Synthesis and Studies of Glucosamine Conjugated BF2-Oxasmaragdyrin

Kandala Laxman; B. Pradeep K. Reddy; Andrea Robinson; Rohit Srivastava; Mangalampalli Ravikanth

doi:10.1002/slct.201903986

Synthesis and Studies of Glucosamine Conjugated BF₂-Oxasmaragdyrin

Kandala Laxman, B. Pradeep K. Reddy, Andrea Robinson, Rohit Srivastava, Mangalampalli Ravikanth

School of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

Abstract

A value addition to the existing NIR fluorescence imaging agents has been synthesized in the form of glucosamine conjugated BF₂-oxasmaragdyrin by treating meso-p-carboxyphenyl BF₂-oxasmaragdyrin with 6-amine-6-deoxy-1-O-Boc-2-N-Boc-β-D-glucosamine in the presence of HBTU. The glucosamine conjugated BF₂-oxasmaragdyrin was thoroughly characterized by HRMS, 1D, and 2D NMR spectroscopy. The photophysical studies revealed that the conjugates are highly stable, absorb in visible- far-red region (400-700 nm) and emits in far-red region (715 nm) with moderate quantum yields. The electrochemical studies showed that the molecules are stable under redox conditions with one reversible reduction and three reversible oxidations. The glucosamine conjugated BF₂-oxasmaragdyrin was found to be highly biocompatible with good cellular uptake in L929 and MDA-MB-231 cells.

Original language	English
Pages (from-to)	938-943
Number of pages	6
Journal	ChemistrySelect
Volume	5
Issue number	3
DOIs	https://doi.org/10.1002/slct.201903986
Publication status	Published - 23 Jan 2020

Keywords

BF-Oxasmaragdyrin
Covalent conjugates
Glucosamine
Macrocycles
NIR fluorescence

Cite this

Laxman, K., Reddy, B. P. K., Robinson, A., Srivastava, R., & Ravikanth, M. (2020). Synthesis and Studies of Glucosamine Conjugated BF₂-Oxasmaragdyrin. ChemistrySelect, 5(3), 938-943. https://doi.org/10.1002/slct.201903986

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abstract = "A value addition to the existing NIR fluorescence imaging agents has been synthesized in the form of glucosamine conjugated BF2-oxasmaragdyrin by treating meso-p-carboxyphenyl BF2-oxasmaragdyrin with 6-amine-6-deoxy-1-O-Boc-2-N-Boc-β-D-glucosamine in the presence of HBTU. The glucosamine conjugated BF2-oxasmaragdyrin was thoroughly characterized by HRMS, 1D, and 2D NMR spectroscopy. The photophysical studies revealed that the conjugates are highly stable, absorb in visible- far-red region (400-700 nm) and emits in far-red region (715 nm) with moderate quantum yields. The electrochemical studies showed that the molecules are stable under redox conditions with one reversible reduction and three reversible oxidations. The glucosamine conjugated BF2-oxasmaragdyrin was found to be highly biocompatible with good cellular uptake in L929 and MDA-MB-231 cells.",

keywords = "BF-Oxasmaragdyrin, Covalent conjugates, Glucosamine, Macrocycles, NIR fluorescence",

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AU - Laxman, Kandala

AU - Reddy, B. Pradeep K.

AU - Robinson, Andrea

AU - Srivastava, Rohit

AU - Ravikanth, Mangalampalli

PY - 2020/1/23

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N2 - A value addition to the existing NIR fluorescence imaging agents has been synthesized in the form of glucosamine conjugated BF2-oxasmaragdyrin by treating meso-p-carboxyphenyl BF2-oxasmaragdyrin with 6-amine-6-deoxy-1-O-Boc-2-N-Boc-β-D-glucosamine in the presence of HBTU. The glucosamine conjugated BF2-oxasmaragdyrin was thoroughly characterized by HRMS, 1D, and 2D NMR spectroscopy. The photophysical studies revealed that the conjugates are highly stable, absorb in visible- far-red region (400-700 nm) and emits in far-red region (715 nm) with moderate quantum yields. The electrochemical studies showed that the molecules are stable under redox conditions with one reversible reduction and three reversible oxidations. The glucosamine conjugated BF2-oxasmaragdyrin was found to be highly biocompatible with good cellular uptake in L929 and MDA-MB-231 cells.

AB - A value addition to the existing NIR fluorescence imaging agents has been synthesized in the form of glucosamine conjugated BF2-oxasmaragdyrin by treating meso-p-carboxyphenyl BF2-oxasmaragdyrin with 6-amine-6-deoxy-1-O-Boc-2-N-Boc-β-D-glucosamine in the presence of HBTU. The glucosamine conjugated BF2-oxasmaragdyrin was thoroughly characterized by HRMS, 1D, and 2D NMR spectroscopy. The photophysical studies revealed that the conjugates are highly stable, absorb in visible- far-red region (400-700 nm) and emits in far-red region (715 nm) with moderate quantum yields. The electrochemical studies showed that the molecules are stable under redox conditions with one reversible reduction and three reversible oxidations. The glucosamine conjugated BF2-oxasmaragdyrin was found to be highly biocompatible with good cellular uptake in L929 and MDA-MB-231 cells.

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10.1002/slct.201903986

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