当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Design and synthesis of a cephalosporin-retinoic acid prodrug activated by a monoclonal antibody-beta-lactamase conjugate.

Design and synthesis of a cephalosporin-retinoic acid prodrug activated by a monoclonal antibody-beta-lactamase conjugate.

Abstract：

:Two novel series of all-trans-beta-retinoic acid derivatives were synthesized and found to possess anticancer activity. The first series, cephalosporin 3'-retinoic esters 6 and 7 were, respectively, obtained by the condensation of all-trans-beta-retinoic acid (2) with cephalosporins 4 and 5. The second series, 7-(retinamido)cephalosporins 11 and 12, were synthesized, respectively, by the condensation of 2 with cephalosporins 9 and 10. These four heretofore undescribed compounds 6, 7, 11, and 12 showed inhibitory activity against murine leukemias (L1210 and P388), sarcoma 180, breast carcinoma (MCF7), and human T-lymphocytes (Molt4/C8 and CEM/0). They also inhibited squamous metaplasia and keratinization in tracheal organ cultures derived from vitamin-A-deficient hamsters. Moreover, cephalosporin 3'-retinoic ester 7 exhibited enhanced activity against keratinization with ED(50)=3.91 x 10(-11) M in the presence of a beta-lactamase from Staphylococcus aureus 95. A tumor targeting fusion protein (dsFv3-beta-lactamase) was also used in conjunction with cephem-based retinoid 7 and the potency of 7 toward L1210, P388, and MCF7 was found to approach that of the free retinoic acid (2). In the presence of dsFv3-beta-lactamase, tumor cells were found to be much more susceptible to retinoid 7 than normal human embryonic lung cells. These notions provide a new approach to the use of beta-retinoic acid for antitumor therapy.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Hakimelahi GH,Ly TW,Yu SF,Zakerinia M,Khalafi-Nezhad A,Soltani MN,Gorgani MN,Chadegani AR,Moosavi-Movahedi AA

doi

10.1016/s0968-0896(01)00127-4

subject

Has Abstract

pub_date

2001-08-01 00:00:00

pages

2139-47

issue

8

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(01)00127-4

journal_volume

9

pub_type

杂志文章

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