Fullerene–amino acid interactions. A theoretical study

León, Aned de; Jalbout, Abraham F.; Basiuk, Vladimir A.

doi:10.1016/j.cplett.2007.12.065

Cited by 51 publications

(29 citation statements)

References 37 publications

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“…The hydrophobic interaction between the Met181 residues and the fullerene surface is the main cause of the strong binding to the Na v Ab channel. In density functional calculations, the free energy of dissociation of methionine from a C 60 fullerene is −12.121 kcal/mol [47]. …”

Section: Resultsmentioning

confidence: 99%

Designing a C84 fullerene as a specific voltage-gated sodium channel blocker

Hilder

Chung

2013

Nanoscale Res Lett

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Fullerene derivatives demonstrate considerable potential for numerous biological applications, such as the effective inhibition of HIV protease. Recently, they were identified for their ability to indiscriminately block biological ion channels. A fullerene derivative which specifically blocks a particular ion channel could lead to a new set of drug leads for the treatment of various ion channel-related diseases. Here, we demonstrate their extraordinary potential by designing a fullerene which mimics some of the functions of μ-conotoxin, a peptide derived from cone snail venom which potently binds to the bacterial voltage-gated sodium channel (NavAb). We show, using molecular dynamics simulations, that the C84 fullerene with six lysine derivatives uniformly attached to its surface is selective to NavAb over a voltage-gated potassium channel (Kv1.3). The side chain of one of the lysine residues protrudes into the selectivity filter of the channel, while the methionine residues located just outside of the channel form hydrophobic contacts with the carbon atoms of the fullerene. The modified C84 fullerene strongly binds to the NavAb channel with an affinity of 46 nM but binds weakly to Kv1.3 with an affinity of 3 mM. This potent blocker of NavAb may serve as a structural template from which potent compounds can be designed for the targeting of mammalian Nav channels. There is a genuine need to target mammalian Nav channels as a form of treatment of various diseases which have been linked to their malfunction, such as epilepsy and chronic pain.

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Section: Resultsmentioning

confidence: 99%

Designing a C84 fullerene as a specific voltage-gated sodium channel blocker

Hilder

Chung

2013

Nanoscale Res Lett

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“…Table 1 presents the DR which is the off-center displacement of Li in the fullerene structure in Å , GAP AA which is the HOMO/LUMO band gap of the amino acids, GAP C60-AA that is the HOMO/LUMO band gap of the C 60 -amino acid complexes and finally DE is the dissociation energy. Also shown are the BLYP results reported for the fullereneamino acid complexes without an endohedral metal atom [32]. In the majority of the cases examined the Mulliken charge is around 0.92 as computed with our DFT methods.…”

Section: Methodsmentioning

confidence: 94%

Li@C60 complexes with amino acids: A theoretical analysis

Jalbout

2008

Journal of Organometallic Chemistry

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“…The reactivity of amino acids, for example, with SWNT species is directly related to several properties. In our group we have investigated the stability of amino acids with fullerenes [17], lithium encapsulated in fullerenes (or Li@C 60 ) [18], and the armchair (5,5) SWNT [19]. Such calculations reveal favorable interaction energies with the amino acids.…”

Section: Introductionmentioning

confidence: 99%

Endo[metallo] SWNT‐amino acid interactions: A theoretical study

Jalbout

2009

Int J of Quantum Chemistry

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ABSTRACT:We propose that an atom of calcium (Ca) which is an alkaline earth metal on encapsulation inside of a metallic armchair (5,5) (SWNT) species can have stronger amino acid interactions. From our calculations of various physical parameters we depict several configurations in which such an endo[metallo] SWNT can be modified by an internally placed Ca atom. Density functional theory (DFT) calculations reveal that the most favorable interactions of the SWNT system is with tryptophan, tyrosine, and phenylalanine that can be directly correlated to the backbone geometry of the amino acid species.

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Fullerene–amino acid interactions. A theoretical study

Cited by 51 publications

References 37 publications

Designing a C84 fullerene as a specific voltage-gated sodium channel blocker

Designing a C84 fullerene as a specific voltage-gated sodium channel blocker

Li@C60 complexes with amino acids: A theoretical analysis

Endo[metallo] SWNT‐amino acid interactions: A theoretical study

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