Synthesis of a Conjugate of Gossypol with Doxorubicin

Synthesis of a Conjugate of Gossypol with Doxorubicin Full article

Journal

Current Organic Chemistry
ISSN: 1385-2728 , E-ISSN: 1875-5348

Output data

Year: 2025, Volume: 29, DOI: 10.2174/0113852728358616241226064825

Authors

Stepanov Andrey V. ¹ , Krayushkin Mikhail M. ¹ , Tretyakov Evgeny V. ¹ , Ilyushenkova Valentina V. ¹ , Shchekotikhin Andrey E. ^2,3 , Akchurin Igor O. ^2,3 , Dezhenkova Lyubov G. ³ , Yarovenko Vladimir N. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninskii Prosp., 119991 Moscow, Russian Federation
2	D.I. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russian Federation
3	G.F. Gause Institute of New Antibiotics, 119021 Moscow, Russian Federation

Gossypol has been shown to be a promising natural product for the anticancer drug development for treating leukemia, lymphoma, colon carcinoma, breast cancer, and other malignant disease. It is known that the conversion of aldehyde groups of gossypol into iminofragments by the treatment of various amines can reduce the toxicity of the derivative and simultaneously increase their pharmacological efficacy. This article describes the preparation and screening of antiproliferative properties of a conjugate of gossypol with antitumor antibiotic doxorubicin. It has been shown that the reaction of the amino group of doxorubicin with the aldehyde groups of gossypol gives the condensation product in which two pharmacophores are linked via enamine– enamine moieties. However, this conjugation decreased the antiproliferative activity of paternal doxorubicin and gossypol against chronic myeloid leukemia cells K562 and led to dramatic loss of potency against MDRsubline K-562/4 with expression of Р-glycoprotein (Р-gp).

Stepanov A.V. , Krayushkin M.M. , Tretyakov E.V. , Ilyushenkova V.V. , Shchekotikhin A.E. , Akchurin I.O. , Dezhenkova L.G. , Yarovenko V.N.
Synthesis of a Conjugate of Gossypol with Doxorubicin
Current Organic Chemistry. 2025. V.29. DOI: 10.2174/0113852728358616241226064825 OpenAlex

OpenAlex:

W4406930486

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