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© 2013 International Maillard Reaction Society 1
IMARS
HIGHLIGHTS
Research Commentaries for the Members of
The International Maillard Reaction Society
A Non-profit Research and Education Organization in Biomedicine and Food Science
Volume 13
Number 2
March 22, 2018
IMARS Highlights www.imars.org Volume 13, Number 2
March 22, 2018
© 2013 International Maillard Reaction Society 2
IMARS HIGHLIGHTS
Research Commentaries for the Members of
The International Maillard Reaction Society
A Non-profit Research and Education Organization in Biomedicine and Food Science
Volume 13
Number 2
March 22, 2018
Editor Reiko Inagi (JP) Contributing Editors Josephine M. Forbes (AUS) Vincenzo Fogliano (IT) Alejandro Gugliucci (USA) Toshio Miyata (JP) Monika Pischetsrieder (DE) Alan Stitt (NI) Varoujan Yaylayan (CA) Rosario Zamora (ES) Ryoji Nagai (JP) Fred Tessier (FR) Norma Frizzell (USA) Kiyotaka Nakagawa (JP) Yukio Fujiwara (JP) IMARS Established in 2005, the International Maillard Reaction Society gathers researchers and clinicians involved in the field of carbonyl reactions in foods, biology and medicine. It promotes research on Maillard Reaction and protein glycation and their numerous applications. It also organizes regular international congresses on the same theme, in addition to those that have been taken place since 1979. www.imars.org
IMARS Highlights www.imars.org Volume 13, Number 2
March 22, 2018
IMARS HIGHLIGHTS
Volume 13, Number 2, March 22, 2018
CONTENTS OF THIS ISSUE: - Editorial comment
Reiko Inagi - Potential usability of Amadori-glycated phosphatidylethanolamine as a
glycoconjugated biomaterial Taiki Miyazawa, Reina Kamiyoshihara, Teruo Miyazawa and Kiyotaka Nakagawa
- Highlights of the glycation literature (January 2018-March 2018)
16 11
5
4
IMARS Highlights www.imars.org Volume 13, Number 2
March 22, 2018
4
Editorial comments
In this issue, Prof. Kiyotaka Nakagawa and his colleagues at Graduate School of Agricultural Science, Tohoku University, Sendai, Japan, kindly published the mini review, entitled “Potential usability of Amadori-glycated phosphatidylethanolamine as a glycoconjugated biomaterial”. This article highlights the potential use of Amadori-glycated phosphatidylethanolamine (Amadori-PE) as a glycoconjugated biomaterial for targeting glucose transporter-mediated transport. Of note, the liposomes containing Amadori-PE are predominantly taken up by the cells, which highly express glucose transporters. They demonstrated that Amadori-PE may be significantly beneficial as biomaterials.
In this year, the 13th International Symposium on the Maillard reaction (ISMR) will be held in Montreal, Canada (September 10-13). On behalf of the IMARS president Prof. Varoujan A. Yaylayan, I would like to invite all of the IMARS members to submit your abstracts.
IMARS committees are very much looking forward to seeing you and to deepening our fruitful scientific discussion in Montreal!
Reiko Inagi,Ph.D. Division of Chronic Kidney Disease Pathophysiology, The University of Tokyo Graduate School of Medicine email: [email protected]
IMARS Highlights www.imars.org Volume 13, Number 2
March 22, 2018
5
Potential usability of Amadori-glycated phosphatidylethanolamine as a glycoconjugated biomaterial
(short review) Taiki Miyazawa1, Reina Kamiyoshihara2, Teruo Miyazawa3,4, Kiyotaka Nakagawa2*
1Institute of Biomaterials & Bioengineering, Tokyo Medical and Dental University,
Tokyo 101-0062, Japan 2Food and Biodynamic Chemistry Laboratory, Graduate School of Agricultural
Science, Tohoku University, Sendai 980-0845, Japan 3Food and Biotechnology Innovation Project, New Industry Creation Hatchery Center
(NICHe), Tohoku University, Sendai 980-8579, Japan 4Food and Health Science Research Unit, Graduate School of Agricultural Science,
Tohoku University, Sendai 980-0845, Japan
*Corresponding author. Tel: +81-22-757-4416 Fax: +81-22-757-4417.
E-mail address: [email protected] (K. Nakagawa).
