Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines

Halil ŞENOL, (Bezmialem Vakıf Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Bölümü, İstanbul, Türkiye)
Aydan DAĞ, (Bezmialem Vakıf Üniversitesi, Eczacılık Fakültesi, Farmasötik Kimya Bölümü, İstanbul, Türkiye)
Kübra ÇOKULUDAĞ, (Bezmialem Vakıf Üniversitesi ,Eczacılık Fakültesi, İstanbul, Türkiye)
Asude Sena AKTAŞ, (Bezmialem Vakıf Üniversitesi ,Eczacılık Fakültesi, İstanbul, Türkiye)
Sezen ATASOY, (Bezmialem Vakıf Üniversitesi ,Eczacılık Fakültesi ,Biyokimya Anabilim Dalı,İstanbul, Türkiye)
Gülaçtı TOPÇU (Bezmialem Vakıf Üniversitesi ,Eczacılık Fakültesi ,Farmakognozi Anabilim Dalı,İstanbul, Türkiye)
Organic Communications
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Yıl: 2020 Cilt: 13 Sayı: 3 Sayfa Aralığı: 114 - 126 Metin Dili: İngilizce DOI: 10.25135/acg.oc.84.20.09.1792 İndeks Tarihi: 02-11-2020

Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines

Öz:
In this study, 12 new oleanane and ursane derivative triterpene compounds,havingfatty acids in the form of esters with carbon numbers of 12, 13, 18, 19, 24 and 25,were synthesized starting from naturalproductsoleanolic and ursolic acids. Initially,3-methylerythrodiol (3β-methoxyolean-12-en-28-ol) and 3-methyluvaol(3β-methoxyurs-12-en-28-ol) were synthesized from oleanolic acid and ursolic acid,respectively. For this purpose,secondary OH group at C-3 of oleanolic and ursolic acidswereprotected as methyl ether and,then,theircarboxylic acidmoietieswere reduced by aluminum hydride. New fatty acid derivatives5a-fand 8a-fwere synthesized through thereaction of 3-methylerythrodiol/3-methyluvaol and corresponding fatty acid halides. In vitrocytotoxic activitiesof the all synthesized compoundswere investigated on 3T3 fibroblast cells and PC3 prostate cancer cell lines. While all the compounds showedat least 70% inhibition on PC3 prostate cancer cells at a concentration of 25 μM, theyhadaverage of 50% inhibition on 3T3 fibroblast human healthy cells at the same concentration.Compounds5cand 8cdemonstrated the least toxic effect on 3T3 fibroblast human healthy cells and the highest toxic effect on PC3 prostate cancer cellsat a concentration of 12.5 μM.Moreover, compounds 8cand 8ehad the least toxic effect on 3T3 fibroblast human healthy cells and the highest toxic effect on PC3 prostate cancer cells at the same concentration.
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APA ŞENOL H, Dag A, Çokuludağ K, Aktaş A, Atasoy S, Topcu G (2020). Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines. , 114 - 126. 10.25135/acg.oc.84.20.09.1792
Chicago ŞENOL Halil,Dag Aydan,Çokuludağ Kübra,Aktaş Asude Sena,Atasoy Sezen,Topcu Gulacti Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines. (2020): 114 - 126. 10.25135/acg.oc.84.20.09.1792
MLA ŞENOL Halil,Dag Aydan,Çokuludağ Kübra,Aktaş Asude Sena,Atasoy Sezen,Topcu Gulacti Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines. , 2020, ss.114 - 126. 10.25135/acg.oc.84.20.09.1792
AMA ŞENOL H,Dag A,Çokuludağ K,Aktaş A,Atasoy S,Topcu G Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines. . 2020; 114 - 126. 10.25135/acg.oc.84.20.09.1792
Vancouver ŞENOL H,Dag A,Çokuludağ K,Aktaş A,Atasoy S,Topcu G Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines. . 2020; 114 - 126. 10.25135/acg.oc.84.20.09.1792
IEEE ŞENOL H,Dag A,Çokuludağ K,Aktaş A,Atasoy S,Topcu G "Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines." , ss.114 - 126, 2020. 10.25135/acg.oc.84.20.09.1792
ISNAD ŞENOL, Halil vd. "Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines". (2020), 114-126. https://doi.org/10.25135/acg.oc.84.20.09.1792
APA ŞENOL H, Dag A, Çokuludağ K, Aktaş A, Atasoy S, Topcu G (2020). Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines. Organic Communications, 13(3), 114 - 126. 10.25135/acg.oc.84.20.09.1792
Chicago ŞENOL Halil,Dag Aydan,Çokuludağ Kübra,Aktaş Asude Sena,Atasoy Sezen,Topcu Gulacti Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines. Organic Communications 13, no.3 (2020): 114 - 126. 10.25135/acg.oc.84.20.09.1792
MLA ŞENOL Halil,Dag Aydan,Çokuludağ Kübra,Aktaş Asude Sena,Atasoy Sezen,Topcu Gulacti Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines. Organic Communications, vol.13, no.3, 2020, ss.114 - 126. 10.25135/acg.oc.84.20.09.1792
AMA ŞENOL H,Dag A,Çokuludağ K,Aktaş A,Atasoy S,Topcu G Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines. Organic Communications. 2020; 13(3): 114 - 126. 10.25135/acg.oc.84.20.09.1792
Vancouver ŞENOL H,Dag A,Çokuludağ K,Aktaş A,Atasoy S,Topcu G Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines. Organic Communications. 2020; 13(3): 114 - 126. 10.25135/acg.oc.84.20.09.1792
IEEE ŞENOL H,Dag A,Çokuludağ K,Aktaş A,Atasoy S,Topcu G "Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines." Organic Communications, 13, ss.114 - 126, 2020. 10.25135/acg.oc.84.20.09.1792
ISNAD ŞENOL, Halil vd. "Synthesis of new fatty acid derivatives of oleanane and ursane triterpenoids and investigation of their in vitrocytotoxic effects on 3T3 fibroblast and PC3 prostate cancer cell lines". Organic Communications 13/3 (2020), 114-126. https://doi.org/10.25135/acg.oc.84.20.09.1792
Sayfa Oluşturulma Tarihi
23-04-2024 14:39

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