Novel derivatives of deoxycholic acid bearing aliphatic or cyclic diamine moieties at the C-3 position

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Novel derivatives of deoxycholic acid bearing aliphatic or cyclic diamine moieties at the C-3 position : Synthesis and evaluation of anti-proliferative activity. / Popadyuk, Irina I.; Markov, Andrey V.; Babich, Valeriya O. et al.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 27, No. 16, 15.08.2017, p. 3755-3759.

Research output: Contribution to journal › Article › peer-review

Harvard

Popadyuk, II, Markov, AV, Babich, VO, Salomatina, OV, Logashenko, EB, Zenkova, MA & Salakhutdinov, NF 2017, 'Novel derivatives of deoxycholic acid bearing aliphatic or cyclic diamine moieties at the C-3 position: Synthesis and evaluation of anti-proliferative activity', Bioorganic and Medicinal Chemistry Letters, vol. 27, no. 16, pp. 3755-3759. https://doi.org/10.1016/j.bmcl.2017.06.072

APA

Popadyuk, I. I., Markov, A. V., Babich, V. O., Salomatina, O. V., Logashenko, E. B., Zenkova, M. A., & Salakhutdinov, N. F. (2017). Novel derivatives of deoxycholic acid bearing aliphatic or cyclic diamine moieties at the C-3 position: Synthesis and evaluation of anti-proliferative activity. Bioorganic and Medicinal Chemistry Letters, 27(16), 3755-3759. https://doi.org/10.1016/j.bmcl.2017.06.072

Vancouver

Popadyuk II, Markov AV, Babich VO, Salomatina OV, Logashenko EB, Zenkova MA et al. Novel derivatives of deoxycholic acid bearing aliphatic or cyclic diamine moieties at the C-3 position: Synthesis and evaluation of anti-proliferative activity. Bioorganic and Medicinal Chemistry Letters. 2017 Aug 15;27(16):3755-3759. doi: 10.1016/j.bmcl.2017.06.072

Author

Popadyuk, Irina I. ; Markov, Andrey V. ; Babich, Valeriya O. et al. / Novel derivatives of deoxycholic acid bearing aliphatic or cyclic diamine moieties at the C-3 position : Synthesis and evaluation of anti-proliferative activity. In: Bioorganic and Medicinal Chemistry Letters. 2017 ; Vol. 27, No. 16. pp. 3755-3759.

BibTeX

@article{516fae80108d478b831a28384efd58c5,

title = "Novel derivatives of deoxycholic acid bearing aliphatic or cyclic diamine moieties at the C-3 position: Synthesis and evaluation of anti-proliferative activity",

abstract = "A new library of deoxycholic acid derivatives bearing nitrogen-containing moieties at the C-3 position was synthesised from epoxy derivative 1 via an epoxide ring-opening reaction promoted by aliphatic or cyclic diamines and fully characterised by NMR and mass-spectroscopy. The synthesised compounds were screened for cytotoxicity against four human tumour cell lines. The results showed that some of the novel diamine-bearing derivatives displayed improved anti-proliferative activities over the parent compound DCA. Among them, a 1-methylpiperazine containing compound (6) showed promising activity and the highest selectivity against tumour cells of enterohepatic origin (HepG2: IC50 = 3.6 µM, SI = 9.0; HuTu-80: IC50 = 4.6 µM, SI = 6.9) and was identified as a lead molecule.",

keywords = "Anti-proliferative activity, Cytotoxicity, Deoxycholic acid derivatives, Diamines, Epoxides, Humans, Diamines/chemical synthesis, Structure-Activity Relationship, Antineoplastic Agents/chemical synthesis, Dose-Response Relationship, Drug, Cell Line, Tumor, Molecular Structure, Cell Proliferation/drug effects, Deoxycholic Acid/chemical synthesis, Drug Screening Assays, Antitumor, CHOLIC-ACID, DESIGN, CELL-LINES, CANCER, CHAIN, AGENTS, ANTIMICROBIAL ACTIVITY, BILE-ACIDS, CARBONIC-ANHYDRASE INHIBITORS",

