Citation:
Jin-Hong Liu, Zi-Fei Zhu, Jia Tang, Ai-Qin Jiang, Liu-Fang Hu, Li Chen. Novel NO-releasing derivatives of betulinic acid with antitumor activity[J]. Chinese Chemical Letters,
;2015, 26(6): 759-762.
doi:
10.1016/j.cclet.2015.04.002
-
Thirteen novel NO-releasing derivatives of betulinic acid (BA) bearing two types of NO-donors (nitrates and furoxans) were synthesized and evaluated for their antitumor activity. The results showed that furoxan-based derivatives exhibited higher antitumor activity than nitrate-based derivatives, with compounds 11a and 11b displaying promising potency against B16 cell lines and HepG2 cell lines (IC50 < 1 μmol/L). Wesupposed that NO-releasing amount of these derivatives which can be detected by Griess method may contribute more to their antitumor activity. As a result, furoxan-based derivatives released larger amount of NO than that of nitrate-based derivatives, which partially explained the higher anti-tumor activity of the former.
-
Keywords:
- Betulinic acid (BA),
- Derivatives,
- NO-releasing,
- Anti-tumor,
- NO donors
-
-
-
[1]
[1] S. Moncada, Nitric oxide: discovery and impact on clinical medicine, J. R. Soc. Med. 92 (1999) 164-169.
-
[2]
[2] P.J. Andrew, B. Mayer, Enzymatic function of nitric oxide synthases, Cardiovasc. Res. 43 (1999) 521-531.
-
[3]
[3] J.O. Lundberg, E. Weitzberg, NO generation from nitrite and its role in vascular control, Arterioscler. Thromb. Vasc. Biol. 25 (2005) 915-922.
-
[4]
[4] R.M. Touyz, E.L. Schiffrin, Reactive oxygen species in vascular biology: implications in hypertension, Histochem. Cell Biol. 122 (2004) 339-352.
-
[5]
[5] J.E. Albina, J.S. Reichner, Role of nitric oxide in mediation of macrophage cytotoxicity and apoptosis, Cancer Metastasis Rev. 17 (1998) 39-53.
-
[6]
[6] F. Dodd, M. Limoges, R.T.M. Boudreau, et al., L-Arginine inhibits apoptosis via a NO-dependent mechanism in Nb2 lymphoma cells, J. Cell. Biochem. 77 (2000) 624-634.
-
[7]
[7] L.A. Ridnour, K.M. Barasch, A.N. Windhausen, et al., Nitric oxide synthase and breast cancer: role of TIMP-1 in NO-mediated Akt activation, PLoS ONE 7 (2012) e44081.
-
[8]
[8] V. Umansky, V. Schirrmacher, Nitric oxide-induced apoptosis in tumor cells, Adv. Cancer Res. 82 (2001) 107-131.
-
[9]
[9] D.D. Thomas, M.G. Espey, L.A. Ridnour, et al., Hypoxic inducible factor 1a, extracellular signal-regulated kinase, and p53 are regulated by distinct threshold concentrations of nitric oxide, Proc. Natl. Acad. Sci. U. S. A. 101 (2004) 8894-8899.
-
[10]
[10] L.A. Ridnour, D.D. Thomas, C. Switzer, et al., Molecular mechanisms for discrete nitric oxide levels in cancer, Nitric Oxide 19 (2008) 73-76.
-
[11]
[11] S. Mocellin, V. Bronte, D. Nitti, Nitric oxide, a double edged sword in cancer biology: searching for therapeutic opportunities, Med. Res. Rev. 27 (2007) 317-352.
-
[12]
[12] S. Korde Choudhari, G. Sridharan, A. Gadbail, V. Poornima, Nitric oxide and oral cancer: a review, Oral Oncol. 48 (2012) 475-483.
-
[13]
[13] S.Y. Ryu, S.U. Choi, S.H. Lee, et al., Antitumor triterpenes from medicinal plants, Arch. Pharm. Res. 17 (1994) 375-377.
-
[14]
[14] Y. Kashiwada, F. Hashimoto, L.M. Cosentino, et al., Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents, J. Med. Chem. 39 (1996) 1016-1017.
-
[15]
[15] F. Li, R. Goila-Gaur, K. Salzwedel, et al., PA-457: a potent HIV inhibitor that disrupts core condensation by targeting a late step in Gag processing, Proc. Natl. Acad. Sci. U. S. A. 100 (2003) 13555-13560.
-
[16]
[16] E. Pisha, H. Chai, I.S. Lee, et al., Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis, Nat. Med. 1 (1995) 1046-1051.
-
[17]
[17] L. Fang, Y.H. Zhang, J. Lehmann, et al., Design and synthesis of furoxan-based nitric oxide-releasing glucocorticoid derivatives with potent anti-inflammatory activity and improved safety, Bioorg. Med. Chem. Lett. 17 (2007) 1062-1066.
