WO1995000130A1 - Utilisation de carotenoides hydrophiles dans la fabrication d'un medicament s'appliquant au traitement de maladies possedant un mecanisme d'oxygenation - Google Patents

Utilisation de carotenoides hydrophiles dans la fabrication d'un medicament s'appliquant au traitement de maladies possedant un mecanisme d'oxygenation Download PDF

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Publication number
WO1995000130A1
WO1995000130A1 PCT/GB1994/001402 GB9401402W WO9500130A1 WO 1995000130 A1 WO1995000130 A1 WO 1995000130A1 GB 9401402 W GB9401402 W GB 9401402W WO 9500130 A1 WO9500130 A1 WO 9500130A1
Authority
WO
WIPO (PCT)
Prior art keywords
hca
disease
carotenoid
treatment
lutein
Prior art date
Application number
PCT/GB1994/001402
Other languages
English (en)
Inventor
Alan Norman Howard
David I. Thurnham
Original Assignee
The Howard Foundation
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.)
Filing date
Publication date
Priority claimed from GB939313266A external-priority patent/GB9313266D0/en
Application filed by The Howard Foundation filed Critical The Howard Foundation
Priority to AU70056/94A priority Critical patent/AU7005694A/en
Publication of WO1995000130A1 publication Critical patent/WO1995000130A1/fr

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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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/07—Retinol compounds, e.g. vitamin A
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/34—Copper; Compounds thereof

