to form filaments or films by contact with a coagulant o1- evaporation of the solvent, i.e. using ice wet spinning or dry-spinning techniques. The films and filaments are strengthened and rendered less soluble by stretching.
The filaments are useful sutures and the films may be sliced to form sutures or used as absorbable panels in surgery.
The invention is illustrated by the following example.
EXAMPLE A mixture of 1 gram of L-proline N-carboxy anhydride and 11.93 grams of 'y-methyl L- glutamate N-carboxy anhydride was dissolved with warming in a mix ture of ethyl acetate (19.4 ml.) and methylene chloride (35.8 ml.). The initiator, 9.5 ml. of N/lO tri-n-butylamine in methylene chloride, was added and the polymerisation took place over a period of 15 hours at 40 C.
The polypeptide solution could be cast into films or spun into filaments by extrusion into coagulants such as ether or ether/ acetone mixtures. The unstretched filaments were found to be insoluble in water, readily soluble in dichloroacetic acid and trifluoracetic acid, and sparingly soluble in glacial acetic acid, formic acid, chloroform, methylene chloride and N,N-dimethyl formamide. The filaments were stretched by 400 percent and this has the effect of reducing their solubility in all the above-mentioned solvents, as well as increasing the filament tenacity to 1.6- gram/ denier.
The absovbability of the sutures of the filamentary polypeptide was tested in vitro by incubation in media containing proteolytic enzymes such as trypsin and papain. The method used was that employed by Lennox & Forss (Journal of the Society of Leather Trades Chemists, 36, 322) in their examination of the digestion of tanned collagen by enzymes. The results of these determinations showed that the polypeptide had a rate of proteolysis similar to that of chromicised cat-gut.
When a strand of the polypeptide was immersed in the papain solution at 50 C. for one hour, it sutfered a loss of weight of 11.4 percent.
What Iclaim is:
' 1. A solid, fiber forming, water insoluble polypeptide copolymer capable of proteolysis consisting essentially of an L-imino acid selected from the group consisting of L-proline and L-hydroxy proline and an L-amino acid selected from the group consisting of L-glutamic acid and L-alanine.
2. The copolymer claimed in claim 1 in which the proportion of L-imino acid is between about 5 and about 15% by weight and the proportion of L-amino acid is between about and about by weight.
3. A filament formed from the copolymer of claim 1.
4. A film formed from the copolymer of claim 1.
References Cited UNITED STATES PATENTS 3,052,655 9/1962 Fox et al. 26078 3,076,790 2/1963 Fox et al. 260 78 3,089,749 5/1963 Ballard 260'-78 WILLIAM H. SHORT, Primary Examiner.
H. D. ANDERSON, Assistant Examiner.
Claims (1)
1. A SOLID, FIBER FORMING, WATER INSOLUBLE POLYPEPTIDE COPOLYMER CAPABLE OF PROTEOLYSIS CONSISTING ESSENTIALLY OF AN L-IMINO ACID SELECTED FROM THE GROUP CONSISTING OF L-PROLINE AND L-HYDROXY PROLINE AND AN L-AMINO ACID SELECTED FROM THE GROUP CONSISTING OF L-GLUTAMIC ACID AND L-ALININE.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB32561/62A GB1049290A (en) | 1962-08-24 | 1962-08-24 | Synthetic polypeptides |
Publications (1)
Publication Number | Publication Date |
---|---|
US3331814A true US3331814A (en) | 1967-07-18 |
Family
ID=10340564
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US295223A Expired - Lifetime US3331814A (en) | 1962-08-24 | 1963-07-15 | Synthetic polypeptides of an l-imino acid and an l-amino acid |
Country Status (9)
Country | Link |
---|---|
US (1) | US3331814A (en) |
AT (1) | AT262517B (en) |
BE (1) | BE636530A (en) |
CH (1) | CH431552A (en) |
DE (1) | DE1495312A1 (en) |
FR (1) | FR1367282A (en) |
GB (1) | GB1049290A (en) |
NL (1) | NL297020A (en) |
SE (1) | SE303832B (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3626948A (en) * | 1968-12-23 | 1971-12-14 | American Cyanamid Co | Absorbable polyglycolic acid suture of enhanced in-vivo strength retention |
US3867520A (en) * | 1971-04-14 | 1975-02-18 | Ajinomoto Kk | Medicated polyamino acid film for occlusive dressing therapy |
US4351337A (en) * | 1973-05-17 | 1982-09-28 | Arthur D. Little, Inc. | Biodegradable, implantable drug delivery device, and process for preparing and using the same |
US4915893A (en) * | 1982-07-16 | 1990-04-10 | Medtronic, Inc. | Method of preparing polyester filament material |
US4955913A (en) * | 1985-03-28 | 1990-09-11 | Robinson Walter C | Surgical tie |
US5101011A (en) * | 1990-07-20 | 1992-03-31 | Ajinomoto Co., Inc. | Aligning agent for liquid crystals comprising poly alpha-amino acid having no optical activity |
US5110852A (en) * | 1982-07-16 | 1992-05-05 | Rijksuniversiteit Te Groningen | Filament material polylactide mixtures |
WO2000052078A1 (en) * | 1999-03-05 | 2000-09-08 | Innovative Technologies, Llc | Use of protein conformation for the protection and release of chemical compounds |
US20020128177A1 (en) * | 1999-03-05 | 2002-09-12 | Kirk Randal J. | Use of protein conformation for the protection and release of chemical compounds |
US6716452B1 (en) | 2000-08-22 | 2004-04-06 | New River Pharmaceuticals Inc. | Active agent delivery systems and methods for protecting and administering active agents |
