OK, great. DMR is still FM and relatively wide band. SSB or CW would easily top those distances on UHF.
DMR in simplex single slot mode is only 6.25 khz wide. And %95 of all user radios ignore the timeslot when in simplex, so the max distance is only limited by the decoder, which I saw someone do the math for once, and UHF can travel over 65,000 km in the time between the on/off slot.
To stay on topic, I have done 70cm DMR simplex text msging over 100 miles in SoCal regoin (lots of hills and bldgs), on flat ground, not on the hill tops.
From San Diego to Long Beach did voice DMR at 5 watts, and text msg'ing (100 miles) Used beams on both sides, both horizontal.
From San Diego to Santa Monica did voice DMR at 40 watts into a home made folded dipole. Other station was running a dual band vertical. (120 miles).
Next test is going to be 200+ miles flat land. (not mountain to mountain)
My assumtion is, a DMR text msg could easily propagate as far as UHF SSB. DMR voice will likely carry as far as SSB as well. You'll need more power to get there, but in the end, it's RF just the same. You got line of sight, or refraction, or ducting, you're not going to ever reach the upper limit of the time slotting, and even if you did, it probably wouldn't matter in simplex, only in a dual slot repeater.
A satellite running a transponder designed to take DMR in, and return it down on another frequency should work just fine. It's when you try to squeeze both slots into the same frequency that distance becomes a problem, and it's due to the time sync, not the signals themselves.