1. Introduction
A large number of biomaterials (e.g. liposomes, micelles and nanoparticles)
have been used for treatment in various diseases such as cancer [1, 2], because these
biomaterials have held a several beneficial abilities by modifying their formulation
and surfaces. On the other hand, Amadori-glycated phosphatidylethanolamine
(Amadori-PE, Figure 1B, D) is a Maillard reaction product that contains a saccharide
moiety in its chemical structure [3-9]. Because of its chemical structure, it has a
potential for use as biomaterials. In this short review, we focused on the potential use
of Amadori-PE as a glycoconjugated biomaterial for targeting glucose transporter
(GLUT)-mediated transport.
2. Prevalence of GLUT on cancer cells
Otto Heinrich Warburg, Nobel prize winner (1931) a German physiologist,
found that cancer tissues consume large amounts of glucose compared to normal
tissue and high amounts of aerobic glycolysis [10]. This phenomenon is called
“Warburg effect” and it is well recognized as characteristic of cancer [11]. Based on
this phenomenon, GLUT is widely overexpressed on cancer cells.
3. Glycoconjugated drug for cancer treatment
Cellular transporters are well known as important determinants governing
drug uptake into target organs. Among them, glycoconjugation-mediated cancer
treatment via GLUT is one of the investigated approaches. A glucose analog, 2-deoxy-
2-(18F) fluoro-D-glucose (18F-FDG, Figure 1E) is used to visualize tumors by positron
IMARS Highlights www.imars.org Volume 13, Number 2
March 22, 2018
6
emission tomography (PET) [12]. In addition, clinical approaches for glycoconjugated
anticancer drugs are on the way. 1-β-D-glucose conjugated ifosfamide mustard,
Glufosfamide (Figure 1F), is already in human clinical trials. For example, 13
Japanese patients with various solid tumors (colorectal cancer, non-small cell lung
cancer, thymic cancer, thymoma, gallbladder cancer, gastric cancer and uterine
corpus-endometrial cancer) who relapsed after standard chemotherapy or no effective
standard therapy were subjected to human clinical trial of Glufosfamide [13]. As a
result, 8 patients showed disease stabilization, 4 patients showed progressive disease
and one patient showed partial response. However, our knowledge concerning the
clinical dynamics of glycoconjugated anticancer drug is still scarce. More
investigation for clarifying the effectiveness of these glycoconjugated drugs would be
of vital importance.
Figure 1. Chemical structures of related compounds in this review.
4. Amadori-glycated PE as a liposome carrier for cancer treatment
In this section, we introduce our recent research related to Amadori-PE [14].
As mentioned in the introduction, liposomes are well known biomaterial for
controlling the retention of encapsulated drugs in circulation, sustained release,
dispersibility, delivery to specific tissues and so on by modifying its chemical
structure of the lipid formulation and associated surfaces [2]. Generally, liposomes are
prepared from phosphatidylcholine (PC, Figure 1A). However, liposomes comprised
of 100% PC exhibit poor membrane fusion, cellular uptake, and selective targeting
capacities [15, 16]. To overcome these limitations, we focused on preparing liposomes
HN
OH
CH2OH
OH
OHO
HN
OH
CH2OH
OH
O
OO
OH
OHOH
CH2OH
OP
O
O
O
OR1
O
O
R2
OH
OP
O
O
O
OR1
O
O
R2
OH
H2NO
P
O
O
O
OR1
O
O
R2
OH
N+
OP
O
O
O
OR1
O
O
R2
OH
OHO
18F
OHOH
CH2OH
P
O HN
NH Cl
Cl
OO
OH
OHOH
CH2OH
Phosphatidylcholine(PC)
Phosphatidylethanolamine(PE)
Amadori-glycated phosphatidylethanolamine(reacted with glucose, GPE)
Amadori-glycated phosphatidylethanolamine(reacted with lactose, LPE)
2-Deoxy-2-(18F) fluoro-D-glucose(18F-FDG)
Glufosfamide
A B
C D
E F
R = R = Palmitic acid
1 2
IMARS Highlights www.imars.org Volume 13, Number 2
March 22, 2018
7
from mixtures of PC and 2 kinds of Amadori-PE (glucose-PE (GPE) and lactose-PE
(LPE), Figure 1B, D). We hypothesized that liposomes prepared from mixtures of PC
and Amadori-PE should exhibit enhanced membrane fusion and cellular uptake
capacities due to the presence of the phosphatidylethanolamine (PE, Figure1C) sites
[15], while the presence of the saccharide moiety would allow for targeting of cells
that highly express GLUTs on their membranes [17]. Thus, we examined the uptake
of GPE and LPE containing liposomes into cells, to evaluate their potential for use in
biomaterials. To confirm the cellular uptake capacity of liposomes, we used human
intestinal epithelial (Caco-2) cells as a model cancer cells and lipophilic polyphenol
curcumin (CUR) as a model drug [18, 19].
