Synthesis of cardiolipin derivatives with protection of the free hydroxyl: Its application to the study of cardiolipin stimulation of cytochrome c oxidase

Marsha P. Dale, Neal C. Robinson

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

Cardiolipin derivatives retaining the free hydroxyl on the polar head group were synthesized. With the use of a tetrahydropyranyl ether to protect this hydroxyl, fatty acyl substitutions were made at both of the 2-positions of cardiolipin (CL). The disubstituted derivatives were obtained in high yields. The stimulation of delipidated cytochrome c oxidase activity shows a hyperbolic dependence on the concentration of these CL derivatives. Both activation parameters, the apparent dissociation constant (Kd,app) and the maximum change in molecular activity (ΔActmax), depend on the chain length of the tails, with less dependence on the degree of saturation. Natural CL (92% C18:2, 8% C18:1) and CL disubstituted with oleic acid (47% C18:2, 52% C18:1) were equally effective at stimulating cytochrome c oxidase activity, with an apparent dissociation constant of approximately 1 μM when incubated in 0.3% Triton X-100 and assayed in lauryl maltoside. CL disubstituted with hexanoic acid, however, is a poorer activator, with an apparent dissociation constant of 6.8 μM and a ΔActmax that is 50% of that achieved with natural CL. Dilysocardiolipin, with complete removal of two of the fatty acid tails, shows negligible stimulation of cytochrome c oxidase activity.

Original languageEnglish (US)
Pages (from-to)8270-8275
Number of pages6
JournalBiochemistry
Volume27
Issue number21
StatePublished - 1988

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Cardiolipins
Electron Transport Complex IV
Hydroxyl Radical
Derivatives
Octoxynol
Oleic Acid
Chain length
Application programs
Ether
Substitution reactions
Fatty Acids
Chemical activation

ASJC Scopus subject areas

  • Biochemistry

Cite this

Synthesis of cardiolipin derivatives with protection of the free hydroxyl : Its application to the study of cardiolipin stimulation of cytochrome c oxidase. / Dale, Marsha P.; Robinson, Neal C.

In: Biochemistry, Vol. 27, No. 21, 1988, p. 8270-8275.

Research output: Contribution to journalArticle

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abstract = "Cardiolipin derivatives retaining the free hydroxyl on the polar head group were synthesized. With the use of a tetrahydropyranyl ether to protect this hydroxyl, fatty acyl substitutions were made at both of the 2-positions of cardiolipin (CL). The disubstituted derivatives were obtained in high yields. The stimulation of delipidated cytochrome c oxidase activity shows a hyperbolic dependence on the concentration of these CL derivatives. Both activation parameters, the apparent dissociation constant (Kd,app) and the maximum change in molecular activity (ΔActmax), depend on the chain length of the tails, with less dependence on the degree of saturation. Natural CL (92{\%} C18:2, 8{\%} C18:1) and CL disubstituted with oleic acid (47{\%} C18:2, 52{\%} C18:1) were equally effective at stimulating cytochrome c oxidase activity, with an apparent dissociation constant of approximately 1 μM when incubated in 0.3{\%} Triton X-100 and assayed in lauryl maltoside. CL disubstituted with hexanoic acid, however, is a poorer activator, with an apparent dissociation constant of 6.8 μM and a ΔActmax that is 50{\%} of that achieved with natural CL. Dilysocardiolipin, with complete removal of two of the fatty acid tails, shows negligible stimulation of cytochrome c oxidase activity.",
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N2 - Cardiolipin derivatives retaining the free hydroxyl on the polar head group were synthesized. With the use of a tetrahydropyranyl ether to protect this hydroxyl, fatty acyl substitutions were made at both of the 2-positions of cardiolipin (CL). The disubstituted derivatives were obtained in high yields. The stimulation of delipidated cytochrome c oxidase activity shows a hyperbolic dependence on the concentration of these CL derivatives. Both activation parameters, the apparent dissociation constant (Kd,app) and the maximum change in molecular activity (ΔActmax), depend on the chain length of the tails, with less dependence on the degree of saturation. Natural CL (92% C18:2, 8% C18:1) and CL disubstituted with oleic acid (47% C18:2, 52% C18:1) were equally effective at stimulating cytochrome c oxidase activity, with an apparent dissociation constant of approximately 1 μM when incubated in 0.3% Triton X-100 and assayed in lauryl maltoside. CL disubstituted with hexanoic acid, however, is a poorer activator, with an apparent dissociation constant of 6.8 μM and a ΔActmax that is 50% of that achieved with natural CL. Dilysocardiolipin, with complete removal of two of the fatty acid tails, shows negligible stimulation of cytochrome c oxidase activity.

AB - Cardiolipin derivatives retaining the free hydroxyl on the polar head group were synthesized. With the use of a tetrahydropyranyl ether to protect this hydroxyl, fatty acyl substitutions were made at both of the 2-positions of cardiolipin (CL). The disubstituted derivatives were obtained in high yields. The stimulation of delipidated cytochrome c oxidase activity shows a hyperbolic dependence on the concentration of these CL derivatives. Both activation parameters, the apparent dissociation constant (Kd,app) and the maximum change in molecular activity (ΔActmax), depend on the chain length of the tails, with less dependence on the degree of saturation. Natural CL (92% C18:2, 8% C18:1) and CL disubstituted with oleic acid (47% C18:2, 52% C18:1) were equally effective at stimulating cytochrome c oxidase activity, with an apparent dissociation constant of approximately 1 μM when incubated in 0.3% Triton X-100 and assayed in lauryl maltoside. CL disubstituted with hexanoic acid, however, is a poorer activator, with an apparent dissociation constant of 6.8 μM and a ΔActmax that is 50% of that achieved with natural CL. Dilysocardiolipin, with complete removal of two of the fatty acid tails, shows negligible stimulation of cytochrome c oxidase activity.

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