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Results: 4

1.
Scheme 1

Scheme 1. From: Tetrakis (hydroxylmethyl) phosphonium chloride as a covalent crosslinking agent for cell encapsulation within protein-based hydrogels.

Suggested THPC reaction mechanism: (A) formation of formaldehyde to initiate hydroxymethyl arm replacement, (B) amine-formaldehyde reaction to yield an immonium ion in a Mannich-type reaction, and (C) phosphorus reaction with the immonium ion to complete the amine coupling.

Cindy Chung, et al. Biomacromolecules. ;13(12):3912-3916.
2.
Figure 1

Figure 1. From: Tetrakis (hydroxylmethyl) phosphonium chloride as a covalent crosslinking agent for cell encapsulation within protein-based hydrogels.

(A) Spontaneous formaldehyde (HCOH) generation positively correlates with THPC concentration. (B) Formaldehyde generation from various amino acids: lysine, glycine, proline, and cysteine alone (−) or reacted in the presence of 0.43 M THPC (+). (C) 31P NMR of THPC alone compared to THPC reacted with proline (Pro), glycine (Gly), or lysine (Lys), where chemical shifts are referenced to 85% phosphoric acid, which is assigned a chemical shift of 0. (D) Extent of THPC-lysine reaction as a function of THPC to lysine reactive group molar ratio.

Cindy Chung, et al. Biomacromolecules. ;13(12):3912-3916.
3.
Figure 2

Figure 2. From: Tetrakis (hydroxylmethyl) phosphonium chloride as a covalent crosslinking agent for cell encapsulation within protein-based hydrogels.

(A) Schematic of elastin-like protein (ELP). (B) Time to gelation of 5 wt% ELP hydrogels with various THPC:ELP reactive group molar ratios. Statistical significance is represented by letters above each column, with different letters signifying distinct statistical groups, p < 0.05. (C) Storage modulus, G′, of 5 wt% ELP hydrogels for 0.5:1 (gray circle) and 1:1 (gray squares) crosslinking density groups during frequency sweeps at a shear strain of 0.7%, which was determined to be within the linear viscoelastic regime. (D) Storage moduli, G′, of ELP hydrogels containing 3 (black circles), 5 (gray squares), and 10 (clear diamonds) weight percent ELP at 1:1 crosslinking density.

Cindy Chung, et al. Biomacromolecules. ;13(12):3912-3916.
4.
Figure 3

Figure 3. From: Tetrakis (hydroxylmethyl) phosphonium chloride as a covalent crosslinking agent for cell encapsulation within protein-based hydrogels.

(A) Representative live (green)/dead (red) projections of encapsulated mouse embryoid bodies in 5 wt% ELP hydrogels (2 mm in diameter, 0.5 mm in height) of varying THPC:ELP reactive group molar ratios immediately after encapsulation and after 7 days of culture. Hydrogels with 0.5:1, 1:1, and 2:1 crosslinking density correspond to storage moduli of ~260, 2200, and 1400 Pa, respectively. By day 7, cellular outgrowth of the lowest crosslinking density hydrogel (0.5:1) encompassed the entire hydrogel. Scale bar = 250 microns. (B) Cardiomyocyte differentiation of an encapsulated mouse embryoid body, in a 5 wt% ELP hydrogel with 0.5:1 crosslinking density, was visualized by expression of GFP-tagged alpha-myosin heavy chain (α-MHC) reporter (green) and counterstained with DAPI (blue) for nuclei visualization after 8 days of culture. Scale bar = 100 microns. (C) Encapsulated chick dorsal root ganglion (DRG), in a 3 wt% ELP hydrogel with 1:1 crosslinking density (modulus ~1500 Pa), cultured for 7 days, and stained for neuronal marker, β-tubulin (red), and glial marker, S100 (green), with Hoescht (blue) for nuclei visualization. Scale bar = 500 microns.

Cindy Chung, et al. Biomacromolecules. ;13(12):3912-3916.

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