- Preparation and application of polyaspartyl - RGDF - anti-tumor drug complex
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The invention discloses a polyasparagine-RGDF compound represented by the formula and a three dimensional morphology of the compound under a neutral condition or a condition of pH 5.4, a polyasparagine-RGDF-antitumor drug compound, wherein the mole ratio
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Paragraph 0023; 0025-0026; 0029-0030
(2021/07/09)
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- Catalytic dehydrative peptide synthesis with gem-diboronic acids
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Alkane-gem-diboronic acids have emerged as versatile organoboron catalysts for dehydrative amidation of α-Amino acids. A phenol-substituted multiboron catalyst with a B-C-B structure outperformed simple arylboronic acids in the condensation of α-Amino acids with suppressed epimerization of electrophiles. gem-diboronic acid catalysis were compatible with various O, N, and S-functionalized α-Amino acids bearing N-protecting groups including common carbamates used in peptide synthesis (Boc, Cbz, Fmoc). N-Trifluoroacetyl protection enabled an unprecedented catalytic dehydrative peptide synthesis at room temperature. Preliminary mechanistic studies revealed carboxylate-binding nature of gem-diboronic acids, orthogonal to the activation of carboxylic acids by arylboronic acids. The distinctive reactivity of the gem-diboronic acids would open prospects for mild catalytic peptide condensation.
- Michigami, Kenichi,Sakaguchi, Tatsuhiko,Takemoto, Yoshiji
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p. 683 - 688
(2020/01/02)
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- Thrombus targeting release of the antithrombotic RGDF [...] - RGDF synthesis and application of
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The invention relates to polyaspartoyl-RGDF capable of achieving RGDF targeting release in thrombus, relates to a preparation method of the polyaspartoyl-RGDF, relates to the targeting antithrombotic function of the polyaspartoyl-RGDF on a rat thrombus mo
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Paragraph 0028; 0031-0033; 0036-0037
(2018/09/26)
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- Poly-α,β-aspartyl-Arg-Gly-Asp-Phe: A novel polymeric nanomedicine
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Thrombosis is a pathological condition and has been one of the most prominent causes of morbidity and mortality. Poly-α,β-aspartic acid is a biodegradable polymer, and RGD-tetrapeptides target thrombus. These led to the design of poly-α,β-aspartyl-Arg-Gly
- Chen, Shuangling,Wang, Yuji,Li, Shan,Wang, Yaonan,Zhao, Ming,Zhu, Haimei,Wu, Jianhui,Peng, Shiqi
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supporting information
p. 182 - 186
(2015/02/18)
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- RGD-peptides modifying dexamethasone: to enhance the anti-inflammatory efficacy and limit the risk of osteoporosis
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Dexamethasone (Dex) is one of the most effective anti-inflammatory glucocorticoids, while the side effect, osteoporosis seriously limits its clinical use. Cell adhesion is involved in the onset of inflammation and osteoporosis, and RGD-peptides are well k
- Yu, Hualong,Mei, Shenghui,Zhao, Li,Zhao, Ming,Wang, Yuji,Zhu, Haimei,Wang, Yaonan,Wu, Jianhui,Cui, Chunying,Xu, Wenyun,Peng, Shiqi
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supporting information
p. 1345 - 1351
(2015/07/15)
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- NOVEL COMPOUND WITH EFFECTS OF THROMBOLYSIS, FREE RADICAL SCAVENGING AND THROMBUS-TARGETING AS WELL AS PREPARATION METHOD AND USE THEREOF
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The present invention discloses a novel compound with effects of thrombolysis, free radical scavenging and thrombus-targeting, as well as a preparation method and use thereof. The compound is a ternary conjugate formed by conjugating a thrombolytic peptide, a free radical scavenger and a thrombus-targeting/antithrombotic peptide together via a linking arm. The present invention also discloses a pharmaceutical composition containing the compounds, wherein the compounds form a nanospherical structure.
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Paragraph 0117
(2015/11/03)
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- Synthesis, evaluation and 3D QSAR analysis of novel estradiol-RGD octapeptide conjugates with oral anti-osteoporosis activity
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To enhance the potency, reduce the side effects and improve oral property of estradiol in estrogen replacement therapy (ERT), 6 novel estradiol-RGD octapeptide conjugates have been prepared. In an ovariectomized mouse osteoporotic model, at an oral dosage
- Liu, Jiangyuan,Zhang, Xiaoyi,Zhao, Ming,Peng, Shiqi
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experimental part
p. 1689 - 1704
(2009/05/26)
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- 3D QSAR of novel estrogen-RGD peptide conjugates: Getting insight into structural dependence of anti-osteoporosis activity and side effect of estrogen in ERT
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To explore the structural dependence of the oral potency and side effect of estrogen-RGD peptide conjugates, here six novel conjugates were prepared via introducing RGD-tetrapeptides into both 3- and 17-positions of estradiol, and introducing RGD-octapept
- Zhao, Ming,Liu, Jiangyuan,Zhang, Xiaoyi,Peng, Li,Li, Chunyu,Peng, Shiqi
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supporting information; experimental part
p. 3680 - 3689
(2009/10/17)
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- Improved anti-osteoporosis potency and reduced endometrial membrane hyperplasia during hormone replacement therapy with estrogen-RGD peptide conjugates
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To improve the specificity and potency of estrogen replacement therapy therapeutics while also minimizing the side effects such as bone resorption and thickening of the uterine wall, a series of novel estrogen-derived conjugates estradiol-3-RGD, estradiol
- Xiong, Yu,Zhao, Ming,Wang, Chao,Heng, Wei Chang,Peng, Shiqi
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p. 3340 - 3353
(2008/02/12)
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- New ion-exchange cum separation technique: A study for the synthesis of ω-guanidine containing peptides using ω-amino acid as surrogate
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This article describes a systematic study for the introduction of ω-guanidine function at a late stage of synthesis using a protected amino group as a surrogate to improve overall yield. This concept was used to design and synthesize pseudo-peptides as GP IIb-IIIa receptor antagonist wherein glycine in endogenous ligand Arg-Gly-Asp (RGD) is replaced by 2-amino-thiazole-4-ylacetic acid (Tha) as a spacer. Further, we describe here a unique salt exchange cum purification technology based on reverse phase (RP-18) medium-pressure liquid chromatography. Copyright Taylor & Francis Group, LLC.
