JP2009528833A - 同位体修飾化合物およびフードサプリメントとしてのそれらの使用 - Google Patents
同位体修飾化合物およびフードサプリメントとしてのそれらの使用 Download PDFInfo
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Abstract
Description
本発明は、同位体修飾化合物およびフードサプリメントとしてのそれらの使用に関する。
加齢に関する現今の定説は、細胞機構における不可逆的変化ならびに呼吸プロセスの一部として細胞に通常存在するフリーラジカルおよび他の活性酸素種(ROS)または活性窒素種(RNS)の有害な作用に対する代謝プロセスの低下した効率が原因であるとする。ROSおよびRNSは、DNA、タンパク質、脂質および他の細胞構成成分を酸化/ニトロ化する。これらのうち、アルギニン、リシン、スレオニン、トリプトファンおよびプロリンを対応するカルボニル化合物に変換するタンパク質酸化は、特定の閾値数のアミノ酸残基が酸化された後ではプロテアーゼにより修復することができない。
本発明は、摂取された場合、機能的に通常の身体構成物質に等価であるが、分解/有害なプロセス(例えば、ROSおよびRNSまたは放射線により媒介されるプロセス)に対してより耐性を有する、身体構成物質(例えば、タンパク質、核酸、脂質、炭水化物など)の形成を生じるクラスの化合物を合成するために、同位体置換を使用できる、という事実に基づいている。そのため、本発明によれば、栄養組成物は、少なくとも1つの変換可能なH原子が2Hであり、かつ/または少なくとも1つのC原子が13Cである必須栄養素を含む栄養組成物を含む。
図1から4は各々必須栄養素を分解する反応を示す。
本発明は、必須サプリメントが酸化、窒素化などの不可逆的化学変換を受け、老化または疾患の発現を導きうる、という事実に関する。必須食品成分は、生物体(例えば、哺乳動物、霊長類またはヒト)によりデノボ合成することができず、そのため食餌で供給される必要がある。本明細書の目的のために、核酸は必須であるが、条件付きで必須と記載されることがより適切でありうる。条件付きで必須な栄養素は、特定の条件下、食餌で供給される必要がある。
塩化第一銅−ジオキシゲン−ピリジン系に触媒される酸素による直接酸化(Nicolaouら、Synthesis(1986)453〜461;Capdevielleら、Tet.Lett.(1990)31:3305〜3308)
ブロモコハク酸イミドを使用する直接変換(Gottardi、Monatsh.Chem.(1973)104:1690〜1695)
直接ヨードソベンゼン酸化(Moriartyら、Tet.Lett.(1988)29:6913〜6916)
ジ−トシル誘導体およびヨード誘導体を介する2段階変換(DeChristopherら、JACS(1969)91:2384〜2385)。
13C6−グルコース(99%濃縮;Sigma)を大腸菌(Escherichia coli)の培養のための炭素飼料源として使用し、対照は12C6−グルコースを除いて同じであった。C.エレガンス(N2、野生型)を、上記のとおりに調製された大腸菌を播種した標準(ペプトン、塩およびコレステロール)培地で培養した。対応する13C−誘導体が入手不可能であったため、大腸菌を除く唯一の炭素含有成分は、12C−コレステロール(Sigma;C.エレガンスに必須であるホルモン前駆体)であった。したがって、線虫を15〜25℃の温度範囲で、各プール50〜100匹の蠕虫で「重」および「軽」(対照)飼料により培養した。両飼料を与えた動物は正常に成長し、すべての主要な特性は非常に類似していた。
使用した無菌培地の基本構成成分は(Lu & Goetsch Nematologica(1993)39:303〜311)によった。水溶性およびTEA可溶性成分(ビタミンおよび成長因子)、塩、非必須アミノ酸、核酸置換基、他の成長因子およびエネルギー源を記載のとおりに調製した(2倍の0.5L)。これに必須アミノ酸:0.98g L−(D2)−Arg(上記参照);0.283g L−Hys;1.05g L−(D2)−Lys(下記参照);0.184g L−Trp;0.389g L−Met;0.717g L−Thr;1.439g L−Leu;0.861g L−Ile;1.02g L−Valおよび0.623g L−Pheを含む(2倍量として0.5L)混合物を添加した。残りの成分を添加する前に、この混合物を55℃で4時間、透明な溶液が形成されるまで攪拌し、次いで室温まで冷却した。
12C−NGM飼料は5,5−ジ−重水素化−アルギニンおよび6,6−ジ−重水素化−リシン、11,11−ジ−重水素化−リノール酸(18:2)ならびに8−D−デオキシグアノシンを豊富に含んだ。C.エレガンスを、1g/Lの各重水素化化合物の総濃度になるように重水素「補強された」誘導体(上記参照)を添加した、上記のとおりに調製した大腸菌を播種した標準(ペプトン、塩およびコレステロール)培地で培養した。したがって、線虫を「重」および「軽」(対照、非重水素化L−アルギニン、L−リシン、リノール酸(18:2)およびデオキシグアノシンを1g/Lの濃度で重水素化アナログの代わりに使用した)飼料で、15〜25℃の温度範囲で、各プール中50〜100匹の蠕虫で培養した。生存期間のデータを実施例10に記載したとおりにプリズムソフトウェアパッケージを使用して解析した。
Claims (18)
