214706-38-4Relevant academic research and scientific papers
Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation
Burstein, Sumner,Salmonsen, Rebecca
, p. 9644 - 9651 (2008)
A series of amide derivatives of long-chain fatty acids has been studied for their effects on the proliferation of cancer cells in vitro. Fatty acids ranged from palmitic to higher polyunsaturated types containing 22 carbon atoms. The amino portions of the molecules included ammonia, ethanolamine, various amino acids and dopamine. Several cell lines were used as models and these included HTB-125 (normal human breast cells), HTB-126 (human breast cancer cells), HeLa (cervical cancer cells), WI-38 (human embryonic lung cells), RAW264.7 (mouse macrophage tumor cells) and RBL-2H3 (rat basophilic leukemia cells). The HTB lines were obtained from the same donor, so, could be considered a matched pair, that is, normal control versus cancer cells and thus, provide a model for testing specificity of action for the acylamido analogs. While many compounds were efficacious in inhibiting the proliferation of various cell lines, only two analogs showed a high degree of specificity in the matched HTB cell lines. N-palmitoyl dopamine and N-palmitoyl tyrosine each demonstrated complete specificity of action at a concentration of 10 μM and were highly efficacious in both cases. No clear structure-activity pattern could be derived from these studies since the intensity of the inhibitory action seemed to depend on three factors, namely, the fatty acid, the amine group and the cell type.
In search of bioinspired hydrogels from amphiphilic peptides: A template for nanoparticle stabilization for the sustained release of anticancer drugs
Mehra, Radha Rani,Tiwari, Priyanka,Basu, Anindya,Duttkonar, Anita
, p. 11666 - 11678 (2019/07/31)
The development of potent stimuli-responsive hydrogels has rapidly expanded in the last decades due to their diversified applications in the field of biomedicines. In accordance with this drift, herein, we aimed at modulating a series of amphiphilic peptide analogues with the general formula Me-(CH2)14-CO-NH-CH(X)-COOH, where X = CH2Ph in hydrogelators I (l-Phe) and II (d-Phe) and X = CH2Ph(OH) in hydrogelator III (l-Tyr), which displayed an excellent propensity to immobilize water at room temperature with a minimum gelation concentration of 0.04%/0.05%/0.02% w/v for hydrogelators I-III, respectively, regardless of their configuration at the C-terminal centre. To validate this threshold concentration difference, we performed computational analysis that demonstrated the ability of the side-chains of hydrogelators I and III to remain highly planar with the methylene units of the amphiphile and aromatic rings, promoting favourable correspondence through van der Waals forces and pi-pi stacking. Consequently hydrogelators I and III self-assembled in an ordered organisation superior to hydrogelator II. Furthermore, the spectroscopic and microscopic experiments revealed that the hydrogelators manifested a β-sheet conformation and nanofibrous morphology at the supramolecular level. As observed visually and additionally confirmed by differential scanning calorimetry (DSC) and rheological measurements, the hydrogels exhibited thermo-reversibility, injectability and high mechanical strength. Importantly, these biomaterials were also found to be resistant towards proteolytic degradation and non-cytotoxic in the cell line HEK 293 using a dose-dependant cell viability assay. To date, the development of a structured approach for the release of drugs in a predictable manner from an optimised formulation, using peptide-based hydrogel nanoparticles as a delivery system remains in its infancy. Hence, we developed hydrogel nanoparticles (HNPs) with our fabricated amphiphilic peptides that exploited the weak noncovalent interactions for their fabrication, unlike other cross-linked polymers that require strong covalent or ionic bonds for their formation. Interestingly, the as-synthesized nanoparticles showed an unprecedented ability to release the anticancer drugs 5-fluoro uracil/doxorubicin at physiological conditions depending on the physico-chemical parameters of the drugs. We believe that the reported injectable, biocompatible, amphiphilic peptide-based hydrogels hold future promise as a potential tool to transport drugs to a targeted site at a greater concentration, thus relieving the patient from surgical injury and simultaneously aiding in a faster recovery.
