CA2075705A1 - Anti-oxidative and anti-inflammatory metal:peptide complexes and uses thereof - Google Patents
Anti-oxidative and anti-inflammatory metal:peptide complexes and uses thereofInfo
- Publication number
- CA2075705A1 CA2075705A1 CA002075705A CA2075705A CA2075705A1 CA 2075705 A1 CA2075705 A1 CA 2075705A1 CA 002075705 A CA002075705 A CA 002075705A CA 2075705 A CA2075705 A CA 2075705A CA 2075705 A1 CA2075705 A1 CA 2075705A1
- Authority
- CA
- Canada
- Prior art keywords
- histidyl
- moiety containing
- carbon atoms
- metal
- tryptophan
- 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.)
- Abandoned
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 117
- 239000002184 metal Substances 0.000 title claims abstract description 117
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- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 74
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- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 36
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- 150000001413 amino acids Chemical class 0.000 claims description 30
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- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- IFGCUJZIWBUILZ-UHFFFAOYSA-N sodium 2-[[2-[[hydroxy-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid Chemical group [Na+].C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(CC(C)C)NP(O)(=O)OC1OC(C)C(O)C(O)C1O IFGCUJZIWBUILZ-UHFFFAOYSA-N 0.000 claims description 21
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- 150000002978 peroxides Chemical class 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/478,091 US5118665A (en) | 1990-02-09 | 1990-02-09 | Anti-oxidative and anti-inflammatory metal:peptide complexes and uses thereof |
| US478,091 | 1990-02-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2075705A1 true CA2075705A1 (en) | 1991-08-10 |
Family
ID=23898480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002075705A Abandoned CA2075705A1 (en) | 1990-02-09 | 1991-02-07 | Anti-oxidative and anti-inflammatory metal:peptide complexes and uses thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5118665A (enExample) |
| EP (1) | EP0514460A1 (enExample) |
| JP (1) | JPH05503939A (enExample) |
| AU (1) | AU7254491A (enExample) |
| CA (1) | CA2075705A1 (enExample) |
| TW (1) | TW296387B (enExample) |
| WO (1) | WO1991012267A1 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2062233A1 (en) * | 1991-03-12 | 1992-09-13 | Atsunori Mori | Catalyst for asymmetric induction |
| US5382431A (en) * | 1992-09-29 | 1995-01-17 | Skin Biology, Inc. | Tissue protective and regenerative compositions |
| WO1994018230A1 (en) * | 1993-02-02 | 1994-08-18 | Procyte Corporation | Inhibition of hiv replication by peptide-copper complexes |
| WO1995026192A1 (en) * | 1994-03-28 | 1995-10-05 | Skin Biology, Inc. | Starch-metal complexes for skin and hair |
| JPH07316192A (ja) * | 1994-05-27 | 1995-12-05 | Hoechst Japan Ltd | Ｌ−リシル−グリシル−ｌ−ヒスチジンおよびこれを含有する創傷治療剤 |
| US7404967B2 (en) * | 1994-12-21 | 2008-07-29 | Cosmederm, Inc. | Topical product formulations containing strontium for reducing skin irritation |
| US6139850A (en) * | 1994-12-21 | 2000-10-31 | Cosmederm Technologies | Formulations and methods for reducing skin irritation |
| US5830993A (en) * | 1995-04-10 | 1998-11-03 | Kansas State University Research Foundation | Synthetic antimicrobial peptide |
| US5891418A (en) * | 1995-06-07 | 1999-04-06 | Rhomed Incorporated | Peptide-metal ion pharmaceutical constructs and applications |
| FR2741075B1 (fr) * | 1995-11-15 | 1998-01-30 | Rech De Pathologie Appliquee S | Conjugues peptidiques, leur utilisation a titre de medicament et compositions les contenant |
| US6331285B1 (en) | 1996-06-05 | 2001-12-18 | Palatin Technologies, Inc. | Structurally determined cyclic metallo-constructs and applications |
| US5698184A (en) * | 1996-08-23 | 1997-12-16 | Skin Biology, Inc. | Compositions and methods for skin tanning and protection |
| US5888522A (en) * | 1996-08-23 | 1999-03-30 | Skin Biology, Inc. | Tissue protective and regenerative compositions |
| US6096861A (en) * | 1997-03-18 | 2000-08-01 | The Regents Of The University Of California | Peptide-peptoid metal complexes |
