Synthesis of some novel hydrazide-hydrazones derived from etodolac as potential anti-prostate cancer agents

İrem Atlıhan; Oya Orun; Ş.güniz Küçükgüzel

Makale detayları

Synthesis of some novel hydrazide-hydrazones derived from etodolac as potential anti-prostate cancer agents

Yazarlar:

İrem Atlıhan | Oya Orun | Ş.güniz Küçükgüzel

Yayıncı:

Marmara University

Ana Başlıklar:

Pharmaceutical Chemistry

Dergi:

Journal of Research in Pharmacy Vol.26 Issue 1, pp.1-12

Belge Tipi:

Makale

Yayın Tarihi:

6/2025

Belge Dili:

İngilizce

Document ID (Org No.):

2001346098

pISSN:

2630-6344

Anahtar kelimeler:

Özet:

 R,S-Etodolac 1,8-diethyl-1,3,4,9-tetrahydrapyrano3,4-bindole-1-acetic acid is a nonsteroidal antiinflammatory drug that contains carboxylic acid group with the structure of pyrano3,4-bindole. In this study, a series of novel R,S-Etodolac derivatives 3a-l bearing hydrazide-hydrazone moiety were synthesized. The structures of these compounds were characterized by spectral 1H-NMR and FT-IR analyses methods. All synthesized compounds were screened for anticancer activity against androgen-independent prostate adenocarcinoma PC-3, DU-145 and androgen-dependent prostate adenocarcinoma LNCaP cell lines by using WST-8 colorimetric method. This method was used for cell viability and cytotoxicity analysis. Compound 3b SGK-720 2-1,8-diethyl-1,3,4,9tetrahydropyrano3,4-bindole-1-ylacetic acid2,6-dichlorophenylmethylenehydrazides showed 10.36, 5.24, 15.53 µM anticancer activity against PC3, DU145, LNCaP cancer cell lines, respectively. According to JC-1 mitochondrial membrane potential test and Annexin VPI staining, 3b was found to have apoptotic effect on these cancer cells. It is concluded that compound 3b containing 2,6-dichloro substituents may be one of the candidate molecules to cope with prostate cancer.

 R,S-Etodolac 1,8-diethyl-1,3,4,9-tetrahydrapyrano3,4-bindole-1-acetic acid is a nonsteroidal antiinflammatory drug that contains carboxylic acid group with the structure of pyrano3,4-bindole. In this study, a series of novel R,S-Etodolac derivatives 3a-l bearing hydrazide-hydrazone moiety were synthesized. The structures of these compounds were characterized by spectral 1H-NMR and FT-IR analyses methods. All synthesized compounds were screened for anticancer activity against androgen-independent prostate adenocarcinoma PC-3, DU-145 and androgen-dependent prostate adenocarcinoma LNCaP cell lines by using WST-8 colorimetric method. This method was used for cell viability and cytotoxicity analysis. Compound 3b SGK-720 2-1,8-diethyl-1,3,4,9tetrahydropyrano3,4-bindole-1-ylacetic acid2,6-dichlorophenylmethylenehydrazides showed 10.36, 5.24, 15.53 µM anticancer activity against PC3, DU145, LNCaP cancer cell lines, respectively. According to JC-1 mitochondrial membrane potential test and Annexin VPI staining, 3b was found to have apoptotic effect on these cancer cells. It is concluded that compound 3b containing 2,6-dichloro substituents may be one of the candidate molecules to cope with prostate cancer.

