Glycyl-lysine
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| Category | Others |
| Catalog number | BBF-05674 |
| CAS | 997-62-6 |
| Molecular Weight | 203.24 |
| Molecular Formula | C8H17N3O3 |
| Purity | ≥95% |
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Description
Glycyl-lysine is a dipeptide composed of glycine and lysine. It is an incomplete breakdown product of protein digestion or protein catabolism.
Specification
| Related CAS | 31461-63-9 (hydrochloride) |
| Synonyms | glycyllysine; Gly-Lys; L-Lysine, glycyl-; L-Lysine, N2-glycyl-; Glycyl-L-lysine; N2-Glycyllysine; Nalpha-Glycyl-L-lysine; H-GK-OH; (S)-6-Amino-2-(2-amino-acetylamino)-hexanoic acid |
| Sequence | H-Gly-Lys-OH |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-6-amino-2-[(2-aminoacetyl)amino]hexanoic acid |
| Canonical SMILES | C(CCN)CC(C(=O)O)NC(=O)CN |
| InChI | InChI=1S/C8H17N3O3/c9-4-2-1-3-6(8(13)14)11-7(12)5-10/h6H,1-5,9-10H2,(H,11,12)(H,13,14)/t6-/m0/s1 |
| InChI Key | IKAIKUBBJHFNBZ-LURJTMIESA-N |
Properties
| Appearance | Solid |
| Boiling Point | 477.8°C at 760 mmHg |
| Density | 1.203 g/cm3 |
| Solubility | Soluble in DMSO, Water |
Reference Reading
1. Cellular Uptake and Distribution of Gemini Surfactant Nanoparticles Used as Gene Delivery Agents
Wei Jin, Mays Al-Dulaymi, Ildiko Badea, Scot C Leary, Jeveria Rehman, Anas El-Aneed AAPS J. 2019 Aug 6;21(5):98. doi: 10.1208/s12248-019-0367-1.
Gemini surfactants are promising molecules utilized as non-viral gene delivery vectors. However, little is known about their cellular uptake and distribution after they release their therapeutic cargo. Therefore, we quantitatively evaluated the cellular uptake and distribution of three gemini surfactants: unsubstituted (16-3-16), with pyridinium head groups (16(Py)-S-2-S-16(Py)) and substituted with a glycyl-lysine di-peptide (16-7N(GK)-16). We also assessed the relationship between cellular uptake and distribution of each gemini surfactant and its overall efficiency and toxicity. Epidermal keratinocytes PAM 212 were treated with gemini surfactant nanoparticles formulated with plasmid DNA and harvested at various time points to collect the enriched nuclear, mitochondrial, plasma membrane, and cytosolic fractions. Gemini surfactants were then extracted from each subcellular fraction and quantified using a validated flow injection analysis-tandem mass spectrometry (FIA-MS/MS) method. Mass spectrometry is superior to the use of fluorescent tags that alter the physicochemical properties and pharmacokinetics of the nanoparticles and can be cleaved from the gemini surfactant molecules within biological systems. Overall, a significantly higher cellular uptake was observed for 16-7N(GK)-16 (17.0%) compared with 16-3-6 (3.6%) and 16(Py)-S-2-S-16(Py) (1.4%), which explained the relatively higher transfection efficiency of 16-7N(GK)-16. Gemini surfactants 16-3-16 and 16(Py)-S-2-S-16(Py) displayed similar subcellular distribution patterns, with major accumulation in the nucleus, followed by the mitochondrion, cytosol, and plasma membrane. In contrast, 16-7N(GK)-16 was relatively evenly distributed across all four subcellular fractions. However, accumulation within the nucleus after 5 h of treatment was the highest for 16(Py)-S-2-S-16(Py) (50.3%), followed by 16-3-16 (41.8%) and then 16-7N(GK)-16 (33.4%), possibly leading to its relatively higher toxicity.
