Opioid peptide interactions with lipid bilayer membranes

Ramaswami, Varadarajan; Haaseth, Ronald C.; Matsunaga, Terry O.; Hruby, Victor J.; O’Brien, David F.

doi:10.1016/0005-2736(92)90083-x

Cited by 22 publications

(18 citation statements)

References 20 publications

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“…Large unilamellar vesicles (LUV) with diameter of 160 nm were obtained by extrusion of multilamellar lipid suspensions through Nuclepore polycarbonate membranes. As shown earlier by quasielastic light scattering (QELS) and supported by negative stain electron microscopy (5), predominantly unilamellar liposomes of uniform size and narrow polydispersity were formed by this extrusion method. The lipid mixture (20 mg) was hydrated in 1 mL buffer and vortexed extensively to form a homogeneous suspention.…”

Section: Preparation Of Liposomessupporting

confidence: 64%

“…The successful development of peptides as novel therapeutic agents requires potent biological activity as well as a means of effective delivery to the site of action. A large amount of work has been done to investigate the structure–activity relationships (1–4), but the corresponding structural factors that effect transport are less well understood (5–10). The nature of transport across cell membranes is a major question of importance to medicine, pharmacology, cell biology and biochemistry.…”

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confidence: 99%

“…Ramaswami et al . (5) examined the permeability of the potent opioid peptide C[ d ‐Pen 2 – d ‐Pen 5 ]enkephalin (DPDPE) and its acyclic analog. It was found that the acyclic peptide was six times more permeable than DPDPE.…”

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confidence: 99%

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Effect of peptide conformation on membrane permeability

Boguslavsky

Hruby

O’Brien

et al. 2003

The Journal of Peptide Research

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The effect of peptide conformational constraint on the peptide permeation across the model membranes was examined by determining the permeability of pairs of cyclic and acyclic peptides related to c[d-Pen2, d-Pen5] enkephalin (DPDPE). The peptides were cyclized by formation of an intramolecular disulfide bridge between the second and fifth residues composed of either d-penicillamine or cysteine. In each case the acyclic peptide was three to seven times more permeable than corresponding cyclic peptide. The possibility that the differences in permeability of cyclic and acyclic peptides is based on the greater conformational freedom of the acyclic peptides in the presence of membrane was examined in more detail by isothermal titration calorimetric studies of Trp6-DPDPE and its acyclic analog. The membrane binding of the acyclic peptide is a more exothermic process than binding of its cyclic Trp6-DPDPE. The transfer of acyclic peptide from water to membrane is an enthalpy driven process, whereas the transfer of the cyclic peptide is driven by entropy.

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Section: Preparation Of Liposomessupporting

confidence: 64%

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confidence: 99%

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Effect of peptide conformation on membrane permeability

Boguslavsky

Hruby

O’Brien

et al. 2003

The Journal of Peptide Research

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“…Já para os peptídeos cíclicos (análogos), essa interação com a membrana é um processo entropicamente guiado e controlado pela ressolvatação do peptídeo conformacionalmente restrito. 27 Os procedimentos de isolamento dos peptídeos vegetais são muito diferentes dos empregados para outras matrizes biológicas, pois a biomassa vegetal é complexa, composta por muitas outras classes de substâncias (pigmentos, açúcares, gorduras, taninos etc). Para Claeson et al existem três razões para se intensificarem estudos sobre procedimentos de extração e purificação de peptídeos de biomassa vegetal: as plantas acumulam peptídeos únicos e de reconhecido interesse farmacológico; usam peptídeos como moléculas sinalizadoras; as ferramentas da biologia molecular são disponíveis para manipulação desses compostos.…”

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Peptídeos cíclicos de biomassa vegetal: características, diversidade, biossíntese e atividades biológicas