- 少なくとも1つの交換可能なH原子が2Hであり、かつ/または少なくとも1つのC原子が13Cである必須栄養素を含む栄養組成物。
- 必須栄養素が、天然の核酸、脂肪酸もしくはアミノ酸であるか、または前記物質を含む請求項1に記載の組成物。
- 最も酸化されやすい位置でC原子に結合された1つのH原子または各H原子が2Hである、請求項2に記載の組成物。
- C原子が13Cである、請求項3に記載の組成物。
- 酸化が酵素的カルボニル化である、請求項3または4に記載の組成物。
- 前記2Hもしくは13C原子、または各2Hもしくは13C原子が、活性酸素種と反応しやすい位置にある、前記請求項のいずれかに記載の組成物。
- 必須栄養素が、Phe、Val、Trp、Pro、Thr、Ile、Met、His、Arg、LysおよびLeuから選択されるアミノ酸であるか、または前記アミノ酸を含む、請求項2から5のいずれかに記載の組成物。
- アミノ酸が、2,6−ジアミノヘキサン−6,6−D2または明細書中に式が挙げられる別の標識アミノ酸である、請求項7に記載の組成物。
- 必須栄養素がペプチドである、前記請求項のいずれかに記載の組成物。
- 栄養素が核酸またはヌクレオチドである、請求項2から6のいずれかに記載の組成物。
- 栄養素がω−3またはω−6脂肪酸である、請求項2から6のいずれかに記載の組成物。
- 植物性物質を含む、前記請求項のいずれかに記載の組成物。
- 微生物物質を含む、前記請求項のいずれかに記載の組成物。
- 前記請求項のいずれかに記載の組成物である培地中、必須栄養素が生物体により生成される生成物中に同化されるような条件下で生物体を培養する工程を含む食品を調製するための方法。
- 栄養素中に、少なくとも1つの交換可能なH原子が2Hであり、かつ/または少なくとも1つのC原子が13Cである必須栄養素を含める工程を含む対象の栄養摂取の方法。
- 必須栄養素が請求項2から9のいずれかに定義されたとおりである、請求項15に記載の方法。
- 対象がヒトである、請求項15または16に記載の方法。
- 対象が商業用動物または家畜である、請求項15または16に記載の方法。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019501135A (ja) * | 2015-11-23 | 2019-01-17 | レトロトップ、 インコーポレイテッドRetrotope, Inc. | 1,4−ジエン系の部位特異的同位体標識 |
US11779910B2 (en) | 2020-02-21 | 2023-10-10 | Biojiva Llc | Processes for isotopic modification of polyunsaturated fatty acids and derivatives thereof |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0604647D0 (en) | 2006-03-08 | 2006-04-19 | Shchepinov Mikhail | Stabilized food supplements and their derivatives |
WO2009114809A1 (en) * | 2008-03-14 | 2009-09-17 | Retrotope, Inc. | Therapies for cancer using isotopically substituted lysine |
WO2009114814A2 (en) * | 2008-03-14 | 2009-09-17 | Retrotope, Inc. | Therapeutic substances that modulate genome methylation |
CA2777827C (en) * | 2009-10-30 | 2020-08-18 | Retrotope, Inc. | Alleviating oxidative stress disorders with pufa derivatives |
DK2588144T3 (en) | 2010-07-02 | 2018-07-23 | Ventana Med Syst Inc | Detection of targets using mass markers and mass spectrometry |
EP3689342A1 (en) | 2011-04-26 | 2020-08-05 | Retrotope, Inc. | Oxidative retinal diseases |
KR102110175B1 (ko) | 2011-04-26 | 2020-05-13 | 레트로토프 인코포레이티드 | Pufa 산화와 관련된 장애 |
AU2012249917B2 (en) | 2011-04-26 | 2017-06-15 | Biojiva Llc | Neurodegenerative disorders and muscle diseases implicating PUFAs |
JP6093756B2 (ja) | 2011-04-26 | 2017-03-08 | レトロトップ、 インコーポレイテッドRetrotope, Inc. | 損なわれたエネルギー処理障害およびミトコンドリア欠損症 |
WO2013176958A1 (en) * | 2012-05-21 | 2013-11-28 | Sequenom, Inc. | Methods and compositions for analyzing nucleic acid |
