Synthesis and antitumor activity of novel dibutyltin carboxylates of aminoglucosyl derivatives.
In this study, di-n-butyltin(IV) oxide was reacted with the amino glucose analog, cis-4-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl)imido]-4-oxo-2-butenoic acid (1a) and o-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl) carbamoyl] benzoic acid (2a) to give the complexes bis-{cis-4-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl)imido-4-oxo-2-butenoic acid]-di-n-butyltin} carboxylate (1) and bis-{o-[N-(1',3',4',6'-tetra-O-benzoyl-2-deoxy-glucopyranosyl) carbamoyl-benzoic acid]-di-n-butyltin}carboxylate (2). These two compounds were then characterized by IR, NMR and MS. In vitro tests showed that both compounds have high cytotoxicity in four tumor cell lines (P388, HL-60, A549 and BEL-7402). Clonogenic assays demonstrated that both compounds 1 and 2 have hematopoietic cell toxicity at 10(-6) M.
Li
Wei
W
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Pharmacy, Ocean University of China, Qingdao, China.
Zhang
Zhong-Wei
ZW
Ren
Su-Mei
SM
Sibiril
Yann
Y
Parent Massin
Dominique
D
Jiang
Tao
T
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D006801:Humans; D009947:Organotin Compounds / Q000138:chemical synthesis* / Q000737:chemistry* / Q000633:toxicity
D000970:Antineoplastic Agents; D005960:Glucosides; D009947:Organotin Compounds; C544207:bis(2-(N-(1',3',4',6'-tetra-O-benzoyl-2-deoxyglucopyranosyl)carbamoylbenzoic acid)-di-n-butyltin)carboxylate; C544206:bis(4-(N-(1',3',4',6'-tetra-O-benzoyl-2-deoxyglucopyranosyl)imido-4-oxo-2-butenoic acid)-di-n-butyltin)carboxylate; C056189:di-n-butyltin; D005947:Glucose