Picchi¹,

Altei²,

Saito³

et al. 2009

Quím. Nova

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Recebido em 7/4/08; aceito em 23/9/08; publicado na web em 30/4/09 CYCLIC PEPTIDE FROM PLANT BIOMASS: CHEMICAL FEATURES AND DIVERSITY, BIOSYNTHESIS AND BIOLOGICAL ACTIVITIES. Natural peptides are outstanding as the most promising macromolecules in the search for new drugs, especially those of cyclic nature. The higher plants revealed a very peculiar composition of their cyclic peptides, which distinguish themselves by a "head-to-tail" cyclization. It is possible to define two groups of cyclic peptides from plant biomass. Those called in this review as Eucyclopeptides formed by 2-12 amino acid, and Cyclotides considered as circular polypeptides, composed of 29-37 amino acid that retain three disulfides bridges in an arrangement known as cyclic cystine knot. Searching for plant peptides should form into a subject for scientific research in the forefront of great importance for bioprospecting natural products macromolecular.Keywords: cyclic peptides; eucyclopeptides; cyclotides. INTRODUÇÃO"Para todos os alvos moleculares importantes no corpo humano existem compostos naturais em outras espécies e em mais de uma em especial". Com essa afirmação Tulp & Bohlin propõem um apropriado paradigma para a química de produtos naturais e para a farmacologia. 1 Esses autores reconhecem que a validade desta citação depende do conhecimento dos mecanismos e funções moleculares e da especificidade de cada receptor biológico, além da elucidação de todos os produtos naturais existentes. Embora a proposta possa parecer ousada, não encontrou muita resistência da comunidade científica. 2,3 Talvez o principal alicerce desse novo paradigma seja a similaridade genética entre as espécies. Nosso código genético armazena cerca de 30.000 genes, dos quais 289 foram relacionados à doenças humanas. Surpreendentemente, quase a metade desses genes (ligados à doenças) tem um correspondente em Arabidopsis thaliana (L.) Heynh. 4 Com as descobertas do código genético humano além de outros organismos e os últimos desenvolvimentos sobre o estudos "-oma" (genoma, transcriptoma, proteoma e metaboloma) e tudo que diz respeito às reações bioquímicas responsáveis pela complexidade celular, as substâncias proteicas tornaram-se objeto de pesquisa multidisciplinar envolvendo química e biologia, principalmente. Dessa forma, discute-se cada vez mais a aplicação das ferramentas da biologia molecular na química de produtos naturais, onde o escopo principal pode ser proteínas e peptídeos. 5 Acredita-se que na era pós-genômica a quimio-genômica será uma alternativa eficiente na busca de fármacos para o tratamento de doenças de origem gené-tica e também de medicamentos com ação direta em determinados receptores celulares.Nesse contexto, os peptídeos de origem natural destacam-se como macromoléculas promissoras na busca de novos fármacos, especialmente os de natureza cíclica. Nos últimos anos as descobertas de peptídeos bioativos cresceram de forma exponencial. Newmann et al. revelam que de um total de 868 de fármacos indicados para uso médico entre 1981-2001, apenas 91 ...

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“…The design and synthesis of peptides which preferentially assume biologically active conformations has produced ligands with high selectivity for the different classes of receptors (3)(4)(5). However, such a constrained water-soluble peptide, optimized in the sense of its interaction with receptor, has a relatively low lipid membrane permeability, thereby limiting its passive diffusion from the blood stream to the brain (9). This strategy led to c[D-Pen2, D-Pedlenkephalin (DPDPE), which is noted for its high potency and selectivity for opioid 6 receptors (4).…”

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confidence: 99%

Lipid membrane permeability of modified c[D‐Pen², D‐pen⁵]enkephalin peptides

Ramaswami

Zhu

Romanowski

et al. 1996

International Journal of Peptide and Protein Research

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Permeability coefficients of a series of analogues of a potent opioid peptide, c[D-Pen', ~-Pen']enkephalin, were measured in a model membrane system. The analogues included hydrophobic amino acid substitutions on position 3. Liposomes of a mixed composition consisting of zwitterionic lipids and cholesterol served as the model membranes. The obtained permeability coefficients range between 0.38 x lo-'' and 2.9 x lo-'' cm/s. These data were correlated with the hydrophobicity scale of Nozaki and Tanford (J. Biol. Chem. 246, 1971, 221 1-2217) (correlation coefficient=0.9933) and with determinations of lipid order perturbation by differential scanning calorimetry (correlation coefficient = -0.9779). The reasonably good correlation obtained within the family of analogues substituted on position 3 (Gly, Ala, Leu, Phe) indicates that changes in permeabilities are primarily related to increases in the partition coefficient of the peptide. However, Phe residue added on the N-terminal end of the peptide (position 0) does not appear to follow the observed trend, showing stronger lipid perturbation and lower permeability compared to the Phe3 analog. This observation demonstrates that each class of peptide modifications requires a new basis of permeability analysis and predictions. 0 Munksgaard 1996.

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Opioid peptide interactions with lipid bilayer membranes

Cited by 22 publications

References 20 publications

Effect of peptide conformation on membrane permeability

Effect of peptide conformation on membrane permeability

Peptídeos cíclicos de biomassa vegetal: características, diversidade, biossíntese e atividades biológicas

Lipid membrane permeability of modified c[D‐Pen², D‐pen⁵]enkephalin peptides

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Opioid peptide interactions with lipid bilayer membranes

Cited by 22 publications

References 20 publications

Effect of peptide conformation on membrane permeability

Effect of peptide conformation on membrane permeability

Peptídeos cíclicos de biomassa vegetal: características, diversidade, biossíntese e atividades biológicas

Lipid membrane permeability of modified c[D‐Pen2, D‐pen5]enkephalin peptides

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Lipid membrane permeability of modified c[D‐Pen², D‐pen⁵]enkephalin peptides