WO1999011251A1 - Medicament for improvement of duration of muscle function or treatment of muscle disorders or diseases - Google Patents

Medicament for improvement of duration of muscle function or treatment of muscle disorders or diseases Download PDF

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Publication number
WO1999011251A1
WO1999011251A1 PCT/SE1998/001526 SE9801526W WO9911251A1 WO 1999011251 A1 WO1999011251 A1 WO 1999011251A1 SE 9801526 W SE9801526 W SE 9801526W WO 9911251 A1 WO9911251 A1 WO 9911251A1
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Prior art keywords
astaxanthin
medicament
mammalian muscle
diseases
duration
Prior art date
Application number
PCT/SE1998/001526
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French (fr)
Inventor
Åke Lignell
Original Assignee
Astacarotene Ab
Priority date (The priority date 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 date listed.)
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Publication date
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Priority to JP2000508354A priority Critical patent/JP3660244B2/en
Priority to AU90989/98A priority patent/AU727349B2/en
Priority to EP98943128A priority patent/EP1011653B1/en
Priority to US09/485,704 priority patent/US6245818B1/en
Priority to DK98943128T priority patent/DK1011653T3/en
Application filed by Astacarotene Ab filed Critical Astacarotene Ab
Priority to CA002299366A priority patent/CA2299366C/en
Priority to DE69810784T priority patent/DE69810784T2/en
Priority to PL98338982A priority patent/PL338982A1/en
Priority to AT98943128T priority patent/ATE230985T1/en
Publication of WO1999011251A1 publication Critical patent/WO1999011251A1/en
Priority to NO20001087A priority patent/NO20001087L/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/12—Ketones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Neurology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Fodder In General (AREA)

Abstract

Medicament for the prophylactic and/or therapeutic improvement of the duration of mammalian muscle function and/or treatment of mammalian muscle disorders or diseases, e.g. equine Exertional Rhabdomyolysis, comprising at least one type of xanthophylles, e.g. astaxanthin, is described. Further, the use of xanthophylles in the preparation of such medicaments, and a method of prophylactic and/or therapeutic improvement of the duration of mammalian muscle function and/or treatment of mammalian muscle disorders or diseases, are disclosed.

