88932-69-8Relevant academic research and scientific papers
Remarkable shape-sustaining, load-bearing, and self-healing properties displayed by a supramolecular gel derived from a bis-pyridyl-bis-amide of L -phenyl alanine
Das, Uttam Kumar,Banerjee, Subhabrata,Dastidar, Parthasarathi
supporting information, p. 2475 - 2482 (2014/10/15)
A series of bis-amides decorated with pyridyl and phenyl moieties derived from L-amino acids having an innocent side chain (L-alanine and L-phenyl alanine) were synthesized as potential low-molecular-weight gelators (LMWGs). Both protic and aprotic solven
Hydrogelation through self-assembly of fmoc-peptide functionalized cationic amphiphiles: Potent antibacterial agent
Debnath, Sisir,Shome, Anshupriya,Das, Dibyendu,Das, Prasanta Kumar
experimental part, p. 4407 - 4415 (2010/09/04)
The present work reports a new class of antibacterial hydrogelators based on anti-inflammatory N-fluorenyl-9-methoxycarbonyl (Fmoc) amino acid/peptides functionalized cationic amphiphiles. These positively charged hydrogelators were rationally designed and developed by the incorporation of a pyridinium moiety at the C-terminal of Fmoc amino acid/peptides, because the pyridinium-based amphiphiles are a known antibacterial agent due to their cell membrane penetration properties. The Fmoc amino acid/peptide-based cationic amphiphiles efficiently gelate (minimum gelation concentration ～0.6-2.2%, w/v) water at room temperature. Judicious variation of amino acid and their sequences revealed the architectural dependence of the molecules on their gelation ability. Several microscopic techniques like field-emission scanning electron microscopy (FESEM) and atomic force microscopy (AFM) were used to obtain the visual insight of the morphology of the gel network. A number of spectroscopic techniques like circular dichroism, FTIR, photoluminescence, and XRD were utilized to know the involvement of several noncovalent interactions and participation of the different segments of the molecules during gelation. Spectroscopic results showed that the - Interaction and intermolecular hydrogen bonding are the major responsible factors for the self-assembled gelation process that are oriented through an antiparallel β-sheet arrangement of the peptide backbone. These Fmoc-based cationic molecules exhibited efficient antibacterial activity against both Gram-positive and Gram-negative bacteria.
Development of potent bifunctional endomorphin-2 analogues with mixed μ-/δ-opioid agonist and δ-opioid antagonist properties
Fujita, Yoshio,Tsuda, Yuko,Li, Tingyou,Motoyama, Takashi,Takahashi, Motohiro,Shimizu, Yoshiro,Yokoi, Toshio,Sasaki, Yusuke,Ambo, Akihiro,Kita, Atsuko,Jinsmaa, Yunden,Bryant, Sharon D.,Lazarus, Lawrence H.,Okada, Yoshio
, p. 3591 - 3599 (2007/10/03)
The C terminus of endomorphin-2 (EM-2) analogues (Tyr-Pro-Phe-NH-X) was modified with aromatic, heteroaromatic, or aliphatic groups (X = phenethyl,benzyl, phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, tert-butyl, cyclohexyl, or adamantyl; 3-18) to study their effect on opioid activity. Only 9 (1-naphthyl), 11 (5-quinolyl), 16 (cyclohexyl), and 18 (2-adamantyl) exhibited μ-opioid receptor affinity in the nanomolar range (Ki = 2.41-6.59 nM), which, however, was 3-to 10-fold less than the parent peptide. Replacement of Tyr1 by Dmt (2′,6′-dimethyl-L-tyrosine) (19-32) exerted profound effects: (i) acquisition of high μ-opioid receptor affinity (Ki = 0.11-0.52 nM) except 23 (Ph); (ii) presence of potent functional μ-opioid receptor agonism (IC50 1]EM-2), 27 (1-naphthyl), 29 (5-quinolyl), and 32 (5-isolquinolyl); (iii) association of weak δ-opioid antagonist activity (pA2 = 5.41-7.18) except 19 ([Dmt1]EM-2), 20 (H), 27 (1-naphthyl), and in particular 29 (5-quinolyl) with its potent δ-agonism (IC50 = 0.62 nM, pA2 = 5.88); (iv) production of antinociception after ic administration of 32 (5-isoquinolyl) in mice, a bioactivity absent in the corresponding Tyr1 analogue (14); and (v) preferential cis orientation (cis/trans = 3:2 to 7:3) at the Dmt-Pro amide bond, in contrast to the Tyr-Pro amide trans orientation (cis/trans = 1:2 to 1:3). Thus, [Dmt1]EM-2 analogues with hydrophobic C-terminal extensions provide model compounds with potent μ-opioid receptor bioactivity and dual functional agonism.
Synthesis of Pyridine Derivatives of L-Phenylalanine as Antisickling Reagents
Altman, Janina,Gorecki, Marian,Wilchek, Meir,Votano, Joseph R.,Rich, Alexander
, p. 596 - 600 (2007/10/02)
Several bicyclic agents composed of L-phenylalanine coupled to various pyridines were synthesized: 2-, 3-, and 4-(L-phenylalanylamino)pyridine.All three compounds at 3 mM gave positive morphological antisickling effects on homozygous SS cells under reduce