2. Gemini surfactant-based nanoparticles T-box1 gene delivery as a novel approach to promote epithelial stem cells differentiation and dental enamel formation
Fatemeh Mohabatpour, Mays Al-Dulaymi, Liubov Lobanova, Brittany Scutchings, Silvana Papagerakis, Ildiko Badea, Xiongbiao Chen, Petros Papagerakis Biomater Adv. 2022 Jun;137:212844. doi: 10.1016/j.bioadv.2022.212844. Epub 2022 May 9.
Enamel is the highest mineralized tissue in the body protecting teeth from external stimuli, infections, and injuries. Enamel lacks the ability to self-repair due to the absence of enamel-producing cells in the erupted teeth. Here, we reported a novel approach to promote enamel-like tissue formation via the delivery of a key ameloblast inducer, T-box1 gene, into a rat dental epithelial stem cell line, HAT-7, using non-viral gene delivery systems based on cationic lipids. We comparatively assessed the lipoplexes prepared from glycyl-lysine-modified gemini surfactants and commercially available 1,2-dioleoyl-3-trimethylammonium-propane lipids at three nitrogen-to phosphate (N/P) ratios of 2.5, 5 and 10. Our findings revealed that physico-chemical characteristics and biological activities of the gemini surfactant-based lipoplexes with a N/P ratio of 5 provide the most optimal outcomes among those examined. HAT-7 cells were transfected with T-box1 gene using the optimal formulation then cultured in conventional 2D cell culture systems. Ameloblast differentiation, mineralization, bio-enamel interface and structure were assessed at different time points over 28 days. Our results showed that our gemini transfection system provides superior gene expression compared to the benchmark agent, while keeping low cytotoxicity levels. T-box1-transfected HAT-7 cells strongly expressed markers of secretory and maturation stages of the ameloblasts, deposited minerals, and produced enamel-like crystals when compared to control cells. Taken together, our gemini surfactant-based T-box1 gene delivery system is effective to accelerate and guide ameloblastic differentiation of dental epithelial stem cells and promote enamel-like tissue formation. This study would represent a significant advance towards the tissue engineering and regeneration of dental enamel.
3. Mass Spectrometric Detection and Characterization of Metabolites of Gemini Surfactants Used as Gene Delivery Vectors
Wei Jin, Randy Purves, Ed Krol, Ildiko Badea, Anas El-Aneed J Am Soc Mass Spectrom. 2020 Feb 5;31(2):366-378. doi: 10.1021/jasms.9b00004. Epub 2020 Jan 10.
Gemini surfactants are a class of lipid molecules that have been successfully used in vitro and in vivo as nonviral gene delivery vectors. However, the biological fate of gemini surfactants has not been well investigated. In particular, the metabolism of gemini surfactants after they enter cells as gene delivery vehicles is unknown. In this work, we used a high-resolution quadrupole-Orbitrap mass spectrometry (Q-Exactive) instrument to detect the metabolites of three model gemini surfactants, namely, (a) unsubstituted (16-3-16), (b) with pyridinium head groups (16(Py)-S-2-S-16(Py)), and (c) substituted with a glycyl-lysine di-peptide (16-7N(GK)-16). The metabolites were characterized, and structures were proposed, based on accurate masses and characteristic product ions. The metabolism of the three gemini surfactants was very different as 16-3-16 was not metabolized in PAM 212 cells, whereas 16(Py)-S-2-S-16(Py) was metabolized primarily via phase I reactions, including oxidation and dealkylation, producing metabolites that could be linked to its observed high toxicity. The third gemini surfactant 16-7N(GK)-16 was metabolized mainly via phase II reactions, including methylation, acetylation, glucose conjugation, palmityl conjugation, and stearyl conjugation. The metabolism of gemini surfactants provides insight for future directions in the design and development of more effective gemini surfactants with lower toxicity. The reported approach can also be applied to study the metabolism of other structurally related gemini surfactants.
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