The Lipoic Acid Analogue 1,2-Diselenolane-3-pentanoic Acid Protects Human Low Density Lipoprotein against Oxidative Modification Mediated by Copper Ion

Matsugo, Seiichi; Lv, Yan; Konishi, Tetsuya; Youn, Hwa Young; Lodge, John K.; Ulrich, Heinz; Packer, Lester

doi:10.1006/bbrc.1997.7711

Cited by 22 publications

(8 citation statements)

References 25 publications

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“…α-Lipoic acid (ALA) is a strong antioxidant, and has both a hydrophobic and a hydrophilic part ( Figure 2 ). ALA has a partition coefficient of approximately 4/1 ( o / w ) [ 10 ], meaning that ALA, unlike other antioxidants, is soluble in both aqueous and non-aqueous media. ALA has a relatively weak affinity for CDs [ 11 ], so it is difficult to accurately analyze the spectral changes using UV or FT-IR spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Studies of R(+)-α-Lipoic Acid—Cyclodextrin Complexes

Ikuta

Otsubo

Ogawa

et al. 2014

IJMS

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α-Lipoic acid (ALA) has a chiral center at the C6 position, and exists as two enantiomers, R(+)-ALA (RALA) and S(−)-ALA (SALA). RALA is naturally occurring, and is a cofactor for mitochondrial enzymes, therefore playing a major role in energy metabolism. However, RALA cannot be used for pharmaceuticals or nutraceuticals because it readily polymerizes via a 1,2-dithiolane ring-opening when exposed to light or heat. So, it is highly desired to find out the method to stabilize RALA. The purpose of this study is to provide the spectroscopic information of stabilized RALA and SALA through complexation with cyclodextrins (CDs), α-CD, β-CD and γ-CD and to examine the physical characteristics of the resultant complexes in the solid state. The RALA-CD structures were elucidated based on the micro fourier transform infrared (FT-IR) and Raman analyses. The FT-IR results showed that the C=O stretching vibration of RALA appeared at 1717 cm−1 and then shifted on formation of the RALA-CD complexes. The Raman spectra showed that the S–S and C–S stretching vibrations for RALA at 511 cm−1 (S–S), 631 cm−1 (C–S) and 675 cm−1 (C–S) drastically weakened and almost disappeared upon complexation with CDs. Several peaks indicative of O–H vibrations also shifted or changed in intensity. These results indicate that RALA and CDs form host-guest complexes by interacting with one another.

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Section: Introductionmentioning

confidence: 99%

Spectroscopic Studies of R(+)-α-Lipoic Acid—Cyclodextrin Complexes

Ikuta

Otsubo

Ogawa

et al. 2014

IJMS

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“…Dihydro-RALA reduces glutathione, which is an important antioxidant for many physiological processes, plays an essential role in detoxification of xenobiotics and is needed for signal transduction. As an amphiphilic molecule, RALA has a partition coefficient of approximately 4/1 (o/w) [3], meaning that RALA, unlike other antioxidants, is soluble in both aqueous and non-aqueous media. These qualities make RALA a central player in the antioxidant network, which is why ALA is used as a treatment for age-associated diseases, such as diabetes and neurodegenerative diseases [4–6].…”

Section: Introductionmentioning

confidence: 99%

Analysis of the Enhanced Stability of R(+)-Alpha Lipoic Acid by the Complex Formation with Cyclodextrins

Ikuta

Sugiyama

Shimosegawa³

et al. 2013

IJMS

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R(+)-alpha lipoic acid (RALA) is one of the cofactors for mitochondrial enzymes and, therefore, plays a central role in energy metabolism. RALA is unstable when exposed to low pH or heat, and therefore, it is difficult to use enantiopure RALA as a pharma- and nutra-ceutical. In this study, we have aimed to stabilize RALA through complex formation with cyclodextrins (CDs). α-CD, β-CD and γ-CD were used for the formation of these RALA-CD complexes. We confirmed the complex formation using differential scanning calorimetry and showed by using HPLC analysis that complexed RALA is more stable than free RALA when subjected to humidity and high temperature or acidic pH conditions. Scanning electron microscopy studies showed that the particle size and shape differed depending on the cyclodextrin used for complexation. Further, the complexes of CD and RALA showed a different particle size distribution pattern compared with that of CD itself or that of the physical mixture of RALA and CD.

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“…However, lipoic acid is also considered beneficial when mused as a food supplement as its antioxidant function has been previously reported and several studies have revealed its protective effects in cases such as aging, diabetes mellitus, and vascular and neurodegenerative diseases all in which free radicals are involved [19–23]. Studies are generally dealing with the biological consequences of lipoic acid administration in cases associated with oxidative stress or the differences between the antioxidant activities of lipoic acid and its derivatives [19, 22, 24, 25]. Data on the efficacy and biological activity of α -lipoic acid on malathion intoxication are not available.…”

Section: Introductionmentioning

confidence: 99%

Physiological and Histopathological Investigations on the Effects of-Lipoic Acid in Rats Exposed to Malathion

Al-Attar¹

2010

Journal of Biomedicine and Biotechnology

43
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29
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The present study was designed to evaluate the influence of α-lipoic acid treatment in rats exposed to malathion. Forty adult male rats were used in this study and distributed into four groups. Animals of group 1 were untreated and served as control. Rats of group 2 were orally given malathion at a dose level of 100 mg/kg body weight (BW) for a period of one month. Experimental animals of group 3 were orally given α-lipoic acid at a dose level of 20 mg/kg BW and after 3 hours exposed to malathion at the same dose given to group 2. Rats of group 4 were supplemented with α-lipoic acid at the same dose given to group 3. The activities of serum glutamic oxaloacetic acid transaminase (GOT), glutamic pyruvic acid transaminase (GPT), alkaline phosphatase (ALP), and acid phosphatase (ACP), and the values of creatinine, urea, and uric acid were statistically increased, while the values of total protein and total albumin were significantly decreased in rats exposed to malathion. Moreover, administration of malathion for one month resulted in damage of liver and kidney structures. Administration of α-lipoic acid before malathion exposure to rat can prevent severe alterations of hematobiochemical parameters and disruptions of liver and kidney structures. In conclusion, this study obviously demonstrated that pretreatment with α-lipoic acid significantly attenuated the physiological and histopathological alterations induced by malathion. Also, the present study identifies new areas of research for development of better therapeutic agents for liver, kidney, and other organs' dysfunctions and diseases.

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The Lipoic Acid Analogue 1,2-Diselenolane-3-pentanoic Acid Protects Human Low Density Lipoprotein against Oxidative Modification Mediated by Copper Ion

Cited by 22 publications

References 25 publications

Spectroscopic Studies of R(+)-α-Lipoic Acid—Cyclodextrin Complexes

Spectroscopic Studies of R(+)-α-Lipoic Acid—Cyclodextrin Complexes

Analysis of the Enhanced Stability of R(+)-Alpha Lipoic Acid by the Complex Formation with Cyclodextrins

Physiological and Histopathological Investigations on the Effects of-Lipoic Acid in Rats Exposed to Malathion

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