Definitions

  • hydrophilic carotenoids for the manufacture of a medicament for the treatment of diseases having an oxygenation mechanism.
  • the present invention relates to hydroxy carotenoid antioxidants (HCA) active against reactive oxygen species (ROS) and free radicals which cause oxidative damage to lipids, lipoproteins, proteins and DNA.
  • HCA hydroxy carotenoid antioxidants
  • ROS reactive oxygen species
  • the invention is particularly but not exclusively concerned with carotenoid antioxidants for use in the treatment by therapy or prophylaxis of coronary heart disease (CHD) in particular by a mechanism involving antioxidative protection of lipoproteins, especially low density lipoproteins (LDL) .
  • Antioxidant nutrients such as vitamin E, vitamin C and betacarotene are considered to have important potential in the prevention of several human diseases, in particular cardiovascular and cerebrovascular disease, some forms of cancer, diabetes, rheumatoid arthritis, Parkinson's disease, Down's syndrome, Alzheimer's disease and several other age-related disorders such as cataracts.
  • Carotenoids are known to act as anti-oxidants in vitro. To date there have been few practical proposals for a formulation for use as an antioxidant.
  • One such is Redoxon Protector sold in the UK by Roche Nicholas Consumer Health Care and comprising beta carotene combined with vitamins C and E put up as one-a-day capsules.
  • European Patent Application No 0 385 335 discloses stabilised fat-soluble vitamin compositions which have a wide range of applications, such as in medicines and food additives.
  • the disclosed compositions basically comprise a fat-soluble vitamin in combination with a carotenoid compound as stabiliser.
  • the invention approaches the prevention or cure of disease involving an oxidation mechanism such as oxidation of lipids, lipoproteins, proteins and DNA from a novel standpoint based on the use of at least one hydrophilic carotenoid compound.
  • the invention provides hydrophilic carotenoids, in particular lutein, which are effective in the treatment by prevention or cure of coronary heart disease.
  • the present invention provides a novel treatment to prevent the onset of coronary heart disease based on the use of at least one hydrophilic carotenoid, especially lutein.
  • carotenoid namely a hydrophilic carotenoid, especially a mono- or di-hydroxy carotenoid such as lutein, or an ester thereof
  • significant and better antioxidant properties can be brought into play within any particular preventative or curative context.
  • lutein or the like has identical properties to betacarotene it would be thought according to the teaching of Sies et al, that lutein or the like should have equal activity. However, this has been shown manifestly not to be the case.
  • the present invention in one aspect provides a compound for use as a pharmaceutical or food supplement, particularly in the prevention or cure of disease involving an oxidation mechanism such as oxidation of lipids, lipoproteins, proteins or DNA, which compound comprises a hydrophilic carotenoid or a mixture thereof.
  • ketonic carotenoids can exist in a keto/enol equilibrium, thus effectively or potentially being themselves hydroxy carotenoids.
  • the compounds of the invention are especially useful in the prevention or treatment of cardiovascular or cerebrovascular disease, cancer, diabetes, rheumatoid arthritis, Parkinson's disease, Down's syndrome, Alzheimer's disease or cataracts or other age related changes.
  • esters are C ⁇ to C g esters e.g. ethyl esters, and esters with long chain fatty acids e.g. stearic, palmitic and linoleic esters or naturally occurring esters such as lutein ester from certain plants e.g. marigold.
  • the invention provides a food supplement or pharmaceutical composition, which composition comprises as an active agent a hydrophilic carotenoid, especially a mono- or di-hydroxy carotenoid such as lutein, or an ester thereof, a ketonic carotenoid, or a mixture of the same, together with a food supplement or pharmaceutically- acceptable diluent or carrier.
  • a hydrophilic carotenoid especially a mono- or di-hydroxy carotenoid such as lutein, or an ester thereof, a ketonic carotenoid, or a mixture of the same, together with a food supplement or pharmaceutically- acceptable diluent or carrier.
  • compositions may be in bulk form or, more preferably, unit dosage form.
  • the composition may be formulated as a tablet, capsule, powder, solution or suspension.