Description

MEDICAMENT FOR IMPROVEMENT OF DURATION OF MUSCLE FUNCTION OR TREATMENT OF MUSCLE DISORDERS OR DISEASES.
The present invention relates to a medicament for the prophylactic and/or therapeutic improvement of the duration of mammalian muscle function and/or treatment of mammalian muscle disorders or diseases, comprising at least one type of xanthophylles, especially astaxanthin. The invention also relates to the use of at least one type of xanthophylles for the production of such a medicament and to a method of prophylactic and/or therapeutic improvement of the duration of mammalian muscle function and/or treatment of mammalian muscle disorders or diseases, e.g. equine Exertional Rhabdomyolysis.
Background of the invention
Exertional rhabdomyolysis, also referred to as exertional myopathy, tying-up syndrome, azoturia, or Monday morning disease, is probably the most common muscle disorder in horses. Predisposing or associated factors that have been implicated in the pathogenesis of this condition include electrolyte imbalances, hypothyroidism, and vitamin E-selenium deficiency. Therefore, treatment of horses affected by exertional rhabdomyolysis have included pain relief, rehydration and correction of electrolyte abnormalities (See e.g. The Horse: Diseases and Clinical Management, edited by C. N. Kolbluk, T. R. Ames, R. J. Geor, W.B. Saunders Company, Philadelphia, 1995, pp. 809-810).
Xanthophylles, including astaxanthin, is a large group of carotenoids containing oxygen in the molecule in addition to carbon and hydrogen. The carotenoids are produced de novo by plants, fungi and some bacteria. Astaxanthin, in the form of naturally produced algal meal of cultured Haematococcus sp., has been marketed as antioxidant for mammals, especially humans. Description of the invention
The present invention provides a medicament for the prophylactic and/or therapeutic improvement of the duration of mammalian muscle function and/or treatment of mammalian muscle disorders or diseases, comprising at least one type of xanthophylles.
In a preferred embodiment the type of xanthophyll is astaxanthin, particularly in a form esterified with fatty acids.
In a most preferred embodiment the astaxanthin in esterified form with fatty acids is algal meal of cultured Haematococcus sp.
Examples of mammalian muscle disorders or diseases include human myopaties and connective tissue diseases, as well as equine myopaties and connective tissue diseases.
In a particular embodiment of the invention, the mammalian muscle disorder is equine Exertional Rhabdomyolysis.
The medicament according to the invention may comprise a mixture of different types of xanthophylles or different forms of the same xanthophyll, such as a mixture of synthetic astaxanthin and naturally produced astaxanthin.
The medicament of the invention may comprise additional ingredients which are pharmacologically acceptable inactive or active in prophylactic and/or therapeutic use, such as flavoring agents, excipients, diluents, carriers, etc., and it may be presented in a separate unit dose or in admixture with food or feed. Examples of separate unit doses are tablets, gelatin capsules and predetermined amounts of solutions, e. g. oil solutions, or emulsions, e.g. water-in- oil or oil-in-water emulsions. Examples of food in which the preparation of the invention may be incorporated is dairy products, such as joughurt, chocolate and cereals. The daily doses of the xanthophyll in the medicament of the invention will normally be in the range of 0.01 to 1 mg per kg body weight.
The present invention also comprises the use of at least one type of xanthophylles in the preparation of a medicament for the prophylactic and/or therapeutic improvement of the duration of mammalian muscle function and/or treatment of mammalian muscle disorders or diseases. Once again, the preferred type of xanthophyll is astaxanthin, particularly in a form esterified with fatty acids, e.g. in the form of algal meal of cultured Haematococcus sp. ; and in a specific embodiment the mammalian muscle disorder is equine Exertional Rhabdomyolysis.
Further, the invention comprises a method of prophylactic and/or therapeutic improvement of the duration of mammalian muscle function and/or treatment of mammalian muscle disorders or diseases, e.g. equine Exertional Rhabdomyolysis, comprising administration to said mammal of a prophylactically and/or therapeutically effective dose of a medicament according to the invention.
Short description of the drawings
Figure 1 is a diagram showing the up-take of different carotenoids, e.g. astaxanthin, in rat muscle. Figure 2 is a diagram showing the up-take of different carotenoids, e.g. astaxanthin, in rat heart.
Figure 3 is a diagram showing the carotenoid content in different rat organs after feed supplementation with astaxanthin. Experiments
The medicament used in the experiments is the xanthophyll astaxanthin which was produced via culturing of the algae Haematococcus sp. by AstaCarotene AB, Gustavsberg, Sweden.
Astaxanthin from other sources, and other xanthophylles as well, are expected to be similarly useful for the purposes of the invention. An advantage of using astaxanthin from algae is, however, that the astaxanthin exists in a form esterified with fatty acids [Renstrδm B. et al, 1981 , Phytochem 20(11) :2561-2564], which esterified astaxanthin thereby is more stable during handling and storage than free astaxanthin.