author = "Popadyuk, {Irina I.} and Markov, {Andrey V.} and Babich, {Valeriya O.} and Salomatina, {Oksana V.} and Logashenko, {Evgeniya B.} and Zenkova, {Marina A.} and Salakhutdinov, {Nariman F.}",

year = "2017",

month = aug,

day = "15",

doi = "10.1016/j.bmcl.2017.06.072",

language = "English",

volume = "27",

pages = "3755--3759",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "16",

}

RIS

TY - JOUR

T1 - Novel derivatives of deoxycholic acid bearing aliphatic or cyclic diamine moieties at the C-3 position

T2 - Synthesis and evaluation of anti-proliferative activity

AU - Popadyuk, Irina I.

AU - Markov, Andrey V.

AU - Babich, Valeriya O.

AU - Salomatina, Oksana V.

AU - Logashenko, Evgeniya B.

AU - Zenkova, Marina A.

AU - Salakhutdinov, Nariman F.

PY - 2017/8/15

Y1 - 2017/8/15

N2 - A new library of deoxycholic acid derivatives bearing nitrogen-containing moieties at the C-3 position was synthesised from epoxy derivative 1 via an epoxide ring-opening reaction promoted by aliphatic or cyclic diamines and fully characterised by NMR and mass-spectroscopy. The synthesised compounds were screened for cytotoxicity against four human tumour cell lines. The results showed that some of the novel diamine-bearing derivatives displayed improved anti-proliferative activities over the parent compound DCA. Among them, a 1-methylpiperazine containing compound (6) showed promising activity and the highest selectivity against tumour cells of enterohepatic origin (HepG2: IC50 = 3.6 µM, SI = 9.0; HuTu-80: IC50 = 4.6 µM, SI = 6.9) and was identified as a lead molecule.

AB - A new library of deoxycholic acid derivatives bearing nitrogen-containing moieties at the C-3 position was synthesised from epoxy derivative 1 via an epoxide ring-opening reaction promoted by aliphatic or cyclic diamines and fully characterised by NMR and mass-spectroscopy. The synthesised compounds were screened for cytotoxicity against four human tumour cell lines. The results showed that some of the novel diamine-bearing derivatives displayed improved anti-proliferative activities over the parent compound DCA. Among them, a 1-methylpiperazine containing compound (6) showed promising activity and the highest selectivity against tumour cells of enterohepatic origin (HepG2: IC50 = 3.6 µM, SI = 9.0; HuTu-80: IC50 = 4.6 µM, SI = 6.9) and was identified as a lead molecule.

KW - Anti-proliferative activity

KW - Cytotoxicity

KW - Deoxycholic acid derivatives

KW - Diamines

KW - Epoxides

KW - Humans

KW - Diamines/chemical synthesis

KW - Structure-Activity Relationship

KW - Antineoplastic Agents/chemical synthesis

KW - Dose-Response Relationship, Drug

KW - Cell Line, Tumor

KW - Molecular Structure

KW - Cell Proliferation/drug effects

KW - Deoxycholic Acid/chemical synthesis

KW - Drug Screening Assays, Antitumor

KW - CHOLIC-ACID

KW - DESIGN

KW - CELL-LINES

KW - CANCER

KW - CHAIN

KW - AGENTS

KW - ANTIMICROBIAL ACTIVITY

KW - BILE-ACIDS

KW - CARBONIC-ANHYDRASE INHIBITORS

UR - http://www.scopus.com/inward/record.url?scp=85021831648&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2017.06.072

DO - 10.1016/j.bmcl.2017.06.072

M3 - Article

C2 - 28688958

AN - SCOPUS:85021831648

VL - 27

SP - 3755

EP - 3759

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 16

ER -

ID: 9561011