  • compositions in accordance with the invention may be prepared using the carotenoid or ester active agent in accordance with conventional food supplement or pharmaceutical practice.
  • the diluents, excipients or carriers etc. which may be used are well known in the formulation art and the form chosen for any particular regimen will depend on the given context and the formulator's choice.
  • the active agent may be a ono-hydroxy carotenoid, a di-hydroxy carotenoid or a ketonic carotenoid per se or an ester thereof, preferably a carotenoid as described below.
  • Astacene (di-hydroxy and di-keto) Astaxanthin (di-hydroxy and di-keto) Capsanthin (dihydroxy and mono-keto) Capsorubin (dihydroxy, di-keto) Canthaxanthin (which can be in a di-keto or di ⁇ hydroxy form)
  • Keto moieties can enolize to give hydroxy groups.
  • the hydrophilic carotenoid used in the invention is a di-hydroxy carotenoid, especially lutein.
  • the active hydrophilic carotenoid may be used together with other active agents.
  • other active agents there may be mentioned, for example, the following, namely:
  • Another carotenoid such as:
  • Alpha, beta, gamma or delta carotene Alpha, beta, gamma or delta carotene.
  • antioxidants or anti- inflammatory agents namely:
  • Vitamin A Vitamin C
  • Vitamin E ( -tocopherol and other active tocopherols)
  • hydrophilic carotenoid e.g. lutein
  • the hydrophilic carotenoid as active agent may be used in a dosage regimen between about 0.5 and about 50 mg per day, typically about 1 to about 30 mg.
  • the hydroxycarotenoids are partially destroyed in the gastrointestinal tract by oxidation. By adding Vitamin E and/or Vitamin C and/or salicylates this process is inhibited and more hydroxycarotenoid is absorbed.
  • the inhibitor may be included as part of a composition according to the invention or administered separately.
  • a unit dosage form such as say a 750 mg tablet or say an 800 mg capsule to be used on a one-a-day basis may contain between about 0.1% and about 4% by weight of lutein and other ingredients may comprise:
  • Beta carotene about 2 to about 20 mg e.g. about 5 mg Vitamin A about 400 to about 600 RE e.g. about 500 RE
  • Vitamin C about 75 to about 250 mg e.g. about 100 mg
  • Salicylic acid about 10 to about 150 mg e.g. about 50 mg
  • Carrier about 150 to about 250 mg e.g. about 175 or about 200 mg.
  • the invention includes the use of a hydrophilic carotenoid, especially a mono- or di-hydroxy carotenoid such as lutein or an ester thereof, a ketonic carotenoid, or a mixture of the same for the manufacture of a food supplement or medicament for the prevention or treatment of disease involving oxidation of lipids, lipoproteins, proteins or DNA.
  • a hydrophilic carotenoid especially a mono- or di-hydroxy carotenoid such as lutein or an ester thereof, a ketonic carotenoid, or a mixture of the same for the manufacture of a food supplement or medicament for the prevention or treatment of disease involving oxidation of lipids, lipoproteins, proteins or DNA.
  • the invention includes a process for the manufacture of a food supplement or medicament for use in the treatment of disease involving oxidation of lipids, lipoproteins, proteins or DNA which process comprises formulating a hydrophilic carotenoid, especially a mono- or di-hydroxy carotenoid such as lutein or an ester thereof, a ketonic carotenoid, or a mixture of the same for use in such treatment.
  • a hydrophilic carotenoid especially a mono- or di-hydroxy carotenoid such as lutein or an ester thereof, a ketonic carotenoid, or a mixture of the same for use in such treatment.
  • the invention includes a method for the prevention or treatment of cardiovascular or cerebrovascular disease, cancer, diabetes, rheumatoid arthritis, Parkinson's disease, Down's syndrome, Alzheimer's disease or cataracts or for delaying other age- related changes which method comprising administering an effective amount of a hydrophilic carotenoid, especially a mono- or di-hydroxy carotenoid such as lutein or an ester thereof, a ketonic carotenoid, or a mixture of the same as active agent.
  • a hydrophilic carotenoid especially a mono- or di-hydroxy carotenoid such as lutein or an ester thereof, a ketonic carotenoid, or a mixture of the same as active agent.
  • Results are mean ⁇ SEM (n) , or mean (95% confidence interval) (n) ⁇ ⁇ Results were log transformed prior to analysis
  • P is the significance determined by two-tailed unpaired t-test
  • jS-carotene has been shown to be a pro-oxidant compared with lutein and lycopene which are antioxidants.