Uptake of astaxanthin in rat
The experiment was conducted to establish if astaxanthin in the form of algal meal was taken up by rat and to see in which organs and tissues astaxanthin is accumulated.
Performance
A medicament in the form of feed containing 100 mg astaxanthin per kg feed in the form of algal meal was prepared.
Twenty-four male rats were divided into two groups; one group received feed without algal meal, and the other group received the feed containing algal meal. After three weeks 6 rats from each group were sacrificed, and the remaining rats were sacrificed after 6 weeks.
At slaughter organs were excised, i. a. thigh muscle and heart, and they were freezed for later analysis of the content of carotenoids with the aid of HPLC. Results
Astaxanthin could be demonstrated in both thigh muscle (see Fig. 1) and heart (see
Fig. 2) of those rats that had received the feed supplemented with algal meal. In the control group, astaxanthin was not detectable.
Muscular tissue and particularly heart showed amongst the highest levels of astaxanthin after supplementation compared to the rest of the examined organs (see
Fig. 3)
Effect of astaxanthin in horse
This preliminary experiment was conducted to establish if astaxanthin is taken up by horses and if supplementation with astaxanthin in the form of algal meal would improve the physical performance of trotting-horses.
Dosage
The horses received 100 mg astaxanthin per horse (approx. 500 kg) per day in the form of algal meal. The meal was supplied to the horses either sprinkled on concentrated feed or in the form of oil suspension.
Uptake
Astaxanthin could be demonstrated in muscles from horses that had received supplementation with the algal meal. The analyses were performed with the aid of HPLC on muscle biopsies. Astaxanthin could also be demonstrated in plasma samples from horses who had received the supplementation.
Effects
The most striking effect of the supplementation has been on horses suffering from muscle problems, so-called Exertional Rhabdomyolysis. In some horses this disorder appears when they are trained and raced regularly. It is not known what it is that causes the problems, but it is believed that the muscles are tightened and therefore the circulation is impaired, resulting in degradation of the muscular tissue. Today, there is no remedy for the problem except rest and increased dosage of vitamin E in the feed.
Problem-horses who have received the astaxanthin-supplementation have been free from the symptom after 2 - 3 weeks, and they have been able to train and race in a normal way. In cases where the supplementation has been stopped or the dosage has been less than 30 mg astaxanthin per day, the septum has reoccurred after approximately 2 weeks. The algal meal supplement has been given to a total of 8 so- called problem-horses, and they have all responded positively to the supplementation.
Effect of astaxanthin on the physical performance of humans
The experiment was conducted so that for a period of 6 months, 20 healthy volunteers received 1 capsule containing 4 mg astaxanthin in the form of algal meal each morning in association with food, and 20 healthy volunteers received 1 capsule containing placebo.
Before the experiment was started, reference values were registered for each person with regard to strength/endurance, strength/explosiveness, condition, and weight.
Performance
The strength/endurance was estimated when a person made a maximum number of knee-bending in a Smith-machine with 40 kg load under standardized conditions.
The strength/explosiveness was tested under standardized conditions in a
Wingate-machine with individually-adapted load and registration of maximum effect during 30 seconds. The values were related to effect/ kg of body weight.
The condition was tested by a step test with 17 kg load and bench height of 32 cm until steady state pulse was reached. (I.e. the pulse did not differ more than three strokes from the measurement of the previous minute). The weight difference between before and after the experiment was checked with a digital scale.
Results No significant difference was established between the astaxanthin group and the placebo group in any of the tested parameters due to the small number of test persons.
With regard to condition (VO2 max./kg, minute) there was no significant difference between the groups; a reduction of 1.75% for the astaxanthin group and 1.37% for the placebo group.
A reduction was also seen for both groups in the (strength/explosiveness) Wingate test (W 7 kg); - 4.13% for the astaxanthin group and - 5.81% for the placebo group.
Both groups gained weight ; 1.0% for the astaxanthin group and 2.1% for the placebo group. However, the individual differences were quite large, and no tendency could be established.
However, there was a clear difference between the groups in the strength/endurance test; 61.74% for the astaxanthin group and 23.78% for the placebo group.
In summary, the positive performance effect that was attributed to astaxanthin by individual athletes does not seem to be related to an increased condition or explosive strength but to strength/endurance according to this experiment.