| US7632803B2 (en) | 1999-10-01 | 2009-12-15 | Dmi Life Sciences, Inc. | Metal-binding compounds and uses therefor |
| US20030158111A1 (en) * | 1999-10-01 | 2003-08-21 | David Bar-Or | Methods and products for oral care |
| US20030130185A1 (en) * | 2000-09-29 | 2003-07-10 | David Bar-Or | Metal-binding compounds and uses therefor |
| ATE553116T1 (de) | 1999-10-01 | 2012-04-15 | Dmi Biosciences Inc | Metall bindende verbindungen und ihre verwendungen |
| US7592304B2 (en) * | 1999-10-01 | 2009-09-22 | Dmi Life Sciences, Inc. | Metal-binding compounds and uses therefor |
| DE19958121A1 (de) * | 1999-12-02 | 2001-06-28 | Max Planck Gesellschaft | Tyrosin- und tryptophanhaltige Peptide als Antioxidantien |
| US20030166510A1 (en) * | 2000-10-11 | 2003-09-04 | Pickart Loren R. | Methods and compositions for increasing skin remodeling |
| US7385025B2 (en) * | 2000-12-19 | 2008-06-10 | Palatin Technologies, Inc. | Metallopeptide compounds |
| US6428461B1 (en) | 2001-04-24 | 2002-08-06 | Kraft Foods Holdings, Inc. | Method for inhibiting oxidation of polyunsaturated lipids |
| US20030148927A1 (en) * | 2001-10-05 | 2003-08-07 | Procyte Corporation | Stable solutions of peptide copper complexes and cosmetic and pharmaceutical formulations produced therefrom |
| US20040180102A1 (en) * | 2002-07-31 | 2004-09-16 | Procyte Corporation | Compositions containing peptide copper complexes and phytochemical compounds, and methods related thereto |
| US20040142853A1 (en) * | 2002-11-07 | 2004-07-22 | Procyte Corporation | Stimulation of hair growth by compositions containing peptide copper complexes and minoxidil |
| US20040138103A1 (en) * | 2002-11-07 | 2004-07-15 | Procyte Corporation | Compositions containing peptide copper complexes and metalloproteinase inhibitors and methods related thereto |
| US7128923B2 (en) * | 2003-03-31 | 2006-10-31 | Procyte Corporation | Preserved and stable compositions containing peptide copper complexes and method related thereto |
| US6927205B2 (en) * | 2003-04-28 | 2005-08-09 | Procyte Corporation | Compositions and methods for treatment of psoriasis |
| US6927206B2 (en) * | 2003-06-06 | 2005-08-09 | Procyte Corporation | Compositions and methods for treatment of rosacea |
| US20050260275A1 (en) * | 2004-04-01 | 2005-11-24 | Procyte Corporation | Encapsulated peptide copper complexes and compositions and methods related thereto |
| US20060018851A1 (en) * | 2004-06-28 | 2006-01-26 | Procyte Corporation | Methods and compositions for preventing and treating hyperpigmentation of skin |
| WO2006023465A1 (en) * | 2004-08-18 | 2006-03-02 | Procyte Corporation | Polyethylene glycol-peptide copper complexes and compositions and methods related thereto |
| WO2006101855A2 (en) * | 2005-03-16 | 2006-09-28 | Procyte Corporation | Methods and compositions for preventing and treating aging or photodamaged skin |
| US7687650B2 (en) | 2006-02-03 | 2010-03-30 | Jr Chem, Llc | Chemical compositions and methods of making them |
| JP5038331B2 (ja) | 2006-02-03 | 2012-10-03 | ジェイアール ケム エルエルシー | 銅と亜鉛の組成物を用いた老化防止治療 |
| US7897800B2 (en) | 2006-02-03 | 2011-03-01 | Jr Chem, Llc | Chemical compositions and methods of making them |
| WO2007087738A1 (de) * | 2006-02-03 | 2007-08-09 | Pentapharm Ag | Biologisch aktive tripeptide, deren kupferkomplexe und salze |
| ES2283212B1 (es) * | 2006-03-31 | 2008-08-16 | Lipotec S.A. | Peptidos sinteticos utiles en el tratamiento de la piel y su uso en composiciones cosmeticas o dermofarmaceuticas. |
| US7867522B2 (en) | 2006-09-28 | 2011-01-11 | Jr Chem, Llc | Method of wound/burn healing using copper-zinc compositions |
| US8273791B2 (en) | 2008-01-04 | 2012-09-25 | Jr Chem, Llc | Compositions, kits and regimens for the treatment of skin, especially décolletage |
| WO2010085753A1 (en) | 2009-01-23 | 2010-07-29 | Jr Chem, Llc | Rosacea treatments and kits for performing them |
| US8952057B2 (en) | 2011-01-11 | 2015-02-10 | Jr Chem, Llc | Compositions for anorectal use and methods for treating anorectal disorders |
