83392-10-3Relevant articles and documents
SYNTHESIS OF N4-ACYLSPERMIDINES
Sundaramoorthi, Rajeswari,Marazano, Christian,Fourrey, Jean-Louis,Das, C. Bhupesh
, p. 3191 - 3194 (1984)
N4-Acylspermidines have been synthesised in good yields from γ-aminobutyric acid and from spermidine.
Synthesis and in vitro antitumor activity of novel acylspermidine derivative N-(4-aminobutyl)-N-(3-aminopropyl)-8-hydroxy-dodecanamide (AAHD)against HepG2 cells
Al-Malki, Abdulrahman L.,Razvi, Syed Shoeb,Mohammed, Furkhan Ahmed,Zamzami, Mazin A.,Choudhry, Hani,Kumosani, Taha A.,Balamash, Khadijah S.,Alshubaily, Fawzia A.,ALGhamdi, Shareefa A.,Abualnaja, Khalid O.,Abdulaal, Wesam H.,Zeyadi, Mustafa A.,Al-Zahrani, Maryam H.,Alhosin, Mahmoud,Asami, Tadao,Moselhy, Said S.
, (2019)
Naturally occurring polyamines like Putrescine, Spermidine, and Spermine are polycations which bind to the DNA, hence stabilizing it and promoting the essential cellular processes. Many synthetic polyamine analogues have been synthesized in the past few years, which have shown cytotoxic effects on different tumours. In the present study, we evaluated the antiproliferative effect of a novel, acylspermidine derivative, (N-(4-aminobutyl)-N-(3-aminopropyl)-8-hydroxy-dodecanamide)(AAHD)on HepG2 cells. Fluorescence staining was performed with nuclear stain (Hoechst 33342)and acridine orange/ethidium bromide double staining. Dose and the time-dependent antiproliferative effect were observed by WST-1 assays, and radical scavenging activity was measured by ROS. Morphological changes such as cell shrinkage & blebbing were analyzed by fluorescent microscopy. It was found that AAHD markedly suppressed the growth of HepG2 cells in a dose- and time-dependent manner. It was also noted that the modulation of ROS levels confirmed the radical scavenging activity. In the near future, AAHD can be a promising drug candidate in chalking out a neoplastic strategy to control the proliferation of tumour cells. This study indicated that AAHD induced anti-proliferative and pro-apoptotic activities on HCC. Since AAHD was active at micromolar concentrations without any adverse effects on the healthy cells (Fibroblasts), it is worthy of further clinical investigations.
An approach to use an unusual adenosine transporter to selectively deliver polyamine analogues to trypanosomes
Tye, Ching-Kim,Kasinathan, Ganasan,Barrett, Michael P.,Brun, Reto,Doyle, Valerie E.,Fairlamb, Alan H.,Weaver, Richard,Gilbert, Ian H.
, p. 811 - 816 (1998)
In this paper we describe an approach to selectively deliver compounds to trypanosomes using an adenosine transporter which is unique to the trypanosome. Various polyamine analogues have been attached to known substrates of this adenosine transporter. The compounds prepared interact specifically with the adenosine transporter, some with a similar efficiency to berenil, a known substrate.
Synthesis, screening and pro-apoptotic activity of novel acyl spermidine derivatives on human cancer cell lines
Razvi, Syed Shoeb,Choudhry, Hany,Moselhy, Said Salama,Kumosani, Taha Abduallah,Hasan, Mohammed Nihal,Zamzami, Mazin A.,Abualnaja, Khalid Omer,Al-Malki, Abdulrahman Labeed,Alhosin, Mahmoud,Asami, Tadao
, p. 190 - 201 (2017)
The polyamines putrescine, spermidine, and spermine are polycationic, alkyl polyamines which play a significant role in eukaryotic cell proliferation. The polyamine metabolism and function are dysregulated in tumor cells making them an attractive therapeutic target by employing polyamine analogs. These analogs have a high degree of similarity with the structure of polyamines but not with their function. Multidrug resistance is a major factor in the failure of many chemotherapeutic drugs which necessitates further research and exploration of better novel alternatives. In the present study, Twenty-six novel acylspermidine derivatives were synthesized and evaluated for their anti-proliferative and pro-apoptotic activities on human breast cancer cells and T-lymphoblastic leukemia cells. The cell proliferation and apoptosis assays using WST-1 and annexin-V/7AAD staining respectively suggest that Compound 1 (C19H41N3O2) Compound 7(C25H51N3O2) and Compound 8 (C29H59N3O) significantly reduced cancer cell viability in a dose- and time-dependent manner. Interestingly, compounds 7, 8 and 9 had slight or no effect on cell proliferation of non-cancerous cells. These studies speculate that these novel acylspermidine derivatives could be promising candidates in designing an anti-proliferative drug, targeting both solid and blood cancer cells.
Method for synthesizing spermidine hydrochloride
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Paragraph 0024-0025; 0034-0035; 0037-0038, (2020/07/13)
The invention relates to a method for synthesizing spermidine hydrochloride. The reaction formula is shown as the following formula (I) which is described in the specification. In the formula (I), theprotective group R1 of amino in 4-amino-1-butanol of a compound 2 is one of tert-butyloxycarboryl Boc-, triphenylmethyl Trt- and p-methoxytriphenylmethyl Mmt-, and a protective group R2 of propane diamine of the compound is one of tert-butyloxycarbonyl Boc-, triphenylmethyl Trt- and p-methoxytriphenylmethyl (Mmt-). A reagent used in the Mitsunobo reaction condition is one of triphenylphosphine, di-tert-butyl azodicarboxylate, diethyl azodicarboxylate and diisopropyl azodicarboxylate. The preparation method disclosed by the invention is simple in required process condition, mild in reaction condition, capable of effectively obtaining spermidine hydrochloride, relatively short in synthesis step and relatively high in synthesis yield.