Claims

1. Medicament for the prophylactic and/or therapeutic improvement of the duration of mammalian muscle function and/or treatment of mammalian muscle disorders or diseases, comprising at least one type of xanthophylles.
2. Medicament according to claim 1 , wherein the type of xanthophyll is astaxanthin.
3. Medicament according to claim 2, wherein the astaxanthin is in a form esterified with fatty acids.
4. Medicament according to claim 3, wherein the astaxanthin in esterified form with fatty acids is algal meal of cultured Haematococcus sp.
5. Medicament according to any one of claims 1 - 4, wherein the mammalian muscle disorder is equine Exertional Rhabdomyolysis.
6. Use of at least one type of xanthophylles in the preparation of a medicament for the prophylactic and/or therapeutic improvement of the duration of mammalian muscle function and/or treatment of mammalian muscle disorders or diseases.
7. Use according to claim 6, wherein the type of xanthophyll is astaxanthin.
8. Use according to claim 7, wherein the astaxanthin is in a form esterified with fatty acids.
9. Use according to claim 8, wherein the astaxanthin in esterified form with fatty acids is algal meal of cultured Haematococcus sp.
10. Use according to any one of claims 1 - 9 , wherein the mammalian muscle disorder is equine Exertional Rhabdomyolysis.
11. Method of prophylactic and/or therapeutic improvement of the duration of mammalian muscle function and/or treatment of mammalian muscle disorders or diseases, comprising administration to said mammal of a prophylactically and/or therapeutically effective dose of a medicament according to any one of claims 1 - 4.
12. Method according to claim 9, wherein said mammalian muscle disorder is equine Exertional Rhabdomyolysis.
PCT/SE1998/001526 1997-09-04 1998-08-26 Medicament for improvement of duration of muscle function or treatment of muscle disorders or diseases WO1999011251A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
AT98943128T ATE230985T1 (en) 1997-09-04 1998-08-26 USE OF XANTHOPHYLLES IN THE PRODUCTION OF MEDICINAL PRODUCTS TO IMPROVE MUSCLE FUNCTIONAL DURATION OR TO TREAT MUSCLE DISORDERS OR DISEASES
AU90989/98A AU727349B2 (en) 1997-09-04 1998-08-26 Medicament for improvement of duration of muscle function or treatment of muscle disorders or diseases
EP98943128A EP1011653B1 (en) 1997-09-04 1998-08-26 Use of xanthophylles in medicaments for improvement of duration of muscle function or treatment of muscle disorders or diseases
US09/485,704 US6245818B1 (en) 1997-09-04 1998-08-26 Medicament for improvement of duration of muscle function or treatment of muscle disorders or diseases
DK98943128T DK1011653T3 (en) 1997-09-04 1998-08-26 Use of xanthophylls in medications to improve the duration of muscle function or treatment of muscle disorders or disorders
JP2000508354A JP3660244B2 (en) 1997-09-04 1998-08-26 Medications to improve the duration of muscle function or to treat muscle disorders or diseases
CA002299366A CA2299366C (en) 1997-09-04 1998-08-26 Use of xanthophylls for improvement of duration of muscle function or treatment of muscle disorders or diseases
DE69810784T DE69810784T2 (en) 1997-09-04 1998-08-26 USE OF XANTHOPHYLLES FOR THE PRODUCTION OF MEDICINAL PRODUCTS FOR THE IMPROVEMENT OF THE MUSCLE FUNCTIONAL PERIOD OR FOR THE TREATMENT OF MUSCLE DISORDER OR DISEASES
PL98338982A PL338982A1 (en) 1997-09-04 1998-08-26 Drug for improving duration of muscle action or for treating muscular disorders or diseases
NO20001087A NO20001087L (en) 1997-09-04 2000-03-02 Medication for the extension of muscle function or treatment of muscle disorders or diseases

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9703191-8 1997-09-04
SE9703191A SE512531C2 (en) 1997-09-04 1997-09-04 Use of at least one type of xanthophyll for the manufacture of a medicament for the prophylactic and / or therapeutic improvement of mammalian muscle function and / or treatment of mammalian muscle disorders or disorders

Publications (1)

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WO1999011251A1 true WO1999011251A1 (en) 1999-03-11

