Helix stabilization of amphipathic peptides by hydrocarbon stapling increases cholesterol efflux by the ABCA1 transporter

Biochemical and Biophysical Research Communications

Volumn 410, Issue 3, 2011, Pages 446-451

  Sviridov, D O ^a   Ikpot, I Z ^a   Stonik, J ^a   Drake, S K ^b   Amar, M ^a   Osei Hwedieh, D O ^a   Piszczek, G ^a   Turner, S ^c   Remaley, A T ^a  

^a NATIONAL HEART LUNG AND BLOOD INSTITUTE   (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

^c KINEMED INC   (United States)

Author keywords

Apolipoproteins; Atherosclerosis; Cholesterol efflux; High density lipoproteins; Peptides

Indexed keywords

ABC TRANSPORTER A1; AMPHIPATHIC PEPTIDE; APOLIPOPROTEIN A1; BUFFER; HELIX LOOP HELIX PROTEIN; HYDROCARBON; PEPSIN A; PEPTIDE; S1A10 PEPTIDE; S2A10 PEPTIDE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL CELL; AQUEOUS SOLUTION; ARTICLE; CELL STRAIN BHK; CHOLESTEROL TRANSPORT; CIRCULAR DICHROISM; CONTROLLED STUDY; COVALENT BOND; HELIX STABILIZATION; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN FOLDING; PROTEIN METABOLISM; PROTEIN MODIFICATION; PROTEIN STABILITY; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; SOLID PHASE SYNTHESIS; TEMPERATURE;

APOLIPOPROTEIN A-I; ATP-BINDING CASSETTE TRANSPORTERS; BIOMIMETIC MATERIALS; CHOLESTEROL; HUMANS; HYDROCARBONS; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN CONFORMATION; PROTEIN STABILITY; PROTEIN STRUCTURE, SECONDARY;

EID: 79960067062     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2011.05.154     Document Type: Article

References (33)