-
[1]
-
-
-
[1]
Yang Liu , Yan Liu , Kaiyin Yang , Zhiruo Zhang , Wenbo Zhang , Bingyou Yang , Hua Li , Lixia Chen . A selective HK2 degrader suppresses SW480 cancer cell growth by degrading HK2. Chinese Chemical Letters, 2024, 35(8): 109264-. doi: 10.1016/j.cclet.2023.109264
-
[2]
Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
-
[3]
Xiaoru LIU , Jinlian SHI , Yajia ZHENG , Shuangcun MO , Zhongxuan XU . Two Ni-based frameworks with helices and dinuclear units constructed from semi-rigid carboxylic acid and imidazole derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 797-808. doi: 10.11862/CJIC.20240328
-
[4]
Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
-
[5]
Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
-
[6]
Shunyu Wang , Yanan Zhu , Yang Zhao , Wanli Nie , Hong Meng . Steric effects and electronic manipulation of multiple donors on S0/S1 transition of Dn-A emitters. Chinese Chemical Letters, 2025, 36(4): 110555-. doi: 10.1016/j.cclet.2024.110555
-
[7]
Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
-
[8]
Fangwen Peng , Zhen Luo , Yingjin Ma , Haibo Ma . Theoretical study of aromaticity reversal in dimethyldihydropyrene derivatives. Chinese Journal of Structural Chemistry, 2024, 43(5): 100273-100273. doi: 10.1016/j.cjsc.2024.100273
-
[9]
Yadan SUN , Xinfeng LI , Qiang LIU , Oshio Hiroki , Yinshan MENG . Structures and magnetism of dinuclear Co complexes based on imine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2212-2220. doi: 10.11862/CJIC.20240131
-
[10]
Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
-
[11]
Fei-Yan Gao , Yan Wu , Ling Yang , Zhong-Yi Ma , Yi Chen , Xiao-Man Mao , Xu-Fei Bian , Pei Tang , Chong Li . Orally delivered berberine derivatives for dual therapy in diabetic complications with MRSA infections. Chinese Chemical Letters, 2025, 36(4): 109917-. doi: 10.1016/j.cclet.2024.109917
-
[12]
Fengyun Li , Zerong Pei , Shuting Chen , Gen li , Mengyang Liu , Liqin Ding , Jingbo Liu , Feng Qiu . Multifunctional nano-herb based on tumor microenvironment for enhanced tumor therapy of gambogic acid. Chinese Chemical Letters, 2024, 35(5): 108752-. doi: 10.1016/j.cclet.2023.108752
-
[13]
Shuying Li , Weiwei ZhuGe , Xuan Sun , Chongzhen Sun , Zhaojun Liu , Chenghe Xiong , Min Xiao , Guofeng Gu . Convergent synthesis and immunological study of oligosaccharide derivatives related to galactomannan from Antrodia cinnamomea. Chinese Chemical Letters, 2024, 35(5): 109089-. doi: 10.1016/j.cclet.2023.109089
-
[14]
Tao Wei , Jiahao Lu , Pan Zhang , Qi Zhang , Guang Yang , Ruizhi Yang , Daifen Chen , Qian Wang , Yongfu Tang . An intermittent lithium deposition model based on bimetallic MOFs derivatives for dendrite-free lithium anode with ultrahigh areal capacity. Chinese Chemical Letters, 2024, 35(8): 109122-. doi: 10.1016/j.cclet.2023.109122
-
[15]
Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
-
[16]
Jun-Ming Cao , Kai-Yang Zhang , Jia-Lin Yang , Zhen-Yi Gu , Xing-Long Wu . Differential bonding behaviors of sodium/potassium-ion storage in sawdust waste carbon derivatives. Chinese Chemical Letters, 2024, 35(4): 109304-. doi: 10.1016/j.cclet.2023.109304
-
[17]
Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
-
[18]
Liping Zhao , Xixi Guo , Zhimeng Zhang , Xi Lu , Qingxuan Zeng , Tianyun Fan , Xintong Zhang , Fenbei Chen , Mengyi Xu , Min Yuan , Zhenjun Li , Jiandong Jiang , Jing Pang , Xuefu You , Yanxiang Wang , Danqing Song . Novel berberine derivatives as adjuvants in the battle against Acinetobacter baumannii: A promising strategy for combating multi-drug resistance. Chinese Chemical Letters, 2024, 35(10): 109506-. doi: 10.1016/j.cclet.2024.109506
-
[19]
Yu Hong , Yuqian Jiang , Chenhuan Yuan , Decai Wang , Yimeng Sun , Jian Jiang . Unraveling temperature-dependent supramolecular polymorphism of naphthalimide-substituted benzene-1,3,5-tricarboxamide derivatives. Chinese Chemical Letters, 2024, 35(12): 109909-. doi: 10.1016/j.cclet.2024.109909
-
[20]
Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(619)
- HTML views(4)