Nε-Z-D-lysine benzyl ester hydrochloride
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Nε-Z-D-lysine benzyl ester hydrochloride

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Category
CBZ-Amino Acids
Catalog number
BAT-003268
CAS number
156917-23-6
Molecular Formula
C21H26N2O4·HCl
Molecular Weight
406.90
Nε-Z-D-lysine benzyl ester hydrochloride
IUPAC Name
benzyl (2R)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate;hydrochloride
Synonyms
D-Lys(Z)-OBzl HCl
Appearance
White solid
Purity
≥ 99% (TLC)
Storage
Store at 2-8 °C
InChI
InChI=1S/C21H26N2O4.ClH/c22-19(20(24)26-15-17-9-3-1-4-10-17)13-7-8-14-23-21(25)27-16-18-11-5-2-6-12-18;/h1-6,9-12,19H,7-8,13-16,22H2,(H,23,25);1H/t19-;/m1./s1
InChI Key
XHBTZNKKLKICJY-FSRHSHDFSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)C(CCCCNC(=O)OCC2=CC=CC=C2)N.Cl
1. Accumulation of porphyrins in Propionibacterium acnes by 5-aminolevulinic acid and its esters
Arisa Ogata, Yuya Hasunuma, Emii Kikuchi, Takuya Ishii, Masahiro Ishizuka, Yoshikazu Tokuoka Photodiagnosis Photodyn Ther. 2017 Sep;19:167-169. doi: 10.1016/j.pdpdt.2017.06.004. Epub 2017 Jun 15.
We have investigated the accumulation of porphyrins in Propionibacterium acnes (P.acnes) by 5-aminolevulinic acid hydrochloride (ALA) and its esters, ALA methyl ester hydrochloride (mALA), ALA octyl ester hydrochloride (oALA), and ALA benzyl ester hydrochloride (bALA). From the fluorescence spectra of porphyrins accumulated in P.acnes, the order of porphyrin accumulation is as follows: ALA≫mALA≈bALA>oALA (≈0). Moreover, the PDT efficacy is reduced in the order of ALA>mALA≈bALA>oALA (≈without additives). These results confirm that ALA is superior to ALA esters in accumulating porphyrins in P.acnes.
2. New 2-[(4-Amino-6- N-substituted-1,3,5-triazin-2-yl)methylthio]- N-(imidazolidin-2-ylidene)-4-chloro-5-methylbenzenesulfonamide Derivatives, Design, Synthesis and Anticancer Evaluation
Łukasz Tomorowicz, Beata Żołnowska, Krzysztof Szafrański, Jarosław Chojnacki, Ryszard Konopiński, Ewa A Grzybowska, Jarosław Sławiński, Anna Kawiak Int J Mol Sci. 2022 Jun 28;23(13):7178. doi: 10.3390/ijms23137178.
In the search for new compounds with antitumor activity, new potential anticancer agents were designed as molecular hybrids containing the structures of a triazine ring and a sulfonamide fragment. Applying the synthesis in solution, a base of new sulfonamide derivatives 20-162 was obtained by the reaction of the corresponding esters 11-19 with appropriate biguanide hydrochlorides. The structures of the compounds were confirmed by spectroscopy (IR, NMR), mass spectrometry (HRMS or MALDI-TOF/TOF), elemental analysis (C,H,N) and X-ray crystallography. The cytotoxic activity of the obtained compounds toward three tumor cell lines, HCT-116, MCF-7 and HeLa, was examined. The results showed that some of the most active compounds belonged to the R1 = 4-trifluoromethylbenzyl and R1 = 3,5-bis(trifluoromethyl)benzyl series and exhibited IC50 values ranging from 3.6 µM to 11.0 µM. The SAR relationships were described, indicating the key role of the R2 = 4-phenylpiperazin-1-yl substituent for the cytotoxic activity against the HCT-116 and MCF-7 lines. The studies regarding the mechanism of action of the active compounds included the assessment of the inhibition of MDM2-p53 interactions, cell cycle analysis and apoptosis induction examination. The results indicated that the studied compounds did not inhibit MDM2-p53 interactions but induced G0/G1 and G2/M cell cycle arrest in a p53-independent manner. Furthermore, the active compounds induced apoptosis in cells harboring wild-type and mutant p53. The compound design was conducted step by step and assisted by QSAR models that correlated the activity of the compounds against the HCT-116 cell line with molecular descriptors.
3. Charge-reversal nanoparticles: novel targeted drug delivery carriers
Xinli Chen, Lisha Liu, Chen Jiang Acta Pharm Sin B. 2016 Jul;6(4):261-7. doi: 10.1016/j.apsb.2016.05.011. Epub 2016 Jun 8.
Spurred by significant progress in materials chemistry and drug delivery, charge-reversal nanocarriers are being developed to deliver anticancer formulations in spatial-, temporal- and dosage-controlled approaches. Charge-reversal nanoparticles can release their drug payload in response to specific stimuli that alter the charge on their surface. They can elude clearance from the circulation and be activated by protonation, enzymatic cleavage, or a molecular conformational change. In this review, we discuss the physiological basis for, and recent advances in the design of charge-reversal nanoparticles that are able to control drug biodistribution in response to specific stimuli, endogenous factors (changes in pH, redox gradients, or enzyme concentration) or exogenous factors (light or thermos-stimulation).
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