Figure 2. A: Average particle size of liposomes prepared from different ratios of PC and glycated PE (glucose-PE (GPE) and lactose-PE (LPE)). Mean±SD, n=3. Means
significantly differed at **P < 0.01. B: Cellular uptake of Curcumin (CUR)-encapsulated liposomes. Liposomes were prepared from phosphatidylcholine (PC)
and Amadori-glycated phosphatidylethanolamine (Amadori-PE) (glucose-PE (GPE), lactose-PE (LPE)) or non-glycated PE. The ratio of PC to Amadori-PE (or non-
glycated PE) was adjusted to 3:1 in all groups. Statistical significance between groups was assessed by Dunnett’s test. Data are mean±SD, n=3. (Modified from Miyazawa et
al., [14]).
As a result, we optimized the preparation of Amadori-PE (or non-glycated PE)
containing liposomes with around 100 nm mean diameters (Figure 2A) [14]. In
addition, cellular uptake study demonstrated that liposomes containing Amadori-PE
(GPE and LPE) tended to increase the uptake of CUR into Caco-2 cells compared
with liposomes containing non-glycated PE (Figure 2B) [14]. It can be inferred that
liposomes containing Amadori-PE are taken up by Caco-2 cells due to the presence of
the saccharide moiety, which binds to GLUTs [20]. On the other hand, levels of
cellular uptake of liposomes containing GPE tended to be higher than those of
liposomes containing LPE (GPE: P =0.08, LPE: P =0.27, Figure 2B). GLUTs are
known to recognize the structure of monosaccharides at the time of sugar uptake into
PC:PE(3:1)
PC:GPE(3:1)
PC:LPE(3:1)
0
5
10
15
20
25
Am
ount
of
CU
R (
pm
ol/
10
cel
l)
P = 0.08
P = 0.27
10 100 1000 10000
Particle size (nm)
Rel
ativ
e in
ten
sity
(%
)
1
100
0
PC:PE=3:1123±4 nm
PC:GPE=3:1107±3** nm
PC:LPE=3:1120±4 nm
A B
cells [17]. Additionally, site o
recognized by GLUT 5 of certain tumors (including Cac
system [20-22]. Therefore, it is speculated that Amadori
monosaccharide is more easily recognized by
increased cellular uptake compared with LPE, which contains the
(Figure 3). This phenomenon can be utilized to enhance the selective targeting and
subsequent cellular uptake of liposomes.
Figure 3. Assumed behav
5. Conclusion
It is considered that liposomes containing Amadori
cells that highly express GLUTs. These characteristics should allow fo
potential applications, such as increased uptake of encapsulated drugs to target cells
following intravenous injection, and enhancement of absorption of encapsulated
nutrients in the intestine. Taken together, the results of this study suggest that
Amadori-PE may have an imminent potential for use as biomaterials in the future.
6. References
1) Moghimi SM, Hunter AC, Murray JC, Nanomedicine: current status and future
prospects. FASEB J. 19, 311
2) Allen TM, Cullis PR, Liposomal drug delivery systems: from concept t
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3) Oak JH, Nakagawa K, Miyazawa T, UV analysis of Amadori
phosphatidylethanolamine in foods and biological samples.
529 (2002).
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5) Miyazawa T, Oak JH, Nakagawa K, A convenient method for preparation of high
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[17]. Additionally, site of fructosyl moiety of Amadori-PE might be specifically
recognized by GLUT 5 of certain tumors (including Caco-2 cells) and digestive
22]. Therefore, it is speculated that Amadori-PE, which contains the
monosaccharide is more easily recognized by GLUT 5, which resulted in the
increased cellular uptake compared with LPE, which contains the disaccharide
his phenomenon can be utilized to enhance the selective targeting and
subsequent cellular uptake of liposomes.
behavior of liposomes used in the study. (Modified from Miyazawa et al., [14])
It is considered that liposomes containing Amadori-PE are taken up by the
cells that highly express GLUTs. These characteristics should allow fo
ications, such as increased uptake of encapsulated drugs to target cells
following intravenous injection, and enhancement of absorption of encapsulated
nutrients in the intestine. Taken together, the results of this study suggest that
n imminent potential for use as biomaterials in the future.
