Synthsis of hemin and porphyrin derivatives and their evaluation for anticancer activity

Citation
Sm. Sondhi et al., Synthsis of hemin and porphyrin derivatives and their evaluation for anticancer activity, I J CHEM B, 40(2), 2001, pp. 113-119
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
ISSN journal
03764699 → ACNP
Volume
40
Issue
2
Year of publication
2001
Pages
113 - 119
Database
ISI
SICI code
0376-4699(200102)40:2<113:SOHAPD>2.0.ZU;2-U
Abstract
N-Ethylaminoadenosine, histamine, 2-amino-2-thiazoline, 4-aminoantipyrine, sulphathiazole and a number of 3,4-diaryl-2-iminothiazolines are coupled wi th hemin to give bis coupled products 3a, 3b, 3c, 3d, 3e and 3f-m, respecti vely. Mono coupling of 2-amino-2-thiazaline with hemin gives isomeric mixtu re of mono coupled product 4. Deuteroporphyrin IX dicarboxylic acid is coup led with 2-amino-2-thiazoline to give bis coupled product 6 which on treatm ent with MnCl2. 4H(2)O gives compound 7. Compounds 3a-m and 4 have been scr eened for anticancer activity against a small panel of six cancer cell line s consisting of prostate tumour (DU145, PC3), colon carcinoma (HT29 or SW62 0), melanoma (SK-MEL-5, LOX), breast cancer (MCF 7 and adriamycin resistant MCF 7), CNS (U251) and ovarian cancer (IGROV1). Best GI(50) (concentration which inhibits the cell growth by 50%), values are shown by 3f, 6.3 muM (p rostate tumour, cell line DU 145); 3f, 6.1 muM (colon tumor, cell line HT29 ); 4, 2.09 muM (colon tumor, cell line SW620); 3f, 2.2 muM (melanoma tumor, cell line LOX); 3i, 4.4 muM (breast tumor, cell line MCF7/ADR); 3j, 2.68 m uM (ovarian tumor, cell line IGROV1) and 3g, 1.25 muM (CNS tumor, cell line U 251) respectively.