Interconversion of bilayer phase transition temperatures between phosphatidylethanolamines and phosphatidylcholines

Huang, Chunbo; Wang, Zhaoqing; Huo, Lin; Brumbaugh, Erich E.; Li, Shusen

doi:10.1016/0005-2736(94)90273-9

Cited by 36 publications

(33 citation statements)

References 11 publications

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“…In contrast, the chain-end perturbation or ⌬C value of C(22):C(18:1⌬ 13 )PC is smaller than that of C(22):C(17)PC (6.3 versus 6.5). Interestingly, the T m value of the monoenoic lipid is remarkably smaller than the saturated one (16.3°C versus 53.2°C).…”

Section: The Effect Of the Sn-2 Acyl Chain Length On The Phase Transimentioning

confidence: 77%

“…For example, the T m value of the C(22):C(18)PC bilayer is 58.6°C (13), whereas that of the C(22):C(18:1⌬ 13 )PC bilayer is 16.3°C (Table I). Before we offer an answer to this intriguing question, we need to first identify what structural modifications take place in the cis-monounsaturated phosphatidylcholines in comparison with the saturated counterparts and to consider the difference in T m in relation to the structural differences.…”

Section: The Effect Of the Sn-2 Acyl Chain Length On The Phase Transimentioning

confidence: 99%

“…Based on the calorimetric results obtained with 50 molecular species of saturated mixed-chain phosphatidylcholines, it has been demonstrated that the two structural parameters, N and ⌬C, for a given type of saturated mixed-chain phosphatidylcholine molecules packed in the gel-state bilayer can be correlated with the T m value of the lipid bilayer (13,14). Specifically, the T m values are related to N and ⌬C as follows (14): T m ϭ a 0 Ϫ a 1 (1/N) Ϫ a 2 (⌬C/N), where the first term (a 0 ) in the right-hand side of the equation corresponds to the extrapolated maximal T m value, which can be obtained with a lipid bilayer containing an infinitely large value of N; the second term with a negative sign indicates that the T m value of a bilayer increases with increasing values of N; the last term, also with a negative sign, is regarded as the chain-end perturbation term, expressed as a normalized ⌬C value, which shows that the larger the chainend perturbation, the smaller the T m and that the perturbation becomes insignificant as N Ͼ Ͼ ⌬C.…”

Section: The Effect Of the Sn-2 Acyl Chain Length On The Phase Transimentioning

confidence: 99%

“…When a cis ⌬-bond is incorporated into the sn-2 acyl chain of C(22):C(18)PC at C (13), the N value of the gel-state bilayer of C(22):C(18:1⌬ 13 )PC, 38.7 C-C bond lengths, is reduced by 0.8 C-C bond lengths; hence, it is slightly longer than the N value (38.5) of C(22):C(17)PC. In contrast, the chain-end perturbation or ⌬C value of C(22):C(18:1⌬ 13 )PC is smaller than that of C(22):C(17)PC (6.3 versus 6.5).…”

Section: The Effect Of the Sn-2 Acyl Chain Length On The Phase Transimentioning

confidence: 99%

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Phosphatidylcholines with sn-−1 Saturated and sn-−2 cis-Monounsaturated Acyl Chains