Moghimi SM, Hunter AC, Murray JC, Nanomedicine: current status and future
, 311-330 (2005).
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trap tandem mass spectrometric analysis of Amadori
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yazawa T, Oak JH, Nakagawa K, A convenient method for preparation of high
IMARS Highlights , Number 2
March 22, 2018
PE might be specifically
2 cells) and digestive
PE, which contains the
GLUT 5, which resulted in the
disaccharide
his phenomenon can be utilized to enhance the selective targeting and
(Modified from
E are taken up by the
cells that highly express GLUTs. These characteristics should allow for various
ications, such as increased uptake of encapsulated drugs to target cells
following intravenous injection, and enhancement of absorption of encapsulated
nutrients in the intestine. Taken together, the results of this study suggest that
n imminent potential for use as biomaterials in the future.
Moghimi SM, Hunter AC, Murray JC, Nanomedicine: current status and future
Allen TM, Cullis PR, Liposomal drug delivery systems: from concept to clinical
Oak JH, Nakagawa K, Miyazawa T, UV analysis of Amadori-glycated
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yazawa T, Oak JH, Nakagawa K, A convenient method for preparation of high-
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Highlights of the glycation literature (January 2018 - March2018) Papers of Editors’ Choice Rabbani N, Thornalley PJ. Advanced glycation end products in the pathogenesis of
chronic kidney disease. Kidney Int. 2018 Feb 22. [Epub ahead of print] Antoniotti GS, Coughlan M, Salamonsen LA, Evans J. Obesity associated advanced
glycation end products within the human uterine cavity adversely impact endometrial function and embryo implantation competence. Hum Reprod. 2018 Feb 20. [Epub ahead of print]
Tong QH, Yan TY, Tao T, Zhang L, Xie LQ, Lu H. Reductive Amination Combining Dimethylation for Quantitative Analysis of Early Stage Glycated Proteins. Anal Chem. 2018 Feb 21. [Epub ahead of print]
Hagiwara S, Sourris K, Ziemann M, Tieqiao W, Mohan M, McClelland AD, Brennan E, Forbes J, Coughlan M, Harcourt B, Penfold S, Wang B, Higgins G, Pickering R, El-Osta A, Thomas MC, Cooper ME, Kantharidis P. RAGE Deletion Confers Renoprotection by Reducing Responsiveness to Transforming Growth Factor-β and Increasing Resistance to Apoptosis. Diabetes. 2018 Feb 15. [Epub ahead of print]
Taguchi K, Yamagishi SI, Yokoro M, Ito S, Kodama G, Kaida Y, Nakayama Y, Ando R, Yamada-Obara N, Asanuma K, Matsui T, Higashimoto Y, Brooks CR, Ueda S, Okuda S, Fukami K. RAGE-aptamer attenuates deoxycorticosterone acetate/salt-induced renal injury in mice. Sci Rep. 2018 Feb 8;8(1):2686.
Rojas A, Añazco C, González I, Paulina A. Extracellular matrix glycation and RAGE activation. A missing piece in the puzzle of the association between diabetes and cancer. Carcinogenesis. 2018 Jan 24. [Epub ahead of print]
Chen Y, Filipov NM, Guo TL. Dietary Glycation Products Regulate Immune Homeostasis: Early Glycation Products Promote Prostate Cancer Cell Proliferation through Modulating Macrophages. Mol Nutr Food Res. 2018 Feb;62(3).
Niihata K, Takahashi S, Kurita N, Yajima N, Omae K, Fukuma S, Okano T, Nomoto Y, Omori K, Fukuhara S; Sukagawa Study Group. Association Between Accumulation of Advanced Glycation End-Products and Hearing Impairment in Community-Dwelling Older People: A Cross-Sectional Sukagawa Study. J Am Med Dir Assoc. 2018 Mar;19(3):235-239.
Cardoso HB, Wierenga PA, Gruppen H, Schols HA. Maillard induced glycation behaviour of individual milk proteins. Food Chem. 2018 Jun 30;252:311-317.