| RU2475240C2 (ru) * | 2011-02-10 | 2013-02-20 | Государственное научное учреждение Курский научно-исследовательский институт агропромышленного производства Россельхозакадемии | Способ коррекции иммунобиохимического статуса у коров в предродовом и послеродовом периодах |
| WO2012166810A1 (en) * | 2011-05-31 | 2012-12-06 | Amplifi Biotechnologies, Inc. | Biologically active tri-peptide |
| FR3029915B1 (fr) * | 2014-12-16 | 2016-12-09 | Sederma Sa | Tripeptides, compositions les comprenant et utilisations notamment cosmetiques |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3194732A (en) * | 1960-10-03 | 1965-07-13 | Neuhauser Irene | Assisting healing of skin-denuded areas on the body with dried non-fibrous egg-shellmembrane products and compositions therefor |
| US3558770A (en) * | 1967-09-01 | 1971-01-26 | Kraftco Corp | Wound treating composition employing an enzyme modified casein |
| US3551554A (en) * | 1968-08-16 | 1970-12-29 | Crown Zellerbach Corp | Enhancing tissue penetration of physiologically active agents with dmso |
| US3767784A (en) * | 1970-12-01 | 1973-10-23 | S Gluck | Composition for the protection and treatment of injured body tissue and method of utilizing the same |
| US3758682A (en) * | 1972-03-23 | 1973-09-11 | Diagnostics Data Inc | Pharmaceutical compositions comprising orgotein and their use |
| US3832338A (en) * | 1972-03-23 | 1974-08-27 | Diagnostic Data Inc | Orgotein production using a buffer solution containing divalent metal salts |
| US4022888A (en) * | 1975-09-09 | 1977-05-10 | Diagnostic Data, Inc. | Esterified orgotein |
| DE2700043C2 (de) * | 1977-01-03 | 1983-12-08 | Thera Gesellschaft für Patentverwertung mbH, 8036 Herrsching | Mittel zur Verbesserung der Durchblutung und Wundheilung |
| US4167945A (en) * | 1977-01-31 | 1979-09-18 | Gottlieb Sheldon K | Method for enhancing the healing of grafted tissue |
| US4287184A (en) * | 1977-11-23 | 1981-09-01 | The Massachusetts General Hospital | Process for healing wounds |
| US4263428A (en) * | 1978-03-24 | 1981-04-21 | The Regents Of The University Of California | Bis-anthracycline nucleic acid function inhibitors and improved method for administering the same |
| US4440788A (en) * | 1980-05-13 | 1984-04-03 | Mitsubishi Chemical Industries, Limited | Cysteine derivatives |
| US4461724A (en) * | 1981-10-28 | 1984-07-24 | Nippon Zoki Pharmaceutical Co., Ltd. | Peptide compounds, a process for manufacturing them, pharmaceutical compositions containing them, and methods for treating ulcer and thrombus with them |
| HU193289B (en) * | 1984-06-19 | 1987-09-28 | Universal Vegyipari Szoevetkez | Cosmetical composition for treating hair and nail containing blood plasma concentrate as active agent |
| US4760051A (en) * | 1985-01-24 | 1988-07-26 | Pickart Loren R | Use of GHL-Cu as a wound-healing and anti-inflammatory agent |
| US4665054A (en) * | 1985-02-08 | 1987-05-12 | Bioheal, Inc. | Chemical derivatives of GHL-Cu |
| US4767753A (en) * | 1985-02-08 | 1988-08-30 | Procyte Corporation | Methods and compositions for preventing ulcers |
| ATE103608T1 (de) * | 1987-04-20 | 1994-04-15 | Procyte Corp | Chemische derivate von ghl-cu. |
| EP0314755B1 (en) * | 1987-05-11 | 1994-08-24 | Procyte Corporation | Use of derivatives of GHL-Cu for the manufacture of a medicament for stimulating hair growth |
| JPH02500368A (ja) * | 1987-05-11 | 1990-02-08 | プロサイト コーポレイション | 温血動物における腫瘍阻止方法 |
| IN166306B (enExample) * | 1987-08-05 | 1990-04-07 | Hoechst India |
-
1990
- 1990-02-09 US US07/478,091 patent/US5118665A/en not_active Expired - Lifetime
-
1991
- 1991-02-07 WO PCT/US1991/000836 patent/WO1991012267A1/en not_active Ceased
- 1991-02-07 AU AU72544/91A patent/AU7254491A/en not_active Abandoned
- 1991-02-07 EP EP91904268A patent/EP0514460A1/en not_active Ceased
- 1991-02-07 JP JP3504540A patent/JPH05503939A/ja active Pending
- 1991-02-07 CA CA002075705A patent/CA2075705A1/en not_active Abandoned
- 1991-02-12 TW TW080101131A patent/TW296387B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| TW296387B (enExample) | 1997-01-21 |
| AU7254491A (en) | 1991-09-03 |
| EP0514460A1 (en) | 1992-11-25 |
| US5118665A (en) | 1992-06-02 |
| WO1991012267A1 (en) | 1991-08-22 |
| JPH05503939A (ja) | 1993-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |