Antioxidant peptide A
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Antioxidant peptide A

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Antioxidant peptide A is a short peptide that contains alternative aromatic or sulfur-containing amino acids. The side chain of antioxidant peptide A is thought to contribute to the strong free radical scavenging activity of the peptide in tumor cells.

Category
Others
Catalog number
BAT-009293
CAS number
159147-88-3
Molecular Formula
C31H54N12O7S2
Molecular Weight
770.97
Antioxidant peptide A
IUPAC Name
(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2R)-2-[[(2S)-3-(1H-imidazol-5-yl)-2-[[(2S)-pyrrolidine-2-carbonyl]amino]propanoyl]amino]-3-sulfanylpropanoyl]amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylsulfanylbutanoic acid
Synonyms
H-Pro-His-Cys-Lys-Arg-Met-OH; L-prolyl-L-histidyl-L-cysteinyl-L-lysyl-L-arginyl-L-methionine; N-[(2S,5S,8R,11S)-5-(4-Aminobutyl)-2-(3-carbamimidamidopropyl)-1,4,7,10,13-pentahydroxy-11-(1H-imidazol-5-ylmethyl)-13-[(2S)-2-pyrrolidinyl]-8-(sulfanylmethyl)-3,6,9,12-tetraazatrideca-3,6,9,12-tetraen-1-ylidene]methionine
Appearance
White or Off-white Lyophilized Powder
Purity
>95%
Density
1.5±0.1 g/cm3
Boiling Point
1045.7±75.0°C at 760 mmHg
Sequence
PHCKRM
Storage
Store at -20°C
Solubility
Soluble in Water
InChI
InChI=1S/C31H54N12O7S2/c1-52-13-9-22(30(49)50)41-27(46)21(8-5-12-37-31(33)34)39-26(45)20(6-2-3-10-32)40-29(48)24(16-51)43-28(47)23(14-18-15-35-17-38-18)42-25(44)19-7-4-11-36-19/h15,17,19-24,36,51H,2-14,16,32H2,1H3,(H,35,38)(H,39,45)(H,40,48)(H,41,46)(H,42,44)(H,43,47)(H,49,50)(H4,33,34,37)/t19-,20-,21-,22-,23-,24-/m0/s1
InChI Key
NHZJOSHEZUEDBO-BTNSXGMBSA-N
Canonical SMILES
CSCCC(C(=O)O)NC(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(CS)NC(=O)C(CC1=CN=CN1)NC(=O)C2CCCN2
1. Vasonatrin peptide, a synthetic natriuretic peptide, attenuates myocardial injury and oxidative stress in isoprenaline-induced cardiomyocyte hypertrophy
Pan Chang, Xiaomeng Zhang, Weiguo Chen, Jing Zhang, Jianbang Wang, Xihui Wang, Jun Yu, Xiaoling Zhu Peptides. 2021 Mar;137:170474. doi: 10.1016/j.peptides.2020.170474. Epub 2020 Dec 24.
Isoprenaline-induced cardiac hypertrophy can deteriorate to heart failure, which is a leading cause of mortality. Endogenous vasonatrin peptide (VNP) has been reported to be cardioprotective against myocardial ischemia/reperfusion injury in diabetic rats. However, little is known about the effect of exogenous VNP on cardiac hypertrophy. We further explored whether VNP attenuated isoprenaline-induced cardiomyocyte hypertrophy by examining the levels and activities of cGMP and PKG. In this study, we found that VNP significantly attenuated isoprenaline-induced myocardial hypertrophy and cardiac fibroblast activation in vivo. Moreover, VNP effectively halted the activation of apoptosis and oxidative stress in the isoprenaline-treated myocardium. VNP promoted superoxide dismutase (SOD) activity. Further study revealed that the protective effects of VNP might be mediated by the activity of the cGMP-PKG signaling pathway in vivo or in vitro, while the use of agonists and antagonists confirmed these results. Therefore, we demonstrated that the antiapoptosis and antioxidative stress effects of VNP depends on elevated cGMP-PKG signaling activity both in vivo and in vitro. These results suggest that VNP may be used in the treatment of myocardial hypertrophy.