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US (1) US6245818B1 (en)
EP (1) EP1011653B1 (en)
JP (1) JP3660244B2 (en)
AT (1) ATE230985T1 (en)
AU (1) AU727349B2 (en)
CA (1) CA2299366C (en)
DE (1) DE69810784T2 (en)
DK (1) DK1011653T3 (en)
ES (1) ES2191329T3 (en)
NO (1) NO20001087L (en)
PL (1) PL338982A1 (en)
SE (1) SE512531C2 (en)
WO (1) WO1999011251A1 (en)

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WO2001072296A1 (en) * 2000-03-27 2001-10-04 Astacarotene Ab Method of inhibiting the expression of inflammatory cytokines and chemokines
US7078040B2 (en) 2000-03-27 2006-07-18 Fuji Chemical Industry Co., Ltd. Method of inhibiting the expression of inflammatory cytokines and chemokines
US20080269349A1 (en) * 2004-02-04 2008-10-30 Fuji Chemical Industry Co. Ltd. Gene expression regulating agent
US7691901B2 (en) 2004-04-14 2010-04-06 Cardax Pharmaceuticals Inc. Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation
US7727752B2 (en) 2003-07-29 2010-06-01 Life Technologies Corporation Kinase and phosphatase assays
US8034372B2 (en) * 2003-03-05 2011-10-11 Nestec, Ltd. Dietary supplement for athletic pets
US9180111B2 (en) 2005-03-29 2015-11-10 Cardax Pharma, Inc. Reduction in complement activation and inflammation during tissue injury by carotenoids, carotenoid analogs, or derivatives thereof

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US6900324B2 (en) 2000-09-07 2005-05-31 Astrazeneca Ab Process for preparing a substituted imidazopyridine compound
SE0003186D0 (en) * 2000-09-07 2000-09-07 Astrazeneca Ab New process
MXPA05001202A (en) * 2002-07-29 2005-11-23 Hawaii Biotech Inc Structural carotenoid analogs for the inhibition and amelioration of disease.
US20050143475A1 (en) * 2002-07-29 2005-06-30 Lockwood Samuel F. Carotenoid analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury
US20050026874A1 (en) * 2002-07-29 2005-02-03 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for the inhibition and amelioration of liver disease
US7345091B2 (en) 2002-07-29 2008-03-18 Cardax Pharmaceuticals, Inc. Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US20050148517A1 (en) * 2002-07-29 2005-07-07 Lockwood Samuel F. Carotenoid ether analogs or derivatives for controlling connexin 43 expression
US7521584B2 (en) * 2002-07-29 2009-04-21 Cardax Pharmaceuticals, Inc. Carotenoid analogs or derivatives for the inhibition and amelioration of disease
US7375133B2 (en) * 2002-07-29 2008-05-20 Cardax Pharmaceuticals, Inc. Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US20050059635A1 (en) * 2002-07-29 2005-03-17 Lockwood Samuel Fournier Carotenoid ester analogs or derivatives for controlling C-reactive protein levels
US7320997B2 (en) 2002-07-29 2008-01-22 Cardax Pharmaceuticals, Inc. Pharmaceutical compositions including carotenoid ester analogs or derivatives for the inhibition and amelioration of disease
US20050049248A1 (en) * 2002-07-29 2005-03-03 Lockwood Samuel Fournier Carotenoid ether analogs or derivatives for controlling C-reactive protein levels
US7723327B2 (en) 2002-07-29 2010-05-25 Cardax Pharmaceuticals, Inc. Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease
US7763649B2 (en) 2002-07-29 2010-07-27 Cardax Pharmaceuticals, Inc. Carotenoid analogs or derivatives for controlling connexin 43 expression
US20050004235A1 (en) * 2002-07-29 2005-01-06 Lockwood Samuel Fournier Carotenoid analogs or derivatives for the inhibition and amelioration of liver disease
US20050059659A1 (en) * 2002-07-29 2005-03-17 Lockwood Samuel Fournier Carotenoid analogs or derivatives for controlling C-reactive protein levels
AU2002329108A1 (en) * 2002-09-03 2004-03-29 Centro De Investigacion En Alimentacion Y Desarrollo A.C. Method of preparing chitosan microcapsules of astaxanthin and product thus obtained
CN1874772A (en) * 2003-11-03 2006-12-06 阿斯利康(瑞典)有限公司 Imidazo [1,2-a] pyridine derivatives for the treatment of silent gastro-esophageal reflux
SE0303451D0 (en) * 2003-12-18 2003-12-18 Astrazeneca Ab New compounds
US20060058269A1 (en) * 2004-04-14 2006-03-16 Lockwood Samuel F Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation
US20060167319A1 (en) * 2004-10-01 2006-07-27 Lockwood Samuel F Methods for the synthesis of unsaturated ketone intermediates useful for the synthesis of carotenoids
JP5196708B2 (en) * 2005-02-04 2013-05-15 富士化学工業株式会社 Muscle atrophy improving agent and food and drink comprising astaxanthin and / or ester thereof as active ingredients
JP2010270095A (en) * 2008-05-30 2010-12-02 Yamaha Motor Co Ltd Agent for improving cognitive performance
US10867701B1 (en) * 2010-06-28 2020-12-15 Heinrich Anhold System and method for optimizing patient-specific intervention strategies using point of care diagnostics
JP5924592B2 (en) * 2013-04-30 2016-05-25 株式会社ダイセル Anti-fatigue composition
CN112057420A (en) * 2020-09-21 2020-12-11 中国科学院烟台海岸带研究所 Astaxanthin spray and preparation method and use method thereof