 R,S-Etodolac 1,8-diethyl-1,3,4,9-tetrahydrapyrano3,4-bindole-1-acetic acid is a nonsteroidal antiinflammatory drug that contains carboxylic acid group with the structure of pyrano3,4-bindole. In this study, a series of novel R,S-Etodolac derivatives 3a-l bearing hydrazide-hydrazone moiety were synthesized. The structures of these compounds were characterized by spectral 1H-NMR and FT-IR analyses methods. All synthesized compounds were screened for anticancer activity against androgen-independent prostate adenocarcinoma PC-3, DU-145 and androgen-dependent prostate adenocarcinoma LNCaP cell lines by using WST-8 colorimetric method. This method was used for cell viability and cytotoxicity analysis. Compound 3b SGK-720 2-1,8-diethyl-1,3,4,9tetrahydropyrano3,4-bindole-1-ylacetic acid2,6-dichlorophenylmethylenehydrazides showed 10.36, 5.24, 15.53 µM anticancer activity against PC3, DU145, LNCaP cancer cell lines, respectively. According to JC-1 mitochondrial membrane potential test and Annexin VPI staining, 3b was found to have apoptotic effect on these cancer cells. It is concluded that compound 3b containing 2,6-dichloro substituents may be one of the candidate molecules to cope with prostate cancer.

 R,S-Etodolac 1,8-diethyl-1,3,4,9-tetrahydrapyrano3,4-bindole-1-acetic acid is a nonsteroidal antiinflammatory drug that contains carboxylic acid group with the structure of pyrano3,4-bindole. In this study, a series of novel R,S-Etodolac derivatives 3a-l bearing hydrazide-hydrazone moiety were synthesized. The structures of these compounds were characterized by spectral 1H-NMR and FT-IR analyses methods. All synthesized compounds were screened for anticancer activity against androgen-independent prostate adenocarcinoma PC-3, DU-145 and androgen-dependent prostate adenocarcinoma LNCaP cell lines by using WST-8 colorimetric method. This method was used for cell viability and cytotoxicity analysis. Compound 3b SGK-720 2-1,8-diethyl-1,3,4,9tetrahydropyrano3,4-bindole-1-ylacetic acid2,6-dichlorophenylmethylenehydrazides showed 10.36, 5.24, 15.53 µM anticancer activity against PC3, DU145, LNCaP cancer cell lines, respectively. According to JC-1 mitochondrial membrane potential test and Annexin VPI staining, 3b was found to have apoptotic effect on these cancer cells. It is concluded that compound 3b containing 2,6-dichloro substituents may be one of the candidate molecules to cope with prostate cancer.

Makale detayları

Synthesis of some novel hydrazide-hydrazones derived from etodolac as potential anti-prostate cancer agents

Yazarlar:

İrem Atlıhan | Oya Orun | Ş.güniz Küçükgüzel

Yayıncı:

Marmara University

Ana Başlıklar:

Pharmaceutical Chemistry

Dergi:

Journal of Research in Pharmacy Vol.26 Issue 1, pp.1-12

Belge Tipi:

Makale

Yayın Tarihi:

6/2025

Belge Dili:

İngilizce

Document ID (Org No.):

2001346098

pISSN:

2630-6344

Etodolac

hydrazide-hydrazone

anticancer activity

apoptosis

WST-8 colorimetric method

Sayı

Makale detayları

Synthesis of some novel hydrazide-hydrazones derived from etodolac as potential anti-prostate cancer agents

Yazarlar: İrem Atlıhan | Oya Orun | Ş.güniz Küçükgüzel

Yayıncı: Marmara University

Ana Başlıklar: Pharmaceutical Chemistry

Dergi: Journal of Research in Pharmacy Vol.26 Issue 1, pp.1-12

Belge Tipi: Makale

Yayın Tarihi: 6/2025

Belge Dili: İngilizce

Document ID (Org No.): 2001346098

pISSN: 2630-6344

Etodolac

hydrazide-hydrazone

anticancer activity

apoptosis

WST-8 colorimetric method

Sayı

Yazarlar:

İrem Atlıhan | Oya Orun | Ş.güniz Küçükgüzel

Yayıncı:

Marmara University

Ana Başlıklar:

Pharmaceutical Chemistry

Dergi:

Journal of Research in Pharmacy Vol.26 Issue 1, pp.1-12

Belge Tipi:

Makale

Yayın Tarihi:

6/2025

Belge Dili:

İngilizce

Document ID (Org No.):

2001346098

pISSN:

2630-6344