2. A study of the sequential treatment of acute heart failure with sacubitril/valsartan by recombinant human brain natriuretic peptide: A randomized controlled trial
Zhihua Pang, Chang Pan, Zhuhua Yao, Ying Ren, Liuyang Tian, Jian Cui, Ximei Liu, Lijun Zhang, Ying Chen Medicine (Baltimore). 2021 Apr 23;100(16):e25621. doi: 10.1097/MD.0000000000025621.
This study aimed to investigate the effects of the basic treatment for heart failure and sequential treatment with rh-brain natriuretic peptide (rhBNP) alone or the combination of rhBNP and sacubitril/valsartan. Cardiac structure, pulmonary artery pressure, inflammation and oxidative stress in patients with acute heart failure were evaluated.Three hundred patients with acute heart failure were included. According to the random number table method, the patients were divided into 3 groups of 100 patients per group: the standard treatment group (treated with an angiotensin-converting enzyme inhibitor, β receptor blocker, and corticosteroid antagonist), rhBNP group (basic treatment combined with rhBNP) and sequential treatment group (basic treatment for heart failure combined with rhBNP followed by sacubitril/valsartan). The changes in NT-probrain natriuretic peptide (BNP) levels, cardiac troponin T (cTnT) levels, cardiac structure, pulmonary artery pressure, and the levels inflammatory factors and oxidative stress factors were compared among the 3 groups at 1, 4, 12, and 36 weeks after treatment.The sequential treatment group displayed superior outcomes than the standard treatment group and the rhBNP group in terms of left atrium diameter, left ventricular end diastolic volume, left ventricular ejection fraction, pulmonary artery pressure, NT-proBNP levels, and cTnT levels, which respond to damage to the heart structure and myocardium. This result may be related to the decreased levels of inflammatory factors and the correction of oxidative stress imbalance.Sacubitril/valsartan significantly reduce the serum levels of inflammatory factors in patients with acute heart failure while decreasing the levels of oxidizing factors and increasing the levels of antioxidant factors. These changes may be one of the explanations for the better cardiac structure and better pulmonary artery pressure observed in the sequential treatment group.
3. Bio-conjugation of antioxidant peptide on surface-modified gold nanoparticles: a novel approach to enhance the radical scavenging property in cancer cell
Sushma Kalmodia, et al. Cancer Nanotechnol. 2016;7:1. doi: 10.1186/s12645-016-0013-x. Epub 2016 Feb 9.
Background: Functionalized gold nanoparticles are emerging as a promising nanocarrier for target specific delivery of the therapeutic molecules in a cancer cell, as a result it targeted selectively to the cancer cell and minimized the off-target effect. The functionalized nanomaterial (bio conjugate) brings novel functional properties, for example, the high payload of anticancer, antioxidant molecules and selective targeting of the cancer molecular markers. The current study reported the synthesis of multifunctional bioconjugate (GNPs-Pep-A) to target the cancer cell. Methods: The GNPs-Pep-A conjugate was prepared by functionalization of GNPs with peptide-A (Pro-His-Cys-Lys-Arg-Met; Pep-A) using thioctic acid as a linker molecule. The GNPs-Pep-A was characterized and functional efficacy was tested using Retinoblastoma (RB) cancer model in vitro. Results: The GNPs-Pep-A target the reactive oxygen species (ROS) in RB, Y79, cancer cell more effectively, and bring down the ROS up to 70 % relative to control (untreated cells) in vitro. On the other hand, Pep-A and GNPs showed 40 and 9 % reductions in ROS, respectively, compared to control. The effectiveness of bioconjugate indicates the synergistic effect, due to the coexistence of both organic (Pep-A) and inorganic phase (GNPs) in novel GNPs-Pep-A functional material. In addition to this, it modulates the mRNA expression of antioxidant genes glutathione peroxidase (GPX), superoxide dismutase (SOD) and catalase (CAT) by two-threefolds as observed. Conclusions: The effects of GNPs-Pep-A on ROS reduction and regulation of antioxidant genes confirmed that Vitis vinifera L. polyphenol-coated GNPs synergistically improve the radical scavenging properties and enhanced the apoptosis of cancer cell.
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