Synthesis and antitumor activity of novel pyridoxine-based structural analogs of saccharumoside-B

被引：5
作者：
Pugachev, Mikhail V. [1 ]
Agafonova, Maria N. [1 ]
Bastrikova, Oksana A. [1 ]
Gnezdilov, Oleg I. [2 ]
Nikishova, Tatyana V. [1 ]
Balakin, Konstantin V. [1 ]
Shtyrlin, Yurii G. [1 ]
机构：
[1] Kazan Volga Reg Fed Univ, Kremlyovskaya 18, Kazan 420008, Russia
[2] Russian Acad Sci, FRC Kazan Sci Ctr, Zavoisky Phys Tech Inst, Kazan 420111, Russia
来源：
MEDICINAL CHEMISTRY RESEARCH | 2021年 / 30卷 / 05期
关键词：
Drug discovery; Pyridoxine; Vitamin B-6; Saccharumoside-B; Antitumor activity; Cytotoxicity;
D O I：
10.1007/s00044-021-02719-4
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of 11 new pyridoxine-based structural analogs of saccharumoside-B were obtained using original synthetic approach. Antitumor activity of these compounds against nine human tumor cell lines (MCF-7, MDA-MB-231, A-498, SNB-19, M-14, NCI-H322M, HCT-115, HCT-116, and PC-3) was studied, and cytotoxic activity to three normal (HEK-293, Chang Liver, and MSC) cell lines was evaluated. Among the synthesized compounds, 12d, 12e, 13b, 13d, 13e, and 14 exhibited the highest antitumor activity, comparable to that of camptothecin and doxorubicin, but with significantly increased selectivity toward tumor cells. [GRAPHICS] .
引用
收藏
页码：1139 / 1150
页数：12
相关论文
共 34 条
  • [1] Development of pyrrolo[2,1-c][1,4]benzodiazepine β-glucoside prodrugs for selective therapy of cancer
    Adiyala, Praveen Reddy
    Tekumalla, Venkatesh
    Bin Sayeed, Ibrahim
    Nayak, V. Lakshma
    Nagarajan, Apoorva
    Shareef, Mohd Adil
    Nagaraju, Burri
    Kamal, Ahmed
    [J]. BIOORGANIC CHEMISTRY, 2018, 76 : 288 - 293
  • [2] Evaluation of salicin as an antipyretic prodrug that does not cause gastric injury
    Akao, T
    Yoshino, T
    Kobashi, K
    Hattori, M
    [J]. PLANTA MEDICA, 2002, 68 (08) : 714 - 718
  • [3] Synthetic analogues of durantoside I from Citharexylum spinosum L. and their cytotoxic activity
    Apisornopas, Jutamas
    Silalai, Patamawadee
    Kasemsuk, Teerapich
    Athipornchai, Anan
    Sirion, Uthaiwan
    Suksen, Kanoknetr
    Piyachaturawat, Pawinee
    Suksamrarn, Apichart
    Saeeng, Rungnapha
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2018, 28 (09) : 1558 - 1561
  • [4] Antiviral activity and interaction mechanisms study of novel glucopyranoside derivatives
    Chen, Meihang
    Hu, Deyu
    Li, Xiangyang
    Yang, Song
    Zhang, Weiying
    Li, Pei
    Song, Baoan
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (18) : 3840 - 3844
  • [5] An efficient synthesis of benzofurans and their application in the preparation of natural products of the genus Calea
    Cruz, MD
    Tamariz, J
    [J]. TETRAHEDRON, 2005, 61 (42) : 10061 - 10072
  • [6] PLATINUM(II) COMPLEXES CONJUGATED AND ANALOGOUS TO O-GLYCOSIDES: SYNTHESIS, STRUCTURAL CHARACTERIZATION AND ANTITUMOR ACTIVITY
    de Lima, Lidiane M. A.
    Santos, Mirelly D. F.
    Albuquerque, Leonardo S.
    Belian, Monica F.
    Silva, Wagner E.
    Filho, Joao R. F.
    Santos, Jandyson M.
    Aguiar, Jaciana S.
    da Silva, Teresinha G.
    [J]. QUIMICA NOVA, 2020, 43 (06): : 752 - 759
  • [7] Regioselective Protection of Sugars Catalyzed by Dimethyltin Dichloride
    Demizu, Yosuke
    Kubo, Yuki
    Miyoshi, Hiroko
    Maki, Toshihide
    Matsumura, Yoshihiro
    Moriyama, Noriaki
    Onomura, Osamu
    [J]. ORGANIC LETTERS, 2008, 10 (21) : 5075 - 5077
  • [8] Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A
    Duc Thinh Khong
    Judeh, Zaher M. A.
    [J]. TETRAHEDRON LETTERS, 2017, 58 (01) : 109 - 111
  • [9] Synthesis and biological evaluation of the glycoside (25R)-3β,16β-diacetoxy-22-oxocholest-5-en-26-yl β-D-glucopyranoside: A selective anticancer agent in cervicouterine cell lines
    Fernandez-Herrera, Maria A.
    Lopez-Munoz, Hugo
    Hernandez-Vazquez, Jose M. V.
    Lopez-Davila, Moises
    Mohan, Sankar
    Escobar-Sanchez, Maria L.
    Sanchez-Sanchez, Luis
    Pinto, B. Mario
    Sandoval-Ramirez, Jesus
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) : 3877 - 3886
  • [10] Enhancement of antiproliferative activity by molecular simplification of catalpol
    Garcia, Celina
    Leon, Leticia G.
    Pungitore, Carlos R.
    Rios-Luci, Carla
    Daranas, Antonio H.
    Montero, Juan C.
    Pandiella, Atanasio
    Tonn, Carlos E.
    Martin, Victor S.
    Padron, Jose M.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (07) : 2515 - 2523
1234