Building a Macrocyclic Toolbox from C-Linked Carbohydrates Identifies Antiangiogenesis Agents from Zebrafish Assay

Jogula, Srinivas (author)

Dasari, Bhanudas (author)

Khatravath, Mahender (author)

Chandrasekar, Gayathri (author)

Kitambi, Satish Srinivas (author): Karolinska Institutet,Södertörns högskola,Institutionen för naturvetenskap, miljö och teknik,Karolinska institutet

Arya, Prabhat (author)

(creator_code:org_t)

2013-07-04
2013
English.
In: European Journal of Organic Chemistry. - : Wiley. - 1434-193X .- 1099-0690. ; 2013:23, s. 5036-5040

Related links:: https://urn.kb.se/re...; show more...; https://doi.org/10.1...; http://kipublication...; show less...

Abstract Subject headings

We report the synthesis of four different types of macrocyclic-derived glycohybrids from carbohydrates that have an amino acid moiety in the large-ring skeleton. These macrocyclic glycohybrids were obtained from -C-1H- and -C-1H-linked carbohydrates. In one series, we utilized ring-closing metathesis as the stitching technology to obtain two different macrocycles, i.e., trans equatorial-axial C-1H and C-5H and cis axial-axial C-1H and C-5H. The click approach was the key reaction in our second series to obtain two other macrocyclic compounds, i.e., trans equatorial-axial C-1H and C-5H and cis axial-axial C-1H and C-5H. The evaluation of this toolbox resulted in the identification of two unique compounds as antiangiogenesis agents in an embryonic zebrafish assay. Interestingly, in both cases, the macrocyclic compounds that have a cis relationship (i.e., axial-axial orientation) between C-1H and C-5H showed activity and their other diastereomers (i.e., equatorial-axial C-1H and C-5 H) with a trans relationship did not show any effect.

By the author/editor: Jogula, Srinivas; Dasari, Bhanudas; Khatravath, Mahe ...; Chandrasekar, Ga ...; Kitambi, Satish ...; Arya, Prabhat

About the subject

MEDICAL AND HEALTH SCIENCES: MEDICAL AND HEAL ...; and Medical Biotechn ...; and Medical Biotechn ...

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