ES2889874T3 (es) | 2014-03-13 | 2022-01-14 | Retrotope Inc | Tratamiento de neuropatía óptica y reducción del estrés oxidativo inducido por esteroides con sustancias polinsaturadas estabilizadas |
FR3068135A1 (fr) | 2017-06-26 | 2018-12-28 | Ids Group | Marquage et identification isotopiques des animaux et vegetaux |
CA3096035A1 (en) * | 2018-04-04 | 2019-10-10 | Retrotope, Inc. | Isotopically modified composition and therapeutic uses thereof |
KR20240096817A (ko) | 2020-05-19 | 2024-06-26 | 사이빈 아이알엘 리미티드 | 중수소화된 트립타민 유도체 및 사용 방법 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10291955A (ja) * | 1997-04-22 | 1998-11-04 | Sagami Chem Res Center | 13c標識ドコサヘキサエン酸及びその製造方法 |
JP2000290291A (ja) * | 1999-03-31 | 2000-10-17 | Nippon Sanso Corp | 安定同位体標識オリゴヌクレオチド及びオリゴヌクレオチド検出方法 |
JP2001514239A (ja) * | 1997-09-02 | 2001-09-11 | マーテック・バイオサイエンスィズ・コーポレーション | Nmr構造を決定するための方法及び組生物 |
JP2001519355A (ja) * | 1997-10-08 | 2001-10-23 | エス. セルバラージ ナイッカー, | 重水素化シクロスポリンアナログおよび免疫調節剤としてのそれらの使用 |
JP2002513911A (ja) * | 1998-05-06 | 2002-05-14 | アイソテクニカ、インコーポレーテッド | 糖尿病症状の診断及び血糖コントロール監視用13cグルコース呼気試験 |
JP2002536981A (ja) * | 1999-02-18 | 2002-11-05 | プロメガ・コーポレーション | 核酸標的配列の存在を測定する方法およびその応用 |
WO2004029254A1 (ja) * | 2002-09-30 | 2004-04-08 | Ajinomoto Co.,Inc. | 安定同位体標識タンパク質の製造方法 |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3520872A (en) * | 1967-03-24 | 1970-07-21 | Upjohn Co | Process for labelling purine and pyrimidine containing compounds |
JPH07500566A (ja) * | 1989-11-30 | 1995-01-19 | クロダ・インターナショナル・ピーエルシー | ネルボン酸及び長鎖脂肪酸の脱髄疾患の治療のための使用 |
US5244921A (en) | 1990-03-21 | 1993-09-14 | Martek Corporation | Eicosapentaenoic acids and methods for their production |
US5393669A (en) | 1993-02-05 | 1995-02-28 | Martek Biosciences Corp. | Compositions and methods for protein structural determinations |
FR2721518B3 (fr) | 1994-06-28 | 1996-04-12 | Gattefosse Ets Sa | Compositions cosmétiques, pharmaceutiques, diététiques, vétérinaires contenant de l'eau. |
US5578334A (en) * | 1995-04-07 | 1996-11-26 | Brandeis University | Increasing the HDL level and the HDL/LDL ratio in human serum with fat blends |
IT1304406B1 (it) * | 1998-10-21 | 2001-03-19 | Danital Italia S R L | Preparazione per la veicolazione di principi attivi basata su acidigrassi polinsaturi del gruppo omega 3. |
US6503478B2 (en) * | 1999-01-13 | 2003-01-07 | Lightouch Medical, Inc. | Chemically specific imaging of tissue |