- Gangopadhyay, Ashok K.,Lal, Bansi
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p. 1389 - 1419
(2008/02/01)
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- Synthesis and comparison of physicochemical, transport, and antithrombic properties of a cyclic prodrug and the parent RGD peptidomimetic
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Cyclic prodrug 1 was derived from RGD peptidomimetic 2 by linking the amino and carboxylic acid groups via an (acyloxy)alkoxy linker. The formation of a cyclic prodrug can transiently alter the physicochemical properties of the RGD peptidomimetic. Cyclic
- Xu, Christine R.,He, Henry T.,Song, Xiaoping,Siahaan, Teruna J.
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p. 2861 - 2869
(2007/10/03)
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- Synthesis and antiaggregatory activity of RGD-peptidomimetics based on 4-oxo-4-(piperazine-1-yl)butyric acid as Arg-mimetic
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A scheme of synthesis of previously obtained RGDF-peptidomimetic-4-oxo- 4-(piperazine-1-yl)butyrylglycyl-D,L-β-phenyl-β-alanine (I), was simplified. The novel RGDF-peptidomimetic - 4-o-xo-4-(piperazine-1-yl) butyryl-glycyl-L-aspartyl-L-phenylalanine (II was synthesized with the use of 4-oxo-4-(piperazine-1-yl)butyric acid as arginyl mimetic. The obtained pseudopeptides were able to inhibit both platelet aggregation in human blood and binding of fibrinogen to its receptor.
- Andronati, Sergei A.,Krysko, Andrei A.,Kabanov, Vladimir M.,Kabanova, Tatyana A.,Karaseva, Tamara L.,Chugunov, Boris M.,Meshkova, Svetlana B.,Topilova, Zoya M.
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p. 375 - 381
(2007/10/03)
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- Design of a new class of orally active fibrinogen receptor antagonists
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The integrin receptor recognition sequence Arg-Gly-Asp was successfully used as a template from which to develop a series of potent, selective, orally active, peptide-based fibrinogen receptor antagonists with a long duration of action. Simple modifications centered on the Arg and Gly residues quickly led to a modified peptide (1) with significantly enhanced ability to inhibit in vitro platelet aggregation. Substitution of the guanidino group in 1 by piperidine provided 3, which showed not only a further increase in potency but also a modest degree of oral efficacy. Finally, exploration of the nature of the C-terminal amino acid, with respect to its side-chain functionality and the carboxy terminus, yielded a group of molecules that showed excellent in vitro potency for inhibiting platelet aggregation, excellent integrin selectivity, a high level of oral efficacy, and an extended duration of action.
- Klein, Scott I.,Molino, Bruce F.,Czekaj, Mark,Gardner, Charles J.,Chu, Valeria,Brown, Karen,Sabatino, Ralph D.,Bostwick, Jeffrey S.,Kasiewski, Charles,Bentley, Ross,Windisch, Vincent,Perrone, Mark,Dunwiddie, Christopher T.,Leadley, Robert J.
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p. 2492 - 2502
(2007/10/03)
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- Acetic acid derivatives
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Acetic acid derivatives of formula and hydrates, solvates and physiologically acceptable salts thereof are useful to inhibit the binding of adhesive proteins to blood platelets and also to inhibit blood platelet aggregation and cell-cell adhesion.
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- Low molecular weight, non-peptide fibrinogen receptor antagonists
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The tetrapeptide H-Arg-Gly-Asp-Ser-OH (1) (RGDS), representing a recognition sequence of fibrinogen for its platelet receptor GP IIb-IIIa (integrin α(IIb)β3), served as lead compound for the development of highly potent and selective fibrinogen receptor antagonists. Replacement of the N- terminal arginine by p-amidinophenylalanine or the Gly moiety by m- aminobenzoic acid led to compounds which are superior to the lead peptide with regard to activity and selectivity for GP IIb-IIIa vs the closely related vitronectin receptor α(v)β3. By random screening [(p- amidinobenzenesulfonamido)ethyl]-p-phenoxyacetic acid derivatives have been identified as fibrinogen receptor antagonists. Further structure-activity relationship studies culminated in the preparation of N-[N-[N-(p- amidinobenzoyl)-β-alanyl]-L-α-aspartyl]-3-phenyl-L-alanine (29h, Ro 43- 5054) and [[1-[N-(p-amidinobenzoyl)-L-tyrosyl]-4-piperidinyl]oxy]acetic acid (37f, Ro 44-9883), which exhibit very high activity as platelet aggregation inhibitors (IC50s 0.06 and 0.03 μM, respectively, human PRP/ADP) as well as marked selectivity for GP IIb-IIIa vs α(v)β3. Since the activity of 37f in dogs declines according to a two-compartment model with an initial phase having a t( 1/2 ) of 8 min and a second phase with a t( 1/2 ) of 110 min, this compound is a suitable candidate for the development as iv platelet inhibitor.
- Alig,Edenhofer,Hadvary,Hurzeler,Knopp,Muller,Steiner,Trzeciak,Weller
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p. 4393 - 4407
(2007/10/02)
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