56341-65-2Relevant academic research and scientific papers
Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates
Matovi?, Jelena,J?rvinen, Juulia,Sokka, Iris K.,Imlimthan, Surachet,Raitanen, Jan-Erik,Montaser, Ahmed,Maaheimo, Hannu,Huttunen, Kristiina M.,Per?niemi, Sirpa,Airaksinen, Anu J.,Sarparanta, Mirkka,Johansson, Mikael P.,Rautio, Jarkko,Ekholm, Filip S.
, p. 285 - 304 (2020/12/21)
Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers a tumor-targeting selectivity that is difficult to match by other means, the last obstacles preventing the full har
Synthesis of Bradyrhizose from d -Glucose
Ngoje, Philemon,Crich, David
supporting information, p. 523 - 527 (2020/01/21)
We describe the synthesis of the unusual bicyclic sugar bradyrhizose in 14 steps and a 6% overall yield from d-glucose. The synthesis involves the elaboration of a trans-fused carbocyclic ring onto the preexisting glucopyranose framework followed by adjus
Synthesis of the trisaccharide repeating unit of capsular polysaccharide from Klebsiella pneumoniae
Susanto, Woen,Kong, Kah-Hoe,Hua, Kuo-Feng,Wu, Shih-Hsiung,Lam, Yulin
, p. 288 - 291 (2019/01/04)
The incidences of primary, pyrogenic liver abscess complicated by meningitis and septic endophthalmitis caused by Klebsiella pneumoniae has increased globally. Earlier studies have shown that the capsular polysaccharide (CPS) of Klebsiella pneumoniae plays an important role in the resistance to phagocytosis and related pathogenicity. The first chemical synthesis of the trisaccharide repeating unit of this CPS has been achieved via stereoselective glycosylation with orthogonal and appropriate protecting groups. A new method for the pyruvylation of trans diol was developed.
Chemical Approach to Positional Isomers of Glucose-Platinum Conjugates Reveals Specific Cancer Targeting through Glucose-Transporter-Mediated Uptake in Vitro and in Vivo
Patra, Malay,Awuah, Samuel G.,Lippard, Stephen J.
supporting information, p. 12541 - 12551 (2016/10/07)
Glycoconjugation is a promising strategy for specific targeting of cancer. In this study, we investigated the effect of d-glucose substitution position on the biological activity of glucose-platinum conjugates (Glc-Pts). We synthesized and characterized all possible positional isomers (C1α, C1β, C2, C3, C4, and C6) of a Glc-Pt. The synthetic routes presented here could, in principle, be extended to prepare glucose conjugates with different active ingredients, other than platinum. The biological activities of the compounds were evaluated both in vitro and in vivo. We discovered that varying the position of substitution of d-glucose alters not only the cellular uptake and cytotoxicity profile but also the GLUT1 specificity of resulting glycoconjugates, where GLUT1 is glucose transporter 1. The C1α- and C2-substituted Glc-Pts (1α and 2) accumulate in cancer cells most efficiently compared to the others, whereas the C3-Glc-Pt (3) is taken up least efficiently. Compounds 1α and 2 are more potent compared to 3 in DU145 cells. The α- and β-anomers of the C1-Glc-Pt also differ significantly in their cellular uptake and activity profiles. No significant differences in uptake of the Glc-Pts were observed in non-cancerous RWPE2 cells. The GLUT1 specificity of the Glc-Pts was evaluated by determining the cellular uptake in the absence and in the presence of the GLUT1 inhibitor cytochalasin B, and by comparing their anticancer activity in DU145 cells and a GLUT1 knockdown cell line. The results reveal that C2-substituted Glc-Pt 2 has the highest GLUT1-specific internalization, which also reflects the best cancer-targeting ability. In a syngeneic breast cancer mouse model overexpressing GLUT1, compound 2 showed antitumor efficacy and selective uptake in tumors with no observable toxicity. This study thus reveals the synthesis of all positional isomers of d-glucose substitution for platinum warheads with detailed glycotargeting characterization in cancer.
TANNIN INHIBITORS OF HIV
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, (2013/10/07)
The invention provides a method to prevent or treat HIV-infection with synthetic tannins, and pharmaceutical compositions comprising synthetic tannins.
Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity
Zheng, Shaojun,Laraia, Luca,O'Connor, Cornelius J.,Sorrell, David,Tan, Yaw Sing,Xu, Zhaochao,Venkitaraman, Ashok R.,Wu, Wenjun,Spring, David R.
, p. 2590 - 2593 (2012/04/23)
A novel synthesis of the ellagitannin natural product tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to precipitate protein and cellular phenotype in HeLa cel
Indium(III) triflate: A highly efficient catalyst for reactions of sugars
Giri, Santosh Kumar,Verma, Monika,Kartha, K. P. Ravindranathan
scheme or table, p. 464 - 478 (2009/04/06)
Indium(III) trifluoromethanesulfonate has been found to be extremely efficient in catalyzing acyl transfer reactions of various carbohydrates and their derivatives. Selective acetolyses of certain benzyl ethers/isopropylidene acetals of sugars have been possible using In(OTf)3 in Ac2O (neat). Reaction of the per-O-acetate of 2-deoxy-2-phthalimido-D-glucose with benzyl mercaptan in the presence of In(OTf)3 led to the formation of the corresponding thioglycoside in high yield. Facile formation and hydrolysis of the isopropylidene and benzylidene acetals of various carbohydrates have also been achieved very efficiently in the presence of In(OTf)3. The results show great promise for In(OTf)3 in synthetic carbohydrate chemistry.
A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid
Clausen, Mads H.,Jorgensen, Malene R.,Thorsen, Jesper,Madsen, Robert
, p. 543 - 551 (2007/10/03)
The synthesis of monomethyl-esterified trigalacturonans 1-3 is described as part of a general strategy towards pectic oligosaccharides. The necessary monomeric building blocks were all prepared on a large scale from galactose pentaacetate. The glycosylations were carried out between galactose glycosyl donors and acceptors using the n-pentenyl glycosylation technique. Yields of the desired α-anomers were in the 50 to 74% range. The trigalactans thus obtained were then subjected to oxidation at C-6. Depending on the protecting group at this position the oxidation either produced the carboxylic acid or the corresponding methyl ester. Hereby, oligomers of galacturonic acid can be prepared with methyl esters introduced in a regiocontrolled fashion.
An efficient method for the synthesis of a 1,6-anhydro-α-D-galactofuranose derivative and its application in the synthesis of oligosaccharides
Sarkar, Sujit Kumar,Choudhury, Ambar Kumar,Mukhopadhyay, Balaram,Roy, Nirmolendu
, p. 1121 - 1130 (2007/10/03)
Synthesis of 1,6-anhydro-2,3,5-tri-O-benzoyl-β-D-galactofuranose (3) has been achieved in good yield by stannic chloride catalysed ring closure of methyl 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactofuranoside (1). The anhydro compound 3 was converted to the
Syntheses of trehazolin derivatives and evaluation as glycosidase inhibitors
Kobayashi,Shiozaki,Ando
, p. 2570 - 2580 (2007/10/02)
The trehazolin derivatives 9-12 were synthesized from the aminocyclitol (7), which is the degradation product of trehazolin (5). In particular, compounds 9-11 were pseudodisaccharides that underwent replacement of the corresponding nonreducing D-glucose m