US20070203055A1 (en) * | 2003-09-30 | 2007-08-30 | New River Pharmaceuticals Inc. | Compounds and compositions for prevention of overdose of oxycodone |
US20110046226A1 (en) * | 2001-08-22 | 2011-02-24 | Shire Llc | Pharmaceutical compositions for prevention of overdose or abuse |
US8394813B2 (en) | 2000-11-14 | 2013-03-12 | Shire Llc | Active agent delivery systems and methods for protecting and administering active agents |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3773737A (en) * | 1971-06-09 | 1973-11-20 | Sutures Inc | Hydrolyzable polymers of amino acid and hydroxy acids |
CN113150064B (en) * | 2021-04-14 | 2023-04-11 | 中山大学 | Artificial synthesis method and application of antibacterial and insect-resistant peptide |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3052655A (en) * | 1958-08-01 | 1962-09-04 | Sidney W Fox | Thermal polymerization of amino acid mixtures containing aspartic acid or a thermal precursor of aspartic acid |
US3076790A (en) * | 1958-08-01 | 1963-02-05 | Sidney W Fox | Method of making copolymers of amino acids containing glutamic acid |
US3089749A (en) * | 1958-04-21 | 1963-05-14 | Courtaulds Ltd | Production of artificial threads |
-
0
- BE BE636530D patent/BE636530A/xx unknown
- NL NL297020D patent/NL297020A/xx unknown
-
1962
- 1962-08-24 GB GB32561/62A patent/GB1049290A/en not_active Expired
-
1963
- 1963-07-15 US US295223A patent/US3331814A/en not_active Expired - Lifetime
- 1963-07-25 DE DE19631495312 patent/DE1495312A1/en active Pending
- 1963-08-23 AT AT678963A patent/AT262517B/en active
- 1963-08-23 SE SE9241/63A patent/SE303832B/xx unknown
- 1963-08-23 CH CH1044263A patent/CH431552A/en unknown
- 1963-08-23 FR FR945456A patent/FR1367282A/en not_active Expired
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3089749A (en) * | 1958-04-21 | 1963-05-14 | Courtaulds Ltd | Production of artificial threads |
US3052655A (en) * | 1958-08-01 | 1962-09-04 | Sidney W Fox | Thermal polymerization of amino acid mixtures containing aspartic acid or a thermal precursor of aspartic acid |
US3076790A (en) * | 1958-08-01 | 1963-02-05 | Sidney W Fox | Method of making copolymers of amino acids containing glutamic acid |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3626948A (en) * | 1968-12-23 | 1971-12-14 | American Cyanamid Co | Absorbable polyglycolic acid suture of enhanced in-vivo strength retention |
US3867520A (en) * | 1971-04-14 | 1975-02-18 | Ajinomoto Kk | Medicated polyamino acid film for occlusive dressing therapy |
US4351337A (en) * | 1973-05-17 | 1982-09-28 | Arthur D. Little, Inc. | Biodegradable, implantable drug delivery device, and process for preparing and using the same |
US4915893A (en) * | 1982-07-16 | 1990-04-10 | Medtronic, Inc. | Method of preparing polyester filament material |
US5110852A (en) * | 1982-07-16 | 1992-05-05 | Rijksuniversiteit Te Groningen | Filament material polylactide mixtures |
US4955913A (en) * | 1985-03-28 | 1990-09-11 | Robinson Walter C | Surgical tie |
US5101011A (en) * | 1990-07-20 | 1992-03-31 | Ajinomoto Co., Inc. | Aligning agent for liquid crystals comprising poly alpha-amino acid having no optical activity |
US20020128177A1 (en) * | 1999-03-05 | 2002-09-12 | Kirk Randal J. | Use of protein conformation for the protection and release of chemical compounds |
WO2000052078A1 (en) * | 1999-03-05 | 2000-09-08 | Innovative Technologies, Llc | Use of protein conformation for the protection and release of chemical compounds |
AU771188B2 (en) * | 1999-03-05 | 2004-03-18 | Shire Llc | Use of protein conformation for the protection and release of chemical compounds |
US7018654B2 (en) | 1999-03-05 | 2006-03-28 | New River Pharmaceuticals Inc. | Pharmaceutical composition containing an active agent in an amino acid copolymer structure |
US6716452B1 (en) | 2000-08-22 | 2004-04-06 | New River Pharmaceuticals Inc. | Active agent delivery systems and methods for protecting and administering active agents |
US20040127397A1 (en) * | 2000-08-22 | 2004-07-01 | New River Pharmaceuticals Inc. | Active agent delivery systems and methods for protecting and administering active agents |
US8394813B2 (en) | 2000-11-14 | 2013-03-12 | Shire Llc | Active agent delivery systems and methods for protecting and administering active agents |
US20110046226A1 (en) * | 2001-08-22 | 2011-02-24 | Shire Llc | Pharmaceutical compositions for prevention of overdose or abuse |
US8343927B2 (en) | 2001-08-22 | 2013-01-01 | Shire Llc | Pharmaceutical compositions for prevention of overdose or abuse |
US20070203055A1 (en) * | 2003-09-30 | 2007-08-30 | New River Pharmaceuticals Inc. | Compounds and compositions for prevention of overdose of oxycodone |
US8106016B2 (en) | 2003-09-30 | 2012-01-31 | Shire Llc | Compounds and compositions for prevention of overdose of oxycodone |
Also Published As
Publication number | Publication date |
---|---|
NL297020A (en) | |
DE1495312A1 (en) | 1969-03-06 |
FR1367282A (en) | 1964-07-17 |
GB1049290A (en) | 1966-11-23 |
BE636530A (en) | |
SE303832B (en) | 1968-09-09 |
CH431552A (en) | 1967-03-15 |
AT262517B (en) | 1968-06-10 |
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