Baldensperger T, Jost T, Zipprich A, Glomb MA. Novel α-Oxoamide Advanced-Glycation Endproducts within the N(6)-Carboxymethyl Lysine and N(6)-Carboxyethyl Lysine Reaction Cascades. J Agric Food Chem. 2018 Feb 13. [Epub ahead of print]
Sowndhar Rajan B, Manivasagam S, Dhanusu S, Chandrasekar N, Krishna K, Kalaiarasu LP, Babu AA, Vellaichamy E. Diet with high content of advanced glycation end products induces systemic inflammation and weight gain in experimental mice: Protective role of curcumin and gallic acid. Food Chem Toxicol. 2018 Feb 10;114:237-245.
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2. Cheng K, Yang A, Hu X, Zhu D, Liu K. Curcumin Attenuates Pulmonary Inflammation in Lipopolysaccharide Induced Acute Lung Injury in Neonatal Rat
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Model by Activating Peroxisome Proliferator-Activated Receptor γ (PPARγ) Pathway. Med Sci Monit. 2018 Feb 26;24:1178-1184.
3. König A, Vicente Miranda H, Outeiro TF. Alpha-Synuclein Glycation and the Action of Anti-Diabetic Agents in Parkinson's Disease. J Parkinsons Dis. 2018;8(1):33-43.
4. Liu C, Chen K, Lu Y, Fang Z, Yu G. Catalpol provides a protective effect on fibrillary Aβ(1-42) -induced barrier disruption in an in vitro model of the blood-brain barrier. Phytother Res. 2018 Feb 26. [Epub ahead of print].
5. Anwar A, Abruzzo PM, Pasha S, Rajpoot K, Bolotta A, Ghezzo A, Marini M, Posar A, Visconti P, Thornalley PJ, Rabbani N. Advanced glycation endproducts, dityrosine and arginine transporter dysfunction in autism - a source of biomarkers for clinical diagnosis. Mol Autism. 2018 Feb 19;9:3. eCollection 2018.
6. Cournot M, Burillo E, Saulnier PJ, Planesse C, Gand E, Rehman M, Ragot S, Rondeau P, Catan A, Gonthier MP, Feigerlova E, Meilhac O, Hadjadj S. Circulating Concentrations of Redox Biomarkers Do Not Improve the Prediction of Adverse Cardiovascular Events in Patients With Type 2 Diabetes Mellitus. J Am Heart Assoc. 2018 Feb 25;7(5).
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8. Preetha Rani MR, Anupama N, Sreelekshmi M, Raghu KG. Chlorogenic acid attenuates glucotoxicity in H9c2 cells via inhibition of glycation and PKC α upregulation and safeguarding innate antioxidant status. Biomed Pharmacother. 2018 Feb 22;100:467-477.
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13. Thompson K, Chen J, Luo Q, Xiao Y, Cummins TR, Bhatwadekar AD. Advanced glycation end (AGE) product modification of laminin downregulates Kir4.1 in retinal Müller cells. PLoS One. 2018 Feb 23;13(2):e0193280. eCollection 2018.
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16. Krajewska-Włodarczyk M, Owczarczyk-Saczonek A, Placek W, Osowski A, Wojtkiewicz J. Articular Cartilage Aging-Potential Regenerative Capacities of Cell Manipulation and Stem Cell Therapy. Int J Mol Sci. 2018 Feb 22;19(2). pii:
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17. Polverino F, Celli BR, Owen CA. COPD as an endothelial disorder: endothelial injury linking lesions in the lungs and other organs? (2017 Grover Conference Series). Pulm Circ. 2018 Jan-Mar;8(1):2045894018758528.
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19. Schulz BL, Phung TK, Bruschi M, Janusz A, Stewart J, Mehan J, Healy P, Nouwens AS, Fox GP, Vickers CE. Process proteomics of beer reveals a dynamic proteome with extensive modifications. J Proteome Res. 2018 Feb 19. [Epub ahead of print]
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259. Hiroshima Y, Sakamoto E, Yoshida K, Abe K, Naruishi K, Yamamoto T, Shinohara Y, Kido JI, Geczy CL. Advanced glycation end-products and Porphyromonas gingivalis lipopolysaccharide increase calprotectin expression in human gingival epithelial cells. J Cell Biochem. 2018 Feb;119(2):1591-1603.
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275. Kuo HL, Huang CC, Lin TY, Lin CY. IL-17 and CD40 ligand synergistically stimulate the chronicity of diabetic nephropathy. Nephrol Dial Transplant. 2018 Feb 1;33(2):248-256.
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