1. Osei-Hwedieh D.O., Amar M., Sviridov D., et al. Apolipoprotein mimetic peptides: mechanisms of action as anti-atherogenic agents. Pharmacol. Ther. 2011, 130:83-91.
2. Remaley A.T., Thomas F., Stonik J.A., et al. Synthetic amphipathic helical peptides promote lipid efflux from cells by an ABCA1-dependent and an ABCA1-independent pathway. J. Lipid Res. 2003, 44:828-836.
3. Yao X., Dai C., Fredriksson K., et al. 5A, an apolipoprotein A-I mimetic peptide, attenuates the induction of house dust mite-induced asthma. J. Immunol. 2011, 186:576-583.
4. Watson C.E., Weissbach N., Kjems L., et al. Treatment of patients with cardiovascular disease with L-4F, an apo-A1 mimetic, did not improve select biomarkers of HDL function. J. Lipid Res. 2011, 52:361-373.
5. Navab M., Reddy S.T., Van Lenten B.J., et al. HDL and cardiovascular disease: atherogenic and atheroprotective mechanisms. Nat. Rev. Cardiol. 2011.
6. Wool G.D., Reardon C.A., Getz G.S. Apolipoprotein A-I mimetic peptide helix number and helix linker influence potentially anti-atherogenic properties. J. Lipid Res. 2008, 49:1268-1283.
7. Tardif J.C., Gregoire J., L'Allier P.L., et al. Effects of reconstituted high-density lipoprotein infusions on coronary atherosclerosis: a randomized controlled trial. JAMA 2007, 297:1675-1682.
8. Nissen S.E. Effect of intensive lipid lowering on progression of coronary atherosclerosis: evidence for an early benefit from the Reversal of Atherosclerosis with Aggressive Lipid Lowering (REVERSAL) trial. Am. J. Cardiol. 2005, 96:61F-68F.
9. Bloedon L.T., Dunbar R., Duffy D., et al. Safety, pharmacokinetics, and pharmacodynamics of oral apoA-I mimetic peptide D-4F in high-risk cardiovascular patients. J. Lipid Res. 2008, 49:1344-1352.
10. Buga G.M., Frank J.S., Mottino G.A., et al. D-4F decreases brain arteriole inflammation and improves cognitive performance in LDL receptor-null mice on a Western diet. J. Lipid Res. 2006, 47:2148-2160.
11. Yasuda T., Ishida T., Rader D.J. Update on the role of endothelial lipase in high-density lipoprotein metabolism, reverse cholesterol transport, and atherosclerosis. Circ. J. 2010, 74:2263-2270.
12. Yvan-Charvet L., Wang N., Tall A.R. Role of HDL, ABCA1, and ABCG1 transporters in cholesterol efflux and immune responses. Arterioscler. Thromb. Vasc. Biol. 2010, 30:139-143.
13. Khera A.V., Cuchel M., de la Llera-Moya M., et al. Cholesterol efflux capacity, high-density lipoprotein function, and atherosclerosis. N. Engl. J. Med. 2011, 364:127-135.
14. Lund-Katz S., Phillips M.C. High density lipoprotein structure-function and role in reverse cholesterol transport. Subcell. Biochem. 2010, 51:183-227.
15. Remaley A.T., Stonik J.A., Demosky S.J., et al. Apolipoprotein specificity for lipid efflux by the human ABCAI transporter. Biochem. Biophys. Res. Commun. 2001, 280:818-823.
16. D'Souza W., Stonik J.A., Murphy A., et al. Structure/function relationships of apolipoprotein a-I mimetic peptides: implications for antiatherogenic activities of high-density lipoprotein. Circ. Res. 2010, 107:217-227.
17. Frank P.G., Marcel Y.L. Apolipoprotein A-I: structure-function relationships. J. Lipid Res. 2000, 41:853-872.
18. Henchey L.K., Jochim A.L., Arora P.S. Contemporary strategies for the stabilization of peptides in the alpha-helical conformation. Curr. Opin. Chem. Biol. 2008, 12:692-697.
19. Kutchukian P.S., Yang J.S., Verdine G.L., et al. All-atom model for stabilization of alpha-helical structure in peptides by hydrocarbon staples. J. Am. Chem. Soc. 2009, 131:4622-4627.
20. Bhattacharya S., Zhang H., Debnath A.K., et al. Solution structure of a hydrocarbon stapled peptide inhibitor in complex with monomeric C-terminal domain of HIV-1 capsid. J. Biol. Chem. 2008, 283:16274-16278.
21. Panagotopulos S.E., Witting S.R., Horace E.M., et al. The role of apolipoprotein A-I helix 10 in apolipoprotein-mediated cholesterol efflux via the ATP-binding cassette transporter ABCA1. J. Biol. Chem. 2002, 277:39477-39484.
22. Schafmeister C.E., Po J., Verdine G.L. An all-hydrocarbon cross-linking system for enhancing the helicity and metabolic stability of peptides. J. Am. Chem. Soc. 2000, 122:5891-5892.
23. Amar M.J., D'Souza W., Turner S., et al. 5A apolipoprotein mimetic peptide promotes cholesterol efflux and reduces atherosclerosis in mice. J. Pharmacol. Exp. Ther. 2010, 334:634-641.
24. Segrest J.P., Garber D.W., Brouillette C.G., et al. The amphipathic alpha helix: a multifunctional structural motif in plasma apolipoproteins. Adv. Protein Chem. 1994, 45:303-369.
25. Remaley A.T., Amar M., Sviridov D. HDL-replacement therapy: mechanism of action, types of agents and potential clinical indications. Expert Rev. Cardiovasc. Ther. 2008, 6:1203-1215.
26. Sethi A.A., Stonik J.A., Thomas F., J S., et al. Asymmetry in the lipid affinity of bihelical amphipathic peptides. A structural determinant for the specificity of ABCA1-dependent cholesterol efflux by peptides. J. Biol. Chem. 2008, 283:32273-32282.
27. Mendez A.J., Anantharamaiah G.M., Segrest J.P., et al. Synthetic amphipathic helical peptides that mimic apolipoprotein A-I in clearing cellular cholesterol. J. Clin. Invest. 1994, 94:1698-1705.
28. Rothblat G.H., Phillips M.C. High-density lipoprotein heterogeneity and function in reverse cholesterol transport. Curr. Opin. Lipidol. 2010, 21:229-238.
29. Navab M., Ruchala P., Waring A.J., et al. A novel method for oral delivery of apolipoprotein mimetic peptides synthesized from all L-amino acids. J. Lipid Res. 2009, 50:1538-1547.
30. Sethi A.A., Amar M., Shamburek R.D., et al. Apolipoprotein AI mimetic peptides: possible new agents for the treatment of atherosclerosis. Curr. Opin. Invest. Drugs 2007, 8:201-212.
31. Bielicki J.K., Zhang H., Cortez Y., et al. A new HDL mimetic peptide that stimulates cellular cholesterol efflux with high efficiency greatly reduces atherosclerosis in mice. J. Lipid Res. 2010, 51:1496-1503.
32. Neufeld E.B., Stonik J.A., Demosky S.J., et al. The ABCA1 transporter modulates late endocytic trafficking: insights from the correction of the genetic defect in Tangier disease. J. Biol. Chem. 2004, 279:15571-15578.
33. Remaley A.T., Warnick G.R. High-density lipoprotein: what is the best way to measure its antiathrerogenic potential. Expert Opini. Med. Diagn. 2008, 2:773-788.