Wang

Huo

et al. 1995

Journal of Biological Chemistry

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Recently, we have shown by high resolution differential scanning calorimetry that the position of a cis double bond (⌬-bond) in a series of 1-stearoyl-2-octadecenoyl-phosphatidylcholines can affect the phase transition temperature (T m ) or enthalpy (⌬H) of the gelto-liquid crystalline phase transition of this series of lipids in the following manner. The value of T m (or ⌬H) is minimal when the ⌬-bond is positioned at C(11) in the sn-2 acyl chain; in addition, this value increases steadily as the ⌬-bond migrates toward either end of the acyl chain, resulting in a symmetrical, inverted bell-shaped profile (Wang, Z.-q., Lin, H.-n., Li, S., and Huang, C. (1995) J. Biol. Chem. 270, 2014 -2023). In this communication, we have further demonstrated the inverted bell-shaped profile of T m using 1-arachidoyl-2-eicosenoyl-phosphatidylcholines. In addition, we have extended the lipid series of 1-stearoyl-2-octadecenoyl-phosphatidylcholines to include 1-arachidoyl-2-octadecenoyl-phosphatidylcholines and 1-behenoyl-2-octadecenoyl-phosphatidylcholine, each series with a ⌬-bond at varying carbon position of 6, 7, 9, 11, 12, and 13. Calorimetric results obtained with these three series of lipids indicate that the inverted bell-shaped curve shifts toward higher temperatures in a nonuniform manner as the saturated sn-1 acyl chain length increases from 17 to 19 and then to 21 C-C bond lengths. Specifically, the T m (or ⌬H) values are nearly identical for these cis-monoenoic lipids when their ⌬-bonds are positioned at C(13). Based on the height of the rotational energy barrier obtained with molecular mechanics calculations, it is evident that the rotational flexibility of the single C-C bond adjacent to the ⌬-bond in 1-stearoyl-2-octadecenoyl-phosphatidylcholine increases as the ⌬-bond migrates from C(9) to C(13). The differential scanning calorimetry results obtained with the three series of lipids can thus be attributed to an increase in the rotational flexibility of the short chain segment succeeding the C(14) atom in the sn-2 octadecenoyl chain. In this communication, we also propose that in the gel-state bilayer of sn-1 saturated/ sn-2 cis-monounsaturated phosphatidylcholine the entire length of the shorter segment of the sn-2 acyl chain acts as a structural perturbing element; hence, it is mainly responsible for the large lower T m of the monoenoic lipid relative to the saturated counterpart. Finally, two general equations relating T m with the structural parameters of cis-monoenoic phosphatidylcholines are presented. These equations, formulated primarily on the assumption that the short segment of the sn-2 acyl chain acts as a perturbing element, are shown to have strong predictive power in estimating the T m values of the gel-to-liquid crystalline phase transitions for sn-1 saturated/sn-2 cis-monounsaturated phosphatidylcholines.Phosphatidylcholines isolated from the plasma membrane of eukaryotic cells are a structurally diverse group of phospholipids. The bewildering variety of membrane phosphatidylcholines originates fro...

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Section: The Effect Of the Sn-2 Acyl Chain Length On The Phase Transimentioning

confidence: 77%

Section: The Effect Of the Sn-2 Acyl Chain Length On The Phase Transimentioning

confidence: 99%

Section: The Effect Of the Sn-2 Acyl Chain Length On The Phase Transimentioning

confidence: 99%

Section: The Effect Of the Sn-2 Acyl Chain Length On The Phase Transimentioning

confidence: 99%

See 2 more Smart Citations

Phosphatidylcholines with sn-−1 Saturated and sn-−2 cis-Monounsaturated Acyl Chains

Wang

Huo

et al. 1995

Journal of Biological Chemistry

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“…Each lipid has its specific transition temperature at which the acyl chains undergo dramatic conformational change [27]. So, in bilayers at neutral pH, DPPC, DPPS, and DPPE have shown a phasetransition temperature of, respectively, 41.4°C, 53°C, and 63°C while SOPC monounsaturated glycerophospholipids have shown a transition temperature of 5.6°C [28][29][30][31]. In addition, it has been demonstrated that PEG increases the phase-transition temperature of glycerophospholipids, possibly by changing the solvation property of water [32][33][34].…”

Section: Discussionmentioning

confidence: 99%

Polyethylene glycols interact with membrane glycerophospholipids: is this part of their mechanism for hypothermic graft protection?

et al. 2009

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Polyethylene glycol (PEG), a high-molecularweight colloid present in new organ preservation solutions, protects against cold ischemia injuries leading to better graft function of transplanted organs. This protective effect cannot be totally explained by immuno-camouflaging property or signaling-pathway modifications. Therefore, we sought for an alternative mechanism dependent on membrane fluidity. Using the Langmuir-Pockles technique, we show here that PEGs interacted with lipid monolayers of defined composition or constituted by a renal cell lipid extract. High-molecular-weight PEGs stabilized the lipid monolayer at low surface pressure. Paradoxically, at high surface pressure, PEGs destabilized the monolayers. Hypothermia reduced the destabilization of saturated monolayer whereas unsaturated monolayer remained unaffected. Modification of ionic strength and pH induced a stronger stabilizing effect of PEG 35,000 Da which could explain its reported higher effectiveness on cold-induced injuries during organ transplantation. This study sheds a new light on PEG protective effects during organ preservation different from all classical hypotheses.

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Thylakoid Ultrastructure: Visualizing the Photosynthetic Machinery

Steinbeck

O’Mara

Ross

et al. 2017

Chlamydomonas: Biotechnology and Biomedicine

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Interconversion of bilayer phase transition temperatures between phosphatidylethanolamines and phosphatidylcholines

Cited by 36 publications

References 11 publications

Phosphatidylcholines with sn-−1 Saturated and sn-−2 cis-Monounsaturated Acyl Chains

Phosphatidylcholines with sn-−1 Saturated and sn-−2 cis-Monounsaturated Acyl Chains

Polyethylene glycols interact with membrane glycerophospholipids: is this part of their mechanism for hypothermic graft protection?

Thylakoid Ultrastructure: Visualizing the Photosynthetic Machinery

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