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001072296A1 (en) * 2000-03-27 2001-10-04 Astacarotene Ab Method of inhibiting the expression of inflammatory cytokines and chemokines
US7078040B2 (en) 2000-03-27 2006-07-18 Fuji Chemical Industry Co., Ltd. Method of inhibiting the expression of inflammatory cytokines and chemokines
US8034372B2 (en) * 2003-03-05 2011-10-11 Nestec, Ltd. Dietary supplement for athletic pets
US7727752B2 (en) 2003-07-29 2010-06-01 Life Technologies Corporation Kinase and phosphatase assays
US20080269349A1 (en) * 2004-02-04 2008-10-30 Fuji Chemical Industry Co. Ltd. Gene expression regulating agent
US10828269B2 (en) 2004-02-04 2020-11-10 Fuji Chemical Industries Co., Ltd. Reducing muscle atrophy by administering astaxanthin
US7691901B2 (en) 2004-04-14 2010-04-06 Cardax Pharmaceuticals Inc. Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation
US9180111B2 (en) 2005-03-29 2015-11-10 Cardax Pharma, Inc. Reduction in complement activation and inflammation during tissue injury by carotenoids, carotenoid analogs, or derivatives thereof

Also Published As

Publication number Publication date
EP1011653B1 (en) 2003-01-15
EP1011653A1 (en) 2000-06-28
AU727349B2 (en) 2000-12-14
NO20001087D0 (en) 2000-03-02
DE69810784T2 (en) 2003-11-13
JP3660244B2 (en) 2005-06-15
AU9098998A (en) 1999-03-22
PL338982A1 (en) 2000-12-04
SE512531C2 (en) 2000-03-27
ATE230985T1 (en) 2003-02-15
SE9703191L (en) 1999-03-05
CA2299366A1 (en) 1999-03-11
ES2191329T3 (en) 2003-09-01
CA2299366C (en) 2008-04-22
NO20001087L (en) 2000-03-02
DK1011653T3 (en) 2003-05-26
DE69810784D1 (en) 2003-02-20
JP2001514215A (en) 2001-09-11
SE9703191D0 (en) 1997-09-04
US6245818B1 (en) 2001-06-12

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