Home / Publications / Synthesis, physicochemical properties and in vitro cytotoxic activity of aziridine-containing derivatives of 1,3,5-triazine

Synthesis, physicochemical properties and in vitro cytotoxic activity of aziridine-containing derivatives of 1,3,5-triazine

Olga Vladislavovna Mikolaichuk 1, 2
Olga Vladislavovna Mikolaichuk
, 
Alexandra Vladimirovna Protas 1, 2
Alexandra Vladimirovna Protas
, 
Elena Aleksandrovna Popova 1, 2
Elena Aleksandrovna Popova
, 
Olga Sergeevna Shemchuk 1
Olga Sergeevna Shemchuk
, 
Mikhail Denisovich Luttsev 1
Mikhail Denisovich Luttsev
, 
Daler Raufovich Dadadzhanov 3
Daler Raufovich Dadadzhanov
, 
Tigran Armenakovich Vartanyan 3
Tigran Armenakovich Vartanyan
, 
Andrey Vitalievich Petrov 4
Andrey Vitalievich Petrov
, 
Vladimir Vladimirovich Sharoyko 1, 2, 4
Vladimir Vladimirovich Sharoyko
, 
Konstantin Nikolaevich Semenov 1, 2, 4
Konstantin Nikolaevich Semenov
, 
Oleg Evgen'evich Molchanov 2
Oleg Evgen'evich Molchanov
, 
Dmitrii Nikolaevich Maistrenko 2
Dmitrii Nikolaevich Maistrenko
1 I.P. Pavlov First St. Petersburg State Medical University, St. Petersburg, Russian Federation
2 A.M. Granov Russian Research Center for Radiology and Surgical Technologies, St. Petersburg, Russian Federation
3 Infochemistry Scientific Center, ITMO University, St. Petersburg, Russian Federation
4 Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
10.1016/j.mencom.2024.10.028
Published 2024-10-22
Communication , Volume 34, Issue 6, 859-861
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Mikolaichuk O. V. et al. Synthesis, physicochemical properties and in vitro cytotoxic activity of aziridine-containing derivatives of 1,3,5-triazine // Mendeleev Communications. 2024. Vol. 34. No. 6. pp. 859-861.
GOST all authors (up to 50) Copy
Mikolaichuk O. V., Protas A. V., Popova E. A., Shemchuk O. S., Luttsev M. D., Dadadzhanov D. R., Vartanyan T. A., Petrov A. V., Sharoyko V. V., Semenov K. N., Molchanov O. E., Maistrenko D. N. Synthesis, physicochemical properties and in vitro cytotoxic activity of aziridine-containing derivatives of 1,3,5-triazine // Mendeleev Communications. 2024. Vol. 34. No. 6. pp. 859-861.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2024.10.028
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.028
TI - Synthesis, physicochemical properties and in vitro cytotoxic activity of aziridine-containing derivatives of 1,3,5-triazine
T2 - Mendeleev Communications
AU - Mikolaichuk, Olga Vladislavovna
AU - Protas, Alexandra Vladimirovna
AU - Popova, Elena Aleksandrovna
AU - Shemchuk, Olga Sergeevna
AU - Luttsev, Mikhail Denisovich
AU - Dadadzhanov, Daler Raufovich
AU - Vartanyan, Tigran Armenakovich
AU - Petrov, Andrey Vitalievich
AU - Sharoyko, Vladimir Vladimirovich
AU - Semenov, Konstantin Nikolaevich
AU - Molchanov, Oleg Evgen'evich
AU - Maistrenko, Dmitrii Nikolaevich
PY - 2024
DA - 2024/10/22
PB - Mendeleev Communications
SP - 859-861
IS - 6
VL - 34
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2024_Mikolaichuk,
author = {Olga Vladislavovna Mikolaichuk and Alexandra Vladimirovna Protas and Elena Aleksandrovna Popova and Olga Sergeevna Shemchuk and Mikhail Denisovich Luttsev and Daler Raufovich Dadadzhanov and Tigran Armenakovich Vartanyan and Andrey Vitalievich Petrov and Vladimir Vladimirovich Sharoyko and Konstantin Nikolaevich Semenov and Oleg Evgen'evich Molchanov and Dmitrii Nikolaevich Maistrenko},
title = {Synthesis, physicochemical properties and in vitro cytotoxic activity of aziridine-containing derivatives of 1,3,5-triazine},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.028},
number = {6},
pages = {859--861},
doi = {10.1016/j.mencom.2024.10.028}
}
MLA
Cite this
MLA Copy
Mikolaichuk, Olga Vladislavovna, et al. “Synthesis, physicochemical properties and in vitro cytotoxic activity of aziridine-containing derivatives of 1,3,5-triazine.” Mendeleev Communications, vol. 34, no. 6, Oct. 2024, pp. 859-861. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.10.028.

