A conjugate from a laminin-related peptide, Tyr-Ile-Gly-Ser-Arg, and chitosan: efficient and regioselective conjugation and significant inhibitory activity against experimental cancer metastasis

Nishiyama, Yasuhiro; Yoshikawa, Tomohiro; Ohara, Nobumichi; Kurita, Keisuke; Hojo, Keiko; Kamada, Haruhiko; Tsutsumi, Yasuo; Mayumi, Tadanori; Kawasaki, Koichi

doi:10.1039/a908145c

Cited by 26 publications

(10 citation statements)

References 24 publications

(14 reference statements)

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“…L ‐arginine derivatives without protecting groups on the nitrogen atom in δ position as 1 E/Z and 3 , once activated with the coupling agents tend to cyclize to six ring lactams. The amount of lactam that could form depends on several factors among which the coupling agent type ,,. In any case this quantity is inversely proportional to the reactivity of the activated derivative versus amine or, as in our case, hydroxyl groups and maximizes if acid BOC‐derivative is unreactive (see the case of compound 3 ).…”

Section: Resultsmentioning

confidence: 85%

“…The formation of the lactam compounds such as 5 and 5 a is extensively documented in literature . L ‐arginine derivatives without protecting groups on the nitrogen atom in δ position as 1 E/Z and 3 , once activated with the coupling agents tend to cyclize to six ring lactams.…”

Section: Resultsmentioning

confidence: 99%

“…Compound 3 , tautomer of 1 as TLC and NMR analysis asserted, unfortunately proved to be totally unreactive versus 4 in the conditions investigated (DCC and EDC). For not cutting off immediately 3 , which is endowed with high purity, symmetric structure and is achievable in large amount, future further investigations using other promising coupling agents such as benzotriazolol/DCC or pentafluorophenol/DCC systems, benzotriazole methyl sulphonate, diphenylfosphorylazide (DPPA) which is known for minimizing the cyclization side reactions, or 2‐chloro‐ N ‐methyl pyridinium iodide, documented for successful esterification of highly hydroxylated PAMAM derivatives with acid drugs will be designed and performed …”

Section: Discussionmentioning

confidence: 99%

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Tert‐Butoxycarbonyl Protecting Group Location Induces Different Reactive Behaviors in the Five Possible Isoforms of Tri‐Boc‐Arginine

2018

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L‐arginine is often used to decorate several scaffolds in order to obtain biomedical devices with increased efficiency and reduced toxicity, so nitrogen atoms need protection for example with BOC group. It has recently been reported that following three protocols which assured the achievement of the widely described (E)‐αN,ωN,ω’N‐Tri‐BOC‐arginine as pure isoform, additional four isoforms were obtained. As a rational consequence, further investigations about their reactivity were performed and in this work the results that showed as it is influenced by BOC location, isoforms structure and double bond position and geometry were reported. Only one isoform, i. e. rotamer E, shown appreciable reactivity highlighting that only the procedure which provides it is actually valid. From rotamer E, two new first generation arginine dendrons were prepared. These fragments, exploitable for decorating dendrimer, polymer or lipid scaffolds are very appealing for preparing synthetic arginine materials potentially suitable for biomedical application. Their spectral characterization as well as that of three other unreported isolated compounds were also provided.

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Section: Resultsmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Tert‐Butoxycarbonyl Protecting Group Location Induces Different Reactive Behaviors in the Five Possible Isoforms of Tri‐Boc‐Arginine

2018

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“…A peptide containing the Tyr-Ile-Gly-SerArg (YIGSR) sequence, corresponding to a partial sequence of laminin, inhibited angiogenesis and thus depressed tumor growth. Nishiyama et al [39] prepared YIGSR-chitosan conjugate and assayed antimetastatic activity. The conjugate proved to have higher inhibitory activity against experimental lung metastasis of B16BL6 melanoma cells in mice than did the parent peptide.…”

Section: Anti-cancer Activity As a Therapeutic Agentmentioning

confidence: 99%

Anti-Cancer Effects of Chitin and Chitosan Derivatives

Karagozlu

Kim

2014

Handbook of Anticancer Drugs From Marine Origin

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Despite considerable progress in medical research, cancer is still one of the high-ranking causes of death in the world. It is the second most common cause of death due to disease after heart disease and according to World Health Organization it will be cause of death more than 10 million people in 2020. Therefore one of the main research goal for researchers investigating new anticancer agents. But the major complication for the cancer cure without surgeries is side effects. Especially, cytotoxic anti-cancer chemotherapeutic agents generally produce severe side effects, while reducing host resistance to cancer and infections. Therefore, it is important to find new, powerful anti-cancer agents that are highly effective, biodegradable and biocompatible. Chitin and chitosan are biopolymers which have unique structural possibilities for chemical and mechanical modifications to generate novel properties, functions. These biopolymers are biocompatible, biodegradable and non-toxic and their chemical properties allow them easily processed into gels, sponges, membranes, beads and scaffolds forms also. Due to their unique properties, they are excellent candidate for cancer cure or cancer diagnosis.

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“…Chitosan contains a large quantity of primary amino groups ͑-NH 2 ͒ readily available for chemical modification by different biochemical groups such as peptide, 20 sugar, 21 ether, 22 etc. In order to use these micro-nanostructures of chitosan for bionanodevice applications, they have to be modified with the desired chemical groups.…”

mentioning

confidence: 99%

Low temperature, low pressure nanoimprinting of chitosan as a biomaterial for bionanotechnology applications

Park

Cheng

Pisano

et al. 2007

Applied Physics Letters

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Micro- and nanoscale structures of chitosan were fabricated by nanoimprinting lithography and biochemically functionalized for bionanodevice applications. Chitosan solutions were prepared and a nanoimprinting process was developed for it, where chitosan solution is used as a functional resist for nanoimprinting lithography. A low temperature (90°C) and low pressure (5–25psi) nanoimprinting with polydimethylsiloxane mold could achieve not only microscale structures but also nanoscale features such as nanowire and nanodots down to 150nm dimensions. The nanoimprinted structures were chemically modified and used for the immobilization of protein molecules.

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A conjugate from a laminin-related peptide, Tyr-Ile-Gly-Ser-Arg, and chitosan: efficient and regioselective conjugation and significant inhibitory activity against experimental cancer metastasis

Cited by 26 publications

References 24 publications

Tert‐Butoxycarbonyl Protecting Group Location Induces Different Reactive Behaviors in the Five Possible Isoforms of Tri‐Boc‐Arginine

Tert‐Butoxycarbonyl Protecting Group Location Induces Different Reactive Behaviors in the Five Possible Isoforms of Tri‐Boc‐Arginine

Anti-Cancer Effects of Chitin and Chitosan Derivatives

Low temperature, low pressure nanoimprinting of chitosan as a biomaterial for bionanotechnology applications

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