  • lutein may protect LDL directly from oxidation, due to its presence in the lipoprotein particles. -carotene does not prevent copper mediated oxidation of LDL but the reason lutein might be more potent is that the hydroxy groups render the molecule more hydrophillic and lutein is more likely to be present on the surface of LDL . i
  • HDL high density lipoprotein
  • LDL low density lipoprotein
  • the lutein:cholesterol ratio (nmole/mmole) was greater, prior to dosing, in HDL. After dosing, the lutein concentration rose much more in the HDL than LDL fraction such that the ratio of lutein/cholesterol in HDL was over three fold greater than in LDL.
  • HDL acts as an antioxidant for LDL by providing a sink for lipoperoxides. It is possible that one of the active components of HDL might be lutein which is present in higher concentrations than the other carotenoids and which has been demonstrated to possess peroxy radical scavenging activity at atmospheric pressure, in contrast to /3-carotene which is inactive under these conditions.
  • diabetes It is believed that the long term symptoms of diabetes are due to reactive oxygen species. Diabetes is also associated with an increased risk of coronary heart disease (CHD) .
  • CHD coronary heart disease
  • Gran granulocyte
  • antioxidants such as alpha- and beta carotene and lycopene were also reduced.
  • the copper was reduced in mono-nuclear cells and plasma Zinc was reduced in plasma.
  • the copper dependent enzyme SOD Superoxide dismutase was reduced in red blood cells.
  • a mixture was prepared to the formulation set forth above in Example 4 but with the addition of 5 mg/capsule alpha carotene.
  • a capsule was prepared using the following ingredients by simple admixture and routine encapsulation:-
  • a capsule was prepared using the following ingredients by simple admixture and routine encapsulation:-
  • Vitamin C Ascorbic Acid 150 mg 160 - Tocopherol 100 mg 110
  • Example 7 The procedure of Example 7 was repeated except that 30 mg of Coenzyme Q10 was included in the mixture and the mixture encapsulated.
  • a size 12 oval capsule of nominally 800 mg weight was prepared from the following ingredients by simple admixture and routine encapsulation:-
  • Vitamin C Ascorbic Acid 100 mg 105
  • Zinc Gluconate to give 15 mg Zn 117
  • a dry powder formula diet composition was prepared by mixing 150 mg of lutein ester per day with a Cambridge Diet (The Cambridge Diet is a Registered Trade Mark) product obtained from Cambridge Health Plan Limited, Norwich, England.
  • Example 7 was repeated a total of sixteen times, in each case a hydroxycarotenoid from the compounds listed below being included in the encapsulated mixture in an amount of 15mg in substitution for lutein ester:-
  • Example 9 Eight Adults were given orally a daily capsule containing the formulation of Example 9 with an evening meal for 4 weeks. Blood (10 ml) was taken after an overnight fast, before, 2 weeks after and 4 weeks after taking the capsule. Plasma, vitamins and carotenoids were analyzed by HPLC as shown in Table IV. The mean concentration of lutein was increased from 0.309 to 0.667 ⁇ mol/L after 4 weeks administration. In Example 1, the mean concentration of lutein in people fromdoch was 0.54 ⁇ mol/L. Thus the capsule was able to provide in a daily therapeutic dose sufficient to bring the concentration of lutein into a beneficial range. Rather surprisingly retinol (Vitamin A) was unchanged, but the expected increases in plasma, ⁇ - carotene and -tocopherol (also present in the capsule) occurred.
  • a capsule was prepared using the following ingredients by simple admixture and routine encapsulation: -
  • Aspirin can be replaced by salicylic acid, 2,3-dihydroxy benzoic acid or 2, 5-dihydroxy benzoic acid.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La lutéine et autres caroténoïdes hydrophyles, lesquels sont destinés à être utilisés dans le traitement thérapeutique ou prophylaxique de maladies, possèdent un mécanisme d'oxygénation. Les caroténoïdes de l'invention sont notamment utiles dans le traitement de maladies coronariennes et peuvent être combinés avec, par exemple, de l'aspirine.
PCT/GB1994/001402 1993-06-28 1994-06-28 Utilisation de carotenoides hydrophiles dans la fabrication d'un medicament s'appliquant au traitement de maladies possedant un mecanisme d'oxygenation WO1995000130A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU70056/94A AU7005694A (en) 1993-06-28 1994-06-28 Use of hydrophilic carotenoids for the manufacture of a medicament for the treatment of diseases having an oxygenation mechanism