GB9929897D0 (en) * | 1999-12-18 | 2000-02-09 | Slabas Antoni R | Improvements in or relating to conjugated fatty acids and related compounds |
CZ299784B6 (cs) * | 2001-05-30 | 2008-11-26 | Laxdale Limited | Lécivo obsahující EPA a ubichinon pro lécení non-Hodgkinova lymfomu, psychiatrických a neurologických chorob |
JP4836786B2 (ja) | 2003-07-11 | 2011-12-14 | − ツァチェルニュウク、タティアナ、アー. エゴロワ | 生体化合物の安定同位体標識のための組成物及び方法 |
JP2006053100A (ja) * | 2004-08-13 | 2006-02-23 | Institute Of Physical & Chemical Research | 動物の代謝解析方法、ラベル動物の製造方法、ラベル動物、および、動物のnmr測定方法 |
EP1637163A1 (en) * | 2004-09-21 | 2006-03-22 | Andreas Kluge | Indicator of therapeutic compliance |
BRPI0516803A (pt) * | 2004-11-19 | 2008-09-23 | Martek Biosciences Corp | oxilipinas de ácidos graxos polinsaturados de cadeia longa e métodos de produção e uso dos mesmos |
US7250416B2 (en) | 2005-03-11 | 2007-07-31 | Supergen, Inc. | Azacytosine analogs and derivatives |
GB0604647D0 (en) | 2006-03-08 | 2006-04-19 | Shchepinov Mikhail | Stabilized food supplements and their derivatives |
US20080234197A1 (en) * | 2007-03-19 | 2008-09-25 | Undurti N Das | Method(s) of stabilizing and potentiating the actions and administration of brain-derived neurotrophic factor (BDNF) |
CN105330743B (zh) | 2007-08-02 | 2019-05-28 | 吉利德生物制剂公司 | Lox和loxl2抑制剂及其应用 |
US20090069354A1 (en) * | 2007-09-12 | 2009-03-12 | Protia, Llc | Deuterium-enriched gemcitabine |
WO2009114814A2 (en) | 2008-03-14 | 2009-09-17 | Retrotope, Inc. | Therapeutic substances that modulate genome methylation |
WO2009114809A1 (en) | 2008-03-14 | 2009-09-17 | Retrotope, Inc. | Therapies for cancer using isotopically substituted lysine |
-
2006
- 2006-03-08 GB GBGB0604647.8A patent/GB0604647D0/en not_active Ceased
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- 2007-03-08 WO PCT/GB2007/050112 patent/WO2007102030A1/en active Application Filing
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- 2007-03-08 CA CA2645038A patent/CA2645038C/en active Active
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Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10291955A (ja) * | 1997-04-22 | 1998-11-04 | Sagami Chem Res Center | 13c標識ドコサヘキサエン酸及びその製造方法 |
JP2001514239A (ja) * | 1997-09-02 | 2001-09-11 | マーテック・バイオサイエンスィズ・コーポレーション | Nmr構造を決定するための方法及び組生物 |
JP2001519355A (ja) * | 1997-10-08 | 2001-10-23 | エス. セルバラージ ナイッカー, | 重水素化シクロスポリンアナログおよび免疫調節剤としてのそれらの使用 |