Synthesis, physicochemical, and biological activities of novel N-acyl tyrosine monomeric and Gemini surfactants in single and SDS/CTAB–mixed micellar system
Joondan, Nausheen,Jhaumeer-Laulloo, Sabina,Caumul, Prakashanand,Akerman, Matthew
, (2017/09/19)
A series of single-chained N-acyl tyrosine surfactants with varying chain lengths (C10-C18) and degree of unsaturation, as well as an N-acyl Gemini tyrosine surfactant with chain length C12, were synthesized, and the struc
Multi-stimuli responsive self-healing metallo-hydrogels: Tuning of the gel recovery property
Basak, Shibaji,Nanda, Jayanta,Banerjee, Arindam
supporting information, p. 2356 - 2359 (2014/03/21)
A series of amphiphilic tyrosine based self-healable, multi-stimuli responsive metallo-hydrogels have been discovered. Formation of these hydrogels is highly selective to Ni2+ ions. The self-healing property and the stiffness of these metallo-hydrogels can be tuned by varying the chain length of the corresponding gelator amphiphile. The Royal Society of Chemistry 2014.
NOVEL COMPOUND ACCELERATING SECRETION OF HUMAN-DERIVED ANTI-MICROBIAL PEPTIDE, METHOD FOR PREPARING SAME, AND COMPOSITION HAVING SAME AS ACTIVE INGREDIENT
-
Paragraph 0076-0080, (2013/07/31)
The present invention relates to a novel compound having an acceleration effect on the secretion of human β -defensin, LL-37, which is a human-derived anti-microbial peptide, a method for preparing same, and a composition for accelerating the secretion of
NOVEL COMPOUND ACCELERATING SECRETION OF HUMAN-DERIVED ANTI-MICROBIAL PEPTIDE, METHOD FOR PREPARING SAME, AND COMPOSITION HAVING SAME AS ACTIVE INGREDIENT
-
Page/Page column 0061; 0062; 0063, (2013/07/31)
Disclosed is a compound having an acceleration effect on the secretion of human β-defensin, LL-37, which is a human-derived anti-microbial peptide, a method for preparing same, and a composition for accelerating the secretion of anti-microbial peptide hav
Synthesis and structure-activity relationships of tyrosine-based inhibitors of autotaxin (ATX)
East, James E.,Kennedy, Andrew J.,Tomsig, Jose L.,De Leon, Alexandra R.,Lynch, Kevin R.,MacDonald, Timothy L.
supporting information; experimental part, p. 7132 - 7136 (2010/12/25)
Autotaxin (ATX) is a secreted soluble enzyme that generates lysophosphatidic acid (LPA) through its lysophospholipase D activity. Because of LPA's role in neoplastic diseases, ATX is an attractive therapeutic target due to its involvement in LPA biosynthe
Synthesis and biological evaluation of phosphonate derivatives as autotaxin (ATX) inhibitors
Cui, Peng,Tomsig, Jose L.,McCalmont, William F.,Lee, Sangderk,Becker, Christopher J.,Lynch, Kevin R.,Macdonald, Timothy L.
, p. 1634 - 1640 (2007/10/03)
Autotaxin (ATX) is an autocrine motility factor that promotes cancer cell invasion, cell migration, and angiogenesis. ATX, originally discovered as a nucleotide phosphodiesterase, is known now to be responsible for the lysophospholipid-preferring phosphol
Initial structure-activity relationships of lysophosphatidic acid receptor antagonists: Discovery of a high-affinity LPA1/LPA3 receptor antagonist
Heasley, Brian H.,Jarosz, Renata,Lynch, Kevin R.,Macdonald, Timothy L.
, p. 2735 - 2740 (2007/10/03)
A recently reported dual LPA1/LPA3 receptor antagonist (VPC12249, 1) has been modified herein so as to optimize potency and selectivity at LPA receptors. Compounds containing variation in the acyl lipid chain and linker region have been synthesized and screened for activity at individual LPA receptors. LPA1-selective (14b) and LPA 3-selective (10g,m) compounds of modest potency have been discovered. Additionally, 2-pyridyl derivative 10t exhibits a Ki value of 18nM at the LPA1 receptor and is significantly more potent than 1 at the LPA3 receptor. This paper describes the synthetic methods, biological evaluation, and structure-activity relationships (SARs) of LPA receptor antagonists.