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB939313266A GB9313266D0 (en) 1993-06-28 1993-06-28 Antioxidants for lipoproteins
GB9313266.0 1993-06-28
US21989794A 1994-03-30 1994-03-30
US08/219,897 1994-03-30

Publications (1)

Publication Number Publication Date
WO1995000130A1 true WO1995000130A1 (fr) 1995-01-05

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PCT/GB1994/001402 WO1995000130A1 (fr) 1993-06-28 1994-06-28 Utilisation de carotenoides hydrophiles dans la fabrication d'un medicament s'appliquant au traitement de maladies possedant un mecanisme d'oxygenation

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AU (1) AU7005694A (fr)
GB (1) GB2280110B (fr)
IL (1) IL110139A0 (fr)
WO (1) WO1995000130A1 (fr)

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GB2289406A (en) * 1994-04-15 1995-11-22 Britannia Health Products Ltd Vitamin, betacarotene and zinc composition for sperm health
WO1996013255A1 (fr) * 1994-10-27 1996-05-09 Board Of Trustees Of The University Of Illinois Utilisation d'astaxanthine pour ralentir et traiter les lesions oculaires et du systeme nerveux central
EP0793491A1 (fr) * 1994-12-22 1997-09-10 Henkel Corporation Compositions pharmaceutiques comprenant du lycopene
WO1997048388A1 (fr) * 1996-06-17 1997-12-24 The Board Of Trustees Of The University Of Illinois Procede de retardement et d'attenuation d'affections oculaires et du systeme nerveux central
WO1998033494A1 (fr) * 1997-02-04 1998-08-06 Kosbab John V Compositions et procedes destines a la prevention et au traitement de maladies degeneratives vasculaires
WO1998037874A1 (fr) * 1997-02-27 1998-09-03 Astacarotene Ab PREPARATION ORALE POUR LA PROPHYLAXIE ET LE TRAITEMENT DES INFECTIONS PAR $i(HELICOBACTER)
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EP1487774A2 (fr) * 2002-02-25 2004-12-22 Diffusion Pharmaceuticals LLC Sels carotenoides trans bipolaires et leurs utilisations
EP1667954A1 (fr) * 2003-08-25 2006-06-14 Diffusion Pharmaceuticals LLC Sels de carotenoides trans bipolaires et leurs utilisations
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US8030350B2 (en) 2005-02-24 2011-10-04 Diffusion Pharmaceuticals Llc Trans carotenoids, their synthesis, formulation and uses
US8206751B2 (en) 2007-10-31 2012-06-26 Diffusion Pharmaceuticals Llc Class of therapeutics that enhance small molecule diffusion
US8293804B2 (en) 2007-04-13 2012-10-23 Diffusion Pharmaceuticals Llc Use of bipolar trans carotenoids as a pretreatment and in the treatment of peripheral vascular disease
CN103228276A (zh) * 2010-09-30 2013-07-31 北京绿色金可生物技术股份有限公司 岩藻黄素在制备与神经退行性疾病相关的神经保护作用以及改善记忆的产品中的应用
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US8974822B2 (en) 2010-06-02 2015-03-10 Diffusion Pharmaceuticals Llc Oral formulations of bipolar trans carotenoids
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WO2018078399A1 (fr) * 2016-10-31 2018-05-03 Ip Science Limited Compositions comprenant des caroténoïdes et de la phosphatidylcholine
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Cited By (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2289406A (en) * 1994-04-15 1995-11-22 Britannia Health Products Ltd Vitamin, betacarotene and zinc composition for sperm health
WO1996013255A1 (fr) * 1994-10-27 1996-05-09 Board Of Trustees Of The University Of Illinois Utilisation d'astaxanthine pour ralentir et traiter les lesions oculaires et du systeme nerveux central
US6362221B1 (en) 1994-12-22 2002-03-26 Cognis Corporation Compositions containing natural lycopene and natural tocopherol
EP0793491A1 (fr) * 1994-12-22 1997-09-10 Henkel Corporation Compositions pharmaceutiques comprenant du lycopene
EP0793491A4 (fr) * 1994-12-22 2000-01-12 Henkel Corp Compositions pharmaceutiques comprenant du lycopene
US6262109B1 (en) 1995-12-22 2001-07-17 Henkel Corporation Methods of preventing and/or treating high serum levels of cholesterol and/or lipids
WO1997048388A1 (fr) * 1996-06-17 1997-12-24 The Board Of Trustees Of The University Of Illinois Procede de retardement et d'attenuation d'affections oculaires et du systeme nerveux central
EP0966960A1 (fr) * 1996-11-27 1999-12-29 Dainippon Ink And Chemicals, Inc. Medicament pour l'inhibition de la carcinogenèse ou de la métastase de tumeurs
WO1998033494A1 (fr) * 1997-02-04 1998-08-06 Kosbab John V Compositions et procedes destines a la prevention et au traitement de maladies degeneratives vasculaires
US6262316B1 (en) 1997-02-27 2001-07-17 Astacarotene Ab Oral preparation for the prophylactic and therapeutic treatment of Helicobacter sp. infection
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GB2280110A (en) 1995-01-25
GB2280110B (en) 1997-11-12
GB9412938D0 (en) 1994-08-17
AU7005694A (en) 1995-01-17
IL110139A0 (en) 1994-10-07

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