Keywords

1
2-a][1
3
5-triazine
5]triazine
aziridine
biocompatibility
cyanuric chloride
cytotoxic activity.
imidazo[1
interaction with DNA
physicochemical properties

Abstract

6-{[4-(Aziridin-1-yl)-6-chloro-1,3,5-triazin-2-yl]amino}-hexanoic acid methyl ester and sodium salt were synthesized from cyanuric chloride. The sodium salt would interact with free radicals of 2,2-diphenyl-1-picrylhydrazyl (DPPH) and inhibit hemolysis induced by Radachlorin. Both compounds interact with DNA with Kbin values of 1.09 × 107 and 0.99 × 107 dm3 mol−1, respectively; they also demonstrate cytotoxic activity against human cancer cell lines.

References

.
1,3,5-Triazines: A promising scaffold for anticancer drugs development
Cascioferro S., Parrino B., Spanò V., Carbone A., Montalbano A., Barraja P., Diana P., Cirrincione G.
European Journal of Medicinal Chemistry, 2017
.
Studying non-covalent drug–DNA interactions
Rehman S.U., Sarwar T., Husain M.A., Ishqi H.M., Tabish M.
Archives of Biochemistry and Biophysics, 2015
.
Synthesis and Biological Activity of Fullerenols with Various Contents of Hydroxyl Groups
Eropkin M.Y., Melenevskaya E.Y., Nasonova K.V., Bryazzhikova T.S., Eropkina E.M., Danilenko D.M., Kiselev O.I.
Pharmaceutical Chemistry Journal, 2013
.
5-(4,6-Dimorpholino-1,3,5-triazin-2-yl)-4-(trifluoromethyl)pyridin-2-amine (PQR309), a Potent, Brain-Penetrant, Orally Bioavailable, Pan-Class I PI3K/mTOR Inhibitor as Clinical Candidate in Oncology
Beaufils F., Cmiljanovic N., Cmiljanovic V., Bohnacker T., Melone A., Marone R., Jackson E., Zhang X., Sele A., Borsari C., Mestan J., Hebeisen P., Hillmann P., Giese B., Zvelebil M., et. al.
Journal of Medicinal Chemistry, 2017
.
Discovery and Preclinical Characterization of 5-[4,6-Bis({3-oxa-8-azabicyclo[3.2.1]octan-8-yl})-1,3,5-triazin-2-yl]-4-(difluoromethyl)pyridin-2-amine (PQR620), a Highly Potent and Selective mTORC1/2 Inhibitor for Cancer and Neurological Disorders
Rageot D., Bohnacker T., Melone A., Langlois J., Borsari C., Hillmann P., Sele A.M., Beaufils F., Zvelebil M., Hebeisen P., Löscher W., Burke J., Fabbro D., Wymann M.P.
Journal of Medicinal Chemistry, 2018
.
Hybrid molecules based on 1,3,5‐triazine as potential therapeutics: A focused review
Prasher P., Sharma M., Aljabali A.A., Gupta G., Negi P., Kapoor D.N., Singh I., Zacconi F.C., Jesus Andreoli Pinto T., Silva M.W., Bakshi H.A., Chellappan D.K., Tambuwala M.M., Dua K.
Drug Development Research, 2020
.
Recent Advances on the s‐Triazine Scaffold with Emphasis on Synthesis, Structure‐Activity and Pharmacological Aspects: A Concise Review
Majeed Ganai A., Khan Pathan T., Hampannavar G.A., Pawar C., Obakachi V.A., Kushwaha B., Deshwar Kushwaha N., Karpoormath R.
ChemistrySelect, 2021
.
1,3,5‐Triazine: A versatile pharmacophore with diverse biological activities
Singh S., Mandal M.K., Masih A., Saha A., Ghosh S.K., Bhat H.R., Singh U.P.
Archiv der Pharmazie, 2021
.
Risk of Subsequent Malignant Neoplasms in Long-Term Hereditary Retinoblastoma Survivors After Chemotherapy and Radiotherapy
Wong J.R., Morton L.M., Tucker M.A., Abramson D.H., Seddon J.M., Sampson J.N., Kleinerman R.A.
Journal of Clinical Oncology, 2014
.
The cellular effects of novel triazine nitrogen mustards in glioblastoma LBC3, LN-18 and LN-229 cell lines
Krętowski R., Drozdowska D., Kolesińska B., Kamiński Z., Frączyk J., Cechowska-Pasko M.
Investigational New Drugs, 2019
.
Triazine as a promising scaffold for its versatile biological behavior
Singla P., Luxami V., Paul K.
European Journal of Medicinal Chemistry, 2015
.
Discovery of novel 1,3,5-triazine derivatives as potent inhibitor of cervical cancer via dual inhibition of PI3K/mTOR
Hu J., Zhang Y., Tang N., Lu Y., Guo P., Huang Z.
Bioorganic and Medicinal Chemistry, 2021
.
Triazines, tetrazines, and fused ring polyaza systems
Hiebel M., Suzenet F.
Progress in Heterocyclic Chemistry, 2021
.
Mikolaichuk O.V., Shemchuk O.S., Protas A.V., Popova E.A., Ostrovskii V.A., Maystrenko D.N., Molchanov O.E., Sharoyko V.V., Semenov K.N.
Mendeleev Communications, 2023