Analytical and physicochemical characterisation of the senile cataract drug dipeptide β-alanyl-L-histidine (carnosine)

被引:19
|
作者
Abdelkader, Hamdy [1 ,3 ]
Swinden, Julian [1 ]
Pierscionek, Barbara K. [2 ]
Alany, Raid G. [1 ,4 ]
机构
[1] Univ Kingston, Sch Pharm & Chem, Drug Discovery Delivery & Patient DDDPC Theme, London, England
[2] Univ Kingston, Fac Sci Engn & Comp, Vis Cognit & Neurosci Theme, London, England
[3] Menia Univ, Fac Pharm, Dept Pharmaceut, Mina, Egypt
[4] Univ Auckland, Sch Pharm, Auckland 1, New Zealand
关键词
L-carnosine; Senile cataract; Histidine; Dipeptide; Ocular delivery; DELIVERY;
D O I
10.1016/j.jpba.2015.05.025
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
This study presents a simple but sensitive HPLC chromatographic method with a stability-indicating assay for determination and physicochemical characterisation of L-carnosine, a promising senile cataract prophylactic agent. Chromatographic analysis was conducted using a reverse phase (RP)-HPLC system and an isocratic mobile phase of 98% v/v trifluoroacetic acid (0.1% v/v) and 2% v/v acetonitrile with detection at 220 nm. L-carnosine was subjected to stress conditions to force its degradation using chemical and thermal agents and was subsequently detected from its degradation products using ESI-MS. The lipophilicity of the drug and 1:1 drug to phospholipid complex (PC) mol/mol was determined by estimating the partition coefficient (P). Lipophilicity was greatly enhanced when L-carnosine was formulated as a phospholipid complex using the solvent evaporation method. L-carnosine-phospholipid complex could be a promising approach for effective delivery to the human lens as offers a potential novel treatment for senile cataract. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:241 / 246
页数:6
相关论文
共 42 条
  • [31] β-Alanyl-L-Histidine Rescues Cognitive Deficits Caused by Feeding a High Fat Diet in a Transgenic Mouse Model of Alzheimer's Disease
    Herculano, Bruno
    Tamura, Minami
    Ohba, Ayaka
    Shimatani, Mayu
    Kutsuna, Natsumaro
    Hisatsune, Tatsuhiro
    [J]. JOURNAL OF ALZHEIMERS DISEASE, 2013, 33 (04) : 983 - 997
  • [32] From amino acids to dipeptide: The changes in thermal stability and hydration properties of β-alanine, L-histidine and L-carnosine
    Vranes, Milan
    Panic, Jovana
    Tot, Aleksandar
    Papovic, Snezana
    Gadzuric, Slobodan
    Podlipnik, Crtomir
    Bester-Rogac, Marija
    [J]. JOURNAL OF MOLECULAR LIQUIDS, 2021, 328
  • [33] Influence of lipid composition on physicochemical properties of nanoliposomes encapsulating natural dipeptide antioxidant L-carnosine
    Maherani, Behnoush
    Arab-Tehrany, Elmira
    Kheirolomoom, Azadeh
    Cleymand, Franck
    Linder, Michel
    [J]. FOOD CHEMISTRY, 2012, 134 (02) : 632 - 640
  • [34] Effects of Carnosine (Beta-Alanyl-L-Histidine) in an Experimental Rat Model of Acute Kidney Injury Due to Septic Shock
    Sahin, Sabiha
    Donmez, Dilek Burukoglu
    [J]. MEDICAL SCIENCE MONITOR, 2018, 24 : 305 - 316
  • [35] MODEL COMPOUNDS FOR METAL-PROTEIN INTERACTION - CRYSTAL STRUCTURE OF COPPER(2) COMPLEX OF BETA-ALANYL-L-HISTIDINE (CARNOSINE)
    FREEMAN, HC
    SZYMANSKI, JT
    [J]. CHEMICAL COMMUNICATIONS, 1965, (23) : 598 - +
  • [36] ENHANCED CARNOSINE (BETA-ALANYL-L-HISTIDINE) BREAKDOWN AND HISTAMINE-METABOLISM FOLLOWING TREATMENT WITH COMPOUND-48/80
    GREENE, SM
    MARGOLIS, FL
    GRILLO, M
    FISHER, H
    [J]. EUROPEAN JOURNAL OF PHARMACOLOGY, 1984, 99 (01) : 79 - 84
  • [37] METAL-COMPLEXES OF PEPTIDES .4. COBALT(III) COMPLEXES WITH BETA-ALANYL-L-HISTIDINE (CARNOSINE) FUNCTIONING AS A QUADRIDENTATE LIGAND
    AMA, T
    KAWAGUCHI, H
    UCHIJIMA, M
    KOINE, N
    YASUI, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (11) : 3464 - 3468
  • [38] A potentiometric and 51V NMR study of the aqueous H+/H2VO4-/H2O2/L-α-alanyl-L-histidine system
    Schmidt, H
    Andersson, I
    Rehder, D
    Pettersson, L
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (01) : 251 - 257
  • [39] H-1 AND C-13 NMR RELAXATION INVESTIGATION OF THE CALCIUM COMPLEX OF BETA-ALANYL-L-HISTIDINE (CARNOSINE) IN AQUEOUS-SOLUTION
    GAGGELLI, E
    VALENSIN, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (03): : 401 - 406
  • [40] L-CARNOSINE (BETA-ALANYL-L-HISTIDINE) AND CARCININE (BETA-ALANYLHISTAMINE) ACT AS NATURAL ANTIOXIDANTS WITH HYDROXYL-RADICAL-SCAVENGING AND LIPID-PEROXIDASE ACTIVITIES
    BABIZHAYEV, MA
    SEGUIN, MC
    GUEYNE, J
    EVSTIGNEEVA, RP
    AGEYEVA, EA
    ZHELTUKHINA, GA
    [J]. BIOCHEMICAL JOURNAL, 1994, 304 : 509 - 516