JP2002513911A (ja) * | 1998-05-06 | 2002-05-14 | アイソテクニカ、インコーポレーテッド | 糖尿病症状の診断及び血糖コントロール監視用13cグルコース呼気試験 |
JP2002536981A (ja) * | 1999-02-18 | 2002-11-05 | プロメガ・コーポレーション | 核酸標的配列の存在を測定する方法およびその応用 |
JP2000290291A (ja) * | 1999-03-31 | 2000-10-17 | Nippon Sanso Corp | 安定同位体標識オリゴヌクレオチド及びオリゴヌクレオチド検出方法 |
WO2004029254A1 (ja) * | 2002-09-30 | 2004-04-08 | Ajinomoto Co.,Inc. | 安定同位体標識タンパク質の製造方法 |
Non-Patent Citations (6)
Title |
---|
JPN6011043625; J.Nutr.,2004,134,p.806-10 * |
JPN6011043636; J.Nutr.,2002,132,p.936-9 * |
JPN6013000938; Nucleic Acids Res.,2005 Oct 4,33(17),p.5553-64 |
JPN6013000939; J.Biol.Chem.,1981 Jul 25,256(14),p.7155-60 |
JPN6013000940; Bull.Chem.Soc.Jpn.,2001,74,p.2199-205 |
JPN7011003016; Journal of Lipid Research,1990,31,p.1693-1701 * |
Cited By (5)
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JP2019501135A (ja) * | 2015-11-23 | 2019-01-17 | レトロトップ、 インコーポレイテッドRetrotope, Inc. | 1,4−ジエン系の部位特異的同位体標識 |
JP2022046501A (ja) * | 2015-11-23 | 2022-03-23 | レトロトップ、 インコーポレイテッド | 1,4-ジエン系の部位特異的同位体標識 |
JP7048976B2 (ja) | 2015-11-23 | 2022-04-06 | レトロトップ、 インコーポレイテッド | 1,4-ジエン系の部位特異的同位体標識 |
JP7355801B2 (ja) | 2015-11-23 | 2023-10-03 | レトロトップ、 インコーポレイテッド | 1,4-ジエン系の部位特異的同位体標識 |
US11779910B2 (en) | 2020-02-21 | 2023-10-10 | Biojiva Llc | Processes for isotopic modification of polyunsaturated fatty acids and derivatives thereof |
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US20100160248A1 (en) | 2010-06-24 |
EP1991068A1 (en) | 2008-11-19 |
EP1991068B8 (en) | 2018-10-17 |
JP2015146811A (ja) | 2015-08-20 |
US20180303145A1 (en) | 2018-10-25 |
EP3339315C0 (en) | 2023-10-18 |
US10918126B2 (en) | 2021-02-16 |
GB0604647D0 (en) | 2006-04-19 |
US20150147457A1 (en) | 2015-05-28 |
US9320289B2 (en) | 2016-04-26 |
CA2931996A1 (en) | 2007-09-13 |
US8906405B2 (en) | 2014-12-09 |
CA2645038C (en) | 2016-08-16 |
ES2639395T3 (es) | 2017-10-26 |
EP3339315B1 (en) | 2023-10-18 |
JP5844955B2 (ja) | 2016-01-20 |
US9616042B2 (en) | 2017-04-11 |
JP6062470B2 (ja) | 2017-01-18 |
DK1991068T3 (en) | 2017-09-11 |
HK1260326A1 (zh) | 2019-12-20 |
US20160263066A1 (en) | 2016-09-15 |
WO2007102030A1 (en) | 2007-09-13 |
US20170172195A1 (en) | 2017-06-22 |
EP3339315A1 (en) | 2018-06-27 |
CA2645038A1 (en) | 2007-09-13 |
EP1991068B1 (en) | 2017-06-07 |
US10015979B2 (en) | 2018-07-10 |
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