Literature DB >> 26005543

Bis-arylidene oxindole-betulinic Acid conjugate: a fluorescent cancer cell detector with potent anticancer activity.

Abhishek Pal1, Anirban Ganguly2, Sumit Chowdhuri3, Md Yousuf3, Avijit Ghosh3, Ayan Kumar Barui2, Rajesh Kotcherlakota2, Susanta Adhikari3, Rajkumar Banerjee2.   

Abstract

Molecules offering simultaneous detection and killing of cancer cells are advantageous. Hybrid of cancer cell-selective, ROS generator betulinic acid and bis-arylidene oxindole with amino propyl-linker is developed. With intrinsic fluorescence, the molecule exhibited cancer cell-specific residence. Further, it generated ROS, triggered apoptosis, and exhibited potent cytotoxicity in cancer cells selectively. We demonstrate the first example and use of isatins as betulinic acid conjugate for selective detection of cancer and subsequent killing of cancer cells via apoptosis.

Entities:  

Keywords:  Fluorescent oxindole; ROS; apoptosis; betulinic acid; cancer cell detection

Year:  2015        PMID： 26005543      PMCID： PMC4434463          DOI： 10.1021/acsmedchemlett.5b00095

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  25 in total

Review 1.  The hallmarks of cancer.

Authors:  D Hanahan; R A Weinberg
Journal:  Cell       Date:  2000-01-07       Impact factor: 41.582

2.  A specific fluorogenic reaction for tryptophan residues using isatin in organic solvents.

Authors:  C I Trigoso; N Ibañez; J C Stockert
Journal:  J Histochem Cytochem       Date:  1993-10       Impact factor: 2.479

3.  Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells.

Authors:  Valentina Zuco; Rosanna Supino; Sabina C Righetti; Loredana Cleris; Edoardo Marchesi; Carlo Gambacorti-Passerini; Franca Formelli
Journal:  Cancer Lett       Date:  2002-01-10       Impact factor: 8.679

4.  Bis-arylidene oxindoles as anti-breast-cancer agents acting via the estrogen receptor.

Authors:  Abhishek Pal; Anirban Ganguly; Avijit Ghosh; Md Yousuf; Bhowmira Rathore; Rajkumar Banerjee; Susanta Adhikari
Journal:  ChemMedChem       Date:  2014-01-31       Impact factor: 3.466

5.  Betulinic acid-induced programmed cell death in human melanoma cells involves mitogen-activated protein kinase activation.

Authors:  YingMeei Tan; Rong Yu; John M Pezzuto
Journal:  Clin Cancer Res       Date:  2003-07       Impact factor: 12.531

Review 6.  ROS stress in cancer cells and therapeutic implications.

Authors:  Helene Pelicano; Dennis Carney; Peng Huang
Journal:  Drug Resist Updat       Date:  2004-04       Impact factor: 18.500

7.  Cooperation of betulinic acid and TRAIL to induce apoptosis in tumor cells.

Authors:  Simone Fulda; Irmela Jeremias; Klaus-Michael Debatin
Journal:  Oncogene       Date:  2004-10-07       Impact factor: 9.867

8.  Betulinic acid: a new cytotoxic compound against malignant head and neck cancer cells.

Authors:  Dietmar Thurnher; Dritan Turhani; Martina Pelzmann; Bettina Wannemacher; Birgit Knerer; Michael Formanek; Volker Wacheck; Edgar Selzer
Journal:  Head Neck       Date:  2003-09       Impact factor: 3.147

9.  Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis.

Authors:  E Pisha; H Chai; I S Lee; T E Chagwedera; N R Farnsworth; G A Cordell; C W Beecher; H H Fong; A D Kinghorn; D M Brown
Journal:  Nat Med       Date:  1995-10       Impact factor: 53.440

10.  Betulinic acid augments the inhibitory effects of vincristine on growth and lung metastasis of B16F10 melanoma cells in mice.

Authors:  N Sawada; K Kataoka; K Kondo; H Arimochi; H Fujino; Y Takahashi; T Miyoshi; T Kuwahara; Y Monden; Y Ohnishi
Journal:  Br J Cancer       Date:  2004-04-19       Impact factor: 7.640
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  7 in total

1.  Synthesis, Biological Evaluation of Fluorescent 23-Hydroxybetulinic Acid Probes, and Their Cellular Localization Studies.

Authors:  Hong Yao; Guoxiang Wei; Yanpeng Liu; Hequan Yao; Zheying Zhu; Wencai Ye; Xiaoming Wu; Jinyi Xu; Shengtao Xu
Journal:  ACS Med Chem Lett       Date:  2018-09-25       Impact factor: 4.345

2.  Betulinic acid attenuates liver fibrosis by inducing autophagy via the mitogen-activated protein kinase/extracellular signal-regulated kinase pathway.

Authors:  Yuan Liu; Yanmeng Bi; Chan Mo; Ting Zeng; Sha Huang; Lei Gao; Xuegang Sun; Zhiping Lv
Journal:  J Nat Med       Date:  2018-10-30       Impact factor: 2.343

3.  Synthesis and X-ray study of dispiro 8-nitroquinolone analogues and their cytotoxic properties against human cervical cancer HeLa cells.

Authors:  Selvaraj Shyamsivappan; Raju Vivek; Arjunan Saravanan; Thangaraj Arasakumar; Gopalan Subashini; Thangaraj Suresh; Ramasamy Shankar; Palathurai Subramaniam Mohan
Journal:  Medchemcomm       Date:  2019-01-22       Impact factor: 3.597

Review 4.  Recent Progress in the Development of Indole-Based Compounds Active against Malaria, Trypanosomiasis and Leishmaniasis.

Authors:  Paulo A F Pacheco; Maria M M Santos
Journal:  Molecules       Date:  2022-01-05       Impact factor: 4.411

Review 5.  Semisynthetic Derivatives of Pentacyclic Triterpenes Bearing Heterocyclic Moieties with Therapeutic Potential.

Authors:  Gabriela Nistor; Cristina Trandafirescu; Alexandra Prodea; Andreea Milan; Andreea Cristea; Roxana Ghiulai; Roxana Racoviceanu; Alexandra Mioc; Marius Mioc; Viviana Ivan; Codruța Șoica
Journal:  Molecules       Date:  2022-10-03       Impact factor: 4.927

6.  Structurally novel steroidal spirooxindole by241 potently inhibits tumor growth mainly through ROS-mediated mechanisms.

Authors:  Xiao-Jing Shi; Bin Yu; Jun-Wei Wang; Ping-Ping Qi; Kai Tang; Xin Huang; Hong-Min Liu
Journal:  Sci Rep       Date:  2016-08-16       Impact factor: 4.379

7.  Evaluation of Cytotoxicity and α-Glucosidase Inhibitory Activity of Amide and Polyamino-Derivatives of Lupane Triterpenoids.

Authors:  Oxana B Kazakova; Gul'nara V Giniyatullina; Akhat G Mustafin; Denis A Babkov; Elena V Sokolova; Alexander A Spasov
Journal:  Molecules       Date:  2020-10-20       Impact factor: 4.411
  7 in total

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